Comparing our insides to everybody else’s outsides

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Since elementary school, when I felt alone and out of place wandering the playground, I have been someone who hungers for connection, intimacy, and real friendship. Not every founder I have met over the past ten years has been up for that kind of connection and openness, but some have. And coming into real friendship with the people I once idolized has been myth-shattering.

It turns out none of their companies grew consistently up and to the right either. Nor do any other leaders wake up every day feeling calm, composed, and confident. Like me, every other leader I have found myself in truly honest conversation with has confessed feelings of self-doubt, fear, or anxiety. Every leader I have spent time with has confessed feeling sometimes, or often, like an imposter in the role.

Looking back, I can see that in my earliest days as a founder and CEO I was comparing my insides to everybody else’s outsides. Nobody sits down with a reporter and openly confesses their deepest fears and insecurities. Most tell stories about their wins and try bravely to put on a face of optimism and impervious confidence. As a result, those of us reading the stories, wondering how we measure up, find ourselves lacking by comparison. We are comparing our insides to everybody else’s outsides.



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