Man looking into setting sun beside title of Transitions After Selling Your Business

“There’s not really anyone to talk about it with Tricia. No one wants to hear that you have millions in the bank and are slightly depressed. They’re just envious of the millions.”

“I always thought I wanted to retire and play golf.  Now I can play golf all day. After a few weeks, it became boring. Why do I exist now?”


From Dr. Tricia:

I sat on the Zoom call, watching the guest speaker talk about selling her business. “Oh no, I thought. She’s depressed.” It’s not the type of depression that involves crying one’s eyes out or an inability to function; it’s the struggle for purpose I see behind someone’s eyes.

She had achieved what many only dream of—building a profitable business, selling it early, and having the choice to do whatever she wanted for the rest of her life.

What few people recognize, including owners themselves, is that in addition to responsibility and burden, owning a business often brings purpose, creativity, and challenge. Building a business requires a certain type of personality – an interest and willingness to engage risk and work, fear and pleasure, overwhelm and triumph…in a way that is much too unpredictable and uncertain for the average population. And this same personality tends not to do well with unfocused energy. What feels like relaxation to many people will feel boring to entrepreneurs.


Common Business Transitioning Mistakes

1. Underestimating the transition. Most owners focused on selling the business without assessing the changes after the sale.

2. Assuming that they will feel a certain way after selling a business and making plans based on those assumptions.

3. Starting another business to ease the discomfort without taking adequate time to assess the lifestyle they’d like.

4. Volunteering or engaging in many new opportunities because of unstructured open time.

Business Transitioning Recommendations

1. Assume you will have unexpected emotions and frustrations after selling. By doing so, you set yourself up for a successful transition. Maybe your emotions will be easy; that’s okay. It’s just better to plan for a jumble of them.

2. Refrain from making promises about what you will or will not do after you sell the business. Frankly, you will not know exactly what you’ll need regarding time and energy buffers until after the company sells. Try not to make promises out of your assumptions.

3. Wait six months before deciding what comes next, unless you decided on a path BEFORE selling the business. When faced with discomfort, people go back to what they know. This phenomenon occurs across many aspects of life. Seasoned business owners consider “getting a job.” Early retired people struggle to make it through three months of not working. Abused spouses go back to their partners. Make plans to deal with the discomfort. A good rule of thumb is to refrain from making life-altering decisions for six months after a significant life transition. It’s a heuristic, not a fact. In the interim, successful entrepreneurs may decide they WANT to start a new business. However, with enough space, it is an active, conscious decision that differs from reverting to a default to escape emotional discomfort.

AND, It's Not Wrong If You Decide to Start Another Business

Business offers many entrepreneurs a creative outlet and a sense of meaningful challenge. The process of building a business energizes some people. People aren’t workaholics if they decide that they love building businesses. The problem occurs when working on business becomes an unexamined default such that they build businesses to fill a void rather than because they enjoy it.

Create a Multi-Faceted Identity

Jimmy has a succession plan; he plans to sell in a few years. In addition to managing the business at a high level, he goes on trips, levels up his golf game, enjoys his family and has an insatiable curiosity that allows him to fully engage in whatever new type of learning comes his way.

From Tricia:  “I called Jimmy to ask if he’d always had outside interests or if there had been a period of his life when he was business-only. He responded, “I’m on the 18th hole. I’ll call you back.”

Whether Jimmy starts another business after he sells this one, he will be fine. His sense of personal identity and daily activities are varied. Business is part of his life but not the entirety of it.

Creating a multifaceted identity does not mean one needs to have a lot of hobbies. In fact, most business owners don’t have traditional hobbies. Their “hobby” might be reading, learning, or being in a new situation. However, a multifaceted identity means one can extract joy from multiple sources. It may be a sport, a church, a social group, a volunteer opportunity, sitting by yourself with a cup of coffee and a book – it’s the ability to feel whole and complete outside your role as a business owner.

A multifaceted identity also buffers against stress and depression. Creating one as early as possible affords individuals more options about how to create meaning and helps them navigate some of the stressors and uncertainties that come with transition.

Feeling Lost Doesn't Mean that You are a Failure

Most business owners are successful because they have ambition, a plan, and the ability to execute it.

From both an emotional and a lifestyle perspective, the time after selling a business can feel like no man’s land. Emotions vacillate and the plan changes. Some people are exhausted. They expect to feel exhilarated but instead, worry that they won’t get off of the couch again.

One of the most constant and annoying facts of psychology is that healing and transitioning require time and space. It can’t be managed cleanly. If it helps, make a plan that emotions and the “plan” will change every 4 hours one week and every two days the next.

A strategy that helps many people is to put some structure into their day. Implementing the concept of a multi-faceted identity, someone may decide to go to the gym or take a walk for 1 hour each morning.  Someone else decides to read two chapters from a book each evening. The commitments do not need to be time-consuming; rather, small routines can create a sense of predictability and comfort. Most people feel crazy for missing their overloaded schedule, but this is a normal reaction, so the key is to have a little schedule but not to overload it and revert back to the default.