“Your idea of building a community is interesting but I’m not going to join. I’m already part of a membership community that I joined decades ago and so I’m not interested in being a member. I’d be happy to support you by coming out to your dinner but this wouldn’t be for me. I want to make that clear upfront.”

This is what a leader told me when he asked what my business was about. He was upfront, direct and no nonsense. Great. Who doesn’t love someone who can be boldly blunt and firm. He needs nothing from me and so he can be as direct as he likes. I like direct people. But sometimes it burns.

The cliff you jump off with no instructions

They say that when you become a founder, you go from the highest of highs to the lowest of lows. Nobody fully understands what that feels like until you actually become a founder because it’s a job you’ve never held before. There is no training. You can’t really go to school for it (though many try). It’s something you have to do by just diving in. When you jump off the cliff, it’s a black hole and you have no clear idea how you’ll feel until you just do it.

Subscribe now

Your superpower only takes you so far

Every founder has one expertise that they’re innately really good at. I call this the founder’s “superpower.” You have to be really good at this thing or you’re not a very valuable founder. Mine is sales. I’m really good at sales because I have strong communication skills and I build trust with people. I can relate to the customers I’m selling to and share a really good value proposition but that’s only if the customer is right for my business. I realize that not everyone is.

When the doubt creeps in

But when you give your pitch and the conversion doesn’t happen. It drops your optimism score down a notch. With each pitch that goes dry, your optimism drops further, sometimes multiplying faster depending on how many days you’ve had a dry spell. As each day goes by, and sometimes weeks, the doubt starts to creep in and you wonder if you’re truly cut out for this? Maybe your product idea wasn’t as great as you thought it would be? Maybe your value proposition is weak and you’re not aware enough to understand this? Maybe you’re just not good enough, plain and simple.

Every founder has these thoughts in their head every now and then, whether they share that openly or not. There are no guarantees in life, but as a founder, you are truly gambling with the unknown because you’re building from zero to one. You’re not taking on a “job” or being promoted into a new role. There’s no playbook for your idea, and the more unique it is, the more you need to blaze the trail. You are building something from nothing and the only thing you have to keep going is your instincts, your drive, and a belief that sometimes starts to drop and you know you’ve got to hold on.

Then the good days hit

But with bad days, come the good. When you get multiple customers in one month and your numbers go up, it’s the most exhilarating feeling in the world. The truth is, it’s rarely about the dollar amount. To me, it’s more about having conviction about something and finding people that truly felt value in what you were selling. You find your people. And when you’re building a private peer community like I am, it’s amazing that the right people see the value of your business right away. The conversion is quicker than most people think - often one personal conversation.

The loneliness nobody prepares you for

Your journey as an entrepreneur, particularly if you’re a solo entrepreneur, is going to be hard. The hardest part is the loneliness because you need to be your own cheerleader, coach, team player, boss. Some founders seek an executive coach, which is definitely helpful but there are many out there and you’ll need to find the right one. I’m not fond of coaches that are just certified on paper - they can’t help me out of a bind when they’ve never actually been in the arena. I also need to admire the coach in some way or I don’t think I could tolerate their coaching for more than a few sessions.

If you have peers going through the same journey as you, that is definitely helpful. It will allow you to share your thoughts with a confidante and be vulnerable when you spend days and weeks acting like you have all the answers. You often don’t.

If you have a group of peers, now we’re talking. Everyone at the same level, doing what you’re doing, going through the same challenges and stepping out of the isolation for a few hours to gain support, encouragement and sometimes just a soul to share your most challenging moments with. That’s priceless because in the end, we are all human.

This is normal

So if you’re a founder, new or deep into your business, and you have waves of feeling on top of the world, with occasional bouts of demoralizing on-your-knees depression, do not fret. This is normal. You’re building something that doesn’t quite exist the way you built it, and that’s something special. You are taking a risk that most people wouldn’t dream about because they know how difficult it is. You are the main character and as we all know, main characters always go through an exciting, painful, unbelievable journey in their stories. Sometimes they become legends. But they always start off as normal people going from zero to one.

Subscribe now

Leave a comment

I’m Christine. Former CPO, current founder. I run 5 to 9 Society, a leadership community built for founders and operators who are serious about the work. If this resonated with you, you’re probably a leader that needs a community like ours.

I spent years as an employee doing something most of my peers thought was optional: showing up to things when I didn’t need anything from them. No job search driving me there, no pitch I was rehearsing in my head on the way over, no hidden agenda underneath the small talk. Just genuine curiosity about who was in the room and what they were building.

I went to dinners, events, and coffee chats when my calendar didn’t demand it and my career didn’t depend on it. I did it consistently, even when I was exhausted from a full week of back-to-back meetings, even when staying home sounded infinitely better. And honestly, some nights it really did sound better. But I went anyway, because somewhere in the back of my mind I understood that relationships don’t build themselves and timing is rarely convenient.

What I noticed over time was that people remembered me. Not because I was the loudest in the room or the most decorated on paper, but because I kept showing up before I needed to. That consistency builds something you genuinely can’t manufacture on demand. It builds trust, familiarity, and a kind of quiet credibility that follows you into rooms you haven’t even walked into yet.

When I Launched, I Didn’t Start From Zero

When I launched 5 to 9 Society, something happened that didn’t surprise me but definitely surprised people watching from the outside. Members signed up immediately. Sponsors came in early without me having to chase anyone down. Guests showed up to the first event because they already knew me and trusted what I was putting into the world. I hadn’t spent a dime on marketing. I hadn’t cold pitched a single person. I had just spent years being a person worth knowing before I needed anyone to know me.

That doesn’t happen by accident. It happens because of a dinner three years earlier where I sat next to someone and actually listened to what they were working on. It happens because of a coffee I didn’t cancel even when my week was falling apart. It happens because I showed genuine interest in people’s work, remembered the details, followed up when something reminded me of them. None of that is sophisticated strategy. It’s just being present and consistent over a long period of time, with no expectation of return.

None of it would have happened if I had only started reaching out when I needed something.

The Fire Extinguisher Approach Doesn’t Work

I watch a lot of smart, capable people make the same mistake. They treat networking like a fire extinguisher: something you grab when there’s already smoke. They go quiet for years, heads down in execution mode, and then a role disappears or a company hits a wall and suddenly they’re at events they’ve never attended before, asking for introductions from people they’ve never invested in. The energy is off and everyone in the room can feel it. It’s not malicious, it’s just transactional, and people are perceptive enough to know the difference between someone who is genuinely interested in them and someone who needs a favour.

I’ve been in rooms where someone I hadn’t heard from in two years slid into the conversation with a very specific ask within the first three minutes. It’s uncomfortable for everyone. Not because asking for help is wrong, it isn’t, but because there was no foundation there. No history of giving, of showing up, of caring about what the other person was building before they needed them to care back. The goodwill has to exist before you can draw from it.

The data backs this up in a way that should make anyone rethink their approach. Around 70% of jobs are never advertised publicly, and 85% of positions are filled through networking rather than job postings (Novoresume). And yet most people only start networking when they’re already in job search mode. By then, they’re competing for visibility against everyone else who also just realized they need to show up. Referrals make up just 2% of applications but account for 11% of total hires, a conversion rate roughly 10 times higher than any other channel (Wave Connect).

Nobody teaches you that the relationship you need at 38 requires you to show up at 34.

Subscribe now

If You’re an Executive, This Matters Even More

There’s a particular version of this mistake that I see executives make, and it costs them more than they realize. The more senior you get, the easier it is to justify going internal. Your days are full, your calendar is a battlefield, and the idea of adding a networking dinner on top of everything else sounds like a punishment. So you stop. You tell yourself you’ll reconnect with people when things slow down, which they never do.

But executives are precisely the people who should be in the room. You have context, perspective, and access that early-career professionals are hungry for. You have the ability to open doors, make meaningful introductions, and add real value to someone’s path just by sharing how you’ve navigated something they’re currently facing. When a senior leader shows up with that spirit, it’s rare enough that people notice and remember it.

And the cost of stopping is not theoretical. Executives surveyed reported they would lose approximately 28% of their business revenue if they stopped networking entirely (Boomset). That’s not a rounding error. That’s nearly a third of everything, gone, because the relationships that support business development quietly atrophy when you stop feeding them.

When the moment eventually comes where you need the network, because it always does, whether you’re considering a board seat, a transition, a new venture, or a chapter you haven’t named yet, the people who will move for you are the ones who have experienced your generosity firsthand. Not your title, your resume, or your generosity.

I used to tell leaders I respected to treat 20 to 30% of their time as relationship capital. Not sales, recruiting, or deal flow. Just meeting sharp, interesting people with no transactional motive attached. It sounds like a lot until you realize how quietly compounding it is over years.

Go to Give, Not to Get

The mindset shift that changes everything is deceptively simple: go to give, not to get. Go because you are genuinely curious about what someone is building and what’s hard about it right now. Go because you might know someone they should meet, or because you’ve made the exact mistake they’re about to make and you can save them six months of pain. Go because being in a room with smart, driven people who care about their work is actually a privilege, even when it doesn’t feel like one at 7pm on a Thursday when your couch is calling.

We forget that. We get so used to Slack threads and Zoom calls and async everything that we start treating in-person connection like an inefficiency rather than what it actually is: one of the most extraordinary uses of limited time available to us. The conversations that have genuinely changed the direction of my career didn’t happen in a DM. They happened across a table, with food and context and the kind of candor that only comes from being physically present with someone.

Nearly 100% of professionals say that face-to-face meetings build stronger long-term relationships than online interactions (Boomset). We know this intuitively, and yet we keep defaulting to the Slack message, the LinkedIn comment, the async update. Meeting people in real life, with your full attention and no agenda, is a gift you give both of you.

Your Next Co-Founder Won’t Be in a Slack Channel

Here’s something founders especially need to hear. The most consequential professional relationships of your life will almost certainly not come from an application, a platform, or a cold outreach. Think about how you’ve met the people who have actually mattered in your career. It was rarely through a formal process.

Your next co-founder, if you need one, will most likely come from someone you’ve already built a real relationship with, or someone you meet at the right dinner at the right time. Candidates who come through a personal referral are 4x more likely to get an interview than those who apply through a job board, and they get hired up to 70% faster (Apollo Technical). That’s not a marginal advantage. That’s a completely different playing field.

Your most strategic hire, the one who changes the trajectory of your company, will probably come through a specific intro from someone who trusts you enough to put their name behind it. Referred employees perform 33% better than those hired through other channels and are 40% more likely to still be with the company a year later (Electro IQ). The difference between a referral hire and an ATS applicant isn’t just speed or cost. It’s quality, fit, and longevity.

Think about it the same way you think about your personal relationships. You didn’t find your closest friend through a random group chat. You didn’t build your most meaningful partnership through a form submission. Those relationships formed through time, proximity, shared experience, and a series of small moments where someone showed up and paid attention. Your professional network works exactly the same way, it just requires you to treat it with the same intention.

The people who will change your business are already out there. Most of them are in rooms you haven’t walked into yet because you’ve been too busy to go.

Your Future Self Is Asking You to Go

You can’t see the future. But the future has a long memory, and it tends to reward the people who showed up before it asked them to.

So when the event invite lands in your inbox next week and your first instinct is to decline because you’re tired and busy and you’d rather decompress at home, pause for a second. Your present self wants the couch. Your future self is asking you to go.

You can wear the pajamas tomorrow.

Subscribe now

Leave a comment

Sources: Jobvite, Wave Connect / SHRM, CNBC Careers, ERIN App, electroiq.com, Apollo Technical, Boomset, Novoresume

There’s a specific kind of loneliness that doesn’t get talked about enough in founder circles.

It’s not the 2am kind. It’s not the staring-at-a-spreadsheet-wondering-if-you-made-a-mistake kind. It’s the kind that shows up in a Monday morning leadership meeting, surrounded by the people you hired, people who are smart and capable and genuinely trying, and still feeling completely alone in the room.

I’ve watched it happen from the inside, up close, more times than I can count.

I spent years as a Chief People Officer at venture-backed startups. I worked alongside six founders across different companies, different stages, different industries. And almost without exception, the thing they struggled with most wasn’t the market, wasn’t the fundraise, wasn’t the product. It was this: they had built a team, but they hadn’t found a partner.

There’s a difference. A big one.

The problem with most executives

Most executives, even the good ones, operate like elevated employees. They execute within scope. They bring recommendations. They wait for direction on the hard calls. They manage their lane and report upward. This is not a character flaw. It’s what the job description trained them to do, and in many organizations, it’s exactly what’s wanted.

But founders don’t actually want that. They just don’t always know how to say it, or even how to name what’s missing.

What they want is someone who shows up already bought in. Someone who doesn’t need the vision explained because they’ve already internalized it. Someone who can sit across from them in a difficult conversation and engage like a peer, not like a subordinate trying to read the room. Someone who will push back directly and then commit fully, who carries the weight of the company like it’s also theirs.

That person is rare. Genuinely rare. And when a founder finds them, it changes everything.

Subscribe now

What I saw up close

I worked with two founders, at two separate companies, who each had co-founders. On paper, they had partners. In reality, they were operating in constant friction. Misaligned on hiring decisions. Split on remote versus in-office. Divided on who to promote, who to let go, how fast to move, when to hold. The co-founder relationship had become a negotiation, not a partnership. Every decision carried the weight of a disagreement that needed to be managed before anything could actually get done.

When I came in and operated the way I do, direct, honest, already aligned on what actually mattered, willing to have the uncomfortable conversation before it became a crisis, I could see what it did to them. Not just professionally. Personally.

Both of them, at different moments, looked at me the way people look when they’ve been carrying something heavy for a long time and someone finally just takes the other end.

I don’t say this to flatter myself. I say it because I’ve thought about it a lot, and I think it explains something important about what founders actually need and almost never have.

They had found something they hadn’t experienced since the earliest days of building, maybe not even then: someone who was genuinely in it with them. Not reporting to them. Not performing loyalty. Not managing up. Just in it.

The loneliness nobody names

The exec who operates like an employee isn’t doing anything wrong, technically. But there is a version of leadership that goes beyond competence, beyond execution, beyond even trust in the conventional sense. It requires the person across the table to see the whole board, feel the stakes, and engage accordingly, without being asked to, without a job description telling them to, without a performance review as the incentive.

Most founders spend years either not knowing that version exists or quietly grieving the fact that they haven’t found it.

The loneliness that comes from that isn’t dramatic. It doesn’t announce itself. It’s just a low hum underneath everything, the feeling that the decisions that matter most are ones you ultimately make alone, because the people around you are good at their jobs but not quite in the game the way you are.

Why I built what I built

This is exactly why I built 5 to 9 Society.

Not because founders need more networking. Not because they need another room full of impressive titles and polished war stories. But because the specific isolation that comes from building something, from being the one who holds the vision and the weight and the accountability, doesn’t go away just because your team is growing or your metrics are moving in the right direction.

It goes away when you find people who get it. Really get it. Who engage with the hard stuff the way a real partner does, honestly, directly, without ego getting in the way.

The right room doesn’t just make you feel less alone. It makes you sharper. It gives the decisions somewhere to land before you make them. It gives you the thing most founders are starving for without realizing it: someone who treats you like the adult in the room, because they are too.

Subscribe now

Leave a comment

I’m Christine. Former CPO, current founder. I run 5 to 9 Society, a leadership community built for founders and operators who are serious about the work. If this resonated with you, you’re probably a founder that needs a community like ours

.

I’ve paid to be in rooms that were supposed to change my life.

Rooms with impressive names, waiting lists, and member directories full of people who looked like they had it all figured out. The pitch was always the same: surround yourself with peers, be vulnerable, grow together.

What nobody tells you is that the entry requirements contradict the whole thing.

When a community requires you to hit a revenue threshold before you can join, it isn’t curating for growth. It’s curating for optics. You end up in a room full of people who are either already past the hard part or pretending they are. Nobody talks about the real stuff because the real stuff might make them look like they don’t belong. So instead you get a lot of polished war stories, selective transparency, and networking dressed up as connection.

