Entrepreneurs

The Identity Crises of Entrepreneurs

The Identity Crises of Entrepreneurs
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I’ll never forget the freedom I felt walking into my office the first day after we decided to shut down SpaceSplitter and chalk it up to a “failure”. Not feeling like I had to convince myself or anyone else that today’s forecast was better than yesterday’s was incredibly liberating and generally healthy for me. That said, leading up to this point, the social and internal fear was real.

After founding and operating early-stage companies for more than six years, my masochism has rewarded me with invaluable lessons learned and the opportunity to advise and learn from other founders.

When I quit my cushy strategy consulting gig to develop SpaceSplitter with my team, it was my entire world. We were going to fundamentally change the way people lived together. Every aspect of my life was consumed by the business, essentially every waking minute, and rightfully so.

When I was with family and friends, my work was the first, second, and third thing they’d ask about… “How’s SpaceSplitter going?!?”. I was conscious of this self-absorption and how self-absorbed it could make me. I made every attempt to rightfully stay modest by highlighting the hard work ahead.

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Still, the self-imposed pressure of painting the perception that “we’re crushing it!” would only reinforce the merger of my self-identity with that of the business.

After it was clear we weren’t finding product-market fit with SpaceSplitter’s platform after 18 months, we came to the heart-breaking conclusion that it was no longer viable.

Thankfully, we were self-financed and bootstrapped, so we didn’t need to apologize for losing anyone’s money, but still -- we were losing a massive part of who we were for almost two years.

The personal sacrifices that accompany being a founder are undeniable, and that’s something anyone serious about starting a company needs to understand and embrace.

However, the personal relationship that can suffer the most is the sense of self that a founder has in failure, as the business inevitably intertwines itself with the self-identity of its founder(s). When things go well, it’s awesome, and the business’ success boosts the founder’s personal brand value and helps actualize and validate the self-worth they felt prior to “success”. But if you ask some “successful” founders, they’ll admit their self-worth was unsubstantiated until their work and efforts manifested itself into “success”, completely absolving those insecurities.

You are the business, and the business is you.

For better or worse.

Until death or liquidity do you part, just don’t ever undervalue your life without the piece of yourself that your work today brings.

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I caught-up on a call with a friend and fellow founder a while ago, as they went through a tough time dealing with upset customers. This person had trouble sleeping at night thinking about not being able to make those customers happy and how life would be if they were unable to make things right. It went so far that they nearly overdosed on sleeping pills and is lucky a roommate found them.

Once I got off the call I forwarded along Ben Huh’s post from 2011, “When Death Feels Like a Good Option”

A while ago I caught-up at a bar with another friend who recently raised more than $10 million for his company. My buddy modestly and quietly proceeded to mention that in the company’s last board meeting, some board members asked him about stepping down as CEO. The founder identity-crisis strikes again! Leaving this person to wonder, “who the hell am I without this element of me as part of my fabric?!?”.

If you watch HBO’s Silicon Valley, you’re already vicariously familiar with this scenario.

For many, I think this fundamentally comes down to the loss of time. As a founder, the largest cost is often the opportunity cost that accompanies your commitment to the business. For “older” founders, this consideration can weigh particularly heavy as one hopes a considerable portion of their life’s hard work manifests itself with a positive outcome.

Another close CEO friend of mine who has been operating the same company for the past five years and recently went through a bridged down-round to keep the lights on expressed “what am I going to do if this doesn’t work? How many companies would even actually look at me as employable?”.

The reality is that this is someone with a ton of operating and management experience, a huge support network and wouldn’t have any problem being gainfully employed within a month.

Yet this level of self-deprecation persists, clouding the true self-worth of founders.

Founders struggle with self-identity, and I think it’s often a leading contributor to stress, anxiety, and depression among founders. These few stories mentioned are not unique.

Related: 8 Ways to Stay Calm During a Crisis

Mark Woeppel has certainly felt this, and Dr. Michael Freedman has written about it. Even Brad Feld deals with this deep-seated stuff.

The emotional and mental exhaustion of founding a company often makes it impossible to keep things objectively in perspective at times. It takes substantial self-awareness and a conscious effort to remind oneself how good life actually is and how undoubtedly bright the future is, one way or another.

The good news, it turns out, the sky is not actually falling.

Perhaps my favorite piece from Ben Horowitz is his post about how, as CEO, the most difficult skill is managing your own psychology.

I continue to learn this lesson myself, and founders should always remind themselves of the invaluable substance they’re developing by operating in the trenches and figuring stuff out.

We underestimate how many people are wildly capable of accomplishing big things, and it’s particularly tough for that self-determination and belief to endure through failure, despite the reality that founders always have a better vantage point and probability of success, once the lessons learned from the journey are digested.

SpaceSplitter wasn’t working for us. That’s how I, Rob Caucci and the team actually felt about the situation. Until I unraveled the company’s existence with my self-identity, I wasn’t able to make the best possible decisions about my bright future that still very much existed.

I wasn’t able to find peace until I began appreciating the journey being the destination.

Three years later, the journey still continues in the work we’re doing at Pijon.co, and I’ve never been more prepared to embrace and influence the uncertainty of the path that lies ahead.