For most entrepreneurs, building a company is all-consuming. The company rules the founder’s entire life, physically, emotionally, and mentally. So what happens when it’s time to sell? Prepare for some unexpected emotional repercussions.

Loss of Identity

After selling my last company, I didn’t have another project lined up immediately.  I totally enjoyed that first vacation, but the novelty quickly wore off.  I found myself becoming restless and bored, and somewhat cranky.  Although I didn’t realize it at the time, I was dealing with a fundamental loss of identity and a lack of purpose. 

Like most entrepreneurs, running my company had defined my primary relationships (all my social interactions were at the office); the structure of my life (I got up and went to work every day); and my sense of self (if I’m not a CEO, what am I?). 

Simply knowing that an emotional response is natural can do a lot to help you deal with it. It can also help you take seriously the idea that, before the sale, you should give some thought to what you’d like to do next.


All right, your life’s purpose has been closely tied to running your company.  So what is your next purpose going to be?  If you have some idea of what you want the next step in your life to be, it will mitigate the shock of waking up without a full and hectic schedule that defines what you’re meant to accomplish each day.

After a successful sale, you’ll have some money to play with. Perhaps you’d like to become an angel investor and help other entrepreneurs. Maybe you’d like to run with your next big idea and create another start-up.  Or you could use your newfound time to turn a hobby into a passion, and take your car to the race track several times a week instead of just once a month. 

Lack of boundaries

Your family and friends are also used to your old schedule and how that fits in with their lives.  They may not immediately appreciate the new you!

A colleague of mine retired recently.  His wife Bonnie was a stay-at-home mom raising their son. She was also a fantastic cook; it was her passion.  Without much else to do, my colleague pottered around the house, obviously bored out of his mind.  When Bonnie found him in the kitchen, rearranging her spices alphabetically, it was lucky he was ever allowed in the kitchen again.

When I sold my last company I set up shop in my home office. That meant I spent each day in the same house as my wife Kittie, an interior designer.  Kittie was used to having the entire house to herself, working intensely in peace and quiet so that she could get into her “creative zone.”  Now she suddenly had an intruder wandering down the hall every five minutes, saying that perhaps she’d be more productive if she did her invoicing first.  I was still unconsciously in CEO-mode, and assumed that she would need me to give her direction.

At the beginning of the third week, Kittie walked into my study, handed me my car keys, and said, “Honey, I do love you, but I need you to get out of the house. I don’t care where you go, just find somewhere else to be.”

A sense of loss after selling your company is a perfectly natural response. You can prevent much of this by getting educated on the emotional consequences of selling your company and recognizing that you and your family will need to do some adjusting during the process.

After a transition period, I found that selling my last company, eight-and-a-half years ago, has worked out really well. I have capitalized on my experience building four companies, raising money for them, and buying and selling them. Today, my “next purpose” is to use that expertise as an investment banker and help other business owners learn from my experiences.