I’ve sat in those rooms. I’ve watched people work them like a conference floor, collecting contacts, chasing deal flow, performing camaraderie. I’ve also sat in women’s investor circles that were supposed to feel different, more open, more human. They weren’t. Some of the coldest, most judgmental rooms I’ve ever been in had “women supporting women” in the tagline.

Subscribe now

That’s not an accident. It’s what happens when you build a community around status rather than substance.

The people who actually need a peer community, the ones mid-build, hands dirty, figuring it out in real time, are often the ones being screened out. And the people who make it past the velvet rope have too much to lose by being honest once they’re inside.

Vulnerability isn’t a vibe. It’s not something you can mandate with a revenue minimum and a nice venue. It shows up when people feel safe enough to say the thing they haven’t said out loud yet. That rarely happens in rooms designed to impress.

I spent a long time trying to find my room. I walked into a lot of wrong ones first.

I remember sitting at a dinner once, surrounded by women who had all the credentials I was working toward. I thought I’d finally found my people. Instead I spent the evening watching everyone perform for each other. Eye contact that lasted just long enough to assess whether you were useful. Conversations that pivoted the second someone more interesting walked in. Women looking you up and down, and then asking, “So, what do you do?” I left feeling lonelier than when I arrived, but also really turned off with the crowd. All these women who should be networking and supporting one another, but instead, judging while seated smugly with their Hermès bags on their laps. That was the night I stopped looking for a seat at someone else’s table.

I stopped looking for the right room and started building one. It took me longer than I’d like to admit to realize that was always the answer. The people who found their way to what I built get it immediately. They don’t need it explained. And honestly, that tells me everything about who belongs there and who doesn’t.

Subscribe now

Leave a comment

I’m Christine. Former CPO, current founder, permanent skeptic of rooms that require you to already have it figured out. I run 5 to 9 Society, a leadership community for founders and operators who are serious about the work, and I write here about the parts of building that don’t make it into the highlight reel.

There’s a lunch I still think about.

We’d been connected through a mutual contact, and the person across the table from me had an energy I recognized immediately. Animated. Fast-talking. The kind of person who leans in when they speak, who finishes your sentences, who makes you feel like you’re already in the middle of building something just by sitting down with them.

The idea was good. A real partnership. Something I could see working.

For two hours, they laid it all out: the vision, the structure, the audience, what we’d build and how. I walked out of that lunch genuinely excited. Maybe more than I’d been about something in a while.

Then I waited.

And waited.

When I followed up, there were reasons. The timing wasn’t right. Some things needed to fall into place first. There were a few more things they needed to figure out. Each message was reasonable on its own. But together they spelled out the thing no one ever says directly: I’m not going to do this.

They never said that. They just kept adding conditions until the idea died quietly, on its own, without anyone having to take the blame.

I wasn’t angry. I was something worse. I was numb.

Because I’d seen it before.

Subscribe now

The Pattern Nobody Talks About

Here’s what I’ve learned after a decade of working closely with founders, operators and leaders building real things:

Most people are better at describing their future than building it.

They are articulate, passionate, convincing. They can see it. They can tell you exactly how it would work. They talk about their goals with a confidence that makes you believe it too.

And then nothing happens.

Not because the idea was bad. Not because the timing was wrong. But because somewhere between the vision and the first real step, they meet themselves. And they can’t get out of their own way.

The questions start. What if it doesn’t work? What if I’m not ready? What if I need to wait until this one thing lines up? Each question sounds reasonable. Together they become a wall. And most people stand in front of that wall for months, sometimes years, calling it strategy.

I’ve watched brilliant people talk themselves out of extraordinary things. I’ve sat across from someone with a genuinely world-class idea and watched the light leave their eyes in real time as they convinced themselves why now wasn’t the moment.

After a while, it stops surprising you. But it does something to you.

When you’re in the room with enough of those people, their hesitation starts to sound like wisdom. Their caution starts to feel like maturity. And if you’re not careful, you start to adopt it. You start asking their questions instead of your own. You start waiting for conditions that will never be perfect enough to satisfy the fear underneath them.

Doubt, it turns out, is contagious. And the incubation period is short.

Then There’s the Other Kind

I remember the first time I really understood the difference.

I was early in my work with a partnerships leader in sales who I’d met from my network. We were sitting on a virtual call going through a strategic decision. An idea, really. One that, frankly, wasn’t fully mapped out. There were gaps. Real ones. Questions nobody had answers to yet.

I laid out the considerations. The things we knew, the things we didn’t, the risks worth weighing.

She listened. Nodded. And then said something I’ve never forgotten:

“We’ll figure it out as we build it. Let’s launch in 30 days.”

That was it. No waiting for the gaps to close. No committee to consult. No conditions to satisfy. Just a decision, made from conviction, with full knowledge that not everything was lined up.

We launched it. And yes, we figured it out along the way. Not because we were reckless. Because she understood something fundamental: you do not get clarity before you start. You get clarity by starting.

That’s the energy I’m talking about.

It’s not arrogance. It’s not impatience. It’s a different relationship with uncertainty. Where most people see risk as a reason to wait, this kind of person sees it as the terrain. The thing you navigate, not the thing you eliminate before you move.

Being around someone like that changes how you think. They give you permission to trust your instincts instead of auditing them into paralysis. They make the bold move feel like the obvious one.

And when you have two of them in the same room? The impossible stops sounding impossible.

What I Didn’t Understand Until I Started Building

I knew all of this intellectually before I launched 5 to 9 Society. I’d lived it for a decade. I’d seen the difference between the people who do and the people who describe.

But knowing something and feeling it are two very different things.

When I left behind the structure of a senior executive role and started building on my own, there was no buffer anymore. No team absorbing friction. No salary arriving regardless of how the week went. Just me, the thing I was building, and everything I let into my head.

I had a lunch early in those months. Different person, same movie. Big talk, real enthusiasm, and then the slow fade as the excuses started arriving. And this time I didn’t just feel numb. I felt it in my business. I left that conversation slower than I’d entered it. The momentum I’d had that morning had been quietly borrowed and not returned.

That was the moment I understood it wasn’t just about personality fit. This was a performance issue. My performance. What I chose to surround myself with was directly affecting what I was able to build.

The people who drain you aren’t bad people. They’re just fighting a different battle. One that’s mostly internal, mostly invisible, and entirely theirs to figure out. That’s not your job to fix. Your job is to know the difference between someone who’s going to make you better and someone who’s going to slow you down, and act accordingly.

Protecting the Room

This is why 5 to 9 Society is invite-only.

Not to be exclusive. Not as a branding exercise. But because I know what a room feels like when the calibration is right. When everyone in it has already decided to move, has already made a bet on themselves, has already crossed the line from talking to doing.

In that room, you don’t have to defend the premise. You don’t have to convince anyone that bold is worth it. The baseline assumption is already there: we’re building, we’re moving, we’re going to figure it out as we go.

What that room does to your thinking is hard to explain until you’ve felt it. You leave sharper. More decisive. More willing to trust the instinct that’s been right before. Not because everyone agrees with you (they don’t, and that’s valuable). Because disagreement in that room is designed to sharpen you, not stop you.

That’s not something I’m willing to compromise on. I’ve seen what the wrong room costs. I’ve felt it.

The Question Worth Sitting With

There’s someone you’re probably thinking about right now.

Someone who said all the right things, got you genuinely excited, and then disappeared when it was time to actually do the thing. Or someone who’s still in your life, still showing up, still listing reasons, still almost ready, and you keep hoping this is the week they decide to move.

I’m not telling you to cut those people out of your life. That’s not the point.

The point is: who in your life makes you bigger? Who pushes you to launch before you feel ready, not because they’re reckless, but because they’ve learned, like you’re learning, that ready is a moving target and motion is the only way to close the gap?

Find those people. Get in rooms with them. Let their conviction infect you the way other people’s doubt would.

Because the version of you that exists after two people like that sit across a table from you and say “let’s go” is a version that builds things you can’t currently imagine.

I know. I’ve been in that room.

Christine Song is the Founder of 5 to 9 Society, a private invite-only network for founders, operators and investors who are in motion. If you’re building something and you’re ready for that room, you know where to find us.

Subscribe now

When I launched my new business, 5 to 9 Society at the end of June 2025, I noticed something really interesting.

A lot of people were curious about my new venture launch. They asked questions, liked the announcements on social media, and shared that the business idea was so needed in the ecosystem. You definitely felt the love and support.

But curiosity and participation turned out to be two very different things. It’s an early reminder of something many founders eventually learn: building something reveals a lot about how people actually behave.

Curiosity Is Not Commitment

One of the first things founders notice is how much curiosity exists around new ventures.

People want to know what you’re building, who’s involved, how it works and what the long-term vision is. That makes sense, humans are naturally curious and curiosity creates conversations.

But conversations don’t always translate into participation. Oftentimes, you’ll notice people watching from the sidelines, but never actually reaching out. Some will cheer you on, but refrain from becoming a real customer. Some will say they’re interested, but never take the next step.

As a founder, I learned very quickly that curiosity is easy, but commitment is much rarer.

People Like Novelty But Your First Customers Are Often Strangers

From the outside, new ventures often look exciting. The announcements, the momentum, the new communities forming, and of course the interesting conversations happening.

It’s exciting to say, “Yeah, I know the founder, she’s working on some cool shit” but when it comes to supporting the business and actually signing up as a customer, it doesn’t happen easily. In fact, you’ll be surprised that your first customers will probably be people you don’t know personally. Strangers.

Some late nights, I’d often ponder why this is? I would come up with a whole bunch of theories in my head:

Theory #1 - Women Are More Risk Averse

It’s because you’re a woman and men typically buy from men / women typically buy from women…and women are known to be more cautious about spending money on risky things. From my experience, women founders told me that they found it harder to convert women into customers than men. They’re not sure if it’s because women are more careful about spending money? Or maybe most women aren’t used to investing in risky deals (it’s been a man’s world for most of our lives as we know). Or it’s because women want to “wait and see” before they buy, to ensure the business is successful and viable before they take the leap.

Theory #2 - Canadians Are More Risk Averse

Canadians are known to be more risk averse in many things, including investing, buying, sponsoring, purchasing, even building. Maybe Canada is a really conservative country compared to the US. So I wonder if building 5 to 9 Society in Canada first was the way to go. Should I have just started in the US instead? Someone told me Canadians have a “scarcity mindset” - there isn’t enough wealth to go around so they’re tight about spending money from hiring, to building, to investing, whereas Americans have an “abundance mindset” - they give, they refer, they buy. There’s lots to go around so we can all be successful.

Theory #3 - All The Other Reasons Founders Start To Doubt Themselves

And then there’s this, an entire whole other category. I wonder about the same things that every founder wonders about. Am I pricing right? Do I have a good enough product/service? Am I good enough to do this? When doubt creeps in and you start to lose your confidence, it’s hard to sleep at night.

Early Support Often Comes From Unexpected Places

Something I noticed as a founder fairly quickly is that support rarely comes exactly from where you expect it. This goes back to being surprised that your first customers aren’t actually from your own circle of friends or your personal network. I mean, sometimes the people you thought would be deeply involved stay on the sidelines.

I have a very vast network of friends who are all business leaders in my network. I also have over 60k connections on LinkedIn, mostly with people I’ve worked with in the past and people I’ve helped throughout their careers. Most of those people did not sign on to be customers of my business.

So who were the first people to join?

They were mostly people I didn’t know. They might have known me through social media or heard of me through LinkedIn, but the truth is, they were essentially strangers to me. Only 7% of my customers are actually people I knew personally, which I found surprising at first, but not so much now.

And it’s not for not trying. I would talk to people I know personally, share with them the value proposition of my product / service, and they would nod, smile politely, and then say they’ll get back to me (they never would). No conversion. At first I thought maybe my pitch was bad.

But then I’d get a random message from a complete stranger who had only heard of 5 to 9 Society via some random LinkedIn post I made and they would book a call. Naturally, going into these calls, I would assume they’d ask the usual questions and similar to my personal network, never call me again. But they did. And quite quickly. They converted. Complete strangers, and some from parts of the US that I don’t even have a strong network in.

Here’s what’s even more surprising. I’m often introduced to people who are building very similar businesses to mine. Let’s say they’re essentially competitors to 5 to 9 Society. Yet, they are extremely open to how they built their business, and one co-founder of a membership community even showed me his online community on a call, shared valuable lessons, and then introduced me to an agency where he hired his first community manager (he knew I was looking for one).

So when I hear people advise founders should reach out to their network of friends and community to seek out their first customers or investors, I wonder if that’s actually good advice. Trust me, I would never have assumed pitching to strangers would be easier for conversion than pitching to people I personally know.

Building Something Reveals Who Is Comfortable With Uncertainty

So I guess that leads me to a conclusion about people in general. Participation in something new requires tolerance for uncertainty.

Early supporters are often people who are comfortable stepping into something that’s still in build mode. Considering most of my customers are strangers, they didn’t sign up to show support. They believed in something that was really new, almost raw and still forming.

While most people prefer to wait until the concept is proven, the crowd has “arrived,” or the outcome feels more certain, there’s obviously a certain group of people that participate in shaping the outcome. I really love that.

My Reflection

Building something has a strange way of clarifying how the world actually works.

You start noticing the difference between people who observe and people who participate. Between people who are curious and people who commit. Between people who wait for something to be proven and those who are willing to step in while it is still uncertain.

At first I spent a lot of time wondering why certain people didn’t show up the way I expected. Why the people I knew best weren’t necessarily the first to become customers. Why strangers seemed more willing to take a chance.

But over time I realized something important. This isn’t a story about disappointment. It’s a story about signals. When you build something, the market reveals who is comfortable with risk, who believes in ideas early, and who prefers to watch from a safe distance until the outcome is obvious.

And the people who step in early are a very particular kind of person. They’re builders. They’re curious but decisive. They’re comfortable participating before something becomes popular. Those are exactly the kinds of people I want around me anyway.

So while building a company forces you to confront uncertainty, it also does something else. It quietly filters your world. And the people who walk through that filter are the ones worth building with.

If you enjoyed this episode and you want to follow my Founder journey, please subscribe - most Founders are often quite lonely.

Subscribe now

Thanks for reading.

Christine

No one prepares you for the ego shift.

As a former Chief People Officer, I walked into rooms where people expected me to have all the answers. My calendar was full weeks in advance. The CEO considered me their right-hand. My six-figure payroll hit my bank account on schedule. My title carried weight before I opened my mouth.

Then I became a founder. And everything reset.

From Strategic to Scrappy

As an executive, I debated org design, executive comp, M&A diligence. I had leaders to delegate my strategic initiatives, and while I was part of the executive team with my peers, I wasn’t entirely equal to them in hierarchy - I oversaw their performance with the CEO, which put me in a unique outlier position on the org chart.

As a fresh, new founder, I:

• Sent cold DMs on LinkedIn asking people to join a brand new community.

• Followed up on unpaid invoices personally.

• Rewrote landing page copy at midnight

• Integrated my own software like Stripe, Slack and Google Suite.

Today I have:

• No team to delegate to.

• No budget cushion.

• No brand equity to lean on.

• No paycheck (yet).

Just execution.

You literally go from architect to operator overnight. Your system kind of goes through shock therapy as you search through YouTube videos on how to build a website, how to integrate systems, how to design a logo that looks really cool. You can’t delegate someone on your team to build a Google Sheet, explore software options or to reach out to insurance agencies to protect your budding (very-new-and-barely-off-the-ground) business. It’s all on you.

Subscribe now

From Being Sought After to Asking

As an employee, Founders called me to come work for them - I never had to apply. They knew me by reputation and they connected with me on LinkedIn.

Operating leaders wanted my advice, invited me to speaker panels and offered key note presentations to kick off events.

Investors asked for my perspective and made personal requests for me to talk to their portfolio CEOs to provide coaching and advisory support.

Today, as a founder:

• I ask people to subscribe.

