Every business owner leaves eventually, whether by sale, by succession, by stepping back, or by closing the doors, and most never design how they will go. A 2026 report from the McKinsey Institute for Economic Mobility finds that most small-business exits today end in closure rather than a sale. Bo Burlingham's interviews with owners who sold found that roughly half were content and half regretted it, and the difference had more to do with preparation than with price. Harvard Business Review research on succession finds the same pattern at board level, where the leader's own reluctance is one of the biggest barriers. This article lays out six ways an owner can leave, explains why the exit has to be designed while the business is still being built, and introduces The Succession Filter™, a three-part diagnostic (Ready, Right, Remains) for seeing your real options years before you need them.
Introduction
I have spent five decades building things, running them, and handing them over, and the handovers taught me more than the building did.
The end of your ownership is already part of the business you are building, whether you plan it or not. Every decision about who knows what, who decides what, and how much of the operation lives in your head is also a decision about how you will eventually leave.
Most owners treat the exit the way most of us treat writing a will. It is important and sensible, and it can wait. Then the day arrives on its own schedule, and the only option left is whichever one happens to be available that month.
This month we look at the exit while it is still a design question, starting with the simplest one: how many ways out have you actually considered?
Key Takeaways
• Every owner leaves, and most leave by whatever route is available when the day comes.
• Most owners have priced exactly one exit, a sale, and many have not priced even that.
• The research is consistent: owners who leave well start years early and know what they want before anyone makes an offer.
• The Succession Filter™ asks three questions in order: Ready, Right, and Remains.
• Preparing an exit also makes the business stronger if you never leave at all.
The Exit Nobody Plans
When owners picture leaving, they almost always picture a sale. A buyer appears, a number is agreed and the keys change hands. For most businesses, that is not how it ends.
The McKinsey Institute for Economic Mobility studied small-business ownership transitions in a 2026 report. As Fortune reported it, roughly six million small and mid-size businesses in the United States will face an ownership transition by 2035. Of small-business exits today, the report puts 92% as closures, 5% as sales and 3% as transfers to new owners. The coverage does not identify the dataset behind those percentages, so I treat them as a direction rather than a precise count. Read that cautiously, they still say the usual way a small business ends is that the doors close.
Plenty of those businesses had value. What they lacked was any arrangement for that value to outlast the person who created it.
Why Capable Owners Wait
If the exit matters this much, why do capable owners leave it to the last minute? The research gives the same answer at every scale.
Ani Huang, Anthony Nyberg and DJ Schepker studied chief executive succession for Harvard Business Review in 2025, using a survey of 49 public-company directors and 44 in-depth interviews with directors, investors and search consultants. One of the biggest barriers they found was the leader. Some chief executives avoid the subject because they are uncomfortable with retirement, worried about their legacy or afraid of losing control. Only 35% of the directors surveyed thought their board had enough time to finish the work.
Those are large public companies, with boards whose job includes forcing the conversation. Most owners have no board. The person most responsible for planning the exit is the person least comfortable starting it, and nobody sits across the table to insist.
Noam Wasserman described a related tension in "The Founder's Dilemma," a 2008 Harvard Business Review article. Founders, he found, tend to want both the value of what they build and control over it, and the two pull against each other. His research covered technology and life-science start-ups rather than owner-operated businesses, but his question travels well. If you have never decided which of the two matters more to you, every exit option will look wrong, because every option gives up some of one to get more of the other.
What Burlingham Found
Bo Burlingham spent years interviewing owners who had sold their companies and wrote up what he learned in Finish Big. By his account, roughly half were content with how their exit went and roughly half regretted it. In his reporting, price had less to do with which half they landed in than whether they had prepared.
He describes the exit in four stages:
1. Exploratory: learning what the options are, deciding what matters to you, and sketching how much you need and by when.
2. Strategic: building into the business the qualities that the successor or buyer you want would need to see.
3. Execution: doing the deal, whatever form it takes.
4. Transition: the period from closing until you are fully engaged in what comes next.
The deal comes third. Many owners, Burlingham observes, start at execution because an offer arrives or a deadline forces the issue, and so they skip the two stages that would have given them choices. He also points out that the preparation takes years rather than months, and that you cannot start too soon.
Six Ways Out
Here is the exercise for this week. Write down every way you could leave, including the ones you have never seriously considered.
• Sell to an outside buyer, whether an individual, a competitor, or a larger group.
• Sell to people inside, such as a partner, a key employee, or a management team buying you out over time.
• Pass it to a family member who wants it and is ready for it. Those are two separate questions.
• Share ownership with employees gradually, through a structured plan.
