Be weird

In Your Most Improbable Life, Kevin Kelly wrote:

Your life’s goal should be to become the most improbable person you can be. Your path, your character, your life, should be the most unlikely, the most unexpected, the least predictable version you can make. Improbable lives have fewer competitors, more unique rewards, and are harder to replace with AIs, since AIs run on the predictable. This is true whether you favor traditional humanist directions or work on a frontier.

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Here is what you gain with your most improbable life:

The authentic you. Your particular mix of talents, native abilities, personal inclinations, genetic limits, life experiences, and ambitious desires points to a mixture that is distinctly unique – if it is allowed to blossom. The further you move in that direction, the more you-like you become.

The more you-ish you become, the less competition you have, because you are occupying your own niche. Less competition means you don’t have to be in a race; you can relax and focus on your strengths. You have the space to become even more you, and even less likely.

When I was studying accounting and finance in university, people around me were all applying to spring programs and summer internships at big banks. Because that's what you do. Getting into a spring program gets you a summer internship. Getting a summer internship gets you a job at graduation. It is not guaranteed, of course. But without those, your chances are as good as zero.

So, what did I do? I applied for an internship at a small startup in London instead. That internship led me to apply for and land a job at another startup. Eventually, I cofounded a startup for four years. Now, I'm building a business up from scratch again.

Unless there's a parallel universe, I can't know for certain which life would have been better. Friends who took the former path have made way more money than I have, have much more stability than I have, and operate at a much larger scale than I can imagine. Would I have preferred that? I really can't know. I'm happy with my path so far, and perhaps that is enough. (I'm certain I'm doing some self-justification here!)

But the takeaway is not about which path is better. It is to think about what you want and not just let the current of society sweep you along. If you find yourself chasing after what most people around want, ask yourself if that is actually what you want. Most people around me were chasing big bank jobs, but slogging for long hours in a finance corporation to make lots of money didn't interest me. So, I pursued startups, where I could make a smaller but more direct impact for a sufficient amount of money. I'm sure some people thought I was weird.

I have an even weirder friend. He has been pursuing theoretical mathematics, even though there is little prospect for non-applied mathematics in Singapore. To continue pursuing his choice of mathematics, he has lived and worked in the UK, the US, and South America. I often admire how much conviction he has.

Maybe that is the trick. Be weird.