• I ask sponsors to believe in something that barely exists.

• I ask my network to show up, repost, support.

And sometimes they do.
And sometimes they don’t.

There’s a quiet humility in realizing your past influence doesn’t automatically transfer into future traction. Sometimes you quietly lie awake at night as you wonder…is it worse to have had a past life as a successful executive operator vs going straight into entrepreneurship right out of school? I’ve honestly thought about that a lot and the grass always seems a shade greener on the other side.

From Protected to Exposed

As an executive, risk was shared. Regardless of how tough situations became, there was always a layer of comfort and solace knowing that you weren’t alone.

There was an executive team - your peers.

There was a board - your counsel.
There was runway - you were being paid.
There were buffers - a company to fall back on.

As a founder:

• Your revenue is your oxygen.

• Your reputation is your distribution channel.

• Your mistakes are visible and permanent.

There is no HR to absorb the emotional labor. There is no CEO to escalate to. There is no executive team to commiserate with.

As a solo founder, you’re truly alone. At first, you feel solace knowing there’s no more politics to act upon. There’s no more useless meetings in your calendar and you don’t have to spend your days going to one-one-one meetings (the larger your team, the more 1:1s). There’s a sense of relief there…but when problems arise, no matter how big or small, the truth is as a solo founder, no one is coming to save you. You have to realize there’s a problem, diagnose it, figure out a solution, and then execute on getting it done. Every stage belongs to you and you alone.

You have mini panic attacks in bed and then fall into the deepest slumber from pure exhaustion.

The Psychological Shift

In the end, the hardest part wasn’t the work. I was accountable, self-managing and really good at getting things done as a executioner.

It was more about the identity shift.

• No performance review to anchor progress.

• No promotion cycle to validate momentum.

• No internal applause for stamina.

• No LinkedIn posts to share new executive hires, quarterly wins or shiny new funding round announcements.

Just signal from the market. Silence can feel loud. A slow sales week can feel existential, and there’s no BD person to hold accountable. You are business development, account manager, social media specialist, partnerships leader and everything in-between. You are one person and you are everyone at the same time.

You start to realize how much corporate structure insulated you from volatility. You used to “row” as a team, but now, you are the captain of a quiet ship. The only company you have are those who are on the “outside” - external peers, fellow founders, friends and family. They listen, they support, they even advise, but they’re not on the inside. You are in the arena alone and you realize, there are more people who are part of teams than solo building.

You need to find your own reasons to celebrate and stay optimistic.

The Part No One Talks About

There were moments in the first 90 days where I questioned everything.

• Was I early or just naive?

• Did I miscalculate my leverage?

• Was I actually built for this?

• Should I have chosen something else to build?

• Was I good enough to be a founder?

And then there were moments of clarity.

When someone paid (I remember my first “customer” and it was exhilarating).
When someone said, “I’ve been waiting for something like this.”
When a member proudly referred a new member to the community.

When a member said, “Joining 5 to 9 Society was one of the greatest highlights for me in 2025.”

That’s the trade.

Stability for sovereignty. Title for ownership. Predictability for possibility.

The first 90 days are brutal.

But they strip you down to whether you actually want this. I really did. I still do. I know that it’s a marathon, a journey, a mission. When I decided to build 5 to 9 Society, I chose to do something that I could continue to do for the next 10 years. If you can’t imagine yourself doing something for at least a decade, don’t do it. You will give up and you will find any reason to do so.

My final advice to new founders or those who are considering founding a company is that you should keep the title of “Founder” before you take on a title of “CEO.” A CEO is a chief executive officer - the chief of the company and all staff. It sounds larger than life and sometimes, when you’re just starting out, you need to be in pure build mode before you can become an executive with the scope of an executive. That keeps you humble, and you’ll need a lot of humility to get your business off the ground. The title of Founder vs CEO separates you from doing “executive things.” As a founder, you will get your hands dirty, you will get deep into the work, and you will definitely build.

To all new founders out there, stay humble and keep building.

Thanks for reading,

Christine

Very few ex-Chief People Officers leave the “safe” world of employment to start their own ventures.

Less than 5% of HR executives go on to becoming founders.

In fact, when I asked ChatGPT to check how many ex-HR executives left their corporate gig to start their own ventures (outside of independent consulting), it could not find any data related to this topic. In fact, it estimated that the number would be very small at less than 5%.

That’s a pretty somber statistic, and it doesn’t feel very encouraging, but maybe that’s the very reason I decided to do it. I’ll be honest with you, I didn’t have much time to put a business plan together. I didn’t have time to research data and do a risk assessment either. In fact, I had to rush the “soft launch” of 5 to 9 Society over a few short weeks as I had an opportunity from an amazing tech company who offered to sponsor the entire launch party during the height of a startup tech week. I couldn’t say no.

When people learned that I used to be a CPO, they automatically assumed that I must have left the employment world because I didn’t get a “seat at the table.” That maybe I was jaded because I was treated poorly like so many other HR leaders who share their grief on LinkedIn about not getting a seat, but honestly, that wasn’t me.

I had a reserved seat at the table.

The fact is I had a reserved seat at the table and I sat at every board meeting (and the after-board-meetings that followed). I “reported” to the CEO on the company org chart, but I never really “reported” to the CEO. We were true partners and we led the executive team together. In fact, one CEO told me they didn’t feel comfortable completing my performance evaluation because they felt that they were evaluating someone who had much more experience than themselves.

In reality, I had lost the ferver I had to work for companies perhaps 2-3 years earlier. I should have rightfully left around 2022 but I often said “one more gig” because I admired the next founder so much and I really wanted to experience one “exit.” (I never did by the way). The truth is, I should have followed my heart and my desire to do my own thing. The problem was I wasn’t exactly clear why. Now I am.

My personal reasons for leaving.

When you work for a company, you’re all part of a team. Everyone needs to row the boat to move ahead. When the company’s smaller, it’s easier to bring on the best rowers because there’s nowhere to hide as a weak rower. But as companies grow, you add layers and the company starts to bloat - it’s not as easy to identify who’s working hard to get across that ocean versus who’s “slacking.” I can’t remember a time ever slacking so when more people join the company due to its success (maybe you just announced a new round of funding), people want to join the “rocket ship” but not all people want to work hard to see it succeed. The freeloaders and the coat-tail riders chipped away at me, like the worker ants vs the leisurely grasshoppers who always had a voracious appetite.

The political actors made me laugh and die at the same time.

Then there’s the politics. Every company has it, but it’s the larger companies that have it 10-fold. Its worst state is at the executive level. Now that you have a shiny new executive leader that manages a vertical at the company, they are all vying for the CEO’s attention and many know how to “play the game.” You’ll see the theatrics at every executive meeting. The posturing, the pandering, the performative leadership that makes you cringe as you watch the performance silently. And worse yet, as the company “scales,” they’ll start to hire more and more “large company” leaders from McKinsey, the big banks, Fortune 500 companies, and those who graduated from Ivy League schools. There’s nothing wrong with any of the above…as long as they’ve proven they can get results. Sparkling trophies on resumes don’t always get results because these leaders often worked at companies with larger budgets, bigger teams and longer sales cycles. They are the antithesis of what most startup leaders get when they join a not-yet-profitable company counting their burn rate daily. The early startup leaders often end up doing more work than the late-joiners with the shiny resumes.

The consequences that are rarely faced.

Lastly, and the most important point of why I left being an employee, there’s a truth to what Zuckerberg said about moving fast and breaking things. Startups move fast. One year at a startup is like 3+ years at a corporation. They have 6-7 goals each quarter versus large companies that do long range planning for the next 3 years. So when you’re moving that fast, things break internally. Processes aren’t implemented because time won’t allow it. Strategies get stalled as outcomes far outweigh building structures that won’t topple over. Bad behaviours multiply as no one has time to be accountable - there are big stakes at play and “We thankfully have HR to take care of the problems.” That’s where HR is sent - to fix all the broken pieces at a company.

HR becomes the messenger of every bad message. The PR person for every bad Glassdoor review. The counsellor for every terminated employee and the psychiatrist for every executive going through their own PTSD episode. HR has been trained since Day 1 to pick up the mess, clean up the aisles, and come into the office, stoic and courageous. Consequences for bad behaviour are often muted when the problems of the company become the responsibility of HR.

And I really resented that.

That’s probably what turned my heart black faster than any of the other dysfunctions and tireless work that I had to do. I was praised for being “resilient” and celebrated for my stamina, but it was just me trying to survive and not go under water.

In more quieter moments at the end of a long workday, I used to sit with my founder and talk openly about how to treat your best and hardest working employees. They deserved all the rewards. You couldn’t pay them enough for how well they did their jobs because their job level and compensation structure wouldn’t allow it. They were the 20% out of the 80% that kept the company together. And they were so smart, hardworking and capable that they could probably start their own companies and be wildly successful at it.

I do because I know it must be done.

I didn’t realize it at the time but I think a small part of me was talking about myself. I don’t need a boss to keep me accountable. I don’t need training to learn how to figure things out. I don’t need rewards to incentivize me to do good work. I don’t need accolades to prove my worth. I do, because I know it must be done. That’s how a founder operates, and all along, I’ve been a founder that happened to be employed by a company…but I’ve rarely met a founder happy to be employed by someone else.

The essence of every founder is the ability for them to be unleashed, unrestrained and set free. What kills every founder is to be bound by the constraints of someone above them. It’s rare for a founder to yearn for a boss. Most founders started their own company to work for themselves.

I perhaps waited 2-3 years too long to branch off on my own, but better late than never. I’m on the solo founder journey and I have no regrets. I think deep down inside, I was building a new version of myself for when I would be “ready.” Being ready doesn’t mean you have all the answers. It means you build something you’re passionate about and you put your blood, sweat and tears into it. And most importantly, you create the mission, your north star and how the foundations of your company will be built. After decades of fixing other peoples’ problems, I’m ready to build my own thing and lay my own path. I think more HR leaders should build their own companies. God knows, they’ve been the lifeline for so many successful companies that exist today.

And while I didn’t plan to be a solo founder when I ventured off to build 5 to 9 Society, it was the best thing that ever happened to me. My loneliness in building alone is offset by the community I’m building and the people I surround myself with - my Substack community included.

Thanks for following my journey so I don’t take it alone.

Christine

That title made sense when I was sitting inside companies, hired to fix, scale, and stabilize systems built by other people. I had proximity to power, but didn’t always have ownership of the outcome. I could advise, influence, and absorb risk, but ultimately I wasn’t the one signing the checks or carrying the consequences home.

That is no longer true.

I am a founder now. And that shift changed how I see everything.

When you build something yourself, the abstraction disappears. There is no distance between decisions and outcomes. No buffer between optimism and reality. No clean separation between personal judgment and business risk. You feel every mistake faster. You learn what matters by what hurts.

I didn’t lose interest in people, leadership, or organizations. I lost interest in talking about them from a sanitized distance.

So this publication is changing.

Founder, Unfiltered is where I’ll be writing about what building actually looks like. The uncertainty. The second guessing. The tradeoffs that never show up in founder posts or panels. The parts of leadership that aren’t aspirational but unavoidable.

My years as a Chief People Officer still matter. They inform how I see incentives, power, culture, and failure. But they’re no longer the center of the story. They are context.

Going forward, I’ll write about:

• Becoming a founder later in a career, not fresh out of school

• What breaks when you move from operator to owner

• Leadership mistakes I recognize faster now that I carry the downside

• Decisions that look obvious in hindsight and impossible in the moment

• The difference between performative honesty and the real thing

As always, I’ll write when I have something burning in me that I want to share, and it’ll be more deliberate. Not to maintain an audience, but to tell the truth while it’s still unfolding.

Some of you subscribed for HR content. Some of you subscribed because you wanted a real view inside how companies work from the inside. The reality is that my past forms my present and future. This is not a reinvention. It is a progression.

Thanks for reading. The next chapter starts here.

When I was young and growing up, I had a lot of childhood trauma. I know many of us have had our own versions of early life adversity and we all know a small part of those experiences stay with us, even when we grow up as adults. We all look back at our childhood and we learn to move on. At least I did, for many years and never looked back. Until recently.

Earlier this year, for the first time in my life, I decided that I should see a therapist to unpack some issues that I had been carrying for decades. I didn’t start out 2025 thinking that I needed to go to therapy. I actually wanted to seek out a mentor or a coach to get into some better habits, but upon some deep reflection, I realized that I actually had a lot of baggage from my childhood that I probably needed to unpack before I could even consider hiring a coach.

The problem was, how do you find a good therapist? I had no idea so I just asked for a recommendation openly on LinkedIn. I got a ton of referrals and a few comments about how “brave” I was to share this on a public forum as a previous Chief People Officer, but if you know me, I’m rarely afraid of what people might think. I honestly got some great recommendations and I ended up choosing a therapist who was very direct and would “say it like it is,” which is what I always go for. She was perfect.

I ended up talking to her every week for 6 months. There was a lot to unpack and a lot to learn about myself, my behaviours and my actions, which became patterns in my life. Those patterns followed me through my adulthood, into my career, how I raised my kids and how I lived my life. I guess you can say we are all formed from an early age to become the product of how we are raised and the experiences we go through. Here’s a snippet of mine.

My parents got married really early in life. That was probably the norm back in the day, but my mother was really young at 19 and my dad was much older at 27. Both were incompatible as fire and ice. My father had an extremely bad temper and my mother was carrying baggage of her own, being raised by a step-mother who came into her family when her own mother (my maternal grandmother) committed suicide when my mother was eight. In the end, my mom had her own reasons for wanting to escape her family and in her mind, getting married was the only option she had to leave a miserable life.

My mom and dad ultimately got married because my mother got pregnant at 18 with my older sister. Were they ready to have children, never mind be married as a couple? Absolutely not. My father was the second oldest of his 5 siblings and he used to hanging out with “the guys” while my mother, being the second youngest of 7 siblings, was not ready to be a wife, a parent or a responsible adult.

By the time I was born less than 2 years after my sister, my parents were fighting like cats and dogs. Violence was the norm in our household, including yelling, throwing objects and literally screaming bloody murder every day because my mom and dad loathed each other so much.

When I was 2.5 years old, we packed up our bags and moved from Korea to Canada to start a “new” life. That new life was difficult when you have no connections, you can’t speak the language, and the environment is not very friendly to foreigners. There was a lot of open racism when you went to the grocery store, walked down the street or served customers. Everyone thought they were better than you and you just got used to looking at the facial expressions of really mean people who felt superior throwing insults at you (even if you didn’t understand what some of those words were). What was certain was that you could see their expressions of hate in their eyes and that left a huge impression on me. It also put a lot of stress on my parents who were likely regretting coming over to this “promised new land” and realizing that it was really hard to earn a living. Stress from life often seeps into stressful situations at home, where unhappiness becomes the fuel for a lot more rage and violence for an already struggling family.

If my parents weren’t fighting each other, they were directing their anger towards us. Physical violence was typical, but their words were sharper than daggers. Neither my mother or father ever had words of encouragement or praise for us. They often looked down on their kids. They blamed us for many of their hardships and oftentimes, that was simply for being born (something we never asked for or could control to be honest). If there was ever a moment of giggles or joy between the kids, my parents would tell us to be quiet and go to the other room. This was how we grew up. We learned to close every door, be silent and never talk back.

As a child, I went to bed sleeping under my blankets when my parents were fighting. I remember running next door to my uncle’s place when my parents were fighting really bad one day and they started throwing all the good dishes across the room aiming for each other. I saw the broken china from Birks, crashing to the floor. Dinner plates, tea cups, crystal glasses. All shattered and my sister holding my little baby brother who was less than one, in her arms as I ran to get help. I was six at the time and my sister was eight.

When I grew to my teenage years, our finances got better. My parents had bought a few small businesses like grocery stores and started to make real money as business owners for the first time in Canada. They could never get credit cards when they first arrived in Canada, so they always used cash, even when they needed a car. All in cash. They also mortgaged a very large house for the first time in a very swanky neighbourhood where all our neighbours were lawyers, doctors and CEOs. We had finally “made it” but the marriage was still strained and my parents still loathed each other.

