Will the Real Entrepreneur Please Stand Up?

I recently sat on a panel at Ash Kumra’s Confessions of an Entrepreneur event with the super smart and accomplished Kent Healy. Kent is a serial entrepreneur and active real estate investor who has a brilliant quiet confidence and an amazing breadth of knowledge. During our panel, he discussed his hardships. He acknowledged that his first business failed and why it failed. Then he discussed his current success and outlined how he was able to take lessons from the failure and leverage them for success.


I followed his lead and admitted to having some challenges of my own. Being what I call a triple minority (young, female, and black) and starting businesses has been difficult for a variety of reasons. I shared my process for handling insecurities and making my perceived disadvantages work to my advantage.


It’s rare that you see this kind of transparency at events for entrepreneurs. There tends to be a lot of glossing over setbacks and minimizing failures. Many entrepreneurs feel a need to create a façade of success, even when there is none to speak of. There’s a pervasive notion that If we show the slightest hint of weakness or uncertainty, we’ll lose respect and all the things we want. But the truth is that the maintenance of this mask is exhausting. And intellectually, we know it’s not possible for anyone to never have a bad day (or year), lose a deal, or fail. It’s a part of life and business. So why do we spend so much energy managing impressions?


Those familiar with the tech world and the history of the Internet likely heard of Aaron Swartz’s death. He, in my opinion, was a bright person who had tremendous promise. A pending legal case is speculated to be one of the factors that may have led to his suicide. We’ll never know, but what we do know is that when a person sees suicide as a viable option, it’s because they legitimately feel there are no other alternatives. They’ve reached a point where they believe that the size and intensity of their problems exceeds their ability to manage the problems. Mashable writer Christina Warren penned a beautiful piece about her brief interactions with Aaron. It brought me to tears because I’ve wrestled with depression myself, and the idea of being smart enough to do amazing things and build a business yet not control something so fundamental to your well-being is maddening. I get it. It broke my heart for Aaron and everybody else before him who hasn’t seen a way out. I occasionally feel Survivor’s Guilt because I know that without the grace of God and a glimmer of hope, I, too, would be a casualty of suicide.


Because of this, I maintain deep respect and admiration for people who allow themselves to be vulnerable in very public ways. I remember a time several years ago when I reached out to Manisha Thakor. She’s a brilliant financial manager and sought after expert, and yet right there on her bio page, she admits to dealing with depression. It was so inspiring to me that I wrote to her to thank her for her transparency and share how much I admired her work. She wrote back the same night, and we exchanged a few messages. To her, it might have been just another fan writing, but for me, it was a reminder that I wasn’t alone in the dark. I carry the same admiration for Brad Feld. He’s written extensively about his depression with a certain peace and clarity that I’ve found praiseworthy. He’s not pandering for sympathy or playing the victim; he’s just being honest about his realities. Whether he realizes it or not, many of his raving fans adore that about him and are likely liberated to tell their own stories and face another day because of him. He writes about things like vulnerability that elicit respect rather than pity.


The concepts of authenticity, vulnerability, and transparency all tie in here. It’s bigger than baring your soul on Twitter or a blog. It’s about giving yourself permission to be human – even as a high-powered (or wanna be) entrepreneur. It’s about realizing that if you don’t go within (to examine yourself truthfully), you will go without (deprived of things your mind and soul need).  Not only does vulnerability free us from the self-imposed trap of managing impressions, it also frees others. It creates a positive ripple, whether we can see it or not.


In reflecting on things we can do to support each other and ourselves, I identified two important actions:


1. Share your personal story truthfully.

It’s not necessary to edit every part of the story to craft the image of perfection and success. The most compelling stories involve a hero who has failed or met with a tremendous setback only to rise and win. There can be no comeback without a setback. And it’s okay if the “comeback” portion of your story is still being written. In many cases, especially for the overachieving entrepreneur, our expectations of ourselves far exceed those anyone else has of us. It’s okay to tell your truth. It’s a gateway to deeper relationships and more personal integrity.


2. Be more interested than interesting.

In the narcissistic age of social media, camera phones, and personal profiles, it’s easy to be so caught up in our own drama and issues that we miss the cries for help from other people. Granted, it can be difficult to discern the difference between a tough time and a suicidal plea, but if we make sympathy a standard way of relating to everyone, we reduce the likelihood of someone reaching out and not having a hand. In many cases, people moving through dark times don’t even want to burden anyone with their issues. They’re not looking for a handout. They often just need a listening ear or a well-timed reassurance. No matter how successful we become, we all need that at one time or another. There’s no amount of self-sufficiency that can take the place of human connection.


If you’re wrestling with seemingly insurmountable challenges, hang in there. I know firsthand how hopeless it can seem, but I can also say with confidence that it gets better. People who are doing meaningful work they love deserve to live vibrant lives, and the rest of the world deserves the gifts they have to offer. There’s a difference between a loser and a late bloomer; taking the next step is the only way to make sure you’re the latter.