The Dark Side of Entrepreneurship That Nobody Talks About

The Dark Side of Entrepreneurship That Nobody Talks About

Ask any entrepreneur, we don't measure time in weeks or months … but from deadline to deadline, launch to launch, and failure to failure. It's how we gauge our impact on the world.

Remember the pure euphoria of your first launch? Or when you made your first sale? Nothing beats the bliss that came from your first major press mention or reached whatever recent milestone that signaled measurable growth. You felt like you'd cracked the code of how to be successful … and that nothing would be the same again.

We crave these moments and fight for them with a superhuman intensity.

Friends and colleagues cheer as you turn your vision into reality, transform lives, and punch crater-sized dents into the universe.

But nobody talks about how addictive that high is. Or that when left unchecked, we risk losing ourselves like an addict seeking any other drug.

Entrepreneurship can be a grisly, volatile mess of toxic ingredients on the verge of combustion, threatening to consume your health, relationships, and life.

According to the Gallup Wellbeing Index, 45% of entrepreneurs report being stressed, and another survey of 242 entrepreneurs, 30% identified as depressed (compared to the national average, which is 7%), and 72% of entrepreneurs have a family history of mental health conditions.

Entrepreneurial swagger is often a thin veneer masking crippling self-doubt, insecurity, and fear of catastrophic failure. The more successful you are, the more people depend on you, and the more is at stake if you fail.

If you feel like you’re living on the edge of a knife, you are not alone.

The Toxicity of Chronic Stress

“Everyone was telling me how great it is and how amazing life is and how they are hiring a bunch of people and closing out rounds of funding. And it was like, okay, yeah, I get that, but let’s have a real conversation.”

“I found it very difficult to find people in my life who were willing to let their guard down and be honest and real.”

Brian Bordainick, Founder of Dinner Labs,

Temporary stress is normal and can be healthy, but as the saying goes, everything in moderation.

Chronic stress, on the other hand, is where the physiological effects become more dangerous:

  • Headaches
  • High blood pressure
  • Heart problems
  • A suppressed immune response
  • And much more

Prolonged exposure to chronic stress can lead to memory loss, anxiety, irritability, depression, substance abuse, social withdrawal, weight gain, insomnia, suicidal thoughts or worse.

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We've all heard stories about the devastating toll this takes on relationships with spouses, children, colleagues, and family. But what's really going on inside the body?

Your endocrine system — responsible for regulating your “flight or fight” response in stressful situations — isn’t returning to a healthy state.

It overrides everything the brain deems not critical (like your sleep, digestive, and reproductive systems) while enhancing the systems that are useful to getting you out of danger (like your muscular and cardiovascular systems).

Prolonged activation can have some very nasty physical side-effects.

When I’m stressed, I clench my jaw … even while I sleep. During one particularly stressful month in 2015, I woke up unable to turn my neck to either side without intense pain. Weeks of tension took its toll. Fortunately, after several days and a few deep tissue massages, I was able to move my neck like a human being again.

Of course, this can be far worse.

For Austen Heinz, the founder and CEO of Cambrian Genomics, Ilya Zhitomirskiy of Diaspora, and many others, prolonged stress — likely coupled with a lack of rest and deep depression — resulted in suicide.

It’s a hard thing to talk about and an even harder thing to admit.

Fortunately, there are entrepreneurs who are speaking out and sharing their own experiences.

“Loneliness, darkness, hopelessness … those words don’t capture the feeling of the profound self-doubt that sets in after a failure. Loneliness. Darkness. Hopelessness.”

“Those words describe the environment of depression. Self-doubt? That shakes you to the core and starts a fracture in your identity that makes you question if you should even exist anymore.”

Ben Huh, “When Death Feels Like a Good Option

You Are Not Your Work

For those of us who monetize our passion, these are hard words to internalize. But it needs repeating:

You are not your work.

You need outlets and hobbies outside of your work to be a healthy human being.

At the risk of sounding cliche, one study showed that having a creative hobby, such as playing the piano or pottery resulted in a measurable decrease in cortisol levels after the activity was completed.

Studies have also found spending time walking in nature has helped people become happier, more attentive, and “present.”

When "you are your business," you set yourself up for a massive existential crisis every time your business changes — which is inevitable on the path to success.

You’re also setting yourself up for a potential crisis once your business is wildly successful; risking micromanagement, forgetting to share praise with your team, and overcommitting to new opportunities.

Relying on any single facet of your life for the entirety of your personal fulfillment is unhealthy and unrealistic. Mark Woeppel found solace in playing music during his business’s downturn:

“I used to be like, 'My work is me.' Then you fail. And you find out that your kids still love you. Your wife still loves you. Your dog still loves you.”