I remember calling the police on my father for the first time when I was twelve years old. The 911 operator asked if it was a real emergency and I said, “Yes, my dad is dragging my mother down the stairs by her hair - hurry!” Two police officers arrived at our house and sat down with my parents. They assessed the situation and told my parents to go seek “legal counsel” and figure out what they wanted to do. My mother’s hair was pulled out in clumps and my dad had red scratches all over his neck. Things got progressively worse over the years.

When I was sixteen years old, my parents sat me and my sister down and told us that they wanted to return to Korea to start a business there. They missed their country and felt that there was a great opportunity to start a business there. They asked us if we could manage on our own and that they would ensure there was money in the bank to pay the bills and feed ourselves. My sister was eighteen and my younger brother was ten. We said we could. Great, my parents told me they would buy me a car so I could drive my siblings to school (my older sister didn’t have her license yet). In a few weeks, they packed up a small bag and left.

Over the next five years, my parents left us to fend for ourselves. Nobody knew the truth about what was going on with our family and we made every excuse to make it seem like we were a “normal” family. I made breakfast for my little brother every day and drove him to school. Then I went to high school and pretended everything was “normal.” I went grocery shopping like an adult and paid the bills like my parents taught us. I went to all my brother’s parent/teacher interviews and lied that my parents couldn’t speak English so I was there to take their place. I forged the signatures of my parents for all school stuff and lived the life of a parent and adult as a teenage kid. I couldn’t go hang out at the mall or watch a movie when I felt like it because I had responsibilities. I hated it and at the same time, didn’t really want to live with my parents either. That was another kind of hell. Most times, I just really felt sorry for my little brother. He deserved better than this and I tried my best to be a parent for him since he had none.

As expected, there were times when we had an “emergency” and called my parents long distance to ask for help. We often couldn’t reach my father and when we called my mother’s phone, she would just yell that she was busy and “figure it out on your own.” Then she hung up the phone on us. Multiple times. I will never forget the way she used to slam down that phone and the shock I felt each time, when I heard the line go dead. My sister and I would just look at each other in shock. It’s funny but I used to think that when your own parents treat you like this, how could anyone else really hurt you?

By the time my parents came back from Korea, they were finally ready for a divorce and we had grown up into our twenties. They were never around when we needed them the most and they certainly didn’t play the role of a responsible (or even normal) parent. They never held any accountability for what they did to us and we never forgot it.

Today, I don’t really have a relationship with my parents. I tried in my twenties and thirties, but as I got older, I realized that they had a choice in how they behaved as an adult and parent, and they chose to be selfish and consumed by their own needs and desires. As a parent of two kids myself, I could never imagine doing this to my own children. And I never have.

So this brings me back full circle to my therapy sessions. Why did I feel the need to go to therapy and bring up these painful memories that I had buried for decades? Well, I think that I finally had a moment to take a step back from my job (I had recently departed from my last company as a Chief People Officer) and I was going through a lot of emotions reflecting on myself.

I had built up an amazing career and a really incredible reputation as a “resilient” HR leader. I was admired by startup founders as someone who could manage all the “hard things” and I did those hard things very well. I often coached and mentored some of these CEOs and they thought I had it all figured out. But the reality was, I was deeply unhappy. The reason why I was always able to figure out what to do when things went awry was because in my childhood, that was also my responsibility. No one was coming to save me, not even my parents. I was responsible for my destiny, my future, my life. If I didn’t figure things out for myself, God knows where I’d be today.

So you become “resilient” and manage to figure out how to deal with complex situations that you might never have tackled before. I had to problem solve, remain calm and figure out a solution to survive. The ability to manage difficult situations was ingrained in me but it wasn’t something I chose to do. It was all about survival. And that’s how I operated in my CPO roles, often in chaotic, dysfunctional environments where everyone’s hair was on fire. I had to find a way to bring calm to the chaos, and allow the company to scale within a relatively functional environment so people could do their best jobs. In a lot of ways, I was reliving the chaos of my childhood years and trying to replicate the strategy of going from dysfunction to success the way I had lived in my early years.

In many ways, I was reliving my traumatic past over and over again and I didn’t want to do it anymore. I survived my crazy parents by leaving them behind. And I sort of felt like me leaving the craziness of startups was also in a way, saving myself from the insanity that I was living over and over again. People often think deciding to become a founder and entrepreneur is the biggest risk an ordinary person can take, but for me, after everything I had gone through, it was just a natural step to the next thing. And I was ready for it. I was ready to build something for myself.

I’ve never really shared this story publicly before and I didn’t do this to get any sympathy. This is just what my life was and you can’t control who you’re born to, but you can often control to some degree, what you make out of the life you were given. I had a really unhappy childhood, but I also know that my life got significantly better as I grew to adulthood. I once used to say as a kid, I want to grow up as quickly as possible so I can make a better life for myself. And I did.

I am also a huge fan of the underdog and I always will be. I admire people who are able to beat the odds and make something for themselves, even when no one is willing to help you. As I was growing up and trying to become someone I could be proud of, the hardest part of my journey was doing it while pretending I lived a normal life like everyone else. All my friends and even family members thought I had a normal life, but that couldn’t be farther from the truth. That’s probably why I always loved to hire those who had gone through great adversity in life and came out of it winning. No training program can ever teach you to fight your way to win against every odd. Only life teaches you that.

This all goes to say, that even when the first people you meet in your life, this being my parents, treat you like you’re the worst thing that could ever happen to them, you don’t have to let that define who you can become.

I’m grateful for the therapy that I went through and I discovered a lot of things about myself. We each become who we are starting as children, but we choose to become who we do as adults.

Thanks for reading.

Leave a comment

Subscribe now

Making the decision to quit my career, give up my executive salary and jump headfirst into starting my own company was not a big decision for me.

I know it sounds arrogant, as if I’m this ultra-confident person who has no fear or anxiety about doing something they’ve never really done before. But the truth is, I really wasn’t nervous, uncomfortable or even scared. Before I even got to the point of wanting to start something on my own, I had long lost the desire to continue on the same path as I had for the past 20+ years.

My reasons included the following:

1. I no longer had a desire to “do HR” work. In fact, I was so dulled by doing HR that I realized I had been doing turnarounds (mercenary work) for difficult startups that needed transformations more and more often. I eventually started to gain a reputation for being “that HR mercenary” that would go in and do what needs to be done. Oddly, even that eventually got boring. Most of the founders I worked with never ended up replacing me after I moved on. Many told me that they would rather have no HR than try to find someone who could duplicate me.

2. I no longer needed a boss. I’ve had my share of bad bosses like everyone else but for the most part, I really enjoyed working with the majority of Founder CEOs that were my managers. But I realized that I was eventually calling them my “partner” versus my “manager” which to me, signalled that I was really operating as my own boss. I had stopped asking for permission a long time ago and the truth was, many founders I worked with didn’t even know what my job should look like. I crafted my own strategies, my own development and my own rules. After a while, you crave someone who can truly challenge you.

3. I really didn’t like doing the things that a “manager” needed to do. My daily schedules were always the same: Daily standup | 1:1 meetings | Team meetings | Executive meetings | Board Meetings | KPI update | OKR update | Onboarding | Offboarding | LRP Meeting | Post-mortem Meeting | All Hands Deck | Quarterly Town Hall Deck | Board Deck... and then rinse and repeat. Being a manager seemed to involve a lot of talking, not a lot of doing. That killed my soul a lot and dulled my senses. I honestly detest meetings and I need to execute versus talk endlessly about how to execute on the never-ending plan. Just move out of my way and let me move fast (that’s what I’m always thinking during meetings).

4. You don’t really get to choose who you work with. This one is personal for me. Besides having the option to choose your direct reports (at least the ones you didn’t have to adopt), you don’t often choose your peers, your colleagues, your stakeholders. What was tough for me was having to work with people that I felt weren’t good enough (or sometimes good at all). Mediocrity is something that creeps up at a company as headcount increases and the business matures. Without critically holding every individual accountable, “great” becomes “good enough” and that’s how high performing companies start to die. This one hurt me a lot and I found it hard to just accept it. People thought I was weird that this got to me more than the founder. And that’s when I asked myself, why should I care more than they do? The reality is, I shouldn’t. I’m not the founder.

When you think about everything that was going on in my head and the fact that these sentiments were multiplying year over year, it really was no surprise that I would turn my back on working for a company again and burn the boats behind me.

The companies deserved better, and I deserved better. We would be doing each other no service.

So starting 5 to 9 Society was inevitable. My first thought was, maybe this will just be a fun side gig with 20 members and I can diversify my time doing other things. Sounded like a good plan until I realized how interested people were in joining the Society, an exclusive executive network built for high-performance operators, founders and investors. I like to call it the “secret society” to pay homage to how I’ve networked over the past decade - in confidential circles where opportunities were whispered and meetups were through exclusive invites. This was my world outside of work - and now my work is building this world.

Every founder who has ever started their own company builds with purpose. I remember working at companies where employees decided what the core values should be for that company. They wanted a stake in what each core value should be because they were working there. But the truth was, those employees won’t be there forever. They will likely stay on for 2-4 years and move into new companies so why should the core values be something the employees should create? It should be created by the founders because long after everyone has moved on to new jobs, odds are the founders will still be there. Rather than creating values to align with current team members, founders should be creating values that align with the right people who join the company. The alignment will draw the right people to you and repel the wrong people from you.

Building 5 to 9 Society has been energizing and it feels right because I’m exactly where I need to be. The early adopters that have joined the Society weren’t difficult to convince to join. They understood the purpose and aligned with the vision. I didn’t need to influence them beyond one initial phone call (I vet every single member that joins) - they truly understood the assignment because they aligned with the mission.

I appreciate early adopters so much because the truth is, I’m also part of that camp. I’ve been an early adoptor of software, new talent, new founders and early stage startups. If the vision aligns with me, I have faith that it’s headed in the right direction. I don’t need proof, statistics, analysis and data. I believe, and that can be a powerful thing.

Don’t believe me? I get it, so many of us are trained and taught to put data before everything. Sure, to be safe, data will try to give you what you desire as an outcome, but it’s also never guaranteed or we’d all be millionaires. Sometimes enormous wins are often based on a bet. Here are a few examples:

1. Star Wars (1977)

Industry: Film

George Lucas self-financed parts of the project, turned down his director fee for merchandising rights (which the studio thought were worthless), and insisted on creative control.

Why it worked: Vision. The studio had no faith. Test audiences were confused. But Lucas saw the cultural white space. It became a $10+ billion franchise.

2. Spotify Wrapped

Industry: Tech/Product

Wrapped was built in a hack week - not market tested, no data predicting virality. Just intuition that people would want to see and share their listening habits.

Why it worked: It turned a private behavior (music taste) into public identity. Zero playbook. Massive brand lift. Millions share it annually.

3. Humans of New York

Industry: Media/Photography

Brandon Stanton was a failed bond trader with no photography background. He started taking street portraits with no business plan or data proving it would resonate.

Why it worked: Human stories told simply and consistently. No SEO tricks. No data. Just raw, emotional truth that scaled globally.

4. Airbnb (initial concept)

Industry: Tech

Investors laughed at the idea of strangers sleeping on air mattresses in people’s homes. Founders literally sold cereal to fund the business.

Why it worked: Trust, design, and timing collided. There was no demand data to back it - just a painful insight about overpriced hotels.

5. MrBeast YouTube Channel

Industry: Creator Economy

He spent everything he made back into stunts and experiments. Early videos had no proof of success, just weird ideas. Counting to 100,000, giving away money.

Why it worked: Obsession with attention mechanics, not analytics. He saw something in people’s behavior no spreadsheet could.

The bottom line? None of these had market validation when they started. They won by identifying an unspoken desire, leaning into intuition, or breaking a rule everyone else followed. Data may optimize, but it rarely originates great ideas.

5 to 9 Society was built from my experiences leading to the person I am today. I’m creating a network that brings in high achievers, not the mediocre. I’m not looking for the tailcoat riders, the ones who want recognition just for participating, or the politicians who spend more time talking versus getting results. If I wanted to get rich, I would allow everyone to “pay to play” but that’s not my motive here. I reject more members than I accept. I want to create a space where truly smart people can gather IRL to support one another and build opportunities. I want to see the best minds congregate and allow us each to become 10x better. I want the builders, the achievers, the dreamers to all be in the same room - and I want to keep out the complainers, the downers, the ones who are always offended.

Like every bold idea that reshaped its space, this Society wasn’t backed by market research or a safe playbook. It was built on instinct, lived experience, and the belief that something better should exist.

No focus group would’ve predicted Star Wars. No data said the world needed Airbnb or portraits of average New Yorkers. But people took the leap. And it landed.

So here’s my bet. In a world flooded with noise and average, the right people still crave substance, curation, and real connection. I’ve found my place in the Society. If this sounds like the right space for you, reach out to me as an early adopter.

We started in Toronto but we will duplicate our playbook across major cities in Canada (Vancouver, Calgary and Montreal next) and the US (NYC, SF and Chicago next).

I’m always up for meeting new people that are doing fascinating things. Hit me up if you want to chat. And thank you for reading my substack. Don’t forget to subscribe to read about my journey.

I’ve been asked this multiple times by aspiring HR mentees who want to climb the career ladder, as well as by mid-level HR leaders who are still striving to get to where they want to go - to the very top.

Oftentimes it’s hard for me to answer this question because I’ve never really “fit the part” of HR. I’ve been told I’m intense, blunt and direct, which is often the opposite of what most people are looking for in an HR leader.

The irony is that the people who described me by those words were the ones who hired me, promoted me, trusted me, and followed me.

Here’s the kicker. Being direct shouldn’t be applied to only employees and junior staff. I’m talking about being direct with your leadership team, the CEO and even the Board. It’s not easy to be ruthlessly honest but I always operate under one principle at any job I take on - What do I need to do to ensure I’m doing the right thing for the Company to succeed? If you want to be objective and logical when you make business decisions, always ask this question first before you make a call.

The truth is, what made me different was essentially what made me effective. Breaking the mold became my greatest advantage and to do that, you have to have courage. In a lot of ways, you also have to be yourself.

One of my greatest natural strengths was being clear-spoken and direct. I’ve been called blunt, but in hindsight, I now know that it’s earned trust faster than politeness ever did.

So I decided to train other leaders on how to effectively “give feedback.” Anyone who’s made a move from “individual contributor” to “people manager” knows that this is one of the most difficult but critical skills to master. It’s difficult because you’re sharing feedback with people you work closely with every day. People can also be emotional, sometimes sensitive, and it’s really hard to get the tone just right so that you don’t sound obtuse.

When I give feedback, I don’t sugarcoat things because that’s the first thing you can do to becoming a disingenuous leader. Being honest is being kind. It’s not a fancy slogan. It’s the truth because I’d rather be honest and direct with someone than operate in performative politics. I say the thing most people avoid because that’s usually what unblocks the real work.

By operating in this way, I’ve built deep trust with founders and execs by refusing to coddle them and by never pretending to be someone I’m not. For every role I’ve ever taken on, I’ve encouraged the CEO to conduct backdoor reference checks on me. I don’t need to know who they’re contacting but I’m certain that the previous CEOs I’ve worked with will share similar feedback about how I operate. To me, even the spiky edges we come with are good things to understand before making a decision to work together because I want both of us to know what we’re signing up for.

Through this honesty, I’ve been able to navigate high-growth chaos by staying relentlessly clear versus endlessly agreeable. I admit, it wasn’t always easy for my executive peers to hear the raw feedback that I shared with them, but in the end, it was to ensure I was operating with integrity which always comes with a level of straight-talk. The way I see it - it’s better to share feedback with you directly versus talking about you behind your back in other rooms. I expect to be treated the same way in return.

