Truly Free

I first read Kavi’s post on tattoos, which started with how he turned down even a temporary one. I could relate to that, and the post made me wonder what was my discomfort with getting a tattoo.

My immediate thought was optionality. But thanks to some excellent coincidence, right below that post (in my feed) was one by The Marginalian which gave me a different perspective.

We build our lives around structures of certainty — houses to live in, marriages to love in, ideologies to think in — and yet some primal part of us knows that none abides, knows that we pay for these comforting illusions with our very aliveness.

That was a deep insight, and it struck me that though I keep using the word ‘optionality’ I think that was just my mind fooling me, what I really wanted was certainty. And this was the roadblock for the ‘vitality/ aliveness’ I have been after.

As always there is a nuance. I am reasonably fine with uncertainty now where I can ‘afford’ it in terms of time and money – like say, ending up at a restaurant in Bangalore that turns out to be meh, or streaming a movie we end up not liking, or a book that doesn’t work for me. But (for example) when we are traveling, specially abroad, I aim for certainty in the plans, because chances are this would be the only trip we’d make to that part of the world.

In ‘A Little Life’ Hanya Yanagihara said

Fairness is for happy people, for people who have been lucky enough to have lived a life defined more by certainties than by ambiguities

I understand that very well, because I have spent much time reflecting on the choices that have shaped my life and led me to where I am now. And the costs I might have had to pay if I chose wrong. For good and not so good, it has been driven by a scarcity mindset, something I have started pushing back against only late in life.

I have seen friends and acquaintances making travel/eating out plans at the last minute, and not being disappointed if things don’t happen. Recently D’s ex-colleague went to Meghalaya instead of, wait for it, Japan! Because they decided too late, and my scarcity-driven mind couldn’t even process it for a while. But I asked myself later, between me, who seeks optionality by planning ahead, and risking disappointment if things don’t go according to it, and them – who take it as it comes, who is really more free? There are preferences, and trade-offs, but I think the answer was clear!

Optionality to me has been a way to define freedom, but I probably aimed for it and hit certainty. And thus “if I need things to be a certain way, I’m held hostage by them“. 

That brings up a fascinating paradox – of wanting certainty and also wanting freedom. They seem to be sworn enemies.

I think it will take another journey to reduce the addiction to certainty, to go back to doing things without a map, but in the meanwhile, I think I got an action point courtesy Shane Parrish.

People think good decision-making is about being right all the time. It’s not. It’s about lowering the cost of being wrong and changing your mind. When the cost of mistakes is high, we’re paralyzed with fear. When the cost of mistakes is low, we can move fast and adapt. Make mistakes cheap, not rare.

From strict no-mistakes to ok with cheap mistakes to realising mistakes are not large anyway. And being comfortable enough ‘to live in the not-knowing’, as Don Draper would say. Ambitious much?

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