Sell for the right reason, or the right price is still the wrong sale
The reason you sell decides whether any price ever feels like enough. Reasons that pass the six-month test are durable: health, a next chapter that pulls rather than pushes, a successor who is ready. Reasons that fail it (a bad quarter, a tired week, somebody else’s exit) produce sales that money cannot make right.
Here is the uncomfortable part, first: some owners get every bit of the number they asked for and still regret the sale. Not because the deal was bad. Because the reason was. The price is what you negotiate over a few months. The reason is what you live with for the rest of your life, and no number, however handsome, can fix a reason that was never really yours.
Almost everything written about selling assumes the decision is already made and hurries on to the mechanics. We want to sit with the part that comes before, because, across the businesses we have served and run, the reason for selling governs whether any price will ever feel like enough. An owner with a settled reason walks away whole at a fair number. An owner with a borrowed or passing reason walks away restless at any number. Same deal, different afters.
The reasons that pass, and the reasons that hold
Most wrong-reason sales trace back to one of four moments, and every one of them arrives with real feeling attached, which is exactly why they are dangerous. A burnout spike: the worst six weeks of the year speaking on behalf of all the others. One bad quarter: a problem that wanted fixing, answered instead with an ending. A neighbor's sale: someone at church or up the street sold well, and suddenly staying feels like losing. And the flattering phone call: an unsolicited buyer says your business is exactly what they've been looking for, and the timetable quietly becomes theirs. Each of these can start a process. None of them can carry an owner through the after.
The reasons that hold are quieter and older. The energy is truly spent: not a hard season, but a flatness that has persisted through good months as well as bad ones. The next chapter is real: something with a shape you are walking toward, not just this thing you are walking away from. Health, yours or your family's, sets a date, and it is the most honest reason there is. Or there is no successor, you have looked properly, and you have no wish to spend five years building one. Notice what these have in common: they were true last year, and they will be true next year. They do not depend on the mood of the month.
One of the four deserves an extra word, because it is the one owners most often lose to: the flattering phone call. It works because it is true: your business probably is attractive, and the caller probably has done their homework. But notice what the call quietly changes. Yesterday you had no timetable; today you have theirs. Yesterday the question was “should I do anything at all?”; today it has become “should I take this?”, a much smaller question, asked on someone else’s schedule. A serious buyer will still be serious after you have taken the time to find your own reason. We know, because we make calls like that ourselves, and the owners who make us wait are the ones we end up respecting most.
- Today
- A number has appeared (from a caller, a neighbour’s exit, one brutal season) and it is doing your thinking for you.
- The gap
- A price can be right while the sale is wrong; the regret owners report almost never tracks the number.
- What’s possible
- A reason that has held for six months, written down, examined out loud with the people it affects.
- The first move
- Date-stamp your reason today. Read it again in six months, before anything is signed.
The six-month test
You do not need a professional to sort your reason. You need a piece of paper and a little honesty about time. Write the reason down in one plain sentence: “I am selling because…” If it takes a paragraph, it is not yet a reason; it is a mood with paperwork. Then ask the sentence two questions about time, and one about company.
Was it true six months ago? A reason that only showed up after the brutal stretch, the bad quarter, or the phone call has not yet been tested by a single good season. And will it still be true six months from now, if the busy season goes well and the phone never rings again? A durable reason survives an imagined good year. A passing one quietly dissolves in it. Finally: would you say the sentence out loud, to your spouse and to your longest-serving employee? Reasons that hold tend to be sayable. Reasons that pass tend to hide behind “the market” and “the timing.”
An owner writes: “I am selling because last quarter was the worst I have had.” Six months on, the quarter is behind them, two good months have followed, and the sentence no longer reads true. Nothing was wrong with selling as an option. The reason simply had not been tested yet, and the test did what it was built to do.
What the regret actually tracks
Here is the pattern that stands out across the businesses we have served and run, and we offer it as our own judgment, not as a study with a footnote. The regret does not track the price. It tracks the quality of the reason. Owners who sold on a durable reason and got an ordinary number tend to be at peace; the reason keeps answering the quiet moments that money can't. Owners who sold on an impulsive reason and got a strong number tend to circle back to the decision for years, because the season that produced the reason passed, and the reason went with it, and the business did not come back. A strong price is a poor insurance policy against a weak reason, because the things that ache afterward were never priced in the first place. We wrote separately about that in the regret usually isn’t about the price, and the two pieces are really one argument in two halves.
If the reason fails the test
Then don’t sell. Not yet, and possibly not at all. A failed test is not a verdict on selling; it is a verdict on this month’s reason. Fix the bad quarter. Take the vacation the burnout is demanding. Let the neighbor enjoy their sale without it costing you your business. And if the flattering caller is real, they will still be interested in six months. A buyer who evaporates because you asked for time was never planning to be careful with what you built. Selling remains one of three honest answers to “what’s next,” alongside growing and holding, and we laid all three out evenly in the piece this whole cluster starts from. The right reason, when it comes, will not need to hurry you.
Heritage is a buyer. When your answer is “sell, now,” someone like us benefits, so a piece that tells you to wait six months looks noble, and you should not let it. Here is the plainer truth: a seller with a durable, settled reason is better for us. Right-reason sellers make cleaner handoffs, stand behind the transition, and don’t come back a year later wishing the deal undone in ways that hurt the business and the people in it. So our advice and our interest point the same direction on this page, which is rarer than it should be and worth knowing. Our record is what it is: our principals and partners have acquired and operated three businesses, with nothing beyond them to point to yet. And if your reason is simply “the biggest possible number, right now,” a patient holder like us is probably not even your best buyer, and we will say so.
Put the thinking to work
Our interest: A buyer benefits when your reason is urgent, and we are a buyer. That is precisely why the six-month test is worth running away from anyone’s table, including ours.
Where to go from here
Compare the decision, the ownership paths and what should carry forward.
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Capital considers acquisitions as a principal buyer; it does not represent a seller or broker a sale. Service work, The Read included, is a separate relationship: if we become interested in buying a business we are working with, we stop that work and tell the owner plainly before any purchase discussion begins. The Read is optional when a broader diagnostic would help. We agree scope, timing and fees before service work begins.
This article is educational. It is not individual legal, tax or investment advice, an offer or a promise of results. Your accountant, attorney, and family make every real decision with you.