5 years ago was my last day of “work”

5 years ago today I did a crazy thing.

I walked away from a great job to pursue an inkling of an idea. This was a clean (psychotic) break from the first 25 years of my life, during which I played by all the rules, colored inside the lines, and took well-trodden paths. Goodbye to all that.

I didn’t feel compelled to recapitulate the details of what’s transpired since then. Instead, I was going to reflect and summarize what I’ve learned over the past 5 years, but I found myself at a loss for words. What could I possibly say to capture the love and fury and joy and indignation and on-the-brinkness and sheer thrill and terror and sense of purpose I have felt (sometimes all at once) during these years?

Everything boils down to platitudes: be yourself; trust your gut; never give up; get some sleep; hustle; surround yourself with the right people; blah.

The platitudes are true but utterly devoid of meaning until they’re colored by personal experiences (usually mistakes) that you just can’t cheat. Entrepreneurship has a way of making you learn things the hard way and kicking you when you’re down. And then there are these barely perceptible yet completely addictive glimmers of progress that make you feel on top of the world. It’s either sadness or euphoria.

In an acute moment of doubt, a great advisor, and, later, an investor once said to me:  “Well, I like an entrepreneur who burns her ships on the shore. Just keep going.”


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