The Entrepreneur’s Identity

On the unhealthy entrepreneurial rollercoaster When I first decided to become an entrepreneur, I didn’t know I was becoming one. All I knew was I didn’t want to be held back by office politics anymore and that I could build something of my own faster than most.

So, I jumped off the corporate cliff, and, amidst many mistakes, I rocked it.

What I didn’t know was how much of a problem “rocking it” would become later on…

The stories of entrepreneurs are wracked with tales of trouble and triumph. Some Davids go up against their Goliath and win, while others fail and fall into obscurity. Some battles have long been settled (like Foursquare versus Gowalla), while others are still ongoing (like Apple versus Google / Amazon / Samsung / almost everyone).

Viktor Frankl describes this in his book, Man’s Search for Meaning, using an example taken from architecture. He says the way to strengthen a weak and decrepit arch is by “increasing the load which is laid upon it, for thereby the parts are joined more firmly together.”

Frankl was referring to the creative tension that gives us the strength to face both professional and personal challenges in our lives.

As entrepreneurs, we need creative tension to drive our continuous search for progress and meaning.

Without creative tension and putting our backs against the wall, would the greatest creations exist today?

I’ve heard the same story countless times, in conversation with friends, reading a book, or listening to a speaker. Projects have a knack of finally taking off only at the last moment, when everything is on the line.

  • When the team behind the iPod brought the original prototype to Steve Jobs, he threw it into a fish tank. Bubbles came up, proving his belief that there was still space inside the device that could be diminished.
  • Guy Laliberté hit the streets with his accordion and stilts for years before he took his big gamble. In 1987, he bought a ticket for himself and his circus group from Quebec to the Los Angeles Arts Festival with no return fare. Now, we all know his success as the founder of Cirque du Soleil.
  • J.K. Rowling wrote the majority of the Harry Potter series in cafés while she carted around her daughter. As a newly divorced single mother, she relied on welfare for her and her daughter. With her back against the wall, she brought her wizarding story to worldwide success.
  • Matt Wilson of told me the website business finally took off when he had no other choice but to make rent for he and his mother. A few years down the line, his new travel business was born out of his own desperate desire to continuously see new parts of the world.

As true as those stories are, how much creative tension is too much?

According to a Gallup Well-Being Index earlier this year, entrepreneurs are doing pretty well when compared to the rest of the population. We’re happy and healthy, but we’re wracked with stress.

In Life Is What I Say It Is, I discuss how energized we are by the rollercoaster’s highs and how ill-prepared we are for the lows. Hitting rock bottom can be devastatingly jarring. Maybe it’s because we’re so emotionally attached to our creations. Maybe it’s because nobody really talks about the low moments.The pitfalls get a few short sentences, while the award ceremonies get the rest of the chapter.

But it may be something else entirely.

The poll also found that entrepreneurs regularly use their strengths to perform their tasks each day, which may explain everything. Do you know what it feels like to use your “strengths” and fail? Do you know what it feels like to have your “strengths” dissipate?

As an entrepreneur, stress isn’t about getting things done. It’s about the fear of not having it in me to make things happen.

When entrepreneurs create projects they feel passionate about and use their strengths to turn that into reality, it isn’t a matter of dwelling over our failures, of greying hair or sleep loss. It’s a matter of building our identities, of how we see ourselves.

Every entrepreneur that has “rocked it” at some point knows what I’m talking about. Once the excitement of the “big break” wears off, our thoughts become, “Can I really pull this off again?”

Every high becomes more difficult to top, and we wonder if we are the real problem. We wonder if we, as people, are enough.

An entrepreneur’s strength, performance and identity shouldn’t be so closely entwined. We need to untangle them.


When I quit my job and started my own business, I started rocking it. Over the past year and eight months, I’ve written two books, served clients with web design, and helped readers through my writing (or so they say). I’ve also more than doubled my personal income, traveled the US with my husband, and worked out of my own home (currently in gym shorts).

Sounds like a glamorous life tinged with adventure, but the other side of the coin isn’t as pretty. What lifts me up also brings me down.

I’ve suffered a nasty business breakup, been betrayed by a client I thought was my friend, and cried to my family, friends, readers, and almost anyone else who will listen.

When I heard Donald Miller speak at a recent event (called World Domination Summit), it finally all made sense. He shared the following words:

“You are not your failures. You are not your successes.”

My first reaction was: “I’m not? Are you sure?”

That then faded into: “Well, that makes me feel a lot better…”

Which led to: “Why did I feel bad about this in the first place?”

The entrepreneur’s need to perform creates a stress level that has almost become a part of the field’s definition.

  • Organize and operate a business or businesses? Check.
  • Takes on financial risk to do so? Check.
  • Stresses out to the point of exhaustion? Check.

It doesn’t need to be this way. If we’re true to ourselves, if we check in with ourselves constantly and adjust accordingly, if we engage in conversation with the people who can guide us, there has to be a way out of the “I’m-am-nothing-without-the-stress-and-prestige-of-creating-something-legendary” entrepreneurial identity.

This issue is bothering me enough to experiment with fixing it. For the month of August, I’ll be undergoing what I call The Redesign Challenge, which means I’ll be trying to detach my personal identity from my entrepreneurial performance via some crazy exercises:

  • Asking Questions: Investing time and effort in getting to know ourselves is the only way to know what’s going on inside our minds and hearts. To do that, I’ll ask myself tough questions like why I equate being busy with being successful, who I’m trying to serve/help, and more.
  • Conversations: Most people would say that I should talk to people that run in different circles to get a well-rounded perspective on this issue. Nonsense. I’ll have conversations with my people — the ones that believe in me and can trampoline me to new heights. They’re the only ones I can trust to guide me toward the real me, regardless of performance.
  • Personal challenges: One of my favorite times in my life were the first few weeks after I quit my job. I’d wake up at 5:45AM to write for hours, work out, and spend time with family. I want to do all of that again, which requires uprooting my business life to fit a new schedule filled with awesomesauce.

I’ll do it privately and post my final thoughts on my blog each week for the world to see. Follow along if you’d like. It won’t be pretty. Consider yourself warned.

As per usual, Seth Godin says it best:

“Your audacious life goals are fabulous. We’re proud of you for having them. But it’s possible that those goals are designed to distract you from the thing that’s really frightening you—the shift in daily habits that would mean a re–invention of how you see yourself.”

The hope is that through this attempt to redesign my life (a shift in habits), I’ll come to terms with the fact that what I do is a part of me, but it isn’t all of me (a re-invention of how I see myself).

If what you do doesn’t define you, then what does?

PS. Thanks for entertaining a weird challenge-hungry entrepreneurial mind.