If only you could be so lucky as to feel regret
regret maximization
I was getting dinner with a friend the other day who is entering a “transitionary period” in her career, and exploring a lot of existential questions about what to do next. Early in your career you have a lot of options in what to optimize your life around – money, career progress, settling down, exploring, enjoying your life. There’s a reason it’s called The Defining Decade – it really is the first decade (in our current social order) in which you have significant latitude to define what you want your life to be about.
A central theme of our conversation was regret. This friend of mine has an older friend, who is in his thirties, let’s call him Bob. Bob optimized for one kind of life – one that involves freedom and exploring his passions, at the cost of being less financially secure than his peers. Several of his friends own homes now, while he is still living with roommates. Bob wonders, when he visits the homes of his friends, and sees how Nice and Established their lives are, whether he’s made the Right Decisions.
In the past few months I’ve faced similar questions about what I want my life to look like long-term. I recently had a call with an old coworker who is in his late thirties to talk about this. What stood out to me about what he said is that “the 30s is the decade of regrets.” Pretty much everyone he knows regrets something about the life decisions they made. Some people regret working too hard and not enjoying life enough, other people regret neglecting their career and putting themselves in a precarious financial position. My mentor said he feels a little bit of both.
What I’ve begun to wonder over the course of having all of these conversations is whether regret might actually be fine. Not just inevitable but like, a good thing, actually. There are so many things that have to be true for you to feel regret about your life choices. You need to have lived for long enough to have made major decisions and observed their ramifications for your life. Not everyone actually gets to do that! Not only that, but if you are in a position where you feel regret, that actually means things are going well for you, for the most part. You have enough open time and space to reflect on decisions years in the past. When you are in the middle of an emergency—like war or illness or imminent death—regret about your career decisions in your twenties will be the last thing on your mind.
For some people, anticipated regret is a prison. And by some people, I mean me. I don’t know what it is exactly, but I’ve always had this tendency of taking responsibility for everything that happens in my life and believing that if I had planned things better, everything would be fine. In my first few years out of college, I was frustrated and lonely in New York, and I kept blaming myself for having chosen to move to New York where I had very few friends. (Incidentally, when I finally accepted where I was, I started making a lot more friends.)
I’ve had similar-shaped conundrums with relationships, friendships, career decisions, pretty much every decision you can imagine. I make a major decision, and then within a few months I blame myself (and the decision) for anything that hasn’t gone perfectly. There is a character in my head constantly waiting to say “oh my god you completely messed it up and if you had just done this one thing differently everything would be different and you should have known about this.”
This pattern has repeated enough times that now I am able to see it for what it is: a refusal to accept that I cannot control everything. A refusal to just accept things as they are. If I stop fixating on “this thing that happened in the past,” then I will have no choice to face The Unbearable Brightness of Right Now, which is way too bright most of the time. I have been breaking free of this pattern though. I don’t wallow in regret nearly as much as I did five years ago.
Feeling regret just means you’re conscientious and have enough open space to consider “what ifs.” I think of it as reflective of your personality more than the quality of your actual decisions. People often talk about it as, you regret certain things and not others, but I honestly don’t think I have ever made a big decision that I did not question at least once.
The only way out of the kind of regret I’m talking about is reduced self-absorption. There is a grief in all the things you didn’t do, and the mistakes you made, the times you didn’t say “I love you,” and so on. But that grief does not have to stick onto you and take over your life. That is a choice you are always free to make. To embrace the ways that things went wrong, and look beyond yourself.
This is close to things I ponder. Here's where I have settled and for reference I do also see regret as an incredible phenomenon that we all are lucky to get to have, just as we are lucky to get to die. As for regret, I have reasoned there are a million and one ways to regret any particular decision, because I have no control over the final outcome of things. The only variable I have any control over is me, and a strong argument can be made that I don't even have control of that, none of us do. Our brains make decisions "behind our backs" all the time. So what I do is that I just accept regret of some form is possible and make whatever decision that minimizes my feeling of it. Which will I regret more: proposing to her or not proposing? Applying to that school or not? Creating a start-up or not? Accepting this job offer, moving to this far off place, strengthening this relationship, getting the serious surgery, buy a house, etc.,...or not? When I come to crossroads I select the path I forecast as reasonably as possible will produce the least amount of regret. That's a rule of thumb that has worked more times than not for me but it does take self-knowledge and moreover a complete and total willingness to accept any outcome at all once the die is cast. In other words, to draw the sword at the decisive moment of truth already completely ready to die in battle. The not knowing is absolutely part of the process, it is part of the fun of being alive.
Great piece! Here's what I tell myself: You cannot know everything and will never know everything. Wisdom is not a static state but an ongoing process. All the decisions you make are the most coherent one you could've done given your psychic constitution and circumstances at that point in time (it's no bad parts all the way down). Regrets matter in-so-far as it helps shape a wiser, more congruent, more whole self and decisions in the present, so change the you right here right now. Lamenting the past while not doing anything about you right now is to place the burden of change on a you that can fundamentally never be changed, which is a way to avoid ever taking real responsibility. Failure is a felt result of when the finite you comes in dynamic, alive contact with the infinite this. To not fail is to be brittle, inert, and dead.
This reminds me of this idea that the genie produces disastrous results because it's taking the shortest path possible / least levers pulled to the end goal - you wish for wealth and both sets of your grandparents die and you get their inheritance money, and so on.
To have the genie produce the perfect result would require accounting for all of the possible factors in the universe, which is to say that it would be impossible. Perfection isn't something fully grokkable by us, much less reachable, and our noble nature is to strive towards it and inevitably fall short, and then do it again anyway. Given this, failure is inevitable, shortcoming is inevitable, the no-longer-having of the good situation or thing is inevitable.
What matters, it seems to me, is if I can remain grounded in and intimately with the messiness of living, while I continue to be pulled towards the infinite, driven not from a fear of failure but by a love for it, for how I ceaselessly become transformed by being in touch with it.