In 2007, I had a great chance to sell my business, and I did. I asked all the right questions before I made the move, except one: How did I really feel about it? And that was a mistake I regret to this day.

Exiting the company you founded is a natural part of entrepreneurship, and it can provide great financial rewards. It has great consequences for your successors in management and the employees you leave behind. And I made sure to attend to those. But the exit also has consequences for you. I took them too lightly.

Why Selling Seemed Like a Good Idea

In my case, everything pointed towards the wisdom of selling the natural disaster mitigation and reconstruction business I had founded 26 years earlier. I had built the company into a valuable, profitable powerhouse, but I felt I was burning out. My partners were aging.  I sensed opportunities elsewhere, and my efforts to keep the staff together and engaged were wearing me out. I knew I could sell, which made all these headaches seem unnecessary.

Shortly after announcing the sale, we were contacted by three interested parties. Everything went smoothly.  We even managed to miss the 2008 recession and, according to our consultants, we received an above-market price. As a businessman, I had done everything right.

Inside, though, I was wracked by regret. What I forgot to consider were the things I enjoyed at work. I didn’t ask myself the hard questions about why I was selling, what I wanted to gain—and most important, what I would miss if I sold. And I don’t think I’m alone in this oversight. Many of my fellow business owners who jump ship, it seems, likewise failed to ask themselves what they would be giving up.

Before You Do What I Did...

My advice to you—before you do what I did—is to stop and think.  Go back to the fundamentals of your business, way back if you need to. You must first understand why you created your business. And I don’t mean just the value proposition. I mean why are YOU there? What do you gain from continuing to stay with the company and what would you lose if you left? Be honest. If you can fully realize what you will be giving up, you will be able to envision the future.

Finally, go one step further and ask what else matters to you. What else do you want to accomplish in life, and will it be easier to do that with our without your company? This is by no means an easy question, but even success can’t extinguish true passion: This is your chance to chase after your dreams.

I didn’t ask myself these questions, and after I sold the company, I soon realized that to be captain of my own ship was my dream. I missed leading my team, charting the company’s course, and responding to challenges at a moments notice. Today, four years after selling, I have learned that the riches of a successful exit can’t replace the rewards of leadership.

In hindsight, I should have looked to someone outside the organization that could offer me perspective. A coach, perhaps, someone to ask me why I was selling, what I wanted to gain afterwards and most importantly, what I would be missing.

Joanna Flatt contributed to the writing of this article.