Returning to London yesterday after 9 months of travel (from Israel to Costa Rica – the first part of my world tour), I’ve been trying to work out what I want to do next.

I have 3-6 months in London while my knees recover from a kitesurfing accident and a list of interesting projects I could pursue – but where the hell do I start?

Luckily I stumbled across an episode of the Tim Ferriss podcast with Phil Keoghan.

In it, Phil discusses a near-death experience in which his (almost) final words were: “I wish I’d…”

His supposedly final moments on earth drew instantly into consciousness his deepest regrets, and Phil followed these regrets as his life’s new mission (after resuscitation of course…) to ensure he would never have to regret them for real.

Death modelling

I admired Phil’s decision to dedicate his life to pursuing would-be regrets and many others, like Jeff Bezos, use a similar regret minimisation framework to work out how to allocate the time.

The only problem was I wasn’t really sure what I would regret the most.

I needed a near-death experience to force it out of me. Sadly these are hard to come by (without actually dying), so I opted for modelling a near-death experience instead:

Imagine you’re about to die.

Get on your knees. put your hands on your head, imagine there’s a gun to your ear. You tense up, start panting intensely. Take a few minutes to really get into it. Now feel the cold steel against your auricle, the thunderous roar of the bullet…and complete the sentence: “I just wish I’d…”

For me, a bunch of interesting things popped up.

Turns out I would wish I had trained harder to make the Cambridge Varsity boxing team, visited my childhood art teacher to thank her for all her help and gone over to India to spend time with my family. (Amongst other things.)

So I’ve now reprioritised my life to minimise these regrets and pursue these wishes (ordered by emotional intensity of regret).

Used in this way, regret can be a powerful mechanism to direct us towards our most meaningful pursuits in life.

Why regret?

The randomness of my near-death regret/wish list got me thinking about why I regretted certain things more intensely than others.

Why do I feel so obliged to see my childhood art teacher and make the varsity team? Why not hike Mt Everest or fly to space? (Also on the list…)

And for me, I think it comes down to two factors:

  1. Fear: I regret most intensely things that I didn’t do because of fear. When I chose to go to LSE over Cambridge, that was fear of not being good enough to hack it with a bunch of Cambridge nerds. Training for the Cambridge Varsity boxing team is the same thing: there’s this fear that I won’t be good enough, that I’ll get injured again etc. And when you don’t do something you know you should have because fear held you back…that turns into deep regret.
  2. Guilt: I also regret things I feel guilty over. Not thanking my art teacher is something I’ve felt guilty about for so long and to die without her knowing how much her support meant to me…the guilt would eat me up and, again, manifest as deep-seated regret.

Dealing with regret

So that’s where my sentiments of regret comes from, and it’s not all bad.

Regret tells us we’ve made an erroneous decision so we can at least course-correct our futures…but sometimes regret can spiral out of control.

We can spend days rolled up in carpet, cuddling a bottle of whisky, wishing we had chosen differently and fantasising about the life that could’ve been but never will.

This is unhealthy. Obviously. And in times like this it’s important to extract the valuable lesson (e.g. in the future, don’t let fear hold you back from pursuing a goal)…but then accept what happened, and more importantly: accept the person you were who made that decision.

Whatever regret-inducing decision you made 10 years ago, 10 days ago, 10 seconds ago, you can’t change that and you couldn’t have made any other decision because you were the person you were back then. Now you’re a different person who can make better decisions, but don’t get angry at your past self for making a bad decision – that past self couldn’t have made any other decision, he/she was too scared, too lazy, or too poorly informed.

There are 1000s of things I could’ve changed and improved while a child for instance – playing sport, practising piano, reading more. But I just didn’t have the ability to make those decisions back then. And I don’t regret any of those things, they were out of my control and now in the past.

Accept. Learn. Move on.

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