"I don't believe in regrets," some people say, "because my mistakes are what made me who I am."
Yes, obviously, duh. We don’t get to go back and redo anything so it is a waste of emotional energy to dwell on the past.
But this can be taken too far. If we never reflect on our past choices then we run the risk of hurtling blindly through the void and learning nothing. If we never allow ourselves to regret dumb choices then we cut off a vital source of feedback in our lives.
Regret is the mechanism by which we learn from our mistakes. Rumination is the mechanism by which we drown in our mistakes.
We all make mistakes. We hurt other people. We hurt themselves. We miss out on golden opportunities because we're scared, and we sabotage our own dreams and visions. We make poor decisions because we don't understand ourselves enough to make better decisions. Humans do regret-worthy things all the time and we shouldn't be afraid of admitting it.
Now, getting sucked into negative downspiraling rumination upon our failures is toxic, of course. But there is a middle ground between shoegazing our way into our early graves and blithely skipping through the world refusing to look back and learn the most basic lessons from our choices. Toxic positivity is a thing.
The dumbest argument against regretting life choices is the one that goes ‘well if I hadn’t made that decision then maybe my life somehow would have wound up really different in a bad way, so I never regret my choices.’ This is the idea that you back to fix one small thing and accidentally trigger WWIII, or your personal-life equivalent. This argument only bears weight if you actually have a time machine and are considering going back and fiddling with your past.
If I had a time machine, would I go back and make different choices? Absolutely not! My life now is awesome and there’s no way I’d risk screwing it up.
But, and this is a key point many people overlook, time machines aren’t real.
Temporal iatrogenesis is a lame excuse for not allowing ourselves to experience the emotion of regret.
For example, I regret how much time and energy I dumped into projects at work, half of which I can't even remember and several of which never got built. I’m not going to spend a moment fantasizing about having made a different decision, but I am going to accept and use my regret to not be a workaholic in my present.
I can't go back and change these choices I made. But I can think through why I have these feelings of regret, I can imagine what I wish I'd done instead, and I can apply these lessons to my life going forward. If I don't process my regret I'm liable to make the same mistakes again, or rebound too far in the opposite direction because I’m not tempering my emotions with good strategy.
So with all that said, I think the exercise of thinking about what advice I'd give to my younger self is worthwhile. I believe this strongly enough to be writing a book on it, in fact, which I’m probably going to have ready to publish this Fall. I mean winter. Spring 2024?
A few days ago I was wading through the twelfth revision of a chapter and felt like I needed to zoom out a bit. It's all well and good to dump 40,000 words at the question, but what if I could only write a letter? What if instead of going back and having a long conversation with my younger self, I could only send a long email?
So I did that. Here it is:
Dear 25yo Self,
Hi, this is your older self. I'm 37 now, twelve years older than you.
This advice I'm about to give you is not an admonishment for not having figured life out sooner. Most people don't even try very hard. That's actually what I love most about you: you never, not once, for any length of time longer than it takes to get over a hangover, have stopped trying to figure life out. Even when it seems like there's no point to it you keep cranking. I love that about you. I think its badass. There are few things more courageous than trying to make sense out of this bullshit soup we call existence.
You're about to get stuck, though. I'm cool with you making some mistakes, but you get stuck in some real eddies in the flow of life and you just thrash around for years. I hope with this letter to give you the tools you need to kick yourself out.
Here’s the thing. You find it validating to be needed. You find it more validating to be needed than to pursue your own dreams. The validation hits you get from fixing and from being the dumpster fire putter-outer are an addiction. The hits make you feel like there's meaning to life, like your existence is justified....
...in the short term. The effect wears off quickly, and you'll need another hit. You are like a rat in a cage hitting a lever over and over again to stave off the pain of floating alone in the void. You need to learn how to float alone in the void.
This is all unconscious for you at this point. You'll make decisions now that don't make a lot of sense to you. This framework I'm laying out is the best fit model for why you made those decisions.
