Going into this project, I expected to write a story about loss.
When you’ve spent fifteen, twenty, or thirty years building a business, the assumption is that selling will hit hard. You lose the identity, the adrenaline, and the daily rhythm all at once. I thought I’d be hearing from founders about how they grieved their companies.
That’s not what I heard.
I sat down with five owners who’ve sold in the last two to five years:
- Mike, who exited his family’s auto repair business earlier in his career than most owners do
- Karen, who built and sold a small neighborhood restaurant with her husband as a planned five-year venture
- David, the founder of a professional services firm he’d led for decades
- Steve, the longtime owner of a regional contracting business
- Linda, co-owner of a specialty commercial packaging company with a small but deeply tenured production team
These owners ran very different businesses, but the pattern in their reflections was nearly identical.
None of them regret selling. Not one. What they regret is what they didn’t prepare for: the deal structure they signed without fully understanding, the taxes they didn’t proactively model, the undocumented details that got fuzzy two years later, the advisors they pulled in too late.
If you’re an owner one to three years out from a sale, the most useful thing we can offer you is what these five wish someone had told them.
The weight you didn’t know you were carrying
One of the founders, David, said something I’ve been thinking about ever since.
“It was about nine months after the sale,” he told me, “that I said to my wife, the weight is gone. I’m not waking up at night anymore. I didn’t realize how much I was carrying, because I’d carried it for so long that it was just second nature.”
That theme of relief and decompression came up in most of the interviews. One owner’s spouse reported that his blood sugar improved with no change in diet, just a reduction in stress. Another founder’s wife had been telling him for years, “You’re here, but your brain is always somewhere else.” After the sale, his brain came home.
If you’re an owner reading this, you may be underestimating the same thing. The chronic load you’ve adapted to (payroll, culture, key-employee risk, tax surprises) only becomes visible once you set it down.
Most of these founders didn’t grieve the business. They grieved how long they’d been that tired without noticing.
For several of them, faith played a quiet role here too. Knowing their identity wasn’t tied to the company made stepping away feel less like an identity crisis and more like a season change.
Where the real regrets live
This is the section I’d most want a future seller to read carefully.
David: the earnout that left him with no voice. David’s biggest regret was the structure of the deal, not the decision to sell. He signed a two-thirds guaranteed, one-third earnout, assuming he’d stay involved and shape the next chapter. The reality was different. The new owners wanted to run the business their way. He watched decisions get made that he never would have made, with no voice and no leverage. “I would have left money on the table to have it guaranteed,” he said. “I would never, ever have entered that deal again.”
He also got blindsided by imputed interest on the earnout, a tax liability his CPA hadn’t flagged in advance. By the time he learned about it, the letter of intent was already signed. “Nobody told me the structure was a mistake. I just didn’t know what I didn’t know.”
Steve: the details that lived in his head. Steve described a different version of the same problem. The handshake-level details he didn’t bother documenting (a ninety-day labor commitment with no expiration date, miscellaneous tools and equipment, a state insurance refund schedule) became friction points years later. “Some of this stuff was in my head,” he said. “Not as easy for someone else to walk into when a lot of details live in one person’s head.”
Linda: the leaseback that ran too long. Linda signed a ten-year leaseback on her former building. The buyer moved out earlier than expected, leaving her with a costly buyout of the remaining lease. “I wish we’d limited it to five.”
The pattern is consistent. The decision to sell was right. The mechanics of the sale were where the money and the stress leaked out.
The buyer matters more than the price
Steve: lower price, lasting relationship. Steve’s deal came in below market on price. He half-financed it himself at favorable terms so his buyers, people he knew and trusted from his broader community, could afford it. Years later, he and his wife are still close with them, and the business is healthier than ever.
Karen: the slower deal that was the right one. Karen and her husband sold their restaurant to people they trusted, on a timeline they trusted. They had a slightly higher offer that would have stretched the process by another six months. They passed. They still have dinner with old regulars.
Linda: an unexpected buyer who honored the people. Linda’s buyer was a community-rooted organization with a multigenerational planning horizon and a culture-first mindset. They kept her people, raised compensation, and improved benefits. “We cannot imagine a more ideal outcome.”
When an owner felt at peace afterward, the buyer wasn’t the highest bidder. They were the right fit for the people, the culture, and the next chapter of the business. The owners who optimized hardest for headline price had the most regret.
