Why Are We Afraid Of The Entrepreneurship’s Darkside?

Why Are We Afraid Of The Entrepreneurship’s Darkside
Why Are We Afraid Of The Entrepreneurship’s Darkside?

There are days when entrepreneurship spills black ink all over the pages of my life soaking into every corner with self-doubt, fear, and anxiety. Out of nowhere thwack, hit with imposter syndrome. The mantra “past success does not guarantee future performance” rings loudly in my ear. And I wonder can owning a business cause depression? Riding the roller coaster and feeling the excitement of launching new things also comes with the reminder of risk and bad days and weeks. For all of its highs, entrepreneurship has some terrible lows. Why is this topic so rarely discussed?

Most of us started our journeys riding high with excitement for the ways we were going to add significance and change people’s lives and our communities. At some point we are jolted with the reality of our decision, being an entrepreneur is not only difficult but it’s profoundly emotional work. Those who are willing to do the job of sharing their vision know, just as the pendulum swings to excitement and joy, it can swing just as far into darkness. We take on the weight for the success of our service, clients, vendors, and employees. Growing rapidly, learning new skills and crushing through personal barriers then waking up at 3 am mind racing wondering if we still have what it takes.

For many, it’s easier to put on a front as an entrepreneur and pretend that everything is all right. This dark side of entrepreneurship is not exactly fun coffee conversation. It’s easier to use our eternal optimism mask to power through. We use the “fear is just excitement” trick every public speaker uses as they step on stage.

Despite what the gurus and Instagram coaches tell you, not everyone has what it takes to be an entrepreneur. Some days I question if I am. Sure we entrepreneurs get knocked down, and we get back up eventually, it’s in our blood. But some days are hard, fucking hard and I feel this in my bones. There is a heavy weight of charting your path and success. When you own your dreams and passion so immensely, you can fall into a pit of self-blame when things don’t turn out as planned.

Like many people who have carved a path into the ground with persistently working hard to pursue a dream, there are days when the Fraud Police comes to visit.

Punk Cabaret singer-songwriter Amanda Palmer describes it this way.

“The Fraud Police are the imaginary, terrifying force of ‘real’ grown-ups who you believe – at some subconscious level – are going to come knocking on your door in the middle of the night, saying:
We’ve been watching you, and we have evidence that you have NO IDEA WHAT YOU’RE DOING. You stand accused of the crime of completely winging it, you are guilty of making shit up as you go along, you do not deserve your job, we are taking everything away, and we are TELLING EVERYBODY.”

What I know is creative, deep and meaningful entrepreneurial work isn’t free. It’s a heart investment. When we sow into our work and into products and ideas to make our corner of the earth a little better – our dreams and heart can get broken. Failure and the fear of failure, although we are told to accept them, doesn’t make for a good friend.

In my search for answers, the one that most resonated was Holocaust survivor Viktor Frankl’s

“Don’t aim at success. The more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side effect of one’s dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself. Happiness must happen, and the same holds for success: you have to let it happen by not caring about it. I was hoping you could listen to what your conscience commands you to do and go on to carry it out to the best of your knowledge. Then you will live to see that in the long-run—in the long-run, I say!—success will follow you precisely because you had forgotten to think about it…Those who have a ‘why’ to live, can bear with almost any ‘how.’”

So what now? I know bad days and weeks will come and go for both you and me. Maybe it’s time to break the taboo of talking about the dark side of entrepreneurship. I’m not suggesting the faux-authenticity of instacelebs talking about messy hair and wearing only sweatpants. Those are safe and easy admissions. What if we talked about the struggles, stress and mental health of an entrepreneur openly?

I hope this sparks a conversation in your corner of the world. How do you cope with the stress of entrepreneurship? Let us know in the comments below.

photo by Bud JohnsonMike Allebach is a photographer of couples boudoir and tattooed weddings . His book Viral Personal Branding arrives in 2019.  His work has been featured in Offbeat Bride, Cosmopolitan and Huffington Post.  Learn more about weddings and couples boudoir at

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