I’ve made it as a woman in leadership not by softening my thinking, but by sharpening it. We all know there’s no room for fluff and emotions in boardrooms and in war rooms. I don’t operate with platitudes and warm hugs, but I also don’t cut people down and make them want to revolt. The skills you’ll learn to grow as a leader will be sharpened by the skills HR can often teach you about working with people and building a successful company - they must be compatible because even in war, you can’t win a battle if your own team doesn’t respect you.

So in the end, I realized that there’s power in not being what people expect, especially in roles where people think they already know what you should be.

You don’t have to perform a version of leadership to earn trust.

You can be relentless and respected.

You can be honest and human.

You can be unlike anyone else in the room and still be the one they call when it matters.

Thanks for reading, listening and for subscribing.

I started my career in formal corporations, working at the companies that we’ve all heard of. The global matrix organizations that have fancy titles like “Centre of Excellence” which employ hundreds of thousands of employees (when I worked at Loblaw Companies Ltd they were the largest private employer in Canada with 185,000 employees - today they are over 280,000). While that definitely wasn’t my cup of tea, I also had an opportunity to work with really amazing people and leaders. It was also the chapter in my life where I got married, signed up for an awesome ESOP program which allowed me to gain my first mortgage, and allowed me to participate in a parental leave top-up program when I had my 2 kids. I remember a startup CEO that once said, “Knowing your work ethic, Christine, I bet when you had your kids, you only took 2 weeks of mat leave and came right back to work!” No, not true. I took a full year off for my first leave and then I took 2 years off for my second when taking leave beyond 12 months was unheard of in the Canadian employment landscape. The reality is when I do something, I do it all the way and I do it really well. That includes how I take care of my family and raise my kids. I’m not just good at my job, I’m great at raising a family.

The last 10 years of work has been working at startups of all sizes and maturity. Let me tell you, it’s been a ride. I’ve worked with founders and CEOs of all backgrounds and personalities. I’ve had the privilege of working alongside so many leaders that I respected and admired and they taught me so much about building a business as well. I learned to become a very well rounded leader, building HR teams outside of the HR norm and focusing more on outcomes versus governance and rules. Did we take risks as a company and an HR team? For sure we did, but no business worth building becomes great playing by strict rules. I was an HR leader that broke almost every rule that HR was told never to break, and I really enjoyed doing that. I also had the privilege of building the best teams over the last decade. Not everyone agreed with all the decisions I made, but I didn’t make decisions to be popular. I did what was right and that wasn’t always easy.

Now, as I look back and realize that I am leaving this phase of my life as an “employee” forever, I feel a sense of gratitude and in some sense, relief. I know this was the path that I was designed to take and I know this is my time. Branching off to do “my own thing” feels right for me and it’s changed how I view relationships with the people I choose to work with.

Choosing who you decide to work with is an incredibly empowering feeling because you no longer need to work with people that don’t align with your values. I’ve never been someone you would describe as “fluffy” or full of feelings but I’ve always understood what it means to have integrity, even when I’m operating at the highest level of performance. So here’s the playbook I’ve always operated with when I work with people, regardless if I’m an individual contributor, a leader or a business owner. Not much has changed over the past 20 years being an operator and my guess is, not much will change as I complete this last ⅓ of my career moving into entrepreneurship, so here are a few reflections I have as I sit and look at the beautiful blue water ahead of me.

1. Integrity means being honest with people, even when you’re sharing tough news. They don’t have to agree with your decision, but you do need to treat people with respect and integrity and that often starts with being honest with them. A lot of leaders I’ve worked with claimed they were honest and radically candid, but really, they were not. They were often “obnoxiously aggressive” or “ruinously empathetic.” Have courage and speak the truth. People will respect you for that.

2. Don’t stay where you’re not respected. If the people you work the most closely with don’t respect the work you do and how you operate, they never will no matter how hard you try. You know that feeling, I don’t have to explain it to you. There are many jobs, different bosses and tons of ways to make money out there. You don’t have to settle and be disrespected for years. Life is not worth living that way because it truly changes you as a person and youth is too fleeting to be unhappy for so long. Choose to be respected.

3. Being performance oriented is the dream of every leader. The best leaders will challenge you to perform at your best. Greatness never came out of “easy” but there’s a way to motivate people and inspire them to do things they never would have believed in themselves. So ensure your leader is motivating you, not constantly demanding from you. Think about who you would want to be with if your life depended on it - would you trust your current leaders if you were in a life and death situation? I choose only those who would fight to pay my ransom.

4. Think about how you feel at the end of the day when you come home exhausted and completely spent. Ask yourself, have you made an impact and moved the needle based on all the effort you exerted? Are you proud of your work and the results? There’s effort that leads to results and there’s plain hard work that sometimes never makes a dent. Working smarter, not harder is actually a thing - are you and the team actually working smarter? Results don’t lie.

5. Do you think about your relationships with the people you work with. For me, work is more than just a job. The people I work with are in the trenches with me so the relationships I’ve built with many of these team members have continued even after decades have passed. Do you have relationships with team members in this way? Would they step up for you if you called them today?

6. Have you ever felt the mood of the team you work with? I’ve worked in really hard environments. The earlier stage of the startup, the harder the work was because no one knew the company you were working at, you often had a shoestring budget and you had to really roll up your sleeves because you had a bootstrapped team. No doubt, those were hard environments to work in, but our team knew how to have fun! We worked long hours, did hard things and truly struggled (i.e., our restaurant software company revenue went to zero during the height of COVID when the government shut down all restaurants in the country). We laughed, sometimes we cried, but we always felt good around one another. Honestly, if you’re going to spend 80 hour weeks with people, you should genuinely want to be around them a lot.

7. What do people say about you when you’re not in the room? I ask this to almost everyone I know. Do you have a clue what people say about you when you’re not around? I’ve had many people in my network literally call me to say xx said this about you whether on stage, in a group networking dinner or to a potential business partner. I’m not surprised by what they say, but I am choked up sometimes.

8. There’s the old Netflix rule about their talent development process whereby they get managers to answer this one question about people on their team, "Knowing everything I know today, would I hire this employee again?" If the answer is no, they believe it's fairer to everyone to part ways. Fair. So do you also gauge and measure your managers every year and ask yourself if you could work with this leader again, would you? If the answer is no, chances are they either feel the same way about you or they have no idea you are that unhappy…is this how quiet quitting started?

9. Every company has rules. Some rules are meant to keep the peace and scale a company, but some rules are just plain dumb and you have to accept it or be labeled a trouble maker. The reality is, someone made the rule, often in management (CEO or founder) or HR, because either someone more stupid than you broke the peace and a new rule had to be implemented to ensure chaos didn’t reign in or there was a weird rule that leadership believed in and they implemented it because they could. I know I’m a leader and I’m also in HR, but I really despise a lot of rules that are made at companies. How do you feel about them? If I don’t love rules, I guess I wasn’t meant to be part of a big company.

10. Lastly, I know more than anyone that oftentimes a job is more than a paycheck…but money actually does make the world go around. It may not buy happiness, but it sure feels better to cry in a Ferrari than in a dingy subway platform, broke and hungry. So I’ve often asked the highest performers, if you’re so high performing, are you getting what you deserve? Because the reality is, companies live off budgets and if you know anything about the dreaded “bell curve,” you will probably earn anywhere between 2% to 6% each year in salary increases unless you plan to leave your company every couple of years to make a jump in salary increase with each move. Does that inspire you based on how much effort and time you put into your job?

The list above are just a few of my random thoughts that have become my playbook over the years. I think it was written to plan my move away from “company” and more towards “entrepreneurship.” People say to go out on your own is to take on a big risk and it’s not worth it but to be honest, I think it’s worse to stay in a box that no longer fits. I’m not afraid of taking risks or trying new things and chances are, this whole journey could be a flop for me but I’m willing to go all in to find out because unless I try, I’ll truly never know.

So what’s next for me? Going all in with 5 to 9 Society, an exclusive, invite-only networking community that will bring Investors, Founders/CEOs and vetted High Potential Operators together. Expect job/candidate matching for coveted roles, exclusive dinners and events, along with advisory/coaching and referrals to support growing businesses. The website is currently getting ready to launch along with the first group of vetted cohorts who will be the founding members for this exclusive network. I may even start my own Tik Tok and podcast. To my awesome network, stay tuned and follow me for more insights. I just may need to change the name of my Substack now that I’m a recovering Chief People Officer…

Thanks for reading. Glad to have you as part of my journey and don’t forget to follow to learn more about this new venture!

Subscribe now

My own thing could mean many things. With the experience I’ve gained through working “corporate” half my career (think systems, processes and big picture) and working at multiple startups for the other half (think risk-taking, building from 0 to 1, and scaling), I’m a pretty balanced person in terms of experience.

The companies I worked at gave me confidence in knowing what I was good at. I was born to lead. Even when I was an individual contributor, I was leading ideas, projects and things the team had never done before, but when I became a true people leader, I was able to move mountains. There’s a huge difference between “managing” and “leading” and it’s something that many leaders don’t fully understand. I’ve seen executives and CEOs still “managing” when they should be “leading” and it often makes me wonder if it’s because leaders are getting younger and have less experience as leaders so they just haven’t been trained to properly lead in their short work tenure.

I can confidently say, I was born to lead whether at a large, matrix, stuffy corporation or at a scrappy startup that’s newborn and trying to make it in the world. Both take an incredible amount of responsibility, stamina, structure-building and courage, and I’m really good at owning that. They must also have a strong ability to work with people and build strong teams. If you can’t do that, you can’t lead because no one is going to follow you. If you ever want to see if a leader is great, ask them who they personally groomed that became a greater leader than when they started? Hopefully they can name a few.

Subscribe now

Now that I’ve been leading as a “leader” for over a decade, one thing I realized as I moved into more expanding roles in HR was that I was doing more than what a traditional Chief People Officer typically does, and to be honest, I really enjoyed that. I was often being pulled into sales discussions, product discussions, finance discussions and everything else you can imagine when you’re building a company. The more seasoned I became, the less I was involved in HR decision-making and instead, I was moved more into the decisions regarding the “business of running a business.” I wasn’t just invited a seat at the table, I had a permanent seat. The reality is I was no longer fulfilling the narrow role of CPO but rather, building a company.

That really got me thinking, especially over the past few years post-COVID, I knew I couldn’t continue being an HR leader anymore because I had bigger interests outside of HR. I also knew I couldn’t be an “employee” anymore either because to be honest, I’ve always been more than an employee. Working at a company is like an obsession to me. I go all in, or I don’t want to be there at all. I know that sounds really polarizing but it’s how I think about most things. I’m fully interested and will obsess about it or I don’t care at all.

So I know that I’ll probably do one of three things over the next few months:

1. Co-found a company with like-minded founders.

2. Start my own thing and become a solopreuneur.

3. Consult and advise, but only where I want to. Really focused work here (though not actually sure the world needs another consultant).

I just know I will never join a company as an employee again. I know that’s really scary for some people who have worked for companies their whole lives, which includes me as well, but I've learned something over the years that I never really thought about until now.

Working for someone means you are fulfilling a dream they designed. They created the rules and the vision, and you have to live in it, and truly believe in the mission or you are frankly just working a “job” and no one wants that. Humans need inspiration to do aspirational things and that’s why mission-focused companies tend to succeed. But if I’m going to spend countless hours working for a company, I have to have strong conviction in the following 5 areas:

1. The mission. Do I strongly believe in what we are building?

2. The leaders. Do I respect them and is it reciprocated?

3. The way we operate. Is the company being run well?

4. The way we treat people. Do employees feel motivated and respected?

5. Success. Am I seeing tangible success from this business so we can continue to build for the next decade (are we a vitamin or a pain killer that people would gladly pay for)?

I find that when one part of the above is missing, it can be ignored for a while but it always comes back to haunt me. Nobody said building a business is easy but we also forget that you can’t build a business on your own - you need people to build your software, serve your customers and motivate your teams. You always need people. And truthfully, you want the best of the best in people, but one word of caution for founders is that the best can always leave for better companies or build one themselves. They don’t have to work for you so be thoughtful about how you treat your best.

So after 20+ years of working for companies, I’ve made the decision to never join a company again unless I’m co-founding one or starting one myself. It’s something I always knew I was going to do eventually, whether it means building a business with other people or starting something solo that I’m passionate about. And why am I sharing this with any of you?

Because over the last week, I’ve had over 12,000 people read the last chapter of my Diary of a CPO blog and I gained 600 new followers on my substack. I haven’t even counted how many new LinkedIn followers I’ve gained this week. The messages many of you have DM’d to me were about having the same thoughts on leaving the HR industry or leaving company-employment overall. I’m clearly not alone in how I feel and I’m not surprised - considering how much valuable time we spend at work and the countless hours we dedicate to the people we work with, may we all find the journey purposeful and rewarding because if it’s not, perhaps we’re seeking a new chapter for our careers.

Thanks for the read and for the messages. This discovery phase in my career is exactly what I needed right now.

I’ve worked as an HR leader at 7 startups in my career, mostly in the tech industry. The majority of these companies were also led by founders which allowed me to learn so much about what it takes to build a company from the ground up. It’s truly a massive feat and I have such profound respect for each of them.

I recently joined an amazing tech startup and had the opportunity to work with a wonderful co-founder CEO whom I have known and respected for many years. The company had all the usual “problems” that you’ll find in any high-growth tech startup - the need to scale operations, systems, and processes to optimize velocity and agility. The need to stand behind their strong values and adopt a leadership style that could bring out the best in their people. And the need to “unlearn” how things were done in the past so they could “relearn” how best to position themselves for this new phase of growth and maturity.

It was an immensely fortunate opportunity for me, but after 30 days, I felt that maybe this wasn’t the best work that I could be doing at this point in my career. The truth is, I was doing work that I’ve done over and over again for the last 7 companies I worked at. There’s something about the predictable repetitive motion of doing things over again that feels like my soul is slowly dying. That excitement of doing things for the first time, even fixing an ugly problem, was gone. For someone who loves to be curious, try new things, and take massive risks, turning the page on the same playbook became a difficult pill to swallow. My desire to build a company felt strangely like I had built this Lego building before - the anomaly was no longer there because I was managing the same function over again. HR.

And to be honest, HR has beaten me down over the past decade as I found myself doing more of the “hard” things in HR vs the rewarding things. Over the past 5 years alone, the HR function has been mandated to oversee a global pandemic (aka COVID), support team “culture” while witnessing extremely polarizing world events, and deal with the outcomes of economic and political issues that threaten our livelihoods resulting in massive mental health issues. We were all facing this at work together because we are all “employees,” but one function had to own the strategy to deal with all of the above, and that was HR. There’s really no training for this stuff and no one graduates from “HR business school” with a playbook for these critical issues. We’re not talking about a P0 bug that can be fixed in a few hours. And there will certainly be more, fresh new crises to be had, which means the playbook is a living document that grows annually. HR becomes the lucky leader to deal with all of the above because HR “deals with people.”

When a leader loses her temper and yells an F-bomb at her team - it becomes an HR problem. When the company Glassdoor page blows up because a reduction in force occurred due to excessive burn - it becomes an HR problem. When a high performer suddenly becomes a low performer - it becomes an HR problem. When HR has the leanest team in the company because they’re considered “overhead” vs a “revenue generator,” and the work still needs to get done (regardless if the company size has doubled over the past 12 months) - it’s still an HR problem.

I understand why many CPOs are either “burnt out” and choose to leave the industry for something entirely different, or they deliberately go into “fractional” HR so that they can “go in, do their thing, and go out” (or as my fractional CPOs like to call it, “get the fuck out”). With fractional work, you rarely take any baggage home, you don’t feel emotionally depleted at the end of the day, and you have less of an attachment to the human problems in an organization. It just becomes a “job” which I guess allows you to stay in the profession longer, but it sure does feel transactional because you’re not really working for impact, you’re just checking in and checking out. Which is why it doesn’t really appeal to me…but neither do all of the HR issues I mentioned above.

