Sometimes It's Supposed to Hurt

I made the right call and drove home in silence.

Not the good kind of silence. The kind where you don't turn the radio on because you can't stand the idea of a song having an opinion about your day.

I had let someone go. It was the correct decision. I had the documentation, the conversations, the months of runway, the second chances that were real second chances and not a paper trail dressed up as mercy. My boss agreed. HR agreed. Every version of the math I ran came out the same.

And it felt terrible.

For a long time I thought that meant I'd done it wrong. That if I'd been a better leader — more skilled, more prepared, more something — I would have found the version where the right thing also felt right. I went looking for that version for years.

It doesn't exist.

Here's what nobody tells you when they hand you people to lead: we've been sold a story that a right decision should feel good, or at minimum, not hurt. It's a lovely story. It is also completely false. Some right decisions feel wrong the whole way through. Some decisions have no option that feels good — you're choosing between kinds of damage. And some decisions feel great and still don't work out, which is its own particular insult.

I'm an engineer by training. I want the world to behave like an equation. Do the math right, and the answer lands where it's supposed to land. Check your work, and the check confirms you.

But in leadership, some of your variables are people. And that X does not sit still. It wanders off the page. It looks like an X, it usually acts like an X, and then on a Tuesday in March it behaves a lot more like a Q. You can solve the equation perfectly and still not recognize the answer.

So the feedback loop breaks. The feeling stops being evidence. And if you've built your whole career on the idea that discomfort means you've made an error, you will start doing something dangerous — you will start making decisions designed to feel good instead of decisions designed to be right.

I've watched it happen. The manager who won't put someone on a PIP because the conversation is awful, so instead they let the person keep failing publicly for another eight months. The leader who softens a layoff message into fog because clarity feels cruel, and now forty people are decoding a memo instead of grieving and planning. The executive who avoids the hard reorg because the last one hurt, so the whole team carries a broken structure for two more years.

None of that was kindness. That was a leader managing their own discomfort and charging the team for it.

The hurt isn't a sign you did it wrong. The hurt is the receipt for having done something that mattered to a human being.

That's the reframe that let me stop looking for the painless version. When it hurts, it's because a person's life changed and I was the one holding the pen. It should cost me something. If it cost me nothing, I would have to ask what happened to me.

And that's the actual line I watch for now — in myself, and in every leader I coach.

The day it stops hurting is the day to pay attention. Not the day it gets easier — easier is fine, easier is skill, easier is knowing how to sit in a room with someone's worst afternoon and not flinch. That's competence, and you should want it.

But the day you feel nothing? The day you deliver it flat, move to the next meeting, and notice at 6 p.m. that you never thought about them again? Or worse — the day there's a small flicker of satisfaction, a little well, they had it coming?

That's the day to stop leading people.

Because the pain is the part of you that still knows the stakes. It's not weakness leaking through your professionalism. It's the last honest instrument you've got.

So if you are sitting with a decision right now that is correct and awful — the PIP you keep rescheduling, the conversation you've rehearsed nineteen times, the name on a list you wish wasn't yours to sign — I want you to hear this from someone who has done it and drove home in silence afterward:

You're not doing it wrong. You're doing it awake.

Make the call. Let it cost you. Then let it teach you something the easy decisions never could.

I write every Tuesday for leaders who were handed a title and not much else — honest, unpolished, from inside the actual job. If this one landed, come get the rest. Subscribe to the newsletter or work with me if you're carrying a decision you'd rather not carry alone.