Your Life Should Be Optimized To Limit Future Regrets
At the beginning of 2021, I moved willingly into the dark. I quit my full-time job to write a movie with my wife.
It’s going to be a while before I know the outcome of that decision. But for me, the decision was an obvious one.
My wife and I were presented with a positive black swan opportunity (a rare opportunity with massive upside) with a well-known movie producer. I knew that if I didn’t give it all of my attention - my best creative hours - I would regret it for the rest of my life.
So I quit my 9-5 to work on the script instead.
Minimizing regret turns out to be a very strong incentive for change. Some of the greatest entrepreneurs of all time use it to guide their decisions.
The 80-Year-Old Test.
When a young Jeff Bezos went to his boss to tell him about his plans for an internet book store, his boss told him that, while he thought it was a good idea, “I think this would be an even better idea for somebody that didn't already have a good job.”
The pull of a “good job” is one I know well. I’ve been fortunate to be fully employed since I graduated from university with good jobs and good bosses.
But for the last handful of years, I knew, at some point, I wanted to try and build something of my own. I just had to decide what to pursue.
Bezos has a model for these kinds of decisions - what I’ll call the “80-year-old-test.” It’s not a test of the head, but one of the heart.
Here’s Bezos explaining his decision to quit his job and start Amazon:
“For me, the best way to think about it was to project myself forward to age 80 and say, ‘Look, when I'm 80-years-old, I want to have minimized the number of regrets that I have.’ I don't want to be 80-years-old and in a quiet moment of reflection, thinking back over my life, and cataloging a bunch of major regrets.
If it failed, fine. I would be very proud of the fact when I'm 80 that I tried. And I also knew that it would always haunt me if I didn't try. And so that would be a regret, it would be 100 percent chance of regret if I didn't try and basically a zero percent chance of regret if I tried and failed. That's a useful metric for any important life decision.”
I’m in the same boat now that Bezos was in at 30. I’m looking straight at an opportunity that I know my 80-year-old self will regret not going after.
So, I’m going after it. If it fails and I can’t sell the movie, so be it. I tried. Old Thomas will thank me for trying. And if it succeeds, it’s a launching pad to bigger and better things under my own name. I win either way.
Most Regrets are Ones of Omission, Not Commission.
Charlie Munger speaks about the kinds of mistakes he and Warren Buffett have made over the years at Berkshire Hathaway. Most of them are regrets of omission, not commission.
In other words, it’s the things they didn’t do that keep them up at night, not the things they tried to do that failed.
Here’s Munger explaining this during a Q&A at the 2001 Berkshire Hathaway annual meeting:
“The mistakes that have been most extreme in Berkshire's history are mistakes of omission. They don't show up in our figures. They show up in opportunity costs. In other words, we have opportunities, we almost do it. In retrospect, we can tell that we were very much mistaken not to do it...
But practically everywhere in life, and in corporate life, too, what really costs, in comparison with what easily might have been, are the blown opportunities. I mean, it just... it's an awesome amount of money.”
You’ll also find regret in knowing what to do, but not going far enough in doing it. For Buffett, stepping a toe in the water when you know you should dive in is almost more painful than doing nothing.
That’s what I feel about writing this movie. I could have written it with my wife while working full time. But it wouldn’t have my full attention, and these rare opportunities with massive upside deserve your full attention.
Here’s Bezos echoing Munger’s sentiment:
“In most cases our biggest regrets turn out to be acts of omission. It's paths not taken and they haunt us. We wonder what would have happened. I knew that when I'm 80, I would never regret trying this thing that I was super excited about and it failing.”
Trying and failing is not the problem. It’s not trying at all that leaves you burned.
Swing At The Fat Pitch, Not Every Pitch.
This does not mean you go after every opportunity that comes your way. You must be very selective in choosing what to work on.
In Buffett terms, you only “swing at the fat pitch” - the big opportunity that’s entirely in your circle of competence. Go after only the asymmetric opportunities with much greater upside than downside that you understand and that if you miss on your swing, you survive to play again. Be selective.
Here’s Buffett explaining that errors of omission are only errors when they occur inside your circle of competence:
“When we speak of errors of omission, of which we've had plenty, and some very big ones, we don't mean not buying some stock where... a friend runs it, or we know the name and it went from one to 100. That's doesn't mean anything.
We only regard errors as being things that are within our circle of competence… An error is when it's something we understand, and we stand there and stare at it, and we don't do anything. Or worse yet, what really gets me is when we do something very small with it. We do an eyedropper's worth of it, when it could do it very big... Those are huge mistakes.”
The script I’m writing is in my circle of competence. I’ve had a decade of experience in the entertainment industry, and the timing of this particular project couldn’t be better. Plus, we’ve already generated significant interest based on the treatment (a 10-page document detailing the plot and characters) and attached a massively successful producer.
I didn’t quit on a whim. I have resources, back-up plans, and options if things don’t work out. No decision is perfect. Success is never guaranteed. All we can do is make the best choices we can with the limited information we have.
I will keep everyone updated as much as I can in the coming months. I don’t know what will happen, but I sleep easy because, win or loss, I won’t carry this regret on my death bed.
And that’s all that matters.