Kevin Eschleman, an assistant professor of psychology at San Francisco State University, whose research showed that people who are more engaged in creative activities often scored 15-30% higher on performance rankings than people who were less engaged: “We found that in general, the more you engage in creative activities, the better you'll do at work.”

It’s also important to remember that you don’t have to do it all alone. Agencies, freelancers, and virtual assistants can take work off your plate.

For Shopify Plus users, one of the benefits of having a Merchant Success Manager is having someone to function as a sounding board, who can listen without judgment and work as a mentor, as someone with industry knowledge and experience.

Remember to Make Time For Self-Care

It’s a vicious cycle: you’re working so much, that you forget to eat right or go to bed on time, so you wake up late, which puts you behind, so you work late again, and wake up at an even greater deficit.

Soon, you’re burned out and want to avoid working altogether. Creating self-care habits isn’t just a good idea in general, it can also do a lot to reduce stress and its nasty side effects.

But as Brad Feld explains on how he deals with his depression as an entrepreneur

“I make time and space to care for my mental health. I stopped setting my alarm for five a.m. and let myself sleep until I wake up naturally. I observe digital Sabbaths in which I stop checking email, keeping up with the news online, and checking into Foursquare. I travel less. I read and run more.”

“In other words, I do all of the things that the prevailing start-up culture tries to squeeze out of my life. And as a result, I'm far more productive in the business of building and investing in companies.”

You might find it hard to justify spending an hour at the gym, or twenty minutes a day meditating, or even getting to bed at a reasonable hour, but these are all things a doctor and other professionals can help you with.

You’ll wish you’d made time for it when you have to take time off because you’re so sleep deprived you’re making basic errors, or because you physically can’t type without searing nerve pain going from your neck to your wrist (ask me how I know!).

Get Enough Sleep

For most adults, 7-9 hours is the recommended amount, although your personal needs could be a little more or a little less. Sleep is often one of the first things to go during a busy period, but reducing sleep to 4-6 hours a night is shown to have a significant impact on cognitive functioning, which is kind of important if you’re a business owner, no?


Meditating doesn’t have to be a New-Agey experience with crystals and incense; it can be as simple as firing up an app for five or ten minutes in the morning. Shopify’s CEO Tobi Lütke swears by Headspace. It’s well-documented that meditation is great stress relief (with other benefits, to boot), so there’s no any excuse to not be doing it.


Aside from the myriad of health benefits, exercise is yet another way to get relief from stress. You can do something as quick and simple as the seven-minute workout, or you can aim to find a fitness activity that’s both healthy and fun (for me, it’s Brazilian jiu-jitsu — for others I know, it’s running, biking, dance class, or something else entirely).

Good Ergonomics

Not necessarily a habit, but since we’re talking about health and entrepreneurs, it’s worth noting: make sure your workspace is set up properly. Check out this breakdown at Lifehacker for a guide on optimizing your office.

Remember, You Are Not Alone

No matter how much you love your work, it’s not worth sacrificing yourself for.

I know firsthand. At one point I managed to have three nervous breakdowns in a year, largely due to overwork.

Nothing, no amount of cash to roll in, would make me want to be in that spot again, with my body physically rejecting food and, at one point, nearly leaving the house without pants because I was so sleep deprived.

If you’re experiencing serious symptoms of anxiety or depression, talk to a doctor or therapist.

The most obvious ones are changes in sleeping and/or eating patterns, and unshakable feelings of listlessness, panic, paranoia or fear.

But there are plenty more (for both anxiety and depression), and these disorders manifest in odd ways sometimes. During my worst depressive episode, my memory was terrible. I reached the end of a month and realized that I had no memory of that entire month, barring one or two experiences — everything else was sort of a gray mist in my head (and still is, to this day).

In the words of Andrew Solomon, a researcher on depression and mental health:

“One of the first people I interviewed described depression as a slower way of being dead. That was a good thing for me to hear early on because it reminded me that that slow way of being dead can lead to actual deadness, that this is serious business. It's the leading disability worldwide, and people die of it every day.”

With the U.S. facing a suicide epidemic and people with depression especially at risk, the cost of staying quiet is too high.

There’s a very real stigma around talking about mental health in general, along with talking about your struggles in entrepreneurial circles, but if you’re dealing with depression, you need to talk to someone.

Your doctor or therapist can help you come up with a plan that’ll make you feel like you again. And if you need someone to talk to right now, the National Hope Line is one of many options, along with the National Suicide Prevention Lifeline and Crisis Text Line.

Running a business can be the best thing in the world — if you can enjoy it. If you’re running yourself into the ground — sacrificing family, life, things you love, and your own health — it’s not worth it.

The most important thing to remember is that you don’t have to do it alone.

Additional Resources

About the Author

Michelle Nickolaisen runs a freelance writing business as well as a branding and marketing agency. When she's not working on those, she's giving fellow freelancers productivity tips, or watching/writing something related to sci-fi & fantasy.