So going back to my original story, I recently departed this amazing company and CEO (that I really, really admire and respect) so that I could take a step back and dream of what I truly want to do. Choosing to depart a company is one of the hardest things you’ll do in your career, but it’s better than staying somewhere you feel won’t benefit both sides equally. I didn’t leave the company for another job. I left to discover what I wanted to do next.

So I asked myself, if anything were possible, what would I want to do that could be vastly different from what I’ve done in the past? What role could I play where I could do something challenging but exhilarating (is that even possible or are all jobs just hard but predictable)? I mean, maybe HR wasn’t supposed to be my thing forever. Maybe HR is asking me to do a hard pivot. Feels like it…

This will be my time to take a break, reconnect with my closest peers, and find my love for people again. That’s right, sometimes you start to dislike people in general because HR becomes such a thankless job. When was the last time you thanked anyone in HR for the things they do? You probably don’t because you assume they’re just doing their job. While that’s true, it’s the only job at a company where the ink for the “duties & requirements” for the role never dries but rather, grows.

If you know me personally but we haven’t connected in a while because I’ve always been too busy at work, feel free to DM. I’d love to just talk and rebuild some great relationships once again. And thanks for reading.

Subscribe now

I absolutely loved riding my bike, racing down the streets, finding any hill that I could speed down and often scraping my knees, shins and elbows as I hit the pavement. Sure, I cried and tried to wash off the bright red blood as I stared horrified at the raw mess of my skin. But there’s nothing like a great bandaid to patch up the mess and get right back out there again.

I also collected toads, tadpoles, bugs and snails. Most of my friends were boys and they often let me lead the pack because I always had the best ideas. We built forts, got lost in bike trails, snuck a rowboat out to the lake during camping, and we hung out at the comic book store back before it became cool for teens.

When I got older and became a teenager, I started to hang out with more girls. Some girls I met were really spontaneous and didn’t let anything get in their way. Other girls were more insecure and carried a heavy weight of emotions, always worried about what others would think. I tended to gravitate towards the former group and felt like I could be myself without having the burden of my insecurities drag me down. Teenage years aren’t easy for anyone, especially when your hormones are invading your mind for the first time and you’re trying to balance growing into an adult while still wanting to be a kid. I was caught up with wanting to grow up and be a responsible adult while still enjoying the freedom of being that girl that can feel the wind in her hair while riding her bike down a hill.

When I finished school and started working in the real world for the first time, I was excited about building my career. I daydreamed about what I would become in the future and threw myself into my first real office jobs. The jobs were relatively boring and I soon realized that being a cog in the wheel seemed to be just a normal part of work life…gross. I worked in corporate jobs back then, like large public companies that everyone has heard of. The ones that have matrix environments and a company directory of thousands of people that you’ll never meet in real life. I would occasionally see the actual CEO or an executive walk by in the morning but never really get the opportunity to talk to them or spend time with them. If they happened to stop by my cubicle or I happened to be in the elevator with them, I made some awkward exchange and blubbered something dumb that I regretted immediately after walking away and that was the extent of my interaction with a “top leader” at the organization. I also noticed a lot of the executive leaders were men. They were pretty nice and often chatted with good humor. There were also a few women. They weren’t so nice and didn’t bother to say anything when they walked by. It was strange to me considering there were so many women (us) supporting the work for the business.

Regardless, I assumed if I worked really hard and exceeded performance expectations compared to my peers (who didn’t really care if they were working hard or hardly working), I would get an opportunity to move up. The thing about corporate life that people who have never worked in it don’t understand is that things move incredibly slow. The pace of work, the pace of getting things done, the pace of planning, scheduling, discussing, meeting, deliberating, contemplating, de-risking, reviewing, re-reviewing, re-discussing can be incredibly soul crushing for people who just want to get shit done. So with all that time you have, in-between an idea and execution, a lot of corporate life is spent talking to peers and psychologically destroying your confidence. I encountered a lot of “advice” from peers who were mostly women. A lot of the advice I was given sounded like complaints and it was also the first time I heard of the term “glass ceiling.” I had to look it up and learned that it meant women would never fully have the opportunities in their career to move up compared to men.  This also applied to “minorities.” So essentially, I ticked the box twice.

In those early career years, I started to lose my confidence for the first time. The influence around me was stifling and I started to believe that I will probably never be good enough because this is how the world works. So I did my job as best as I could and I tried to block out all the negative energy and gossip that was surrounding me daily. I wasn’t sure if I was depressed because of corporate life or because I was a woman working in a system that would apparently never give me an opportunity to succeed. It was also unfortunate that I never had a mentor, an advisor or someone in a more senior position that could give me some good advice. I mean, I was twenty-something and it wasn’t common to have a mentor back in those days so I was just blind to what I didn’t know.

I started to feel like I was cursed for being born a woman. Why couldn’t I have been born a man? Life would be so much easier, and guys seemed so much more easy going (at least compared to the women I worked with). I saw men going out to have a drink after work, watching sports together in the lunch room and playing golf together at company events. They all seemed to support each other and provide advice, guidance and networking opportunities. I didn’t see that with the women. They all complained that they had to go home and take care of their kids, cook dinner and clean the house. I asked them why didn’t they split up their chores with their husband and the response was always between 2 answers: 

1. They complained that if they didn’t do it, their husbands wouldn’t do it. It just wouldn’t get done.

2. They complained that they were not the breadwinners and so they had to ensure their husbands managed their own careers and brought home the bacon and they will add to it as a supplementary career, but they really wanted to be a stay at home mom.

I wasn’t married at the time, but I thought both reasons weren’t good reasons for a woman to do double duty compared to the men. In my twenty-something single, unmarried and childless brain, I thought, I’m either never going to get married if this is the price of entry, or I will only marry if I can find an equal to myself. I also witnessed so many older women who were getting divorced and had no income or job experience to make a proper living. I saw divorced men who had young new wives beside them driving around in luxurious cars and dressed in dapper suits. And when I talked about this with women in their twenties and thirties, they always assured me that their husbands would never leave them and that the sacrifices they put into their marriage would keep them bonded for life. I’ll bet these 50-year old ex-wives probably thought the same thing when they were 20-year olds. 

My plan was to never marry, build up an incredible career, travel the world and be fabulously glamorous. I often dated men who were a few years older than myself, who had seen and done more than I had and I could learn from them. That was the plan,  until I met this younger guy (6 years younger than  myself) who started off as a buddy of mine that I could punch in the arm and hang out with and totally be myself. My girlfriend was coaching a hockey team at the time and he was one of the players. She would ask me to come watch the game so I did and that’s how I met him. He had a “crush” on me at first, which I didn’t take seriously but after a few hangouts, I realized something about him that was different from the other guys I dated. He genuinely respected everything that was important to me. He didn’t impose his ways of thinking on me like some guys did and he didn’t act like he knew it all. There was a genuine curiosity in him about all things me, and he was actually a lot of fun (if you can make a girl laugh, you will likely win her heart). I told him I never wanted to get married or have kids, and he said no problem. Then one day I woke up and had a change of heart. I told him, I do want to marry and maybe have a kid or two. And he said ok.

We got engaged, then married, and then had our first kid. After 3 years, we had another. And while I doted on my girls and spent an enormous amount of time as a new mom, loving every minute of it, after a few years, I decided I wanted to go hard into finding a career that I was going to love. That’s when I transitioned from corporate to startup. It was at this time that my eyes fully opened up and I felt like I could see things in color for the first time in my life (at least when it comes to my career which is a huge part of my life). The next 10 years of my life goes deep into startup life and anyone who has ever worked in startups (especially early stage) knows how damned hard it is every day. I couldn’t have done what I’ve done in my career without my husband who dedicated the last 10 years picking up the girls, making lunch and dinner for the family, getting groceries on weekends, filling the gas for weekdays, cleaning the house and never complaining about it because he worked in steady corporate which allowed me to work unconventional hours in risky startups. If you want to have an equal partnership with someone who respects you and won’t make excuses, focus on finding the right partner. Your marriage, your career and your kids will thank you for it. Remember, not all men are the same and we don’t have to accept the status quo (at least I won’t).

That first year in startup, I did everything wrong. I worked with a founder who was incredibly dysfunctional, highly emotional and could be elated one minute and then pounding his fist on the table the next. I remember we were on a call once where he didn’t like what I said and a few minutes later, he hung up on me. Like, when was the last time an adult hung up on you? I can’t even remember because it’s so immature and petty but that’s how he was. There were so many more incidents that occurred after that that made me want to roll my eyes into my head each time something came up. Do you remember when we heard that Travis Kalanick, the founder of Uber who was rolling on the floor after video came out of him yelling at the Uber driver? And his executive team was cringed out and so disappointed in him that they just couldn’t work with him anymore? That’s how I felt most days working with this founder. He was eventually removed by the board but I worked with him for almost 2 years. On better days, I surprisingly learned a lot from him as well. He taught me to eat the frog first and get the hard things out of the way. He also shared an incredible amount of feedback with me, which I really appreciated because we never get enough feedback, ever. My ability to grow so quickly in this role was in huge part due to his belief that I could do anything. He gave me my first executive opportunity and I will always be grateful for his belief in me. I also experienced severe burnout for the first time in my life and had to go to the hospital for surgery before I quit my job and recuperated. Upon reflection and hindsight, I know that burnout can occur because you are the most relied upon and highest performing employee on the team. I know now that you can die by being loved to death.

That was my first role at a “crazy” startup and then I followed up by joining 5 more over a decade. My next few startup experiences all varied from early stage to later stage, from small to large, from male founders to female founders, from VC backed to M&As and everything in between. I learned so much about growth, resilience, frustration, depression, loneliness, betrayal, coups and winning against all the odds. They say fact is stranger than fiction and startups can be a strange place. It’s not for the faint of heart and sadly, a lot of women say it’s not made for them. But what if you could learn something great about an environment that is vastly different from what you know or expected? Nobody said startups were easy. Nobody. It’s the exact opposite of that. And most days, everyone finds it difficult, not just women but men alike. For me, the ambiguous environment and the raw lack of processes was refreshing to me and I felt like I could work faster and execute more quickly due to the lack of red tape. But I also had to balance that risk with things that might break and cause issues in the future. Startups are high risk and I’m not sure if some women find that too scary or too risky but I got a thrill from it. 

So this is where I’m going to go full circle back to the beginning of my story. When I was young, I thought being born a girl was a curse. I believe that the world was made for boys and men and we were just here to fill the spaces in between. I believed maybe we were just the supporting cast members but never the main actors. I mostly believe this because the women told me I should. I worked with women that often made me feel small and created an insecurity that I had never felt as a child. And when I grew up, most women didn’t lift me up or give me opportunities to develop and gain confidence. Most of my managers were women HR leaders and they were pretty difficult to work for and with. They had very low self esteem and they protected themselves by making other women feel vulnerable by stripping away their confidence. I started to feel less confident in each role, until I broke out of corporate, joined risky startups (which happened to have less women) and worked within a more male-dominated workforce that just sort of accepted me as one of the guys. The startups were also tech startups, so success was factored on KPIs, OKRs and target outcomes (numbers don’t lie). There was less emotion and more logic and objectivity. Logic and objectivity to make decisions, how beautiful is that?

That’s not to say every day was sunshine and rainbows (remember that first founder that I worked with)? But at least I could be myself and nobody really judged me. Being around guys who were confident made me feel more confident. Being around guys that didn’t talk about insecurities and emotions made me think less about those things. Being around guys that were direct and honest gave me confidence to do the same. So I guess my point is that sometimes, women create the kind of deep seated insecurities that we are trying to avoid by instilling it in others and making us acutely aware of it. The “groupthink” that occurs can discourage our ability to do things we’ve never done before and hinder our ability to succeed. You know that saying when doubt creeps in? The same goes for our deepest insecurities - are we manifesting the stereotypes of women that we are trying to destroy? Men get bashed so much for not supporting women, but in my experience, women have bashed women far more than the men in my lives. I’ve had more women troll me online, bash me behind my back and turn my words around to weaponize them against me. I’ve also had to delete more hateful comments and block more LinkedIn users that were women than men. Twitter (or X) has always been extolled as the most obscene online platform outside of Reddit, but I see more and more women indulging in grotesque and rude comments on other women’s posts versus just scrolling by. It’s disturbing to me and I’m worried about the future of women if this is how we are going to treat one another. Behind all the virtue signaling of women supposedly supporting other women out there, I’ve not seen that to be true.

So going back to my childhood, what I realized coming full circle is that being a woman is amazing. I get to still do all the incredible things that I’ve always enjoyed as a little girl and I get to surround myself with the supporters that will allow me to be me. My supporters have predominantly been men in my life and career, and as a result, I won’t bash them the way women sometimes want me to. The male allies I’ve had in my life and career should be celebrated and they deserve the credit due. Not all men are perfect, far from it, but the majority of them have been my ally. Being a woman is not a curse - it’s a blessing. It’s only a curse if you are the woman that creates discourse for other women while pretending to be their greatest supporter. So to women I say, maybe it’s time we change how we operate so that we could support other women and also find some wins for ourselves. Your daughters and your sisters will thank you for it.

Subscribe now

Note, I’m certain there are some women who will be “offended” by my diary entry here but it’s a diary after all - you just happened to read it.

Leave a comment

Have you ever heard the phrase, “HR is a thankless job?” 

How about, “HR is the complaints department?”

Or this one, “HR is not for the faint of heart?”

For anyone who ever thought going into HR would be fun (how difficult could it be to manage culture in the organization), I say you haven’t done enough of the hard things to be a credible HR leader. Because unless you have occasional bouts where you want to quit your job and contemplate something vastly different, you have only touched the surface of HR.

I once wrote a LinkedIn post on a whim after a very bad day at work. I didn’t put a lot of thought or effort into my post. I simply picked up my phone and typed in how I was feeling that day.

Without planning to, that post generated 2.3 million views, 23,000+ likes, 1,000+ comments and 2,000+ reposts. (If you’re curious about the post, you can read it here).

My opinion is that HR is one of the hardest jobs out there because you have to deal with people. While most jobs focus on one prime thing - sales, technology, product development, finance, etc. HR deals with people. The good, the bad, and the extremely ugly. This is their job and I often call it the “customer service department” of organizations. And we all know customer service is damned hard (insert image of bad customer behaviours throwing coffee at baristas or having a temper tantrum because a customer couldn’t get a refund for their purchase from last year). You know exactly what I’m talking about, and we always secretly think the same things when we witness these incidents, “These customer service agents don’t get paid enough to tolerate this.” We also all know now…the customer is not always right. And neither are all employees.

I remember I once had a coffee chat with a founder/CEO who was building a business and wanted to see how he could build a great culture. I was honest about the things you need to do as a CEO and as a leader to build a thriving company that creates a great culture - and I don’t mean great as in happy employees that are hugging each other all day and being besties. I mean building a great culture of accountability, performance and success. You don’t get all of that just by being nice and giving your employees anything they want, whenever they want. Leaders build accountability, performance and drive success through honest conversations, courageous actions and by challenging people to grow. If you don’t have the courage to do those difficult things, you will ultimately build a company of entitlement, complacency and self-serving motives.

His reaction to my feedback was a smirky grin. He responded by saying, “Oh, I get it, you’re jaded and burnt out.” His confident smirk showed me that he felt he knew better. He continued by sharing that he believed if you create the right type of environment, culture will find its place nicely. Oh, if only it were that easy. A few weeks later, I saw that his company posted a job description for an HR manager. One of the requirements of the job was “to be happy.”

Honestly? Like some sort of creepy toxic positivity mask that their HR leader must wear while going around stocking the snack drawers and booking the pizza parties for lunch so everyone is happy? That one line completely turned me off. This was not a credible job description and you would never add a line like that if you were hiring a finance manager or a marketing manager. 

Well, that company made their hire and things seemed to be going well but in time, their high engagement scores dropped (everyone knows that when you’re small, your eNPS is often high, but when you grow, it’s difficult to keep the momentum going). Employees started to complain, bad behaviours set in and company reviews started to go down. The biggest complaint was that the leadership team didn’t know how to lead apparently. It appears that having a happy HR manager didn’t help their cause afterall.

