First conclusions from reflections on my life

I spent some time over the past weekend reflecting on my life, over the past few years. 

I turned 28 a few months ago. The idea was that I wanted to reflect on what I’ve learned from my 20s, but do it a few years early, so that I can start doing better sooner rather than later. (In general, I think doing post mortems before a project has ended is underutilized.) 

I spent far less time than I had hoped. I budgeted 2 and a half days free from external distractions, but ended up largely overwhelmed by a major internal distraction. I might or might not do more thinking here, but for starters, here are some of my conclusions.

For now I’m going to focus on my specific regrets: things that I wish I had done differently, because I would be in a better place now if I had done them. There are plenty of things that I was wrong about, or mistakes that I made, which I don’t have a sense of disappointment in my heart about, because those mistakes were the sort of thing that either did or could have help propel me forward. But of the things I list here, all of these held me back. I am worse today than I might have been, in a very tangible-to-me way, because of these errors.

I wish that I had made more things

I wish that, when I look over my life from this vantage point, that it was “fuller”, that I could see more things that I accomplished, more specific value that my efforts produced.

I spent huge swaths of time thinking about a bunch of different things over the years, or planning / taking steps on various projects, but they rarely reached fruition. Like most people, I think, My history is littered with places where I started putting effort into something, but now have nothing to show for it.

This seems like a huge waste. 

I was looking through some really rough blog posts that I wrote in 2019 (for instance, this one, which rather than being any refined theory, is closer to a post mortem on a particular afternoon of work). And to my surprise, they were concretely helpful to me, more helpful to me than any blog post that I’ve read by someone else in a while. Past-Eli actually did figure out some stuff, but somehow, I had forgotten it.

I spend a lot of time thinking, but I think that if I don’t produce some kind of artifact, the thinking that I do is not just not shared with the world, but is lost to me. Creating something isn’t an extra step, its the crystallization of the cognitive work itself. If I don’t create an artifact, the cognitive work is transient, it leaves no impression on me or the world. It might as well not have happened.

And aside from that, I would feel better about my life now, if instead of a bunch of things that I thought about, there were a bunch of blog posts that I published, even if they were in shitty draft form. To the extent that I can look over my life and see a bunch (small, bad) things that I did, I feel better about my life.

I would feel much better if every place where I had had a cool idea, I had made something, and I could look over them all, and see what I had done.

Going forward, I’m going to hold to the policy that every project should have a deliverable, even if it is something very simple: a shitty blogpost, a google doc a test session, an explanation of what I learned (recorded, and posted on youtube), an MVP app.

And in support of this, I also want to have a policy that as soon as I feel like I have something that I could write up, I do that immediately, instead of adding it to my todo list. Often, I’ll do some thinking about something, and have the sketch of how to write it up in my head, but there’s a little bit of activation energy required to sit down and do it, and I have a bunch of things on my plate (including other essays that I want to write). But then I’ll wait too long, and by the time I come back to it, it doesn’t feel alive anymore.

This is what happened with some recent thinking that I did about ELK for instance. I did clarify some things for myself, and intended to write it up, but by the time I went to do that, it felt stale. And so an ELK weekend, that I participated in a while back back is one more project where I had new thoughts but mostly nothing will come of them.

For this reason, I’m pushing myself to write up this document, right now. I want to create some crystallization of the meager thinking that I did when reflecting on my life, that puts a stake in the ground so that I don’t realize some things, and then just forget about them.

I wish that I made a point to write down the arguments that I was steering by

From 2018 to early 2020, I did not pursue a project that seemed to me like the obvious thing for me to be doing, because of combination of constraints involving considerations of info security, some philosophy of uncertainty problems, and underlying both of those, some ego-attachments. I was instead sort of in a holding pattern: hoping/planning to go forward with something, but not actually taking action on it.

[I don’t want to undersell the ego stuff as my just being unvirtuous. I think it was tracking some thing that were in fact bad, and if I had had sufficient skill, I could have untangled it, and had courage and agency. But I can’t think of what straightforward policy would have allowed me to do that, given the social context that I was in.]

In retrospect the arguments that I was steering my life by were…just not very good. I think if I had made a point to write them up, to clarify what I was doing, and why I was doing it, this would have caused me to notice that they didn’t really hold up. 

If for no other reason than that I would share my google docs, and people would argue against my points.

And in any case, I had the intention at the time of orienting to those arguments and trying to do original applied philosophy to find solutions, or at least better framings, for those problems. And I did this a tensy weency bit, but I didn’t make solid progress. And I think that I could have. And the main thing that I needed to do was actually write up what I was thinking so I could build on it (and secondarily, so other people could comment on it). 

