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Why Writing About Failure Doesn’t Make You One
Don’t Wait to Be Successful to Write About Failures
People like a winning image.
I believe this, and I see examples of it every day. I feel it too. I don’t like pity parties, sadness, or discouragement; I’m drawn to hope, encouragement, and excitement.
I used to think that this meant people wouldn’t want to read about anything except the W’s.
By extension, that means if you’ve experienced a setback, don’t write about it. Experiences that contain even a whiff of embarrassment, loss, or failure, are all meant to be stuffed away, kept in obscurity, and to be disguised as if they didn’t happen.
The caveat to this is you can reveal a failure after it happened, but only after you’ve won or consider yourself a success. Or so I thought.
This observation became clear to me as I skimmed Sahil Lavingia’s, “Reflecting on My Failure to Build a Billion-Dollar Company,” which was a really great essay (that got him a traditional book deal!), ending on a positive note that he’d redefined success, and that Gumroad had transitioned from a VC-backed hypergrowth company to a sustainable business. This is a belief that Gumroad Lavingia and I shared:
