why the past seems never enough

tl;dr it’s super dumb that our future selves has to inherit the shitty decisions of our past selves

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Part of me believes that if I had the discipline and ambition that I have now when I first went to college, I might have ended up a lot more successful than I am right now. I might have founded a startup that has just received Series B funding (or at least tried to start a startup) instead of doing whatever I did in college that ended up with me doing what I am doing now. It’s not bitterness, just longing.

Then I remember that I actually was quite ambitious when I went to college. I had a lot of plans, although the plans back then are somewhat different from the plans that I have now. I wanted to go into medicine or public policy or something. I didn’t get too far because I wasn’t particularly good at following through with things I was interested in, ranging from reaching out to professors for research opportunities, to scheduling a date from a flirtationship, to transitioning acquaintances to friends. It’s not my life didn’t end up the way I wanted — it’s just that I wish I had done more early and made more mistakes early, so I could’ve become a stronger person at an earlier age to accomplish more today. What I lacked back then — and what I still lack to a certain extent — was resourcefulness and ambition.

There’s this John Legend interview that I watched a little while ago that really changed how I thought about my relationship with writing. He talked about how detachment may momentarily satisfying on a social and personal level (i.e. I am too cool for xyz), but passion gets us a lot further in life. It wasn’t that I was absolutely detached from pursuing anything, but I did allow my passions to be shielded by a layer of detachment. In many ways, I feel like I use my career as a shield to protect me from acknowledging how little progress I have made with my passions. I have not published anything that seriously took dedication. All that I have to show for my writing is a trail of blogposts requiring minimal editing and published on the first draft. My music is even more behind because I didn’t decide to seriously pursue it until recently.

The thing is pursuing passion requires the possibility of failure on an existential level. If you pursue your career, at least you’ll get somewhere at the end of the day even if you don’t end up where you want to be. If you pursue your passion, you could try the hardest you ever could and still fail. When you prioritize your career, then you can check a lot of boxes for things that typically indicate success like financial independence and stability. When you prioritize your passions (assuming your passions aren’t career-driven) then there’s a chance you could be catapulted into public life as a D-list celebrity, but then there’s also the chance that you could end up with nothing. You could devote your entire life to your passions and have no traditional markers of success to show for it.

I think the objective of life is to understand what you want to do at an early age and then follow through with it. Oftentimes in life, our regret falls into two camps:

1. Regret for now pursuing something soon enough
2. Regret for not pursuing something hard enough

There’s always room to start something, but the depth at which you can reach greatly deteriorates the less time you have to follow through on your plans. I was thinking a lot about high school lately, how I wanted to go into medicine without entirely understanding what I was getting myself into, what sacrifices I would have to make, and what else would be available in the world if I didn’t. Eventually, I did figure out that I didn’t want to practice medicine, but in reflection, it took me a lot longer than I wanted. It was time I could’ve used to pursue writing or music instead.

One of my friends told me a while back that she wished they knew what college to wanted to go to when she first got accepted into college. Instead, she had to find out the hard way: by going to college and realizing that the culture did not fit, and then transferring out. At the time, my immediate response was that I was jealous of her. Transferring colleges is like having double the college experience. You have your college experience in one college, and then you have a different college experience in another college. She didn’t see it that way, and I think that taps into something really intrinsic about human nature — that the experience we have had is never enough. When we take our life in one direction, there is another way our lives could’ve gone. We yearn for the fantasy we created from a different life to compare to the dullness of the life that happened.

When I was in college I was doing a local maximization. I had a limited set of knowledge back then, and the choices I made back then were subject to my limited abilities back then.

The thing about immaturity is that nothing seems immature until you reach maturity. It exists in another dimension because we are unable to access our immature selves when we reach maturity. Things seemed a lot more difficult when we were younger because they were. I consider high school the hardest time I’ve ever worked in my life because it was the hardest I’ve ever worked. It was not because it was the most I’ve worked — my 70-hour workweek paired with my part-time Master’s program paired with studying for the CFA ensures that this part of my life is the most I’ve ever worked — but most does not mean hardest. In high school, I was a lot less capable than I am now, and that lack of capability made seemingly easy tasks now a lot more difficult than they should’ve been.

Academically, I worked a lot, but this does not mean that I had the grades to prove it. My studying was not nearly as efficient and focused as it is right now, and it all seems like a waste of time in reflection. I think that might be one difficult part of parenting. It’s hard to explain to kids how lazy they are until they become adults. No matter how much kids think they work, they will never compare to the work ethics of their adult selves. Studying in high school < studying in college, any day of the week.

Socially, I found it a lot harder to make friends and hold conversations than I do now. At a certain point in life, we learn how to feign interest in what other people are saying; this came to me slightly later than it did for most people. It’s weird to think about because I have access to a completely different personality now than I did in the past, but there was a point in my life when I was uncomfortable reaching out to strangers, uncomfortable raising my hand in class, uncomfortable asking people out for coffee or lunch. I can’t describe how I justified to myself now, but if I asked my past self he would have a reason for it. But since this old version of myself has died, all I am left with are the consequences of my older self. He was the one that made the set of decisions that led to my current life. Now, I am the one that has to live with the life he has left me.

But the old Taylor can’t come to the phone right now
Why? Oh, ’cause she’s dead 

Taylor Swift, Look What You Made Me Do

Whenever we make a decision, we make a decision based on the information we have at the time, paired with some emotional factors from environmental circumstances. Things only make sense in retrospect because we are presented with additional information that gives us a more complete image of the life we chose. Because we could never amount to the same capability we have now when we are younger, the past always seems never enough. As long as our future selves accumulate the experience and development our past selves never had, it always will seem like our past selves never lived up to their potential.