Hey, Will here,
About two years ago, I was playing golf with a buddy who'd just sold his business.
Thirty-plus years building one company. He'd been out of it for about a year by then. Sold it on his terms, walked away clean, without that look you see on most operators after they exit.
You know the one I'm talking about.
The look that says the money arrived, but the meaning never did.
He had something else in his eyes. Something I couldn't quite name. I spent the whole round trying to figure out what it was.
I didn't bring it up on the course. It didn't feel right. The question felt bigger than the game, and we were running out of holes anyway.
Two weeks later, we met for lunch. That's when I asked him.
"How did you know it was time?"
I expected the standard answer. The buyer came in at the right number. The market was hot. The kids weren't interested. Something external made the decision for him, and he just caught the wave at the right moment.
That's not what he told me.
He said, "I wrote down a dream ten years before I sold. Specific. Written. On paper. When the offer came, I asked myself one question — is the dream still bigger than my ego?"
He paused. The kind of pause where you can actually hear someone deciding how much of what they're thinking they're willing to say out loud.
"The day my ego got bigger than the dream, I would've stayed. The day the dream was still bigger... I left."
What I took from that — not his exact words, but what I heard underneath them — was that the dream only won by about six months.
Six months.
I've been thinking about that conversation since that lunch. I'm writing this now because I believe it's one of the most valuable things anyone's said to me in the last decade.
But not for the reason I originally thought.
At first, I thought he was showing me how to negotiate an exit on your own terms.
What he was really showing me was how to become one of the few operators who actually get the chance to negotiate at all.
📋 The 60-Second Read
Three things before your coffee goes cold:
✅ The pattern. Half of all business exits are involuntary. The Exit Planning Institute calls it the 5 D's: death, disability, divorce, disagreement, and distress. Of the operators who try to sell on their timeline, 70-80% never find a buyer. Most don't exit on their terms because they never reach the table.
✅ The principle. Your terms aren't a negotiation outcome. Their optionality is built years before the offer arrives. The work that creates the choice is invisible. Most operators never do it.
✅ The prompt. This week's exercise is The Dream Test — the page my friend wrote ten years before he sold. The page is the artifact. The page does the work.
Even if you close this right now, that's what matters this week.
🔍 The Dig
It took me about eighteen months to realize what my friend had actually told me. For some reason, I couldn’t see what he was saying. His dream versus his ego?
I thought he was in the lucky 25% — the operators who exit happy because they got their number. Most don't. The Exit Planning Institute has tracked this for over a decade: 75% report profound regret about their exit within 12 months. Not because the price was bad. Because nothing on the other side looked like they thought it would.
But that's just the visible part. The harder story sits underneath.
About 50% of operators don't choose how they leave at all.
The 5 D's: death, disability, divorce, disagreement, distress. Half of the exits are involuntary. The other half try to sell, and 70-80% of those listings never close.
Read that twice. My read of the math: out of every 100 operators who eventually leave, maybe 8 to 12 actually walk away with the deal they wanted, on the timing they chose, with options on what came next. The other 88 to 92 either exited because life forced it, listed and never sold, or watched a deal collapse during due diligence.
Most exit advice, the kind on every broker's blog and every CEPA's website, is written for operators who have already made it to the table. Pick the right buyer. Time in the market. Negotiate on your terms. All useful. All irrelevant for ninety percent of the people reading it. Because they're never going to sit down at that table.
What got my friend to the table wasn't a negotiation. It was a page in an old notebook.
He wrote his dream down ten years before he sold. Specific. On paper. Updated every couple of years. Was the dream still bigger than the ego? As long as the answer was yes, he stayed and built.
The day the answer was no, he was already prepared to leave. Not because he'd negotiated his exit terms, but because the work the page demanded over a decade was the same work that turned a high-functioning dependency system into a transferable business.
The page wasn't aspirational. It was strategic. Every line pointed to something specific he had to remove from his own desk. And everything he removed made the business worth more, work without him, and survive a 5 D he never wanted to need.
