Be A Fool

Hitting home runs are hard. Being confident is very different from being right.

Yesterday, I was talking to an entrepreneur and he told me his passion, but also his financial conundrum. He wanted to change direction to work on something more monetizable, but ultimately more limiting as a product. I couldn’t help but tell him to pursue his passion, and go all the way. In fact, why be an entrepreneur otherwise?

His concerns were real — cash running out was imminent — he had two months’ runway. We were debating. He drew from his personal experience from the past; similar situation. I shouted, “but that was different,” and quickly realized it was hard for me to counter him without any way to back up my claim.

Only this morning, did I come to realize what had bothered me, and what I should have stated clearer.

Fear of failure was a logical thing. In the next two months, if he didn’t make his company sustainable, he’d be out of business. Naturally, there wouldn’t be any more pursuing of passion left at that point.

The journey, and the things you would discover along the way, was the unpredictable part that would make or break you. I only just started reading Fooled by Randomness, but I bought the idea of a Black Swan. We never knew what was going to make our venture successful. Being confident was different from being right.

In truth, there was no way of telling which venture was more limiting or more risky — but we could tell which was the passion, and which was not.

Be a fool.


Now read this

My Alphabet

NYTimes, Gmail, Facebook, Twitter. These are four websites I visit the most. Every time I need a mental break, I tap “n,” “f,” “t,” into the browser URL and with one pinky action I kill some time. It occurs to me that these handful of... Continue →