Wednesday, 24 April 2013

What would you do if you knew you would fail?

We are reminded, ever so often: Do what you love. Find your passion. Cal Newport improves on this by instead asking "What are you willing to get good at?"

Along the same lines I like to consider, koan-like, two sides of a related question. First:

What would you do if you knew you'd be successful?

If no matter what you chose, it would become huge. Be the new biggest thing. Get written up in the NYTimes. Be so big that people you don't know would email you constantly asking when they could get more X. You, as a person would publically be forever linked with this thing.

That question helped me let go of my career as a musician (maybe just for a while, maybe forever— I certainly don't know) and go into writing apps. I love playing music, of course. And for a number of years after undergrad it was very important to me that I earn a living doing music. But in the last few years the answer to "how can I scale this" has involved doing more of the things I don't particularly love doing: playing weddings, teaching people who aren't really all that interested in learning, admin to keep new work coming in. Instead, I thought, what do I like doing that is scaleable? And of course programming is the obvious answer. Turns out I am okay at it and since lots more people need software developed than know how to do it, no one much cares what your degree is in as long as you can hack teh codez.

Even more liberating, though, is the flip side of the first question:

What would you do if you knew you were going to fail? 

That no matter what you did or how hard you worked, at the end of it you would accomplish nothing, get no recognition, make no more than a minimal amount of money and have no lasting impact? It sounds depressing, but when I imagine having that kind of foreknowledge... and then getting up off the floor and heading out into the world to do something anyway, I imagine it coming with this incredible clarity, this freedom to simply pick something good and interesting and fun, with no anxiety or pressure about it seeming "right" to other people, or it being likely to make you wealthy, or it making people think you're smart when you tell them that is "what you do". 

I also imagine that this kind of knowledge— non-hypothetical in someone like Steve Jobs' case— is what makes creative, visionary leaders able to commit themselves to a project with such single-mindedness. They have looked failure in the face and said... "meh".

Final quote: A friend of mine once, many years ago, when I was trying to get up the nerve to talk to a group of cute girls, said "I think most people have a lot more things they regret not doing than things they regret doing." This is, in my experience, completely true and indicative of a human tendency worth working against. 

(Oh, and for the record, I got absolutely, positively shot down by the cute girls— but its value as an anecdote for not fearing failure still keeps that decision regret-free.)