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Transition: How to Enjoy the Journey of Entrepreneurship

I read an article on a few months ago called The Psychological Price of Entrepreneurship. If you haven’t read it, even if you’re not an entrepreneur, you should. It’s a life changer. Here are some key excerpts for discussion:

Successful entrepreneurs achieve hero status in our culture. We idolize the Mark Zuckerbergs and the Elon Musks. And we celebrate the blazingly fast growth of the Inc. 500 companies. But many of those entrepreneurs, like Smith, harbor secret demons: Before they made it big, they struggled through moments of near-debilitating anxiety and despair — times when it seemed everything might crumble.

Until recently, admitting such sentiments was taboo. Rather than showing vulnerability, business leaders have practiced what social psychiatrists call impression management–also known as “fake it till you make it.” Toby Thomas, CEO of EnSite Solutions (No. 188 on the Inc. 500), explains the phenomenon with his favorite analogy: a man riding a lion. “People look at him and think, This guy’s really got it together! He’s brave!” says Thomas. “And the man riding the lion is thinking, How the hell did I get on a lion, and how do I keep from getting eaten?”

Not everyone who walks through darkness makes it out. In January, well-known founder Jody Sherman, 47, of the e-commerce site Ecomom took his own life. His death shook the start-up community. It also reignited a discussion about entrepreneurship and mental health that began two years earlier after the suicide of Ilya Zhitomirskiy, the 22-year-old co-founder of Diaspora, a social networking site.

Lately, more entrepreneurs have begun speaking out about their internal struggles in an attempt to combat the stigma on depression and anxiety that makes it hard for sufferers to seek help. In a deeply personal post called “When Death Feels Like a Good Option,” Ben Huh, the CEO of the Cheezburger Network humor websites, wrote about his suicidal thoughts following a failed startup in 2001. Sean Percival, a former MySpace vice president and co-founder of the children’s clothing startup Wittlebee, penned a piece called “When It’s Not All Good, Ask for Help” on his website. “I was to the edge and back a few times this past year with my business and own depression,” he wrote. “If you’re about to lose it, please contact me.” (Percival now urges distressed entrepreneurs to seek professional help: Call the National Suicide Prevention Lifeline at 1-800-273-8255.)

Entrepreneurs often juggle many roles and face countless setbacks–lost customers, disputes with partners, increased competition, staffing problems–all while struggling to make payroll. “There are traumatic events all the way along the line,” says psychiatrist and former entrepreneur Michael A. Freeman, who is researching mental health and entrepreneurship.

Complicating matters, new entrepreneurs often make themselves less resilient by neglecting their health. They eat too much or too little. They don’t get enough sleep. They fail to exercise. “You can get into a startup mode, where you push yourself and abuse your body,” Freeman says. “That can trigger mood vulnerability.”

But it may be more than a stressful job that pushes some founders over the edge. According to researchers, many entrepreneurs share innate character traits that make them more vulnerable to mood swings. “People who are on the energetic, motivated, and creative side are both more likely to be entrepreneurial and more likely to have strong emotional states,” says Freeman. Those states may include depression, despair, hopelessness, worthlessness, loss of motivation, and suicidal thinking.

Call it the downside of being up. The same passionate dispositions that drive founders heedlessly toward success can sometimes consume them. Business owners are “vulnerable to the dark side of obsession,” suggest researchers from the Swinburne University of Technology in Melbourne, Australia. They conducted interviews with founders for a study about entrepreneurial passion. The researchers found that many subjects displayed signs of clinical obsession, including strong feelings of distress and anxiety, which have “the potential to lead to impaired functioning,” they wrote in a paper published in the Entrepreneurship Research Journal in April.

The article still sits with me to this day. Why? Well, for starters — it’s true. And what this article doesn’t mention is that it’s especially true for younger people, who are still trying to navigate the murky waters of life — of love, hobbies, friends, spirituality, balance, health, and happiness — with limited groups of friends who actually understand the intricacies of this lifestyle. And if you’re not married or in a serious long term relationship? You’re doing it alone. And good luck finding someone who can or is willing to relate to you or put up with your bullshit when you’re having a manic fit and can’t stop feeling like the weight of the world is on your shoulders.

To illustrate my point, here’s a great anecdote from “The Fearsome Nightmare Entrepreneurs Never Talk About”:

The day began to go wrong long before Dave reached his office. He had finished working out on the treadmill and was grabbing his car keys when Joe called on his cell. His three year old was running a fever so he would not be coming in to work. Joe was his tech-guy, the only person who understood the new CRM package on which they had just spent a king’s ransom. More, their new product launch–a ‘make or break’ for the company–was scheduled for later in the week and 2 million emails needed to go out smoothly.

Joe was apologetic. He promised to work from home and fix the bugs they had identified but Dave felt queasy.

His night receptionist handed him a message when he reached his office. Bob wanted to speak with him immediately. Bob was his lead investor, the guy who had found the other investors for him and promised him that he would back him till the end of the quarter when the results of the product launch were in. If all went well, the company would be able to self-finance for the rest of the year.