So without trying to sound jaded, I’d love to share a CPO’s top 5 things that leaders should not be doing and my advice for what to do instead. Side note, I only share 5 because this article can only be so long, but I could easily share 20.

# 1. You don’t create greatness by showering rewards without earning them.

This is every lesson a new founder or new leader ever learned about culture (the hard way). This is in fact, the worst thing you can do for people. It’s like a toxic form of gentle parenting where you give anything their heart desires without the ability to cope with the hard things that come their way (and they always do). If you have a habit of just giving out trophies without developing the muscles and the minds that receive them, these folks will be in jobs they can’t scale with empty titles, and they will ultimately never be able to compete for similar jobs in the real world where experts are skilled and credible at what they do (remember that Aussie break dancer at the Paris Olympics?).

Rather, leaders should develop skills like critical thinking, conflict management and disciplined approaches, so that people can experience challenges that allow them to thrive in adversity. That is a far greater gift for your employees than just handing out rewards that weren’t fully earned. Honestly, think about some people at your workplace - do their titles really justify their experience? I’ve met COOs that were 25 years old and CTOs that were glorified IT support managers. Giving in to entitlement ultimately hurts the ones that you care about the most because unless the rest of the world is willing to roll out red carpets for them everywhere they go, they will ultimately crash and fail. 

#2. You don’t reward bad behaviours (even when they’re winning at their jobs).

In HR, we often call these folks “brilliant jerks” because most people in this bucket do their jobs really well - they hit their revenue targets and manage their projects with ease. However, their greatest downfall is their bad attitude and behaviours, often showcased to their peers, their teams and even their managers. They create drama (but it’s never their fault) and they lash out to those around them because they feel a sense of entitlement. They are smug in thinking, “Why would anyone punish me if I’m doing a great job at my work?” In the world of assessing who should stay and who must go, these are the first ones that leaders should remove from the company, even before poor performers because they negatively impact so many people.

I often give the advice that if you can’t get them to recognize their behaviours and how it impacts the team in a harmful way, then your only option is to release them. Being terminated from a job that they were doing well in is jarring but it might be just that which will get them to change. The alternative reaction is that they will blame the company and everyone but themselves. Eventually, they join a new company, and guess what happens? History will repeat itself.  The reason why releasing is often the best way to tackle bad behaviour folks is that you can’t force someone to change their behaviour if they don’t want to. The onus sits with that person alone.

#3. You don’t give preferential treatment to poor performers just because you like them as a person.

This one is something that every leader I’ve ever worked with struggled with. In this scenario, there is always someone that either the founder, the CEO, or a senior leader feels strongly attached to. We build relationships all the time as humans and this especially happens at work where we spend the most amount of time with the people we work with. What typically happens is that this leader hires someone that becomes a fixture at the company - they’re often long-standing in tenure, they spent many long nights working on big problems together and they probably made a pact a long time ago that they would take the company to wild success together. They are essentially bonded at work.

But somewhere along the way, this person can no longer keep up with the job. Perhaps they’ve been promoted too quickly, too many times and the job got bigger than them, or they became disengaged and complacent in their belief that they have life-long security in their job. Regardless if it’s the former or the latter, both scenarios not only harm this person’s ability to develop themselves further but the seat that they continue to sit in at the company hurts the company. Any hires you make below them rise up to the level of their leader, and if their leader is an incompetent B performer, they will often hire a C performer under them. This person prevents their own team’s ability to develop and achieve greatness, or they will take advantage of their team by delegating all the work to them while they sit comfortably in their office planning their next vacation or social outing (I’ve spoken to so many employees who claimed they had no idea their boss wasn’t actually doing work during work hours). At the worst, this creates morale issues for the team(s) they lead and for the ones who are doing the work. What’s the fastest way to create an environment of nepotism, preferential treatment and unfairness? Keep rewarding these folks who are only doing 50% of their job.

#4. You don’t have difficult conversations because you want to be liked.

Who doesn’t want to be liked? I think everyone prefers to be liked and keep the boat steady. Why spend an afternoon sharing constructive feedback with a colleague on knowing that they’re going to ruin your weekend (and theirs). But if you’re in the position of a leader, this is what you signed up for. I’m not sure people realize this but as you climb that ladder of management, the more senior you become, the more your job consists of people and problem managing all day, like up to 80%. It doesn’t get easier which is why building up your ability to have really difficult conversations is so critical to your success. HR is there to help and guide you along the way, but this is not their responsibility. It’s yours. Any organization or leader that relies on HR to share bad news are the ones who create the bad reputation of HR as an industry, not to mention you are not worthy of the title of “leader.”

This also goes back to why you need to develop your skills to move up. Being an expert in Finance or Marketing isn’t going to make you an excellent leader if you don’t know how to manage people and give direct feedback, navigate difficult relationships and communicate hard things. Your desire to be liked should be trumped by your desire to be respected.

#5. You always counter an offer when someone threatens to leave.

This is something every manager has had experience with. They have an employee on their team that wants something (a promotion, a salary increase or more vacation time). The person gets declined at this time and then a few months later, they come back to their manager threatening that while they “weren’t looking,” their profile was noticed by a recruiter and they are offering them xx% higher salary or a much more senior position so they felt compelled to bring this forward. The manager runs to HR to state they cannot lose this person and they don’t have time to hire/train their replacement at this time. HR does not advise counter offering this employee, sharing real stats that claim the following:

• 80% of employees who accept a counter offer end up leaving within six months.

• 50% of employees who accept a counter offer regret their decision.

• Only 3% of employees who accept a counter offer stay with the same company for more than two years.

The manager will not be swayed and gains the approval to counter the offer. The employee accepts and if the story ended here happily, there would be no issues regarding counter offers. But the reality is that counter offers rarely succeed in the long run. While the offer may temporarily make the employee happy, eventually their reasons for being dissatisfied in the role or at the company have not changed (if anything, they don’t have the opportunity to complain anymore since they were given what they wanted with the counter offer). So in the end, the employee ends up leaving anyway and in the meantime, the department now has a manager with a reputation of divvying out higher compensation and promotions to keep people. You’ve now set a very loud precedent within your team and your company.

If you’ve read this far, you’re probably wondering why I shared my top 5 things that leaders shouldn’t be doing? 

Going back to the beginning of my article, there are reasons why HR leaders are leaving their jobs at accelerating and alarming rates. It’s not easy dealing with people, especially when they’re managing the complaints, the problems, the issues and the negative opinions directed their way all day, but when leaders (who are the business partners for HR) choose to disregard the advice that HR leaders proactively provide, the issues that follow are inevitable and they are often pivoted back to HR to fix once again. It’s like advising someone not to proceed with a business deal until they’ve read the contract thoroughly but they decide not to heed your advice because they know this person. And then they get bamboozled out of millions for a corrupt deal that could have been avoided and now you’re the one being asked to get this person out of this dilemma. Do you know how many times an HR leader wishes they could say, “I told you so….”

I guess when you’ve been in HR for so many years, you’ve gained a lot of experience not just through solving endless problems and finding creative solutions, but also how to avoid predictable situations in the future. While we can’t all see the future, one thing is certain - the more you deal with people, the more you understand the psychology of people (the good, the bad and the oh so ugly) as well as organizational behaviours. While nothing really surprises HR people anymore (they’ve often seen it all), they are also wiser for it and realize that they also have a choice…to continue repeating the crazy over and over again, or to not. They can choose to leave the company or the industry altogether. And they are, in droves.

The next time you see your HR leader cleaning up someone else’s mistake (maybe yours), consider how to avoid this circumstance in the future because that could possibly retain your HR leader a little longer.

Subscribe now

I don’t think about my career trajectory all that much, but when someone specifically asks me how I rose up in my career, it makes me stop and think.

I’ll be the first to say, I’m not an exceptional “brainiac” and there are many people who have done far greater things than I have. However, I can say I am very good at the things I do, and I think I’ve figured out what has contributed to my success. 

As with anything, there are a variety of skills I honed in on to become great at like learning to articulate myself clearly; using logic and objectivity to validate a point; being careful to look around corners so that I’ve thought of every angle and avoid potential mistakes; learning to collaborate and share ideas with others, etc.

But those are really table stakes. Lots of people do those things, or they can learn to do them and do them well. 

What I think has contributed to my success is something that I didn’t consciously think about until I got older, and that was my innate curiosity.

Think about the people around you or your family members and friends. How truly curious are they? Curious enough to ask questions (even the dumb ones)? Curious enough to take action (even if it means more work for you)? Curious enough to rock the boat (because you know the way we’re doing things now is just wrong)?

The truth is, not all people are curious and they are satisfied to go on with their day-to-day lives without questioning anything or wondering why it simply is the way it is. Some people just aren’t curious enough and so they accept.

When I graduated from university, one of my first jobs was at Dell where I worked as a customer service agent on the phone. I was excited to be joining a hardware tech company and they put a large group of us through a 2 week training program. During one of those training sessions, a manager was trying to explain that when you get a complaint from a customer, you’ll oftentimes need to work with team members from other departments to resolve the issue. For example, if a customer called to say their computer order wasn’t placed properly, you would need to go find the sales rep that took the original order from this customer to resolve the issue. The only problem was, we were instructed that you aren’t allowed to go over to that team member to talk to them face to face, in real life (even though that team sat right next to our team on the same floor).

You would only be allowed to email them.

I thought that was odd, considering we were all physically there together in one building sitting next to one another. This was also a long time ago, prior to software programs that allowed you to text one another like Slack, so emails were really cumbersome when you had to go back and forth to discuss something in detail.

So I asked this training manager, why are we only allowed to email one another? Why can’t we walk over and have a conversation with our colleague, or even call them on the phone to discuss the situation. Wasn’t emailing one another wasting time and effort going back and forth?

She looked at me, smiled smugly and said, “Because Michael Dell wants it that way.”

Seriously…that was her answer to me? That didn’t provide me with any insight into the “why” except for the fact that he sounded completely arrogant and power hungry and this manager sounded content to take Mr. Dell’s command and proudly implement it to everyone. Even if she didn’t agree with him, couldn’t she have thought up a better response to my question, just so that us newbies could be more aligned?

When I looked around the room, everyone just sort of stared at her, nodded and accepted it. Everyone except for me. I still didn’t understand why that was the rule, and I didn’t think it was a good one. It was inefficient. It didn’t allow for close collaboration between teams. It resulted in longer resolution times. It created communication issues that would have been better revolved through a conversation. And it didn’t create an environment where we could all solve problems as one team. We were being trained to work in a bubble and a silo. I mean, why bother even commuting into work if we aren’t allowed to talk to one another?

So I decided that Dell wasn’t the place for me and I left that role shortly after.

Throughout my career, I let my curiosity lead the way. Even early in my career as a new manager where I was given more responsibility and autonomy to do things, I always looked closely at how things worked or why we did things a certain way. If I thought something could be done better, more efficiently or with less mistakes, I would go ahead and “fix” it. I gained great satisfaction seeing the results of my labour and I continued to view the world with this curiosity and how things could be better.

My managers always thought I was just hard working or engaged, but it wasn’t even just that. I’ve always worked incredibly hard and I often choose jobs that engage me, but those weren't the only things that allowed me to succeed. It was and still is the genuine curiosity I have within me to look at something and wonder, is there a better way to do this? What would I do if this was my business? How would I manage this function if I was in that person’s shoes? I wasn’t sure if everyone thinks this way, but those were the things that were always in my head, even to this day. It never gets old.

I was at a hair salon one day getting my hair done. A customer went up to pay and was about to get her jacket from the coat rack near the cash register and she was surprised that it was missing. She asked the cashier and her hairdresser about her jacket, her red leather jacket, and they were all surprised and said someone must have taken it by mistake. A red leather jacket, by mistake? Probably not. But I remember thinking, if I was the owner of this salon, I would never leave customer coats on an open rack for people to freely take. I would have built a coat closet and ensured that customers got a coat check chip to store their belongings safely, just like they do when you go to a restaurant and they take your coat. Why wouldn’t you do the same at a hair salon?

I was lining up at Aritizia and there were no signs to instruct customers of where the line begins and ends. Two  lines started forming, one from one side of the cash counter and one from the other. I knew that eventually, someone from the cash desk would tell one side of the customer line that the line starts on the other side of the counter. That was eventually directed at me and the people behind me, so we had to leave the line that had formed and walk over to the other side to get behind the long line that was formed on that end. Remember, there were no signs, no stickers with arrows on the floor, nothing. This was frustrating for customers and also unnecessary, but for some reason, the cashiers didn’t seem to care and sure enough, every few minutes they had to tell one side of the line to get to the other side, over and over again, probably many times in their 8 hour shift. When I went back a month later, I thought surely they must have put up signs by now, but nope, it was still the same. And they were still telling customers to get to the other side of the line. So why expend so much energy to do this when you could be fixing the situation and making both customers and cashiers happy?

I walked into a HomeSense and thought I would just pick a few small items. I ended up going through every aisle and picking up more and more stuff, little things that kept piling up in my arms. I hadn’t picked up a basket when I entered the store but now, I regretted not doing so because my hands were full. I decided it was time to cash out as I didn’t have the ability to carry anything else. As I stood in line with my purchases, I gazed at the front of the store and wondered, “Why do they only have baskets at the front of the store? Surely if placed baskets at different areas of the store, customers could easily drop their purchases into one and would likely end up buying more and continue shopping longer?” In my mind, I imagined stacking baskets in the middle of the store, the back of the store and maybe near the changing rooms.

So when you think about it, almost everything starts with curiosity. Then, when you ask the questions and gather the facts, you have an opportunity to take action. Once you take action, you have made change. And with change, you have 1. Resolved a problem, 2. Made something more efficient, or 3. You have created a new and refreshing way of doing something.

So think about what you could accomplish by applying this way of working at your job? Imagine how much more efficient you could become by resolving issues that cause friction and pain points and creating better solutions for daily problems at work. 

And better yet, imagine if your manager could witness you doing all these amazing things simply spurred on by curiosity. Doesn’t all of this show initiative? Don’t you become the most valuable player on the team simply because you can and will solve problems? Perhaps you’ll become the MVP because you do what most others don’t…you see something, you do something.

For me, I find my curiosity becomes stronger when I start a new job at a company. During those first 3 months when I come into a job with a fresh set of eyes, I want to know how everything works in my domain. Joining a new company and taking on the function of HR means I have the opportunity to change how we provide services and programs to our employees who are the ones we serve. 

Why are we only providing learning and development programs online? Have we tried looking into more interactive programs or is this just the way it’s always been done?

Why is turnover so high for this vertical/team? Is there an issue with the manager leading this team or are there other concerns we should be looking into?

Why did our engagement score drop by 15 points last year? Was there a major event that occurred that affected employees in a negative way or did we divert our attention from employee engagement?

The reality is, all leaders should be curious so that complacency and comfort doesn’t settle in (we must all avoid going on autopilot), but I truly believe that it’s magnified when you are in an HR role. In HR, you are in a role that requires unbiased judgment calls for almost every aspect of your work because you deal with people the most. In order to have an unbiased view of a situation, you need the facts. In order to get the facts, you have to ask questions, dig into details, probe where things feel misaligned and ensure that no stone has been left unturned. And then you fix. You take action.

Maybe I was always destined to work in HR and be really good at it because I had this innate curiosity to look under every stone. Maybe I just landed in HR and it taught me to be curious, more than I ever was. Or maybe some people are born with it and they make good use of it because not every HR person I’ve known has been truly curious.

My advice to you is to never stop being curious, asking questions and making things better. You can either be a passenger in life or you can be in the driver’s seat. I choose to be in the driver’s seat - it’s way more fun!

Subscribe now

The best leaders are essentially people leaders. What does that mean?

I’ve been working in HR for almost 20 years and I’ve been a people leader for half of that time. During my tenure, I’ve worked in publicly traded companies with massive global matrix environments as well as early stage companies that are trying to find product market fit. I’ve worked at companies that delivered excellent value to their stakeholders and I’ve also worked at companies that had to fold because they could not compete with the competition.

