You Can't Want It More Than They Do

Richard Bach wrote the line I keep coming back to on weeks like that. "Argue for your limitations, and sure enough they're yours." It shows up in Illusions, a small strange book I first read in my twenties and did not really understand until I had run a company long enough to watch smart people defend their ceilings in front of me.

The quote gets shared as a self-improvement line, and it works fine that way. That is not the version I need to write about. The version I need to write about is the other side of it, the one nobody puts on a coffee mug. When someone in front of you is fighting for their limitation, you cannot lift it off them. You can offer the door. You can name what you see. You can build the ramp, pay for the coaching, hold the seat open one more quarter. And they will still, calmly and often politely, choose to keep the limitation, because the limitation is doing a job for them that clarity would take away.

That is the part I had to learn the hard way, more than once, before it stuck.

The Shape It Takes At Work

At Alpine Security and again at Blue Goat Cyber, the pattern was almost always the same. I would see someone who I was sure had another gear. Sharper than their current output. Capable of running a team, or owning a client, or leading a technical track without being asked twice. I would tell them. I would give them the shot. I would set up the scaffolding, protect their calendar, and hand them the reps.

And about a third of the time, they would rise into it and it would be one of the best decisions I ever made as a founder.

The other two-thirds, they would take the title, keep the exact same behavior that had kept them at the previous level, and get quietly frustrated that the outcome did not follow. Then I would coach. Then I would coach harder. Then I would rewrite the role. Then I would eat the cost of my belief in them for another quarter, and another, until the math finally forced the decision I should have made when I first noticed the gap between what they said and what they did.

Every single time, in the exit conversation, they had a well-rehearsed reason it hadn't worked. The market. The team. The tooling. Me. Any explanation except the one that lived closest to home. I don't say that with contempt. I say it because I've done the same thing in my own life about my own limits, and the honest name for it is that a limitation, once you've built an identity around it, is expensive to put down. It has been paying rent for you for years. Losing it costs you the story of who you are.

My job was never to take that story away from them. My job was to stop paying for it on the company's dime.

Why We Try To Save Them Anyway

There is a specific flavor of leadership ego in wanting it more than they do. I've had all of it.

One flavor is genuine care. You like the person. You've had beers with them. You've met their kid. Ending the arrangement feels like betrayal, so you convince yourself one more month of effort will unlock the version of them you can see and they can't.

One flavor is self-image. You want to be the leader who develops people, the one nobody quits on, the one who saw potential where others didn't. Letting them fail feels like a failure of your own brand.

One flavor is sunk cost. You've already spent so much time trying that walking away means admitting the time was wasted. It usually already was, and the only variable left is how much more you're willing to add to the pile.

And one flavor, the ugliest and the truest, is that it feels good to be needed. If you can be the one who finally reaches them, that means something about you. That is not leadership. That is a rescue fantasy wearing a corporate title.

I have used the reframe framework I wrote about last week on exactly this feeling, more than once. The ugly sentence is always some version of: I am about to stop trying to save someone I promised myself I would help, and I feel like a bad leader for it. The truer sentence, once I actually sit with it, is that continuing to try is what would make me the bad leader, because I am now spending the company's runway and the person's own time to protect my self-image.

What The Ironman Version Taught Me

I've paced friends through hard miles in a lot of races. In an Ironman, you can run next to someone at mile 18 when their legs are gone and their head is louder than the crowd. You can hand them a gel. You can talk them through the next mile marker. You can absolutely change the shape of the last hours of their day.

You cannot run the last eight miles for them.

At some point they either take the next step or they sit down on the curb, and that decision is not yours. You can be as prepared, as loving, as experienced, as encouraging as you know how to be, and the finish line will still be exactly as far away for them as it is. The finish line does not negotiate with your effort on someone else's behalf.

Business is the same. Coaching is the same. Marriage is the same, and I say that carefully as someone who used to think the sheer force of my care could carry a relationship one person had already left. It couldn't. It never has. Wanting it more than the other person wants it is not love or leadership. It's a slow way of teaching yourself that your care doesn't count, when the real problem is that you were pouring it into a container that had a hole in the bottom.

What To Do Instead

I won't pretend I have a clean formula for this. I have habits I've earned by getting it wrong enough times.

First, I say the hard thing early, once, in plain language, and I check whether their behavior changes within a defined window. Not their words. Their behavior. Words are cheap in these conversations because everyone involved is trying to protect the relationship.

Second, I stop coaching effort and start coaching evidence. If the pattern hasn't moved in the window, another lecture from me won't move it either. The next move belongs to them, and my job is to hold the seat honestly, not to keep inventing new ways to nudge.

Third, I get honest about who I'm protecting when I hesitate. If the answer is "them," I check that against reality; usually the delay costs them more than the decision would. If the answer is "me," I name it and act anyway. The self-image protection is the tax I owe for having built the ego in the first place.

And fourth, when I do end it, I end it clean. Short. Warm where warmth is honest. No hedging, no over-explaining, no offer I can't stand behind. That is a lesson I keep having to relearn, and I wrote about the shape of one of those endings in an ending isn't a failure, it's time doing its job.

None of this is cold. It is the opposite. Cold is pretending to help someone while quietly resenting them for not becoming the person you decided they should be. Warm is telling them the truth, holding the door for who they actually are, and then respecting the choice they make, even when their choice is a smaller life than you would have picked for them.

The Part That Stays With Me

Bach's line is not really about limits. It's about ownership. If you argue for your ceiling, you own it. That's true of you. It's also true of the people you lead, the people you love, the people you try to help.

Which means the version of leadership I keep having to grow into is not the one where I rescue people from their limitations. It's the one where I offer them a door they can walk through, tell them what I see on the other side, and then, if they decide to stay in the room they're in, I close the door gently and go do my actual work.

I don't get that right every time. I am, on balance, less bad at it than I was ten years ago, mostly because I have paid the tuition of getting it wrong in public. If you're in one of those situations right now, and you can feel yourself trying to want it more than they do, that feeling is the signal. Not to try harder. To stop, look at what you're actually protecting, and decide whether the story you're carrying about them is still true or whether they have been telling you the real one for a while and you just haven't wanted to hear it.

You can love someone and still not save them. You can lead someone and still not carry them. You can be the most patient founder on the planet and still not talk a person out of a ceiling they've decided is theirs. The kindest thing you can do, once you know that, is stop pretending otherwise.