Is your exit plan truly tax-smart?
The “what’s next” question is the real predictor
The single best predictor of post-sale contentment was whether the owner had a clear, energizing next chapter already in view.
Mike: two next chapters already in motion. Mike already had two things waiting before he exited: a new venture and a coaching role he was passionate about. He never went through a regret window.
Linda: the question her advisor kept asking. Linda’s wealth advisor had been asking, for years before the sale, “What does it look like on the other side?” That question forced her to picture life beyond the business well before she had to live it.
David: no regret, but a slower transition. David misses the visionary work of being a founder, the rallying-the-team energy. He has no regrets about selling, but he’s still finding the right outlets for that part of who he is. The transition would have been smoother if he’d named the next chapter before signing the letter of understanding.
If you can’t yet picture what you’d love about life on the other side, you’re not ready to be at peace with it.
If you’re one to three years out
Based on what these five owners would tell their younger selves, here’s where to invest your preparation:
- Build the advisor team early. You need a CPA who’ll model the tax implications of structure choices a year in advance, not just process your return. You need a wealth partner who can back into the number you actually need. And you need an attorney who executes your strategy rather than negotiating it. Bring them together before the letter of intent, not after.
- Pressure-test the structure before the lawyers do. Sit down with the buyer in the honeymoon stage and hammer out the messy details together: earnouts, leasebacks, transition labor, undocumented commitments. Save the legal fees for execution.
- Clean the operational house. Books, inventory, customer lists, key-person dependencies. If important details live only in your head, you’re either lowering your value or storing up future friction.
- Develop your internal leadership team. Several owners said this was their single best pre-sale move. It strengthens the business and widens the range of buyers who can make sense of the deal.
- Picture life on the other side in detail. Test it with someone who knows you well. If you can’t see it, you’re not done planning.
A last thought
If there’s one sentence to take from these five owners, it’s this: they don’t regret selling. They regret what they didn’t prepare for.
The good news is that most of those regrets are preventable. It starts with the right team and enough lead time to ask hard questions about the structure.
If you’re somewhere on that one-to-three-year runway, this is exactly the work we love walking alongside owners through. The decisions you make now will shape what life on the other side actually feels like.
Would you like to map your runway together? Let us know. We’d be glad to start that conversation.
Related Reading
- Life After the Business: Setting Intentions for the Next Chapter Five clarity questions for shaping the next chapter, whether a sale is in view or not.
- Setting Your Retirement Finish Line How to define “enough” before you get there, beyond the dollar amount.
- What Would You Do If Every Day Was a Saturday? On the void that freedom can create without a clear sense of purpose.
- 4 Parts of a Joy-Filled Retirement “Life Portfolio” A simple framework for where to invest your energy after the business.
Craig Hamilton
Strategic Advisor
About the Author
With over 30 years of experience as a Certified Financial Planner, Craig Hamilton joins Alterra as a sort of paternal figure and has a position of respected “special counsel” to the firm. This role is likely familiar to Craig as one of his four children is also a financial advisor. Mr. Hamilton is also a Certified Public Accountant with a degree in Business from Pacific Lutheran University in Tacoma, where he graduated magna cum laude.
Craig was born and raised in the Pacific NW and built a family here that now includes twelve grandchildren. In Craig’s words, “coaching, counseling, and mentoring are in my DNA.” This approach also characterized Craig’s financial career for 20-plus years as an Investment Officer for Russell Investment Services and their later incarnation as The Threshold Group. Throughout that time, Craig approached financial planning as “a critical tool to manage financial priorities and achieve a client’s dreams,” a philosophy perfectly aligned with the Alterra approach.
Craig took an early interest in all things financial, purchasing his first security while still in elementary school. Given his history, it’s not surprising multi-generation investing and legacy planning are his special interest. Listening to the stories of his clients and then helping them along the path to their goals brings Craig personal joy. So, it will likely come as no surprise that Craig was also a college tennis coach for over 20 years. As Craig says, “coaching, counseling, and mentoring are assets” that he will invest in Alterra Advisors.
The “Alterra” name was coined by joining the Latin roots “alter”, the origin of the word “altruism” with “terra” meaning earth or land. This name reflects the company philosophy of “clients before profits” and providing firmly grounded advice.