And nothing else is more important for you to fix. This dynamic is the primary blockage, the root cause for you bashing your head against a brick wall for the next several years. Getting through it will be painful, but maybe with this letter I can help make the process shorter for you than it was for me. Stick with me here. Everything I'm going to say relates to this.
You need autonomy. You need to get clean, you need time and space away from the cotton candy crack of validation hits. Go to all the therapy you want, but if you're in an environment where the validation hits are right there being pushed at you from all directions you're not going to get far. Imagine trying to quit alcohol as an addict but the fridge is full of beer. You need to be able to put miles and years between you and your favorite sources of validation.
Your sources of validation are women and work. You find women who you think need your help, and you find employment where it feels like only you can keep the thing afloat. These are lies, of course: these women don't need you any more than those jobs need you to keep things running. But it feels that way, and you find women who are happy to indulge your fixes and rescues and you find jobs that don't mind you pulling all-nighters and putting in eighty hour weeks, and this maintains the fiction necessary to keep the flow of validation hits coming.
You need to be solo and you need to not have any kind of job. You need this space so that you can face the dragon of what it means to not have constant sources of external validation flowing in.
The detox is going to be rough, bud, there's no other way to put it. The validation hits from women and work is how you convince yourself that it's all right for you to exist.
But there is an end to it, or rather, the path goes through darkness but there is light on the other side and the path keeps going. There is no destination, you know that already, but you can get to more interesting parts of the path.
You need to be solo and you need to not have any kind of job for a spell so that you can learn to put your own two feet on the ground, so that you can learn that you - just you, alone - are enough, that you deserve to live here on this rock as much as the next guy, so that you can learn to love yourself.
Do this, and you won't need the validation hits any more. Do this, and you can have relationships with people as an individual, you can give them your gifts and you can receive theirs. You can get involved in vocations and projects that aren't about flattering your ego by demonstrating the size of dumpster fire you're capable of extinguishing.
You can unclench your fist from the world and as a consequence be flooded in wonder at it.
Here’s how to actually do it.
1. An extreme low cost of living (CoL) is magic. It's the key to everything. By extreme low CoL I mean a four-digit burn rate, all right? Anything under $10k a year. I know that sounds insane but it's actually no, not for you. Figure out how to live well off of less than ten k and the world becomes easy. It's easy to earn enough money to live off of when you spend barely any of it.
2. Learn to 'throw competence at it, not money' [Vicki Robins]. QoL =f($,skills). Most people think QoL=f($). This is only true if (skills) are held constant across the data set. The more appropriate skills you have, the higher QoL you can have for less money. So by "spend less than ten k a year" I'm not telling you to live in a cardboard box under the overpass. I'm telling you to pursue the skills necessary to live a life you are psyched on while spending almost no money. (PS by skills I also mean social skills, not just the ability to adjust a carburetor or cook a meal.)
3. Build up your FU stash. Right now you're at close to zero NW. I screwed up at this point. I indulged in lifestyle inflation. I carried five figure consumer debt for years starting right about where you are now at age 25. Unimaginably stupid, yet so common. Do not do this. With a very low CoL and a regular paycheck you can be building up a buffer of money quickly. You can be saving seven years of living expenses every year of work, all right? Do that! Duh!
4. At some point in the next few years, quit and do anything else. Maybe you'll build up to 30x and never have to money again, maybe you'll build up to 10x and punch out. Either is fine, there’s no one right choice. Do whatever you like. I recommend slow-traveling the world for a few years. As long as your CoL remains super low your options are enormous. But you need a period of time where you aren't working for anyone else. If you do 'work', you can build stuff on spec and if anyone wants to buy it from you, cool. But you cannot have clients or bosses.
5. After a few years of adjusting to autonomy, you’ll figure out what to do with the rest of your life. I don’t have any advice for you other than you’ll figure it out as you go along, and it’s probably impossible to plan ahead for. Right now just focus on leveraging your privilege to gain autonomy from The Machine so you can do something interesting with yourself. The most irresponsible thing you can do with your privilege is waste it following rules that benefit the status quo so, like, don’t.
Good luck.