• Keep ownership and step out of the daily work while someone else runs the operation.
• Wind it down on your own schedule, with your people and customers looked after.
If they are honest, most owners have considered one or two of these. Few have looked at all six with the same seriousness, and you cannot choose an option that never made your list.
Burlingham adds a point that is easy to skip. Buyers are selling themselves to you too, so find out what a particular buyer is after and what they would do with the business once it is theirs. Their plan becomes your legacy once you sign.
The Succession Filter™
To make this practical, I use a three-part diagnostic called The Succession Filter™. It asks three questions in the order they come up in real life:
• Ready: Could this operate without me, and have I ever tested whether it can?
• Right: Who would I refuse to hand this to, and who would actually fit? Owners tend to answer the first half and assume they have answered both.
• Remains: What persists after the handover, the business itself or the people? Almost nobody asks this until it is too late to affect the answer.
The filter tells you where you stand today on a transition that has not happened yet. It will not write your plan for you. We will take one question at a time over the rest of the month.
Starting Late
Some readers are thinking this would all have been easier ten years ago. That is true, and it changes nothing about what to do next. David Bach makes the point in Start Late, Finish Rich, a book about personal finance rather than business exits: starting late is still starting, and deciding to begin today does more good than regretting yesterday.
The same holds here. Burlingham's first two stages, exploring and building, can begin this month, however far away your exit seems.
Jeff Giesea, an entrepreneur who sold his own company, wrote in Harvard Business Review that remarkably little has been written about life after an exit. He suggests sketching a simple plan for the first six months afterward, with three to five areas of focus. You may be years from needing that plan, but it helps to know now that you will.
What This Means in Your Practice
In dentistry, the six ways out look like this.
An outside sale usually means another dentist or a dental group, including a DSO. Each buys for different reasons and has different plans for your team and your patients.
An inside sale usually means an associate who buys in over time, or a partner who buys you out.
Family means a son or daughter who is a dentist, wants the practice, and is ready to lead it.
Sharing ownership with your team works differently in dentistry than in most businesses. In many states, only a licensed dentist can own a dental practice, so this usually means bringing an associate into ownership rather than your hygienists or your front desk. A dental attorney in your state can tell you what applies to you.
Keeping ownership and stepping out of the daily work means an associate leads the clinical day while you continue to own the practice.
Winding down means more than closing the schedule. Patient records, continuity of care, and telling your patients all come with obligations, and your state’s rules govern them.
Most dentists I talk with have pictured one of these: the sale. This week, write all six on a page with your own practice in mind, and next to each one write the name of the person who would make it possible. The blank lines are where your planning starts.
Final Thoughts
You will leave what you built, by design or by default. Designing it today does not commit you to selling, stepping back, or handing it on. It means knowing every option while you still have time to choose among them.
Start with the list. Write down every way out, including the ones that make you uncomfortable. Then ask the first question of The Succession Filter™: could this run without me, and have I ever tested it?
Book Your Free Practice Efficiency Call
How much of your business would keep running if you stepped away for a month? If you are not sure, that is the place to start, and it is what a free 30-minute Practice Efficiency Call is for. We will look at where the business depends on you and where it is losing time or money. https://calendly.com/drmjhanlon/the-hanlon-group-consultation
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Earlier than feels necessary. Burlingham reports that the preparation takes years, not months. The exploratory work of learning your options and deciding what you want costs almost nothing and can start today.
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No. Selling is one of at least six ways out. Planning is how you find out which one fits, and the preparation strengthens the business if you decide to stay.
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A three-part diagnostic for owners. Ready asks whether the business could run without you and whether you have tested it. Right asks who you would refuse and who would actually fit. Remains asks what persists after you leave. Together they show where you stand before a decision is forced on you.
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In Burlingham's interviews, regret came mostly from a lack of preparation rather than from the price. The owners who regretted their exits had not decided what they wanted, given themselves enough time or understood what the buyer intended.
Sources & Further Reading
• Bo Burlingham, Finish Big: How Great Entrepreneurs Exit Their Companies on Top (Portfolio, 2014)
• David Bach, Start Late, Finish Rich (Doubleday, 2005)
• Ani Huang, Anthony J. Nyberg and DJ Schepker, The Pitfalls That Undermine CEO Succession Planning, Harvard Business Review, November 2025
• Noam Wasserman, The Founder's Dilemma, Harvard Business Review, February 2008
• Jeff Giesea, Dealing with the Emotional Fallout of Selling Your Business, Harvard Business Review, September 2015
• McKinsey Institute for Economic Mobility, The Great Ownership Transfer (2026), as reported in Fortune, February 26, 2026