Home Thinking Aloud Dealing With The Dark Side Of Entrepreneurship

Dealing With The Dark Side Of Entrepreneurship


by Dr. Stephen David LeonardPresident and CEO of Lisa Leonard Designs (LLD) and Stephen David Leonard (SDL)

Entrepreneurship isn’t just about our successes, accomplishments, and the rewards of our work. There’s a darker side of entrepreneurial life we don’t like to acknowledge, let alone admit to others. This involves depression, a growing problem among the high achieving and entrepreneurs.

I have endured my own struggles with depression while leading a home-grown startup to multi-million dollar and multi-company success. Tackling this head on yielded powerful results.

Here are my recommendations for managing depression while building your business:

Engage Those Around You.

What should you do if you suspect — or even know — you are battling depression? First, listen to those around you — especially your close circle like your spouse, colleagues, family, and those you trust. If you lack such an inner circle, that should be a red flag. My depression took on a form of irritability and anger. This is fairly common among men. You might experience battles with deep sadness, or despair or any combination of negative emotions. One day my wife came to me and said, “Steve I can’t take your outbursts of anger anymore. Every weekend you get angry and down and it lasts all weekend. You need to get help.”

These are not words that a person wants to hear — I sure didn’t. And I can tell you, I did not respond the first time. Ultimately, we need to listen to the people who know us.

Listen to Yourself.

Many of us are not taught how to listen to our emotions and what they are telling us. Still, try to pay attention to your moods — how often are you angry? When you’re alone do you ever find yourself feeling sad despite success or failure? I wouldn’t have said I was depressed, but I knew something was wrong. I certainly wasn’t happy or lighthearted. Happiness isn’t wishful thinking or putting blinders on. It’s the ability to live in a posture of gratitude, acknowledging the many positive things in your life.

Talk to a Professional.

A great first step is to talk to your doctor or spiritual leader like a pastor, priest or rabbi. But, keep in mind that physicians and spiritual leaders generally receive very little if any psychological training. Deep, longstanding depression warrants seeking professional help. Whether you think you’re “that bad” or not, if you see signs, seek out a local therapist, support group, or therapy retreat center. As a former pastor I was nervous about who to turn to. Then I heard a well know author share his experience at a therapy retreat center. I figured he is a smart guy and it helped him, so maybe it would help me. I went—terrified and not knowing what to expect — and it is one of the single most life changing things I’ve done. The center helped me connect with a therapist in my area and I have attended other similar retreat centers in my own journey.

These steps are simple, but often extremely difficult to take. However, the return on this investment in yourself results in exponential yields. I don’t know your circumstances, but I can share some examples I’ve seen in my life and those I’ve known along the way.

You might just save your marriage or relationship with your significant other. Rather than living at odds, your partner can become your biggest ally. Who knows, they may engage in a similar process and you will grow together as happened in my case.

You will become a more engaged leader as your emotions become a dashboard rather than the driver of your leadership. Emotions, even negative emotions, are not a bad thing. The key is understanding the specific role they play in giving you signals about your experience.

You can strengthen your company. It’s not unusual for a depressed leader (especially a successful one) to maintain a tight grip on the reigns to “keep at least one thing under control in my life.” But we all know that type of leadership and control are illusions hindering the real growth potential of our companies. When you face your depression, you are much more likely to allow the company to become less dependent on your personal strengths and weaknesses by surrounding yourself with other highly capable people.

You will certainly become a better parent. Consider the model you give your children facing their own personal issues. You will show them an example of healthy relationships, healthy conflict and a sense of purpose without having to prove something. What better gift can we give to our children?

Depression is a very real issue facing successful leaders today. If you see the signs, I encourage you to reach out to someone and take one of the steps listed here. I remember the first time I went to my doctor to talk with him about my depression. My heart was racing, my blood pressure was elevated, and I was sweating. When I finally cracked open the reason I was there, he answered saying he understood because of his own struggles with depression. The first step can be terrifying no matter who you are. But you also just might find a level of joy in your life you never knew possible.


As President & CEO of Leonard Group, Dr. Stephen David Leonard has seen the importance of creating meaningful and quality product. Established in 2010, the Leonard Group has grown from home-based business into a multi-million, multi-brand company including lines for men and women, faith-based jewelry, a pet line and American-based manufacturing. Having launched the Stephen David Leonard brand in late 2017, Stephen’s vision is  to help struggling people find their purpose understand their unique identity, experience, skills, and talents so they can live the life they were created to live.


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