Bob, like Joe, was apologetic. He had tried his best but his partners were not very happy with the results so far. He could no longer guarantee that he would be there for Dave as promised. But what about the new product launch, Dave sputtered.

Bob was sympathetic but he was not reassuring. He would do his best but Dave had better start working on a plan B.

Dave got another call from Joe that evening. His child was still sick. He was sorry but the strain was too great. He was quitting, effective immediately.

It took a long time for Dave to fall asleep and he woke up in a cold sweat at 3AM. Steel bands were clamped around his chest and he could barely breathe. Fear, stark uncontrollable fear, permeated every cell and flowed out through every pore. He felt his body stirring, moving involuntarily.

“What’s up dear?” his wife mumbled sleepily.

“Nothing,” he lied.

He found that he had curled up in the fetal position.

I like this anecdote because I’ve witnessed it — with myself, and with some of my entrepreneurial friends.

Life is tough as an entrepreneur, so you hide it. You don’t talk about it. Because it’s not sexy. It’s not powerful. And when you do feel like the weight of the world is on your shoulders, you have to pretend it’s not because there are very few people who can or are willing to try to understand how you feel.

And if you’re a woman? Try harder to find a man who will or can relate to you in a role that isn’t in your “societal nature.” Because women aren’t supposed to be entrepreneurs, after all — are they? I haven’t seen many lately.

I can honestly say that with the exception of a few other friends of mine who happen to also have experience as young entrepreneurs, no one really understands the pressures or the stressors that go into owning a company, let alone trying to grow it, maintain it, or most important of all — sell it — while trying to live the somewhat normal life of a 20 or 30-something.

Yes, I’m saying the latter for a reason.

As a millennial entrepreneur, I can tell you that the only reason I started a company when I was 22 was because it was the only opportunity available to me that even remotely resembled what I thought would make me happy.  The writer’s strike had just hit Hollywood and eliminated opportunities as a Producer, which is what got me to LA in the first place. I was lucky to land a job at a music discovery startup that I thought would take me through the strike and beyond, but while the startup I worked for initially made me love the buzz of “startup culture”, it only taught me to hate corporate culture (and producing) so badly that I never wanted to work for anyone ever again. Ever.

So I started my own company. Because I thought it was easier. I thought it was freedom.

But it’s neither of those things. Over the last seven years, I’ve lived on a roller coaster. I’ve dealt with being over $200,000 in outstanding unpaid client debt, I’ve made it through an economic depression, I’ve kept roofs over countless employees heads while they never worried about a thing, and I’ve seen the highs of closing big deals and the lows of pain in the ass clients who think you owe them the world for $1, deals falling through left and right, and dealing with intense partnership struggles.  Tack on the personal stuff, adding countless important friendships lost and abandoned (especially over the past few weeks), friends who have passed away or been diagnosed with terminal illnesses, and added relationship sutff? It’s a lot for a young person to handle. There’s not a single moment that I can remember in the last seven years that was effortless.

Which is why I don’t want to be an “entrepreneur”.

It took me a long time to realize that I don’t like running a company. I’m not good at it. And I could argue that there are a lot of eccentric CEO’s and Founders that have brilliant ideas and business acumen, but who are also terrible at running a company. Because telling people what to do and dealing with the intricacies of the day-to-day is actually suffocating for people like me, and it never really leads to the best end result.

Owning a company just to be an entrepreneur is one of the most selfish, egotistical things someone can do. I know, because I did it for seven years. While it’s great to say you want to own a company and be successful at doing what you love, one day you’re going to have to pay all your taxes, cash in your non-existent IRA, and find someone to either buy your business, or shrink away into shakey retirement unless you happened to be smarter than 98% of the rest of the moderately successful entrepreneurs who didn’t make it big like Mark Zuckerberg.

So what’s my point?

The key to life is in transition. Change, like death and taxes, is inevitable. How you respond to that change is what makes you who you are. You never know how you’re going to get from Point A to Point B, especially as an entrepreneur, because it always feels like you’re a work in progress. And you are. We all are.

But you do get to Point B, eventually. And when you do, you start to set your sights to Point C.

So enjoy the transition. While I hate running a company, I will never stop being an entrepreneur. I’ve been lucky to have some amazing career opportunities cross my desk that are even more stressful than my entrepreneurial journey thus far; but because I processed the transition, I at least know what I’m willing to accept and what I’m not willing to accept in my life, while keeping an open mind as I embark on the next journey so I continue to learn those things.

I encourage you to do the same. Find the things you do like about entrepreneurship, and try to center your world around those things. It’s the perks that make the negatives bearable — and ultimately, allowing your life to transition, that can get you where you want and need to go.


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Tori Kyes is a Los Angeles-based writer/producer and entrepreneur. She specializes in social media, technology, and entertainment. She's also an advocate for social change, a marathon runner, Ph. D student (Media Psychology), gratitude giver, and lover of life.

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