The human transition of selling your business
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“I get a dozen calls every week from PE companies. I didn’t want to sell, but the calls wore me down. I thought, Okay, let’s see what they’ve got. And besides, three of my buddies sold in the last 16 months, so I know what’s going on. But I didn’t. I had no idea I could get that much money for my company. There was no way I could pass it up. So I hired a broker out of Kansas City. He got us more than I could have hoped for. Five months later, with no further obligations, I turned the keys in. Thirty-seven years, and then everything stopped — like one of those airport people movers on steroids. I stepped off completely disoriented and stumbled into a four-month stupor.”
From day one in business, Jess had run his company as if he were going to sell it. Everything was in meticulous order, everything that is, but himself. Jess was not psychologically ready to sell his company and move on.
Jess’s company was not just an asset; it was his purpose, heart, soul, and at its very core, who he was. And then there were his employees. How would the new company treat them? Would the culture he’d worked so hard to build just disappear? In essence, Jess parachuted into a mile-deep canyon of darkness.
During the five-month sale process, Jess and his wife Christy did have time to plan for one thing, a five-week European vacation. A home remodel project was next.
Although there were moments of temporary panic while in Europe, disorientation set in during the part of the home remodel that no longer required Jess’s carpentry skills.
Jess had acquaintances who sold their companies, and five years later, they were still traveling and engaging in other leisure activities. Nothing wrong with that, but he wasn’t wired that way.
What to make of a life
What to Make of a Life is Jim Collins’s latest book, and the title meets Jess at this pivotal intersection in his life.
Collins’s work in What to Make of a Life is relevant to the identity crisis many founders experience after selling their businesses because Collins is fundamentally asking a deeper question than financial success:
“What is a well-lived life after achievement?”
For many owners, the company became a:
- Structure
- Mission
- Identity
- Tribe
- Scoreboard
- Purpose
- Challenge
- Proof of Usefulness
- Rhythmic Routine
The sale removes all of that at once.
That is why some founders experience disorientation even after a successful exit. The problem is not money. The problem is the sudden absence of meaning, rhythm, and in-frame personal encodings.
Collins emphasizes that a single achievement does not define a life; rather, a continuing process of making meaning through commitment, curiosity, relationships, discipline, and contribution shapes it. He warns against drifting into passive comfort after major success because human beings are wired for engagement and growth. This ties directly into the founder’s transition.
A business owner who spent decades solving difficult problems, leading people, making decisions, building culture, and carrying responsibility often cannot simply “retire to leisure” without consequence. The founder may believe he wants freedom, but after the initial decompression period, he often discovers he still needs: Challenge, purpose, contribution and growth.
Collins’s concept of “cliffs” becomes especially powerful here.
Selling one’s company is a cliff.
A cliff interrupts the trajectory of life and forces choices. The owner stands at the edge of:
- Identity Reconstruction
- Relationship Shifts
- New Freedom
- Uncertainty
- Possibility
The question becomes: “What will I make of this next season?”
Not: “What will I do to stay busy?”
Collins pushes readers toward intentional construction of a meaningful life rather than passive consumption of comfort. For founders, that means the post-sale phase should not be framed as “escaping work,” but as designing the next arena for growth, contribution, and meaning.
That next arena may become:
- Mentoring younger entrepreneurs
- Teaching
- Coaching
- Philanthropy
- Writing
- Investing
- Board leadership
- Craftsmanship
- Exploration
- Family leadership
- Public service
- Spiritual development
- Mastering new disciplines
The important issue is not status.
It is an alignment between:
- Energy
- Curiosity
- Capability
- Values
- Contribution
- Meaning
- Growth
- Relationships
- Challenge
Collins also distinguishes between achievement and meaning. A founder may have built a highly successful company while postponing questions such as:
- Who am I outside the company?
- What relationships matter most?
- What kind of person do I want to become now?
- What gives me deep fulfillment beyond winning?
- What would make the next 30 years meaningful?
This is why many exits fail psychologically, even when they succeed financially.
The founder prepared for the transaction, but not for the human transition.
In many ways, What to Make of a Life reframes the post-exit chapter from “I sold my company,” to “I now have the opportunity — and responsibility — to design the second half of my life intentionally.”
That is a much bigger question than retirement.
In 10 years of research, Collins found no evidence that anyone lacked a cliff in their life. Consequently, this book applies to everyone.
What to Make of a Life is not a self-help book. It’s a self-knowledge book. You simply will not be able to not reflect upon your own lives as you read the case studies based on matched pairs of individuals (Collins used the matched-pair research technique in his seminal book “Good to Great” as well). Use Google or ChatGPT to find a synopsis/review of the book.
For a taste of What to Make of a Life, enter this prompt into your favorite Gen AI (I do favor ChatGPT for its answer) program:
Provide definitions for cliffs, encodings, in-frame, out-of-frame, the arrow of money, inner fire, fog and personal hedgehog as Jim Collins uses in his book What to Make of a Life. Also, provide two examples of each of these words that are not in the book.
Jess and his wife returned from Europe. A few weeks later, Jess found an online mastermind of other owners and former owners who were working through Collins’s book. He joined it, and it made a huge difference in his life.
Collins mentions that one of his best practical suggestions for making use of his book is to engage in conversations with others about it.
What to Make of a Life is my number one book recommendation for 2026.
This article was originally featured in the Summer 2026 edition of ACCA Now Magazine. ACCA members can read the full magazine at https://hvac-blog.acca.org/magazine/.
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Posted In: ACCA Now, Leadership Development
