I’m currently rubbing my left shoulder with a grimace that probably looks like a snarl to the person sitting across from me. I slept on my arm entirely the wrong way last night, pinned under the weight of a restless mind, and now my entire trapezious is screaming. It’s a sharp, persistent reminder that some things just don’t fit where they used to. This physical kink is a perfect, if painful, metaphor for what I’m watching unfold in this glass-walled conference room on the 43rd floor.

I’m sitting in on a strategy session for a company I helped exit just 13 weeks ago. The founder, a man who spent 23 years building this empire from a garage with nothing but a soldering iron and a staggering amount of caffeine, is sitting three chairs down from the head of the table. He is currently an ‘advisor.’ That’s the title they gave him to soften the blow of the check. But as I watch the new CEO-a thirty-something with a very expensive haircut and a penchant for the word ‘optimization’-systematically dismantle the founder’s core culture, I can see the founder’s jaw tightening. He looks exactly how my shoulder feels: misplaced, cramped, and pulsing with a dull ache that won’t go away.

We tell ourselves the lie of the ‘smooth transition’ because it makes the bank feel better about the loan and it makes the buyer feel better about the risk. We think that by staying on for a year, or 23 months, or whatever the earn-out period dictates, we are protecting our legacy. We think we are the bridge. The reality? We are usually just the toll booth that everyone is trying to drive through as fast as possible.

I remember talking to Marie G. about this. Marie isn’t a corporate shark; she’s a wildlife corridor planner. Her entire career is spent figuring out how to let grizzly bears and elk move through human-occupied landscapes without getting hit by a semi-truck or stuck in a fence. We were sitting in a small cafe in a town with a population of about 943, and she told me that the hardest part of her job isn’t the science-it’s the geography of habits. ‘Animals have memory paths,’ she said, gesturing with a fork. ‘If you put a bridge where they don’t want to go, they won’t use it. And if you stand in the middle of their old path, even if you think you’re helping, they’ll either gore you or starve.’

Marie G. understood the physics of migration better than most M&A attorneys I’ve met. When you sell your business, you are migrating. You are moving from ‘Owner’ to ‘Former Owner.’ Attempting to inhabit the space in between-the ‘Advisor’-is like standing in the middle of that wildlife corridor. You are the obstacle. You are the person who remembers why we used to do things the old way, and the new team? They don’t care about the ‘why.’ They only care about the ‘next.’

It’s a brutal realization. You walk into the breakroom and realize they’ve changed the coffee brand. It’s a small thing, a $13 change in the monthly budget, but it feels like a personal insult. You see the 43 employees you hired, people whose kids’ names you know, looking at the new boss for permission to breathe. You want to jump in. You want to say, ‘No, Sarah doesn’t work well under that kind of pressure, you have to approach her differently.’ But you shouldn’t. You can’t. You are a ghost. And there is nothing more frustrating than a ghost who still thinks he has a vote.

I’ve made this mistake myself. Years ago, I stayed on for a 12-month transition after a divestiture. I thought I was being noble. I thought I was ensuring the ship didn’t hit an iceberg. By month 3, I realized I was the iceberg. My presence made it impossible for the new lead to establish authority. Every time a problem arose, the staff looked at me, and I, in my infinite ego, gave them the answer. I was undermining the very leadership I was supposed to be supporting. I was the kink in the neck of the organization.

This is where most deal structures fail. They focus so heavily on the multiples and the EBITDA that they forget the psychological gravity of the ‘Stay-Behind.’ A buyer wants you there because they are scared of what they don’t know. They want you as an insurance policy. But insurance is meant to be tucked away in a drawer, not sitting in the corner office questioning the new marketing spend.

If you find yourself in this position, or if you’re staring at a Letter of Intent that requires a long-term residency, you have to ask yourself: are you actually helping, or are you just afraid of the silence that comes after the sale? The silence is where the real work of the next chapter happens. When I look at how

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approaches these moments, there’s a distinct focus on the post-sale reality. It’s not just about getting the highest number on the page; it’s about ensuring the person behind the number actually survives the transition. They understand that a clean break is often more merciful than a slow amputation.

In Marie G.’s world, if a corridor is designed correctly, the animal moves through it without ever realizing a human was involved. The transition is invisible. In the business world, we should aim for the same. If you’ve built a truly great company, it should be able to survive your absence. If it can’t, then you haven’t built a company; you’ve built a very complex job for yourself.

I watched the founder in the meeting today finally stand up. He didn’t offer a counter-argument to the ‘optimization’ plan. He just picked up his jacket and said he had a 2:03 PM tee time. He walked out. The room felt lighter the moment the door clicked shut. It wasn’t that they didn’t respect him; it was that they could finally start being whatever they were going to become next. They could finally stop looking at the past for permission.

There is a specific kind of grief in that. It’s the grief of realizing the world keeps spinning when you stop pushing it. But there is also a massive, soul-level relief. You don’t have to carry the 43 lives on your back anymore. You don’t have to worry about the 13% dip in Q3 projections. You can just go be a person.

But we fight it. We fight it because we’ve tied our identity to the struggle. We think if we aren’t the one solving the $733k problem, then we aren’t anyone at all. We stay on to prove we’re still needed, only to find out that being needed is often just another word for being stuck.

I’ve seen earn-outs that lasted 33 months turn the most successful people I know into bitter, cynical shells of themselves. They spend three years fighting over things that don’t matter because they can’t handle the fact that they are no longer the protagonist of this particular story. It’s a waste of a good exit.

If you’re going to stay, stay for a specific, narrow purpose. Be the ‘In Case of Emergency’ glass box. Do not be the daily operator. Do not have a desk in the main flow of traffic. In fact, don’t have a desk at all. Work from a coffee shop three blocks away and only come in when there is a specific, technical question that only you can answer. Even then, answer it and leave.

Marie G. told me once that the best corridors are the ones that provide cover. Animals need to feel safe while they move. As a seller, your job in the transition is to provide cover for the new owner while they find their footing-not to stand in the clearing and roar.

My shoulder is still throbbing. I should have moved hours ago, but I stayed in this chair, stuck in a position that wasn’t working. It’s funny how we do that. We stay in the pain because we’re used to the shape of it. We stay in the office because we’re used to the weight of the responsibility.

But the check is in the bank. The 43 people are still getting paid. The corridors are open. The best thing you can do for the legacy you spent 23 years building is to get out of its way. Let it change. Let it become something you don’t recognize. That’s the ultimate proof that you built something that actually matters.

If you’re currently looking at a deal and the ‘Stay-Behind’ clause feels like a noose, trust that instinct. It’s not just nerves; it’s the realization that you’re trying to be two versions of yourself at the same time. You’re trying to be the hunter and the retired observer simultaneously. The woods aren’t big enough for both.

What happens to the company now? That’s not your story anymore. And honestly? That’s the most beautiful part of the whole thing.