How to minimise regrets


Hey friends,

I got an email a few days ago from a high school student in the Philippines (let’s call him Matt) considering applying to medical school. He was worried because it’s such a competitive process – what if he spends years trying and failing to get in? If that were to happen, he would have ‘wasted’ those years of his life.

Jeff Bezos (the founder of Amazon) has a system for decision-making that he calls his Regret Minimisation Framework (yep, seriously). He wants to make decisions in such a way that when he’s 80 years old and looking back on his life, he has as few regrets as possible.

In Jeff’s case, this framework told him that he should probably leave his job at a well-paying hedge fund and start a book store on this thing called The Internet. Had he not done so, he would have regretted not trying.

I like to have this in the back of my mind when making decisions, but there’s another important aspect of minimising regret that I like to call the Win-Win Principle.

The Win-Win Principle

The Win-Win Principle states that whenever we’re trying something new or risky, we should design it so that we win even if we lose. Tim Ferriss did this when setting up his podcast. Even if the podcast flopped, he would have still ‘won’, because he’d have learned audio production and how to be be a better interviewer. His podcast, incidentally, is now one of the most popular in the world (and one of my all-time favourites).

Matt can apply the Win-Win Principle to his conundrum of applying to medical school. Firstly, of course, he should do everything he can to maximise his chances (good grades, reading around the subject, work experience, extra-curricular activities etc). Then even if he doesn’t get in and has to take a gap year, he can use that year to work on his own projects, try out new hobbies, read more books, level-up skills. That’s a year of growth that everyone who got in to medical school that year will be missing out on, because they’ll be spending that time memorising pointless things like the Kreb’s cycle.

So to answer Matt’s question in a roundabout way, he should definitely apply to medical school if that’s what he wants to do, because if he didn’t, he would regret it later in life. And he should work on other stuff alongside his application so that even if he misses out on a place, he’ll still have ‘won’ in his own way.

This way of thinking makes most risky decisions a lot less risky. We can always find a way to turn a loss into a learning experience. We can choose to build systems that mean we win, even if we lose. And if we do this consistently, we might even find that our apparent ‘failures’ set us up for even bigger successes later in life.

Have a great week!


PS: I’m going to do a 100k subscribers Q&A video soon. Normally I ask for questions via Instagram and YouTube but this time I’ll put it to this email list – do you have any questions you’d like to ask?

PPS: As much as I LOVE getting questions about specific grade requirements to study Medicine at Cambridge, or what scholarships are available for international students to study Medicine at Cambridge, I’ll probably prioritise questions where the answer would benefit a broader audience 😉

Stuff I’ve been enjoying this week

(1) A great video about jealousy – Anna Akana

I was going to write an email about this at some point, but this video says everything I would’ve wanted in a wonderfully entertaining way.

(2) My new favourite YouTube channel – Becki and Chris

The branding + personality + amount of effort that goes into each video is incredible. These guys are legit YouTube + couple goals. Also, their interior design is to die for.

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