The floorboards in the office didn’t always groan like this. Or maybe they did, and I was just too busy 4 years ago to notice the discordance. My hand shakes slightly as I reach for the mouse, a micro-tremor that signals the nervous system has finally decided to stage a coup. I missed the bus this morning by exactly 14 seconds. I watched the taillights fade into the grey drizzle, and for a moment, I considered just standing there until the next one came, or until the sidewalk reclaimed me. That’s the vibration of burnout-not a fire, but a slow, damp rot that makes you want to sell the world just to stop hearing the noise. You think that if you could just sign a piece of paper and hand over the keys, the noise would stop. You are wrong.
I’ve watched founders walk into a conference room with the thousand-yard stare of a soldier who’s been in the trenches for 154 days straight. They think the exit is a door. It isn’t. It’s a gauntlet.
When you decide to sell your business because you are ‘done,’ you are effectively deciding to run a marathon with the flu. The process of selling a company-the real, gritty, deep-dive process-requires more emotional intelligence and raw stamina than the day-to-day operations you’re currently failing to manage. You are at your weakest point precisely when you need to be at your strongest, and the market knows it. It smells the exhaustion like blood in the water.
The Lighthouse Keeper’s Warning
“The land looks like a pillow when you’ve been awake for 44 hours. But the land is where the rocks are. If you hit the beach because you’re tired, you don’t find rest. You find a wreck.”
I’ve watched clients like Marcus operate in the logistics space. He had built a revenue beast over 14 years. By the end, he was drinking 14 cups of coffee a day and forgetting his children’s middle names. He wanted the ‘quick, clean close.’ That phrase is a death knell in M&A. When a buyer hears ‘quick and clean,’ they translate it to ‘vulnerable and desperate.’
Lower Offer Accepted
Discount Paid
But Marcus was so tired he saw the signature line as a lifeline. He signed it. He didn’t buy freedom; he bought a new kind of prison at a 44% discount.
/ / / / / / / / / /
[The relief of the signature is a ghost that disappears before the ink dries.]
/ / / / / / / / / /
The Soul Exam (Due Diligence)
What most owners fail to realize is that the due diligence phase is essentially a proctology exam for your soul. It takes an average of 144 days to close a mid-market deal, and every one of those days is filled with questions that challenge your integrity, your competence, and your legacy. If you are already burned out, you will crack. You will snap at a junior analyst over a missing 1094-C form. You will concede on crucial indemnification clauses just to get the meeting over with.
Decision Bankruptcy
You will find yourself agreeing to holdbacks and escrows that you’ll never actually see, just because the light at the end of the tunnel looks like a way out. But it’s usually just an oncoming train.
I made this mistake once, in a smaller way. I was so eager to finish a project 4 years ago that I ignored a glaring red flag in the contract-a tiny clause about recurring liability. I just wanted to go home and sleep for 44 hours. That one moment of ‘exhaustion-based compliance’ cost me 14 months of legal headaches later. I was trying to buy a moment of peace, but I was paying for it with my future tranquility.
The Buffer Zone: Strategic Distance
This is where the structure of support becomes vital. When you are operating from a place of depletion, your perspective is warped. You see the buyer as a savior rather than an adversary. You see the paperwork as a chore rather than a weapon. You need a buffer.
You need someone whose nervous system isn’t fried to stand between you and the wolves. This is precisely why engaging with
is less about the technicalities of the ledger-though those matter-and more about having a steady hand on the tiller when yours is shaking. They act as the lighthouse, much like Emerson A.-M., marking the rocks so you don’t have to guess where they are through the fog of your own fatigue.
If you are energized, you fight those chips with data and posture. If you are burned out, you accept them as the ‘cost of doing business.’ You are literally paying hundreds of thousands of dollars to avoid a few more weeks of discomfort. It’s the ultimate bad trade.
Paying the Price of the Process
I think back to that bus I missed this morning. If I had sprinted, I might have caught it. But I would have arrived at my destination sweaty, panting, and unable to focus. Instead, I stood in the rain for 14 minutes. I let the frustration wash over me and then settle. I realized that my desire to catch the bus was actually just a desire to be ‘finished’ with the commute.
But the commute is the price of the destination. If you aren’t willing to pay the price of the process, you don’t deserve the result.
Selling a business is the most significant financial event of your life. It is the culmination of every 14-hour workday and every 4:00 AM panic attack you’ve ever had. To throw it away in a fit of exhaustion is an insult to your past self.
“You have to love the light even when you hate the tower.”
You might hate your office right now. But don’t let that hatred drive you to the first ‘quick’ exit you find. The exit is not an escape hatch; it is a transition that requires every ounce of focus you have left. If you don’t have it, find someone who does. Find someone who can carry the fire for you until the deal is actually done. Because the only thing worse than being burned out at work is being burned out, broke, and full of regret because you sold your soul for a discount.
The Final Trade-Off
We often seek a single event to solve a systemic problem. We think the ‘Sale’ will fix the ‘Burnout.’ But the burnout is internal; the sale is external. If you don’t fix the internal state before you engage in the external transaction, you will simply carry your exhaustion into a much poorer retirement.
You’ll sit on a beach somewhere, staring at the waves, thinking about the 44% you left on the table because you were too tired to say ‘no.’ The ocean isn’t quiet, and neither is a mind filled with regret. Stand your ground, find your advisors, and don’t mistake the first light you see for the end of the tunnel. It might just be the fire you’re trying to outrun.