Somewhere around month six or seven, sellers start saying some version of the same thing. Not that they regret selling. Not that the price is wrong. Just that they're tired. Tired of the document requests. Tired of the calls that could have been an email. Tired of a process that was supposed to take four months and is now closing in on eleven.
That exhaustion is real, and it deserves to be named honestly instead of waved away. It's also, if left unexamined, one of the more expensive things that can happen in a deal.
Fatigue Is Not the Same as Doubt
This is the distinction that gets lost. An owner who felt certain at signing, genuinely certain, can still find themselves short-tempered, distracted, and just wanting the whole thing to be over by the time closing gets close. That's not the deal going bad. That's not cold feet. It's the natural cost of running a business full time while also running a second, invisible job: answering diligence requests, reviewing redlines, and staying available for a buyer's team that has all the time in the world because it isn't their company on the line.
The adrenaline that carries an owner through the LOI and through signing doesn't last eleven months. It isn't supposed to. What replaces it is a long, flat stretch of waiting and paperwork, and that stretch is exactly where the risk lives, as we wrote about last week in the signing-to-close gap.
What Fatigue Actually Looks Like
It rarely shows up as a feeling anyone announces. It shows up as behavior. Signing off on a document request without reading it closely because reading it closely for the tenth time feels unbearable. Agreeing to a buyer ask on a call, on the spot, without running it by an advisor first, because looping in the advisor feels like one more step in a process that already has too many. Letting a point that would have been worth fighting for in month two quietly go in month nine, not because it stopped mattering, but because the fight itself is what's exhausting now.
None of this looks like weakness from the inside. It looks like efficiency. It looks like finally, finally making progress. That's what makes it dangerous.
Buyers Don't Need to Exploit It to Benefit From It
Most buyers aren't running a strategy to wear a seller down. They don't have to. A worn-down seller is simply easier to close with on the buyer's terms, and buyers who have done several of these deals know that time is on their side by default. The longer the process runs, the more the balance tips, not because anyone engineered it that way, but because fatigue does that work on its own.
This is exactly why the sellers who protect themselves best aren't the ones who never get tired. They're the ones who stay engaged, especially with their advisors, at the moment they least feel like it.
Why the Last Concession Costs More Than the First
A concession made early in a deal is made from a position of leverage and perspective. The seller still has options, still has energy to negotiate, and is weighing the point on its merits. A concession made in week ten, by contrast, is usually made from a position of neither. It doesn't just cost whatever that one point was worth. It tends to compound, because giving on one thing late in a deal makes the next ask easier to make and harder to refuse. The first concession is a negotiation. The last one is often just relief.
How to Catch It in Yourself
The fix is almost embarrassingly simple, and that's exactly why it gets skipped. Say it out loud. Tell an advisor, tell a partner, tell whoever is in the deal with you: I'm exhausted, and I don't trust my own judgment on this point right now. Naming the fatigue is often enough to stop it from quietly making decisions on your behalf.
The owners who move through this stretch cleanly aren't the ones with more stamina than everyone else. They're the ones who recognize the moment they're running low, and lean on their team harder, not less, exactly when it would be easiest to stop.
Enterprise Value Includes This, Too
Protecting enterprise value doesn't stop being the job once a deal is signed, and it isn't only a matter of watching the working capital calculation or chasing down consents. Staying engaged with a seller through the long, unglamorous, exhausting middle of a deal, especially the part where nothing feels like it's happening, is part of the same work. It's less visible than the readiness work done before a process launches, but it protects the same number.