Here’s a question worth asking yourself if retirement is anywhere on your horizon. If your business could run without you from Monday morning on, what would you do on Tuesday? For a lot of owners, that’s harder to answer than anything in the sale paperwork. They have a number in mind for the sale. They have a rough idea of who might take over. What they don’t have is any picture of who they are once the business stops needing them every day.
That question is about to reach a lot of owners at the same time. Census data analyzed by Gallup (opens in new tab) shows that 52.3% of U.S. businesses with employees are owned by someone 55 or older. A 2026 Chase survey (opens in new tab) of about 1,000 small business owners found that 40% plan to retire within the next decade, yet only 8% say they’re fully prepared to hand the business off. Most of the advice about that gap covers valuation, taxes and finding a buyer, and all of that deserves your attention. After 35 years inside more than 500 organizations, though, I’ve watched a different problem stall more transitions than any tax question. The owner can’t picture a version of himself or herself that isn’t the business.
It’s important for them to understand that they are not their business without all the employees that have done such a great job of getting them to where they are at this point.
— Gary Henson, Founder of Gary Henson Group
One of my clients hired me when he was at retirement age and ready to sell. The business was profitable, but the profits weren’t big enough to support the price he wanted. He had already let some people go, and he told me there was one person in the company he believed could be a great leader. Could I develop him and let him lead?
After two or three months of working with that man, I agreed with the owner. He was a great leader. So I went back and told the owner plainly: “Look, you can’t go into your business any longer. Let this gentleman lead the organization, keep putting a team around him that supports higher productivity and higher profitability, and you’ll get what you want.”
He said yes. Then he kept coming back and asserting himself in the business anyway. Every time, I had to have the same hard conversation with him: “No, no, no, stay away. Let this other gentleman actually lead the organization. He has the ability to do that.” This was a man who wanted that sale more than anyone in the building, and he still couldn’t stay out.
I’ve seen that pattern too many times to call it unusual. Years of payroll, customers and emergencies wear the original vision down, and bit by bit the owner’s identity becomes the business. Ask a lot of owners to describe themselves without mentioning their company, and they can barely finish the sentence. That costs more than most of them realize. Culture defaults to the personality of whoever’s running the business, so an owner who can’t step back keeps the whole company organized around his availability. It costs him at the closing table too. Buyers pay less for a company that leans on its owner (it’s one of the first things buyers look for when you’re preparing to sell), and an owner who keeps walking back in is showing every buyer that the business still needs him.
of small business owners say they are fully prepared to transition ownership, even though 40% plan to retire within the next decade. Chase for Business, 2026 Small Business Owner Survey →
Where do you start? Earlier than feels necessary, and with the same seriousness you give the financial side.
First, answer the same question I open every engagement with, only this time about your life instead of your company: what do you want? Write it down the way you’d write a vision statement for the business. Where do you want to spend your time? Who do you want to spend it with? What have you been promising yourself you’ll get to “someday” for the last 15 years?
Second, start building that life now, while you still own the business. The research here is worth a look. A study of more than 93,000 adults aged 65 and older across 16 countries, published in Nature Medicine (opens in new tab) and led by researchers at University College London, found that people with a hobby reported fewer depressive symptoms along with higher happiness, self-reported health and life satisfaction. Those links held after the researchers accounted for income and employment, and life satisfaction showed the strongest connection. It’s an observational study, so it can’t prove hobbies cause the gains, but the pattern was consistent from country to country. The lead author, Dr. Karen Mak, pointed to reasons that should sound familiar to any owner: feeling in control, finding a purpose, and feeling competent at handling daily life.
Most owners I meet get all three of those from the business and nowhere else. If that describes you, pick one new thing and try it this quarter. A class, a club, a volunteer role, the guitar you gave up years ago. You’ll probably be bad at it at first. Good. You’ve spent years telling your people to fail forward. Take your own advice somewhere nobody reports to you.
Third, let the business prove it can run without you, in stages. Take a full week away and don’t call in. Then take two. Each time your team handles it, you’ve shown a future buyer something important, and you get a little more room to find out who you are outside of it. When we get an owner out of the way and let somebody in the organization run it, two things happen. The owner can be there 70% to 80% less, and the business becomes more valuable because it no longer hinges on one person.
Finally, remember who got you here. You are not your business without the employees who’ve done such a great job of getting you to where you are. Seeing that clearly makes it easier to hand them the keys, and easier to believe there’s a whole person waiting once the handoff is done.
If stepping away stirs up something heavier than restlessness, like grief that won’t lift or a low mood that hangs on for weeks, please talk with a licensed counselor or your doctor. That happens to plenty of people during a major life change, and it deserves support from someone trained to give it. For most owners, though, the starting point is one uncomfortable question and an honest written answer. If you want help building the business side of that plan, that’s exactly what we help owners do through the Inside-Out Method.
