Do the Uncomfortable Version

None of what I’m about to tell you guarantees success. I want to be honest about that up front, because most of what gets written for founders promises a formula, and there isn’t one. You can do all seven of these things and still fail. That’s the truth.

But here’s the other truth, and it’s the one I actually care about. If you can’t do these things, you will stall out. Not always loudly. Sometimes you just plateau and call it stability. Sometimes you watch people with half your talent pass you and you tell yourself they got lucky. The avoiding is quiet. That’s what makes it dangerous.

So this is the list. Six things I’ve either done myself or watched founders fail to do from a seat close enough to see everything.

1. Know when and how to fire people

I’ve fired a lot of people. Most of those were hard in the way all firings are hard, but they weren’t the ones that kept me up.

The ones that mattered were the executives. Senior leaders have autonomy, influence, and the ability to do real damage before anyone notices. A bad individual contributor costs you a role. A bad executive costs you a year, a culture, sometimes the company. And the reason they’re so dangerous is the same reason they’re so hard to remove. They’re persuasive. They’ve spent a career learning how to sound right in a room.

My job, for most of my career, was to see around that corner. To recognize the pattern before it fully formed. To know when someone was telling a founder exactly what the founder wanted to hear, and to say out loud that it was bullshit. That skill is uncomfortable to use because it makes you the person who ruined the good vibe in the meeting. Most people won’t do it. They wait for proof. By the time you have proof, the damage is already paid for.

Knowing when to fire someone is really knowing how to trust your read before the evidence is undeniable. If you wait for undeniable, you waited too long.

2. Don’t be embarrassed to reach out to people ten times bigger than you

There’s a name I won’t print here. Big enough that when I said I was going to reach out and ask him to come to one of my dinners, the smart move would have been to assume no. Everyone assumed no. He said yes.

It wasn’t the first time someone larger than life wanted into my orbit because they saw something specific in what I was building. I’m not telling you that to flex. I’m telling you because of what almost stopped me, which is the same thing that stops most people. The fear of the ask.

Here’s the thing about the ask. If you don’t make it, you’ve already given yourself the rejection. You just did it quietly, on his behalf, before he got a chance to. People think they’re protecting themselves from a no. What they’re actually protecting is their ego. They’d rather stay in the safe zone and keep the fantasy intact than risk a real answer.

The people who win reach up constantly and get told no constantly and it costs them nothing, because they were never staking their self-worth on the yes. Decouple the ask from your ego and the whole world gets bigger.

PS: Claude told me this dinner guest wouldn’t even respond to me. Even he was wrong. Don’t believe everything AI tells you either (saving this for a future post).

3. Don’t be ashamed to put yourself out there

I’ve spent years posting on LinkedIn about my own mistakes. About things I believed that rubbed the status quo the wrong way, which in HR is most things worth saying.

It would have been safer to post nothing with a point of view. Safer to stay agreeable, vague, universally palatable. And completely invisible. Because if you don’t stand for anything, no one can find you. You become wallpaper. Pleasant, forgettable wallpaper.

Standing for something means some people will disagree with you, sometimes loudly. That’s not the cost of being visible. That is being visible. The disagreement is the proof you said something real. The founders and operators who matter are drawn to people with a spine, not people optimizing for zero objections. Conviction is the most undervalued asset in a feed full of people trying not to offend anyone.

If you’re worried everyone will agree with you, you’re not saying anything yet.

4. Make decisions fast, with the risk in full view

I once worked closely with someone who told me, repeatedly, that he was blunt. That he was direct. That he genuinely didn’t care what people thought of him. It was part of his whole identity.

He cared enormously. He cared what I thought of him, what working with him felt like for me, what I walked away carrying. The performance of not caring was covering for the fact that he couldn’t sit with an honest read of himself, and a person who can’t be honest about themselves cannot make a clean decision. They flinch. They delay. They reframe the hard call until it becomes someone else’s to make.

Deciding fast isn’t recklessness. It’s the ability to look directly at the risk, name it, accept that you might be wrong, and move anyway. Most people who look indecisive aren’t weighing options. They’re avoiding the discomfort of being accountable for the outcome.

Speed comes from being willing to own the result either way.

And here’s the part I’ll say plainly. Your own version of the truth matters. If someone holds an unflattering view of me, and it’s their honest experience, I can respect that. I don’t need everyone to be flattered to feel solid. What I can’t respect is the person who hides their truth and calls it kindness. Decide from what’s real, including the parts about yourself you’d rather not look at.

5. Hold yourself accountable and work fucking hard

There’s no version of this list where this point gets dressed up.

Nobody is coming to make you do the work. The autonomy that makes founding intoxicating is the same autonomy that lets you quietly underperform for months with no one to answer to. You set the bar, you clear the bar, you decide if you’re lying to yourself about where the bar is. That’s the whole job when no one’s watching, which is most of the time.

I don’t trust the founders who talk more about balance than output, at least not in the years that decide whether the thing lives. There’s time for sustainable later. Early, the work is the moat. The accountability is the moat. Everyone wants the result. Very few want to be the person who holds themselves to it on the days nobody would notice if they didn’t.

6. Know who to listen to, and who to cut off

These two are the same muscle, so I’m treating them as one.

I stopped taking advice from people I wouldn’t want to become.

That’s the filter. Not how confident they sound, not how much they’ve technically achieved. Would I trade my life for theirs? If no, why am I weighting their opinion on how I should live mine? Advice always carries the shape of the life that produced it. Take direction from people whose life you’d actually want.

The harder half is cutting off. I don’t give people a second chance to disrespect me, and I know how that sounds.

We’ve all been trained to extend grace, to assume they didn’t mean it, to forgive on the theory that everyone deserves another shot. I think that’s how good people get walked over repeatedly by the same person.

When someone shows you who they are, believe them. The first time. Not the third, after you’ve spent eighteen months building a case you already had in the opening scene. People reveal themselves early and then spend a long time hoping you weren’t paying attention. Pay attention. Believe what you saw. Then protect your orbit like it’s the asset it is, because who you let close to you is who you slowly become.

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None of this is a guarantee. I’ll say it one more time because the whole piece rests on it.

You can do all six and still not make it. But I’ve never seen someone build anything that lasts while avoiding them. The avoiding doesn’t announce itself. It looks like patience, like grace, like balance, like keeping the peace. It’s mostly just fear wearing better clothes.

Do the uncomfortable version. It’s the only one that compounds.

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I’m Christine. Former Chief People Officer, current founder. I run 5 to 9 Society, a private community for founders and operators. We are built for builders. If this resonated with you, you’re probably a leader who needs a community like ours.