‘Shining’ a Light on the Internal Struggles of the Entrepreneur

The following is an excerpt from “Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom,” in which Gino Wickman and Rob Dube shine a light on the internal struggles of the entrepreneur. Being driven, as all entrepreneurs are, is a blessing and a curse. 

Going Through the Motions

The driven are typically not fully present with the people they love. “Present” means you are focused and engaged in the here and now, not distracted, mentally absent, or drifting. Your mind is always racing, thinking, solving. Think about how this affects your relationships. How unimportant it makes people feel.

This includes forgetting birthdays and anniversaries, showing up late for important family events, and, when at the event, being there in body only.

Brett Kaufman, founder of Kaufman Development, a real estate development company, feels internal pain when he thinks about the times he has not been present with his son: “On multiple occasions, he has said to me, ‘Dad, did you hear me?’ ”

Mark O’Donnell has a similar story. “I have so many examples of my kids saying, ‘Can you play with me?’ and me saying no because I was either exhausted from the day, or actively thinking about a problem or opportunity I wanted to solve.

“It is painful to think about all those times and how it now manifests itself. Eventually, my son stopped asking. He got the brunt of my entrepreneurial career. My first daughter was already born before I started my company, and my second daughter was born after the business was already successful. I had more freedom and a focus on having more balance. I was still distracted from time to time with her but was aware of what I was doing.

“With my son, I had no idea what I was doing and the impact my mental checkout was having.”

Brett and Mark’s stories are not unique, as many driven entrepreneurs are consistently distracted, leading to strained relationships with family and friends.


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Numbing the Pain

Justin Breen, CEO of BrEpic Communications LLC and author of the book “Epic Life: How to Build Collaborative Global Companies While Putting Your Loved Ones First,” wrote an Inc. magazine article addressing common wounds that entrepreneurs have experienced.

He states, “I have yet to meet an entrepreneur who hasn’t experienced at least one of the following:

  1. Bankruptcy or potential bankruptcy
  2. Heightened levels of anxiety
  3. Depression
  4. Traumatic experiences as a child or young adult.”

When Justin shared these four with me in a conversation, my jaw dropped, as I realized I’ve experienced all four.

Add a fifth to Justin’s list: “addiction.”

Addiction is doing something compulsively, in excess, that is not good for you: work, food, porn, drugs, alcohol, gambling, TV, social media, gaming, or shopping, to name a few. These addictions are soothing to driven entrepreneurs because they assist in numbing and distracting you from your internal pain and give you the dopamine hit you so desperately crave.

It might sound crazy to say, but for a driven entrepreneur, building a multimillion-dollar company is soothing. They can get lost and numb themselves in the hustle and bustle of building the business. They never have to stop and look inside themselves, so they never think they are harboring any pain.

The solution is to understand and acknowledge the pain. Accepting it will speed up the process of eliminating it. Soon it will go away.

A 2015 study by Michael A. Freeman, clinical professor of psychiatry at the University of California, San Francisco School of Medicine, and an acknowledged expert on the mental health of entrepreneurs, found that 49% of entrepreneurs had dealt with some kind of mental health challenge:

“People who are on the energetic, motivated and creative side are both more likely to be entrepreneurial and likely to have strong emotional states.”

Freeman also noted that “different people have different strengths and different vulnerabilities. For people in business, if you’re an executive or manager or founder, you need to understand yourself and manage yourself so you can play your strong cards and have strategies to manage your weaknesses.”

Another 10 Discipline client, Mike Sullivan, president and CEO of Loomis, a full-service ad agency, lost half his revenue in 90 days.

“It was terror,” he shared. “Slashing my income, laying off people I loved, and finding the energy to hustle hard to rebuild my business was more than I was equipped to handle.

“I think many entrepreneurs believe they thrive on intense pressure and even wear it as a badge, but that’s a grossly overrated orientation for me. At the time, my winning formula didn’t include a lot of self-care. I learned the hard way that too much stress is brutal on the mind, body, and spirit. It was easily the most miserable time of my life. What’s worse, I didn’t have the scaffolding in place to catch my fall. And boy, did I fall.

“It started with sleepless nights and creeping anxiety that ultimately turned into gut-wrenching, all-consuming stress. So, I did what many self-respecting entrepreneurs do. I went to my doctor for a prescription. I got some clonazepam to calm myself down. I also tried a couple of prescriptions for sleep with varying degrees of effectiveness. I even got some Adderall to help with focus and energy so I could work extra hard and fast to rebuild my business.

“The side effects from the drugs made matters much worse. Before I knew it, I was swallowed up in a severe clinical depression. Then I made a suicide attempt. That earned me a compulsory week’s stay in a hospital psychiatric unit, which, in retrospect, certainly beat the hell out of the alternative. It was a gigantic wake-up call. My business is not worth my life. Nothing was worth the awful toll my coping strategies took on my family. It was a very scary time for all of us.

“In the years since, I’ve shifted my thinking dramatically by incorporating many resources including a great therapist and no more medications.

“A decade later, my business has never been stronger, and, more importantly, I have never been healthier or happier. There have been setbacks in the years since then, as there always are, but my capacity for handling the ups and downs has grown by leaps and bounds.”

This lack of peace in your life isn’t necessary. Nor is the feeling of emptiness. You’re simply trying to fill a hole that can’t be filled with outer world “stuff.”

Using The 10 Disciplines, we are going to show you how to fill that hole and experience a sense of wholeness. For now, the point of this Discovery is to help you become aware of what it means to be driven—the good, the bad, and the ugly.

Reprinted with permission from Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom by Gino Wickman and Rob Dube (BenBella Books, 2024).


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