What 20, 25, or 30 years in business means for what comes next

After 20 or 25 or 30 years running the same business, something shifts. The problems you are solving are the same problems you were solving a decade ago. The business works. It supports your family and your employees and a lot of other people. But you are different. You have been doing this for a long time and you are starting to think, quietly, about what else there is.

That is a reasonable thing to think about. It is also, for most owners, the point where very little actual planning gets done.

According to the Exit Planning Institute’s 2023 national survey of 1,162 business owners, baby boomer owners are the least prepared generation for this moment, despite being the closest to it. Only 13% have a written personal plan for what comes after the business. Only 15% have a written company plan. Yet 57% of boomer owners say they want to step back within 5 years.

Understand the signals that mean it is time to start

The math most owners have not run

Here is the number that tends to change the conversation: 64% of business owners need the proceeds from their business to fund their life after they step back. That is not 64% of people who are planning to sell. That is 64% of all business owners surveyed by the Exit Planning Institute.

For owners who have been building something for 20 or 30 years, the business is often the largest asset they own. Larger than the house. Larger than the retirement accounts, if those even exist. The plan, whether stated or not, is to eventually convert that into money and live on it.

The problem is that most of those owners have not had a formal valuation in the last 2 years. They are carrying a number in their head based on something they heard at a chamber event or a rough revenue multiple. They do not actually know what a buyer would pay today, what it would take to get to the number they need, or how long that would take.

Find out how to get a realistic read on what your business is worth

The identity problem nobody talks about

There is a reason baby boomers are the least prepared generation. It is not laziness or ignorance. It is that after 25 or 30 years, the business stops being something you own and starts being something you are.

The Exit Planning Institute’s research describes it directly: boomer owners “have focused on growing a successful company, not a significant one.” Their identity has become tied to the business. Thinking about what happens after means thinking about who they are without it, which is a harder conversation than any deal structure.

This shows up in the data on post-sale regret. PwC research, cited in the EPI 2023 report, found that 75% of owners who sell their businesses feel deep regret within one year of closing. The same study found that 96% of owners who expressed that regret had no plan for what they would do after the sale. The financial outcome had nothing to do with it.

What changes after 20 years, 25 years, and 30 years

At 20 years, most owners are still in the building phase. They are too busy to think seriously about stepping back, and the business still has obvious upside. This is actually the best time to start building the structures that will eventually make the business transferable, even if a sale is 10 years away.

At 25 years, the questions start becoming more personal. Health is on the mind, even if nothing has happened yet. Key employees who have been there since the beginning are aging too. Customers who built the business are retiring themselves or changing the way they buy. The business is stable, but the world around it is shifting.

At 30 years, the conversation usually gets real. The owner has made it to an age where they can see the end of the road, and the question of what the business is worth and what comes next cannot be put off with “I’ll think about that later.”

The owners who handled each of those transitions well were the ones who started thinking about them before they arrived.

Why 92% of business exits are not sales

This is the number most owners do not know: according to a 2025 McKinsey analysis of Gallup survey data, 92% of small businesses that exit the market close permanently. Only 5% are sold to a new owner.

That does not mean most businesses are worthless. It means most owners run out of time, options, or runway before they can position the business for a real sale. A business that closes because the owner retired without a plan leaves money on the table that could have funded 20 years of a different life.

The owners who do sell are not luckier or smarter. They started earlier. They got a real read on what the business was worth. They reduced the things that made it hard to transfer. And they made a decision before a health event or a market shift made it for them.

See what a 3-year preparation process actually involves

What to do if you are at this point right now

If you have been in business for 20 or more years and you have started thinking about what comes next, the single most useful thing you can do is get a realistic number.

Not a broker’s pitch. Not a revenue multiple you calculated yourself. A real, defensible estimate of what a buyer would pay for the business today, given your financials, your customer base, your management team, and the market you are in.

That number tells you whether you need 2 more years or 7. It tells you what is holding the value back. And it tells you whether the plan you have in your head, the one where the business funds your next chapter, is actually going to work.

That is the starting point. Everything else follows from there.