I’ve worked alongside exceptional leaders who have been groomed to manage companies that lead the stock market as well as entrepreneurial geniuses that have founded the best companies and built breathtaking businesses from zero to one.

I have worked with some of the smartest and most capable leaders, and what I’ve learned that surprised me the most is that the most capable leaders are not the ones we would all assume to take the center stage.

They were not the best engineers who had the perfect code. 

They were not the best finance leaders that spit out the best finance models.

They were not the marketing leaders that created the most unique brands.

The best leaders I ever worked with for any role were the ones that could work best with people. Sure, they had hard skills but they also had a high level of EQ that allowed them to work exceptionally well with the greatest number of people. 

They were true people leaders.

Simple as that.

Subscribe now

The best leaders in my experience, had a set of unique skills that seemed to be the baseline for all the great leaders I experienced in my career. Here’s what they all had in common.

High Collaboration

They collaborated like experts and they even debated in a way that allowed the best ideas to rise to the top because they knew how to engage with people at all levels. They knew that the best ideas must win. It had nothing to do with building power or feeling threatened when others shared innovations that were better than their own. They knew what the best interests were for the company’s mission and that takes a whole lot of humility. Humans are not naturally conditioned to swallow their ego and pride, especially in this competitive world but when your best interests are towards the company versus your self, you have arrived.

Vastly Curious

The best leaders were also wildly curious and unafraid to ask questions. Without curiosity, you are arrogant and presumptuous. You assume you know everything and you wouldn’t in your wildest dreams ask the “stupid” questions. Here’s the surprise, the smartest people always ask the most basic questions because they don’t assume to know everything. They want to learn what you know and they are wildly curious to learn from you. I’ve witnessed executives asking customer service agents the most basic questions because they wanted to learn from ground zero.

Empathy & Logic

The best leaders are the best team members to work with because they can work with people who are just like them, and they can also work with people who are vastly different from them. That means that the best leaders are prepared to have tough conversations that are unpredictable and yet, they will be grounded in their approach. They understand how to balance human empathy with objective logic so that one side never trumps the other. 

Do the Hard Things

The best leaders also have the best engagement on their teams because they know how to work with people and that often means doing the hard things. They will have challenging conversations with you and talk about the difficult things that some leaders shy away from. If your leader can’t dive into the hard conversations because they don’t like to rock the boat, they are not leaders. They are the status quo that like to keep things comfortable and yearn to be liked. In fact, the most junior leaders like to emphasize to their team that they “did their best” to fight for them but HR or the Executive team didn’t agree to that promotion or new hire and so they cop out on real conversations and stay complicit in being the “nice guy” while blaming the leaders above them. This is far from real leadership.

An HR Perspective

So here’s where I’ll add an extra lens, from a personal HR point of view. Sometimes, people mistake great leaders for those who are “people persons.” I think this is the greatest mistake people make about HR leaders. It is harmful to presume that HR leaders should be a “people person” and champion every employee in the organization because their role in HR must mean they are solely people focused. That is simply not true. It’s also harmful to label a leader as “great” just because they like people but they can’t discern the right competencies for their team members to succeed in their roles. When you hire and keep a person who is incompetent in their role, you do a disservice to the entire team because they now have to lean into the incompetencies of your hire to get the job done so the business can move forward.

People come in all shapes and sizes. When you hire employees into a company, you are hiring them for their expertise, their skills, their ability to get the job done. What are their motivations? How do they contribute to the company culture to add to it versus depleting it. It’s also about their attitudes towards work and how they enable others to be successful as one team. We have all worked with a “brilliant jerk” who perhaps generates great value in their role but who is intolerable to work with. We are also familiar with the incompetent team member who doesn’t have the relevant experience to succeed in their job but they interviewed and here they are. Do we take action or turn a blind eye as your company culture erodes.

HR should not blindly be championing all people for the sake that they are focused on people. They should be focusing on the right people with the right attitudes to make all of us better in what we do. For every intolerable jerk out there or the miserable team member that spreads negativity around the office day in and day out, there is someone else out there who is dying to be in your role, who would be highly successful and who would be an epic culture carrier. The fact that HR leaders are expected to celebrate every bad hire that comes into any organization is a fallacy and an insult to organizations. No wonder so many business leaders disrespect HR professionals and see them as social workers who are focused solely on distributing jobs to the public regardless of their skills, effort or behaviours. As an HR leader, I can assure you that many people who are released from companies are not released because of something insignificant - that’s ridiculous. Bad behaviours, bad attitudes and bad actions have led many to their demise but it takes deep self awareness to recognize mistakes you might have made within thyself. Most times, it’s easier to finger point and blame versus reflect and learn.

The truth is that if you can’t work well with people, problem solve with your peers and find harmony to move forward, you probably can’t do this at any company. You are a lone wolf and you’re probably better off being a solo contributor. That’s the truth. You are a disruptor, but not in a good way. You disrupt the business in a negative way and for those who are feeling uncomfortable while reading this, I’ll bet you’ve experienced the negative side of what I’m sharing at a few companies you’ve worked at. I always say, those who feel this familiar discomfort have experienced this before. This is not your first time but hopefully, it will be your last if you can focus on making changes to guide your future.

You can’t expect to join a company and be employed forever just because you feel entitled to a job. You can’t join a new company and comfortably fall back into your bad habits. Every employer has the choice to hire the best team players who will make the company better so the ones that show up entitled, disgruntled or with a basic bad attitude will never succeed at a company that is genuinely interested in building an amazing culture and team environment.

Every great organization wants to hire great people and create great cultures. You would do the same if you started your own company. 

Every employee has the privilege to choose where they work and how they show up. Every employer has the same privilege. It is ultimately up to you to show up as you’d like. Make that choice wisely.

Subscribe now

Share

Leave a comment

I’m in HR and I think that’s why I don’t suffer fools gladly even more than the average person.

The first time I heard this was around 2016 when I took on my first leadership position at a fast-growth SaaS startup company. At that time, we had to do everything fast - fast hiring, fast development and fast execution. Even failures had to occur quickly, swiftly followed by the lessons learned. My first executive job was stressful and exhilarating at the same time, and it was during that time that I started to learn so much about people in general.

I’m not sure if it was because I was finally at a level where I had to interact with so many different people at different levels that you learned to gauge people and their behaviours very quickly. Was it because I was involved in so many more recruitment interviews, hiring for fast growth companies that I learned to quickly assess when someone wasn’t completely genuine in an interview or when that person felt “off” in terms of their character? Was it because I was working with so many executive leaders who were managing their verticals and you had to spend so much time fixing problems, performance managing teams and doing all the hard things about hard things?

What I learned very quickly was that hard technical skills and book smarts will not result in your ideal hire. I’ve reviewed thousands of resumes from shiny candidates with every accreditation and ivy league school graduation letters on their resumes but the majority of them ended up being the worst hires I had ever made. What I learned was that they spoke very well, showed up to the interview extremely confident but they were obviously trained to show confidence, bred to believe they are the best of the best. The only problem was that they couldn’t execute on all that confidence after they were hired for the job. In fact, the majority of them had imposter syndrome quite a lot and they made a lot of excuses to blame others for why they failed to succeed in their role and the majority of them were cons (they had connections to gain flashy jobs but they didn’t earn the true right to be there). This is obviously disappointing for any hiring manager, but worse if you believed that their credentials and their resumes should have resulted in your amazing, high performing hire.

Let’s go back to that saying, “I don’t suffer fools gladly.”

According to the Cambridge Dictionary, it simply means “to have very little patience with people who you think are stupid or have stupid ideas.”

Pretty blunt, right?

I agree, it sounds harsh. So mean. Just so dismissive about people. And shouldn’t HR be the ones to uplift people all the time? Isn’t that our job?

Not for me. Why does HR have to be in the job where they must be unconditionally “for the people” versus “for the mission?” For one, not everyone is here for the mission and some people are just plain unhappy being here. I’m probably one of the few HR leaders out there that truly believes in the mission first before just rah-rahing for the people. I’m not the happy cheerleader that blindly sees the positive in every situation because we all know that we need to look at facts or the truth. No matter how much we want to believe in others, we need to be objective and ensure that we are not viewing the world with rose tinted glasses in some blind and rainbow way. There is such a thing called reality and I’m a firm believer that everyone has an opportunity to achieve their reality if they put in hard work and they’re disciplined in their approach.

Don’t get me wrong, I’m very much a people first HR leader but that doesn’t mean that all people are right all the time. I think meritocracy is an important part of creating an environment where everyone feels they have the opportunity to achieve great things…as long as they put in the work to do so. That also includes myself and I’ve been the first to tell my CEOs, when that day comes when I am no longer servicing the company the best I can, I’ll be the first to step down - you won’t need to tap my shoulder, I will know first. And I mean it.

This has nothing to do with DEI or giving concessions to others because we should. I grew up as an immigrant from South Korea and I landed in Canada when I was 2 years old. At the time, my family had very little to show for themselves as we quickly had to learn the language and navigate a new country that was so different from where we came from. We didn’t have friends or family and my parents had to work hard to integrate into this new society while trying to find work to feed me and my older sister. It was hard and there was rampant racism at the time where you had people who just came up to you on the street to make fun of you for no reason - making gestures and saying cruel things because they thought it was funny and in their right. I remember my mother never cowering away when strangers taunted us. She stood up to them and hurled curse words back at them which startled them even more (I guess they thought she would be more submissive based on the Asian stereotype but she was anything but). I look back at those early years and I don’t blame my mother for how she reacted. At night, when she was putting me to bed, she would say, “Don’t let fools like them make you lose your confidence. Work hard, find your success and never let them take away your pride. Be successful and you show them.” Even as a little girl, scared and unsure of myself, I still remember what my mother told me. And as I grew up, I started to realize something…there are a lot of fools that speak confidently and swagger around like they own the world but more often than not, they are fools. They literally lack all self-awareness and they have no idea how ignorant they look most of the time. They were certainly not what I thought success should look like. 

I wish people respected hard work and discipline more than they do today. That’s the one thing that I think we all are capable of but few of us actually put work into. I feel like so many people complain about what they don’t have versus appreciating what they do, and knowing that they can control many parts of their destiny to get to where they want to go. I hear employees complaining that they want their company to be fully remote so they can work from Portugal but they don’t choose to leave for a remote-first company. I hear people complaining they want to be a leader, but they are the first people to log off at 5pm and they don’t want to be disturbed when there is a company emergency. I hear people saying they want to be a manager of people but then they get upset when they need to share difficult company news and instead blame the executive team as if they had nothing to do with any company decisions. Maybe I grew up in a different time or maybe I grew up with very little, but I really believe that every single one of us has an opportunity to make our dreams come true if we put our minds to it but it takes hard work and it seems like that’s something no one wants to do these days. I’ll share 3 short stories about my childhood that might show a snippet of how I became who I am today.

Story #1: When I was really young, Disney World opened up in Orlando (this was in the 70’s) and it was all the rage. Every kid in my school ended up going to Disney World for vacation at least once and I was so envious! I used to watch Mickey Mouse cartoons on TV and loved all the Disney princess movies back then. I also had parents who worked 7 days a week and never had time for vacations so I knew I would never go as a child. Instead, I had to work part time at my parent’s grocery store and while I didn’t love it, I really learned the power of earning money at a young age. My parents paid me $5 per hour and I tried to work as much as I could over the summer holidays to see how much I could make. I often worked 12 hour days on weekends to see if I could do it (I was 13 years old). I did and I really enjoyed it (making money felt empowering as a kid who had nothing). I ended up visiting Disney World in my 20’s when I met my husband - he grew up in a single parent home raised by his mother after his father died of brain cancer when he was only 10, but his mother decided her 2 sons should experience Disney World and so she saved up enough money to take them. What an amazing mom! I LOVED Disney World when I went for the first time at 27 and I have gone back with my kids at least 10 times since (I still love it but I think more so because I never had a chance to go as a kid). I took my kids many times, not because they wanted to go, but because I felt like I could do something for them that I never had a chance to do myself. It’s something that I’ll probably always carry with me.

Story #2: I had a tough upbringing as a child (one day, I’ll share those stories with you) but I still had a lot of optimism. I remember sitting in my guidance office waiting to speak to my counselor about one of my courses. While I was waiting, there were a few students who were getting ready to graduate that year and they were all waiting to get their acceptance letters from schools like Harvard, Yale and Stanford. I was not one of them, but I also didn’t dream that big. I was more realistic and all I wanted was to graduate from university. Definitely local and definitely not ivy league. I remember years later, lots of students were really angry about having to pay back their student loans. I secretly felt grateful that student loans existed to help kids like me who needed support with tuition fees. It took me many years to pay back my student loans but I did, every single penny and I never complained - I was given a student loan and I knew I had to pay it back. I was grateful I even had a chance to go to university.

Story #3: I remember in my early years working in HR, I understood that if you wanted to climb the career ladder, you had to put in years of hard work and dedication to get to where you wanted to go. You get your entry-level job and then you prove yourself, and you move to that next level, etc. One day, in my HRBP role, I was talking to a colleague and she told me to look at someone’s profile on LinkedIn. This person she pointed to was someone who worked at our head office (we rolled into a large, publicly traded company) and she had recently graduated from her ivy league university. She did not start off in an entry level position. She was automatically put into a managing director position straight out of undergrad. I was perplexed. I asked her why this person was in such a high level position when she had no working experience and she looked at me like I was an idiot. “Don’t you know, some people are just privileged like this, she probably had connections or her dad made a call to the CEO. That’s the way the world works,” she said to me. I was shocked…not so much because I thought things like this just don’t happen, but shocked because I couldn’t believe that you could do things like this and expect people around you to just “accept” it. Why is nepotism tossed around so nonchalantly? Worse yet, what IF this person couldn’t do their job successfully, what would happen then? Would the company just have to accept her mediocrity because that’s the way it works? To me, this was even worse, accepting someone who might be really bad at their job but that shouldn’t matter to anyone else because that’s just the way it is. How sad (I hope she was good).

So when I think about how I don’t suffer fools gladly, I have to admit that I don’t. I think that each of us has the capability to do great things but we all have the opportunity to rise to a level of greatness. The level that we rise to will depend partly on our intelligence, partly on our will and partly on luck. Some of us will rise to extremely high standards and some of us will only rise to a moderate level. I think the part that I find intolerable is when someone is given an opportunity to rise to the occasion and they flop because they relied too much on luck (luck without will only gets you so far), or they didn’t put in the effort required to succeed (you thought that you could succeed without working really hard) or you just couldn’t do the job no matter how hard you tried (you were willing but not able, which is the hardest thing to overcome). 

Where I don’t suffer fools is all the foolishness I see sometimes at work that I find incredibly off putting. People who have a sense of entitlement because they were in their job for a long time. People who chase titles and salaries but they’re hardly worth the titles they chase. People who find every excuse in the book to extol why they didn’t hit their targets but none of their excuses hold themselves accountable. People who claim they should be promoted and how fabulous they would be while they are barely succeeding at the level they’re currently at (I guess a promotion would cure that). I don’t suffer fools gladly. There is a sense of entitlement and expectation that people feel now more than in previous generations and no one witnesses this more than HR. Sometimes, I think that common sense has been lost, replaced by very confident people who are unabashedly asking for the sun, the moon and the stars just because they have no shame.

When you genuinely think of the 80/20 rule, you will understand that most companies are run by the top 20% (I think it’s more like the top 10%) but you will often get the 80% asking for the rewards because sometimes, they think all you need to do is ask and you shall receive. If only it were that easy.

A true meritocracy is what everyone dreams of, but not everyone will put in the hard work and effort to reap the rewards they dream of. Don’t be a fool and ask for something you don’t deserve because the world is extremely competitive and we must all earn our place. Earn your place rightfully and you will also earn the respect of others. I’m in HR and maybe I’ve seen too much but I’ve never suffered fools gladly.

Subscribe now

Share

Leave a comment