Analyzing Regret and its World of Assumptions.
Much like how people wear the "I work 100hrs a week" as a badge of self-validation, having "no regrets" in life is becoming something similar.
Is it possible for someone to have lived life with 0 regrets?
Sure.
Let's say a single decision follows this tree:
A fuck-up is when you learn from acting. Regret is when you learn from not acting.
The movement to embrace and even celebrate fuck-ups seems to be alive and well. At least in Toronto, we have a team of wonderful people who help share such learnings and culture.
Fuck-ups are fine and well in the hands of the popular social movement. I mean, I'd say it's commonplace enough to share fuck-ups, failures, mistakes as early as job interviews, bars, etc... Even on my podcasts, I ask that question to my guests.
When Do I Share Regrets?
What doesn't seem to get shared until much later, maybe as late as the death bed, are regrets. Maybe it's because you can't hide fuck-ups as easily since it actually happened.... whereas a regret.. well.. you didn't act on it so no one is the wiser. It can stay as the secret locked inside your mind.
It's at least been a realization for me. Mistakes are so plain as day but regrets just seem to lag in the back of mind and come up here and then but I can just push it down. Just like what dudes are taught to do with feelings.
Why Aren't Regrets Embraced?
I realized that I don't tend to embrace any regrets. Maybe it's because I'm conditioned to think they're dirty. I mean, if they weren't so dirty.. then why is it that people share regrets closer to their final moments like some confession to a priest?
Maybe a regret just feels dirtier because to have made a mistake... you did something... but a regret... you were just on the sideline. You weren't the "man in the arena". No honour there. Just some movie critic screaming on the sidelines. A mistake at least has some satisfaction with knowing. But regret... it's plagued with rosy assumptions of a life not lived. Just the wonderments of 'what could've been."
But even Jeff Bezos probably has regrets. He has a regret minimization framework. Not a 0 regret framework. He's a smart guy and successful in many parameters so if he is any example, I'd say having regrets are normal.
So I thought about digging into the regrets. The ones that plague my mind in moments of silence.
The Biggest Regret that Plagues My Mind
The one that randomly pops up like some uninvited guest are the missed investments.
The ones where if I had put in a decent amount of my capital in where I would be a millionaire right now. I don't know about most people but I know that $5M is plenty enough for me to live a comfortable life and there have been two specific stocks where if I had put in materially more than I initially had.... well then I would've achieved a form of financial freedom.
Of course, I understand one can't look at them that way. But life is just so different when you experience it vs. when you read about it.
When I initially invested, there were reasons why I didn't bet the house. Given the information available, the decision process made sense then. The prudent thing is to look at it as an independent decision and proceed. But oh man does it nag at you.
I'm sure there are investment books and pundits who'd say it's a waste to regret such situations. And good for them. But, like advice, they aren't living my life so it really doesn't matter what they think or believe. I felt that there seemed to be more than just the investment piece.
Instead, I decided to look deeper into this regret and actually play it out. Kind of like writing a novel with an alternate universe.
This exercise is not too dissimilar from crafting out what I would do if I had financial freedom. Maybe it's because at this current point in writing this piece, the financial peace is top of mind for me.
Regardless, I began to construct the world. Listing out what I imagined myself doing, how I'm spending my time etc.. The immediate world. How the days would look.
The result was quite dull. It constructed of a number of things the money could do like helping my parents financially, constructing my fund, taking my family on vacations.. but also ones that didn't necessarily 'need' the money like starting more podcasts, studying abroad, etc...
Even with the hindsight knowledge of what the stock price became, this world I'm imagining was full of assumptions. Assumptions made with an imagination limited by the set of experiences and learnings I had in my head.
Slowly, the money became distant. It began to hold a view of a world filled with sets of assumptions. The world of imaginations and things I 'think' I'd do. Things I imagine wanting to do. Sure, somethings may require the money I imagine having but there are plenty of things that don't. The latter presented assumptions for testing.
That's how regret... when examined.... could create opportunities.
By the End of It, Many Things Happened
One is that I obtained a little bit of peace. Not that I'm at peace with missing the opportunity. But a little bit of peace is obtained for the present because I have a set of assumptions to test now. Though it's painful at times that we can't reverse time (if only...) pragmatism can take root when the present can be used to test assumptions. Either I will achieve states I had hoped to achieve (hence null-ing the regret) or I realize I wouldn't have even enjoyed that outcome anyways (again.. null-ing the regret).
Another big revelation for me is to be more patient. To be more patient in forming relationships and trust. Though it's been easier to hold stocks for 4-5 years, I've come to realize this mentality has become harder with the current part of my career. Maybe it's because I see it every day... like someone staring at a stock chart. No good can come of the latter and well, the way I work with the former seems to be doing exercises such as this.
I would say that what I have going on now is continuously testing those assumptions but as it's not easy going... sometimes I need to re-do the exercises to re-align my state of mind. Sometimes, other new assumptions arise with the new things I've learned and experienced in life since the last exercise.
The hope here is that over time, the nagging regret will fade after enough assumptions related to it are tested. Then a new one will probably appear. Like always, there will probably be one that dominates my subconscious and pops into my mind as my mind wanders.
Then the process will repeat and I'll try to dig deeper into it and reflect on the assumptions this new regret carries.
It seems to be something of an unending cycle. An uncomfortable cycle at times. But, like many things that make us uncomfortable, I think leaning into it can reveal assumptions worth testing.