Business Transition Lessons Learned: Get Me Out of Here!

This is the story of one business owner, who thought he wanted to sell his business so he could have more free time, but found out that the business he had built was more intertwined with his personal identity than he realized. His story shows us just how important it is for owners to be mentally prepared to exit their businesses, including figuring out how to separate themselves from the business and determining what’s next.


  • The owner of a successful business, in his early 50s, longed to be completely free from the day-to-day grind.
  • He started and ran his business very suc­cessfully for 20+ years.
  • He grew the company to 25 people.
  • He was tired and bored, and he wanted to have fun and enjoy life more before he was too old.
  • He was well-diversified financially, and when you asked him what he intended to do with all of his soon-to-be-found free time, he gave a list a mile long that included his beloved toys: race cars, air boats, fishing boats, etc.

Sound familiar? Well, maybe your list does not involve the same plans or toys, but the desire to leave the daily grind of your business may ring a bell. Maybe you’re sick and tired of being sick and tired?

What Happened:

He put his business up for sale, and after about a year on the market, they found a quality buyer, negotiated a deal, and the big day arrived.

Freedom at last, right? Well, maybe for the first month, but his story doesn’t end there.

He was certain that retirement would be just what he wanted and needed. How could it not be? No employees calling in sick, no warranty work, no bad debts, no payroll to make.

But, he was bored!

His business was all he knew. He missed the employees, the customers, the chal­lenge, the grind. He found himself stopping by to see everyone at lunch. He called his old buddies in the industry, but they were too busy to spend much time with him—they had their own businesses to run. He soon realized that the company had been his life. It was his family, his reason to get up every morning.

After a 12-month sale process and anxiously waiting for his freedom, he found himself wishing he could undo everything!

What Happened?

  • He wasn’t personally prepared. He hadn’t spent enough time separating himself from the business or figured out what he was going to do next. His business was the framework for who he was. As the CEO, he was used to being in charge of everything, and now he was in charge of deciding which fishing hole he wanted to go to!
  • His best friends were all still working.
  • He now had a non-compete agreement that covered a very large area and prevented him from working in the only trade he knew.
  • He felt lost and actually sold the home he loved and moved two hundred miles away to start the business all over again in the same industry!
  • More than 10 years have now passed, and he still owns his second company.
  • Selling was not the right choice for this owner at this time; he wasn’t ready.

What Should’ve Happened?

  • If the owner had taken the time, he could have examined the areas of “pain” that needed to be addressed. He could have eliminated some of his day-to-day responsibilities and possibly changed his role in the company without selling, which would have provided him the needed relief and a succession plan when he was finally ready to call it quits.
  • He would have had a thoughtful plan that took into consideration what he really wanted in his next phase of life and outlined options to achieve those goals and desires.
  • He would still have the same company and his home, and he would not have had to move out of the area.

Start preparing yourself now … even if you are potentially years away from selling your business.

You have worked so hard to grow and run your business. You deserve to exit on your own terms and achieve all of your goals. Our members exit their businesses when they are ready and improve their chances for making their next phase of life the most fulfilling and best yet. Let us show you how.

To your successful exit,

Jane Johnson


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