The key to taking long term decisions

Intellectual Banter: Episode #17

Jul 31, 2022

Welcome to the 10 new members of our tribe who have joined us since last week. If you’re new or missed the last edition, catch up here. And thank you for giving me your time, I appreciate it.

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Greetings, my friends!

Quick personal update: my wife and I’ll be on our way to the hospital tomorrow for our kid’s arrival. Kid’s a bit shy, so we’re gonna have to give “it” a little nudge. It’s also punctual and arriving right on time (very good, kid).

On my mind

Everyone optimizes for pain avoidance.

It’s their primary decision making metric. And I get it, it hurts. So why not?

Cause it sucks.

It’s short sighted (focused literally on the next moment). And you’ll never be able to avoid feeling pain anyways. So as far as decision making models go, it’s horrible.

So what’s a better model to use?

Regret minimization.

Regret is useless as a feeling to cling to. It paralyzes you, makes you mope all day long. And then no one wants to hang out with you.

But it’s excellent as a mental model to review difficult decisions. Especially the ones you ignore and silently hope “sort themselves out”. Minimizing regret is delayed gratification personified. Because pain stings in the moment, but regret lasts forever.

It’s how I decided to leave my job and pursue writing online.

I’d worked in banking for 9 years. I didn’t enjoy it. And was tired of shrugging my shoulders in defeat whenever someone asked me “how’s it going?”. I had money saved up and an earning spouse. And life wasn’t really stopping while I made my decision.

So I took the call to pursue what I would least regret 50 years later (trust me, that time will come).

Here’s what you do:

Back then I just visualized being 80 years old, looking back at my life and asking - “will I regret NOT doing it?”. The answer was fuck yes! So I took the call.

Since then I’ve lived with that decision for 7 months and also read more on this topic. So let me add nuance to it:

1. Don’t be rash: After deciding, make a plan. I didn’t get up one day and say “screw you, I’m leaving!”. I decided, then prepared to leave my job. And made an outline of what I would do (which is this). There’s no bravery in stupidity.

2. Be aware of survivorship bias: Successful people often justify their risky decisions in hindsight. But there’s more randomness in life than you’d like to accept. Doesn’t mean you should stay locked up in your cupboard. Just be aware.

3. Focus on principles you won’t regret pursuing: What drives you? Is it stability for your family or creating a legacy? Neither option is “right”, just different. (H/t: Sahil Bloom)

4. Use a time machine: Use an age progression filter on your photo and paste it in front of where you work. It’ll serve as a daily reminder to your mind. Helps deal with uncertainty and “why TF am I doing this again?!”. (H/t: Derek Sivers)

7 months into my journey, I have zero regrets.

That doesn’t mean it’s been a joy ride the entire time. It’s fucking hard at times and I have to deal with my untrained monkey mind (shhhh!). Face self-doubt and push through a lot.

But it’s a pain I chose.

And I know when my time comes, I will not regret having taken this call.

Un-chuckle worthy quote

To maximize your long-term happiness, prioritize projects you’d most regret not having pursued by the time you’re old and looking back at your life. - Julian Shapiro

Serve your future self, not your present.