That's the whole insight. Dream-prep and exit-prep are the same prep. Most operators don't realize this until ten years too late.
Three types of operators. You're one of them.
🪨 THE DEFERRER. The dream was real once. Got buried under five expansion cycles, three near-exits, and the assumption that the right number would clarify everything. Most likely outcome: a 5 D. Or a listing that doesn't sell.
🛠 THE PROTECTOR. Knows the dream is in there somewhere. Hasn't written it down because writing it makes it accountable, and accountability would force decisions they're not ready to make. Most likely outcome: keeps building until something external forces the exit.
⚡ THE OPERATOR ON TERMS. Wrote the page. Updates it once a year. Built the business to match. Most likely outcome: gets to the table with options. May exit at the right number. May not exit at all. Either way, it's a choice.
✅ Deferrers and Protectors do the same work — they build the business. Operators on Terms do that work plus the dream work. The second job buys the option to choose.
💬 The Quote
You will get to the end one way or another……
🎬 The Move
Start the page.
Sit down. Single piece of paper. Write the answer to one question:
If I sold the business on Friday, what does my Tuesday look like in 18 months?
Specifics. Where you live. What you're working on. Who you're with. Whether you still need the alarm. Whether the work has a paycheck attached or something else — and what the something else actually is.
Not a vision board. Not a five-year plan. One Tuesday, eighteen months out, on one piece of paper.
If the page comes back blank or generic, that's information. The dream needs to be written before any of the operational work makes sense.
If the page fills up quickly, include additional information. Now consider the work between you and that Tuesday. Most of it isn't exit preparation; it's dependency cleanup. The two are essentially the same.
That's it. The page. Before Friday.
🎯 The Prompt
This week's Move starts the page. The Dream Test deepens it.
⏱ 90 seconds + a 10-minute interview · 📋 You need: a quiet hour · ✅ You get: a written page you can update yearly
I've been an business owner/operator for [X years]. I run a [type of
business] doing [revenue range]. I've been thinking about
exit timing — could be one year out, could be ten.
You're a thoughtful interviewer who has helped operators
write the page that holds their actual terms. Walk me
through 6–8 questions designed to extract:
- What I want my Tuesday at 11 AM to look like in 18 months
- What I'd refuse to give up in any deal, regardless of price
- What I need from the next phase that the business
currently provides (purpose, structure, identity, status,
the rhythm of decisions)
- What I'd want to be doing instead — with specificity, not
abstraction
- The number that's high enough to leave on, and the number
below which I'd stay even at a discount
After I answer, write back: the page itself, in plain
language, one page or less. Then list the operational work
between me and what's on the page — the dependencies I'd
need to remove, the people I'd need to develop, the systems
I'd need to encode — so I'd actually have the option to
leave when the page says go.
Don't be motivational. Don't soften. Read me back what I
told you, and tell me the work that earns it.The first read of the output is uncomfortable. That's the point — most operators have never seen their dream and their dependencies on the same page at the same time.
Run it before any conversation about exit, with anyone.
🎤 Open Mic
Three questions, pick one. Reply.
What's the first thing you wrote down when you pictured your Tuesday? One line.
Have you ever actually written your dream down on paper? Honest answer. Most haven't.
If a 5 D hit in the next ninety days — death, disability, divorce, disagreement, distress — does your business survive without you? Anonymous, if you need it to be.
I read every reply. The good ones end up in next week's Open Mic so other operators can see themselves in your answer.
— Will
P.S. The Dream Test is one of forty prompts in The Operator's Prompt Pack.
You won't find most of this stuff on a broker's blog or in some free PDF. These are the prompts a fractional COO uses with one operator at a time — I just sized them down so you can copy and paste.
The Strategy section has five more for the conversations you keep avoiding with yourself. The operators who exit on their terms? They started with a page. Ten years before they sold.
The first version of the page is free — start it tonight on a napkin if you want. The pack is for when you're ready to go deeper. Check it out here!
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