Typical Negative Feelings After the Exit

March 01, 2018Exit Strategies, Family Business, Insights, Selling a Business

Selling your business is the most emotionally involved transaction you will ever make. Even when the sale goes smoothly, it’s not as simple as closing the deal and living happily ever after in retirement. Remember, retirement is a dirty word to entrepreneurs. We don’t want to kick back and relax; we need to be “working” in some sense of the word. What can you expect to feel in the days and months after your exit from business?


Your company was—and still is—the first thing on your mind upon opening your eyes every morning. You might have even been thinking about it in your sleep. Work kept you busy, motivated, inspired and all of the other good things that drive self-worth and self-fulfillment. When you’re no longer running your business, you have all of this newfound free time. At first, you won’t know what to do with it. You might find yourself pacing the house looking for something to do, texting your former employees, and giving into other compulsions or rituals stemming from anxiety. Restlessness after the exit is normal. There is no expectation that a racing horse will sit under a tree once it leaves the track. The more honest you are with yourself and the more thought you put into your retirement lifestyle up front, the better able you will be to keep yourself busy.


Some entrepreneurs find themselves downright dissatisfied and discontent with retirement. If you feel this way at the beginning, try not to meddle in your old business. Join service clubs, boards and other groups to keep your schedule full, knowing that these, too, might leave you wanting more. If that’s the case, by all means, seek a new business endeavor. It doesn’t even have to be one that has a prospect of making you a ton of money; anything entailing a semblance of strategy and growth can fill the void left by selling your business. There are also many mentoring opportunities where recovering business owners can pass their knowledge to newly formed businesses.


The same way some homeowners have “seller’s regret” after selling their house, business owners sometimes wish they hadn’t turned over their business. This is especially likely if the business implodes after their exit. It happened to me. I sold my business to someone, and they proceeded to run it into the ground. I had everything set up perfectly—great staff, all systems in place…it was the ideal business for a buyer to step into. And yet they managed to destroy it all.

Safe to say, I regretted my decision to sell when all of that went down. It felt like my brand was tarnished. A big part of the reason I started Exit Consulting Group is because I wanted to keep my horror story from happening to other business owners. I once heard someone say, “A parent can only be as happy as their saddest child.” The same idea applies to a business owner’s feelings toward their company. If the company succeeds, they feel proud. If it flounders, they feel like they failed. It’s not only the latter that evokes regret, though. If the business flourishes under its new leadership, you might feel regret in the form of wishing you were part of it.


When I found out my business was in shambles under its new owner, I was on the verge of getting into a street fight every day. Again, everything was firing on all cylinders. How could someone screw it up? Let’s face it: ego is a big part of entrepreneurship, and you’re probably going to keep tabs on your business after you sell it. If you find out things aren’t going well, it’s going to get you riled up. This is why it’s so important to have a post-exit plan so you’re not letting something that’s out of your control dramatically impact your mood.

How to Cope

All of the above emotions are common and understandable. They can be especially overwhelming for “lifestyle” business owners, meaning those who are so deeply involved that every aspect of the business touches them. Removing yourself from the work you know and love is a bittersweet milestone; our job at Exit Consulting Group is to help you 1) capture more of the “sweet” things about retirement, and 2) effectively manage the “bitter” aspects. See how we guide business owners through every aspect of an exit or transition.