Sometimes a business doesn’t sell because the price is too high. Sometimes the buyer can’t get financing. Sometimes there are problems with the employees, the lease, the financials, or the business itself.
And sometimes, the problem isn’t any of those things. Sometimes the owner simply isn’t ready to let go.
Being ready to sell a business means more than being financially prepared. It also means being ready for what comes next.
The Business Was Transferable. The Owner Wasn’t Ready.
I once worked with an owner who had spent more than 40 years building a company.
There were key employees in place. Not every customer relationship depended exclusively on the owner. The business wasn’t entirely dependent on the owner to generate its revenue. Economically, there was a path for the business to transfer to new ownership.
On paper, it was a business that could be sold.
The problem wasn’t the purchase price. It wasn’t the buyer. It wasn’t financing, the employees, the lease, or even the transition terms.
The problem was the owner.
The owner was over-identified with the business.
After more than four decades, the business wasn’t simply something the owner owned. It had become an important part of who the owner was.
There were no children preparing to take over the company. There were few interests outside the business and no strong desire to travel, pursue hobbies, or redirect decades of energy toward something new.
The owner had said, “I am ready to retire.”
I believed those words.
But I didn’t pay enough attention to whether the owner’s actions supported them.
I was wrong to bring the business to market.
Financially Ready Doesn’t Always Mean Personally Ready
This experience taught me something I hadn’t fully appreciated before: a business owner can be financially prepared for retirement and still be completely unprepared for the emotional consequences of selling.
For an owner who has spent 20, 30, or 40 years building a company, selling the business isn’t simply a financial transaction.
It can mean giving up a daily routine, relationships, responsibilities, a sense of purpose, and an identity that has been built over decades.
A buyer can solve the financial questions.
What’s the business worth?
Can the buyer obtain financing?
What happens to the employees?
What happens to the lease?
How long will the owner stay during the transition?
But a purchase agreement can’t answer the owner’s most personal question:
“What am I going to do when this business is no longer mine?”
The Deal Never Closed
In this case, the transaction did not close.
Approximately two and a half years later, health issues ultimately caused the owner to close the business.
The business closed.
The owner received nothing for it.
That outcome has stayed with me because the business had once represented decades of work, relationships, and value. There had been an opportunity to transfer that business to a new owner, but the owner wasn’t ready to make that transition.
What I Learned
The biggest lesson I took from this transaction is simple:
The owner has to be ready to sell.
Being able to say, “I want to retire” isn’t necessarily the same as being ready to walk away from the business.
Now, before I take a business to market, I want to know that selling the business is truly one of the owner’s most important short-term priorities.
If an owner cannot look me in the eyes and say, “This is the most important task for me to complete in the short term,” then they may not be ready to become a client.
That isn’t a judgment. It’s an important part of the preparation process.
What Comes After Your Business?
For owners who have spent decades building a company, determining what the business is worth is only part of preparing for an exit.
You also need to think about what comes next.
What will your days look like?
Where will your sense of purpose come from?
What relationships or interests will fill the space the business leaves behind?
What are you looking forward to?
For some owners, those questions are easy to answer.
For others, they may be much harder—and that’s okay.
But they are questions worth answering before putting the business on the market.
Because sometimes the hardest part of selling a business isn’t finding the right buyer.
It’s being ready to let the business go.
If you’re thinking about selling your business, start by asking yourself not only, “What is my business worth?” but also, “What am I ready to do when it’s no longer mine?”
Are You Really Ready to Sell a Business?
If you would like to discuss selling your business, I would love to start that conversation. My name is Hank and I represent Oklahoma business owners. Reach out for a free consultation.