(I’m in particular thinking about some ideas I had in conversation with Scott G at an MSFP. There was a blog-post writing day during that workshop, and I contemplated writing it up (I think actually had a vague intention to write it up sometime), but didn’t because I was tired or something.)

And I think this as been pretty generically true. A lot of my sense of what’s important or how things work seems to have drifted along a seemingly random walk, instead of being a series of specific updates for reasons. 

After I panic-bought, during covid, I made a policy that I don’t move money without at least writing up a one-pager explaining what I’m doing and what my reason for doing it is. This allows me to notice if my reason is stupid (“I just saw some news articles and now I’m panicked”) and it allows me to reflect on my actual thought process, not just the result of my thought process later. (Come to think of it, I think it might be true that my most costly financial decision every might be the only other time that I didn’t follow this policy! I should double check that!)

I think I should have a similar policy here. Any argument or consideration that I’m steering my life by, I should write up as as a google doc, with good argumentative structure. 

The thing that I need, to implement this policy is a the trigger. What would cause me to notice arguments that I’m steering my life by.

I wish I had recorded myself more

[inspired by this tweet]

When I was younger, it was important to me to meet my wife early, so that she could have known me when I was young, to understand what I was like and where I grew from. 

I’ve recently started dating someone, and I wish she was able to know what younger Eli was like. She can read my writing, but the essays and diary entries that I wrote are low bandwidth for getting a sense of a person. 

If I had made a vlog or something, I would have lots and lots of video to watch which would help her get a sense of what I was like.

Similarly, for if I ever have kids, I would like them to be able to know what I was like at their age. 

Furthermore, I spent some time over the past day listening to audio recordings that I made over the last decade. I was shocked by the samples of the way my younger self was, and I wish that I had more of those recorded to compare against.

I feel like I’ve sort of permanently missed the boat on this one. I’ve permanently lost access to some information that I wish I had. But I have a heuristic on a much smaller scale: if I’m in a conversation, and I have the thought “I wish I had been recording this conversation”, I start recording right then. It seems like this same heuristic should apply at the macro scale: if I have the thought “I wish I had been regularly recording myself 10 years ago, I should start doing that now.

I wish that I did more things with discrete time boxes, so that I could notice that I failed

There were very few places where I concretely failed at something, and drew attention to the fact that I failed. As noted, there were lots and lots of projects that never reached fruition, but mostly I just punted on those, intending to continue them. If I had a bad day, I was often afraid to cut my losses and just not do the thing that I had hoped to do.

There are lots of skills that I planned to learn, and then I would attempt (usually in an unfocused way) to learn them in some amount of time, and at the end of that period of time I would not have made much progress. But I would implicitly move out my timeline for learning those things; my failing to make progress did not cause me to give up or allow me to consider not making that skill a part of me at some point. I allowed myself to keep punting my plans to the indefinite future.

This was probably self-fulfilling. Since I knew that if I failed to do or learn something in the short term, I wouldn’t actually count that as a failure in any meaningful sense, I would still be planning to get it somehow, I wasn’t really incentivized to do or learn the thing in that short term.

I think that one thing that would have helped me was planning to do things on specific time horizons (this weekend, this week, this month, whatever), and scheduling a post mortem, ideally with another person, on my calendar, at the end of that time horizon.

Now, I don’t think that this would have worked, directly, I think I still would have squandered that time, or made much slower progress than I hoped. But I by having a crisp demarcation of when I wanted to have a project completed by, scheduled in such a way that I can’t just explain it away as no longer relevant (because I made less progress than I had hoped to make by the time it came around), I would more concretely notice and orient to the fact that something that I had tried to do hadn’t worked. And then I could iterate from there.

I intend to do this going forward. Which concretely means that I should look over my current projects, and timebox out at least one of them, and schedule with someone to postmortem with me.

I should have focused on learning by doing

Most of what I have tried to do over the past decade is acquire skills.

This has not been wholly unsuccessful. I do in fact now posses a number of specific skills that most people don’t, and I have gone from broadly incompetent (but undaunted) to broadly competent, in general.

But most of the specific skill learning that I tried to do seems to have been close to fruitless. Much of what I learned I learned in the process of just working on direct projects. (Though not all of it! I’ve recently noticed how much of my emotional communication and facilitation skills are downstream of doing a lot of Circling, and, I guess, from doing SAS in particular).

 I think that I would have done much better to focus less on building skills and to focus more on just doing concrete things that seemed cool to me. 

(And indeed, I knew this at the time, but didn’t act on it, because of reasons related “choosing projects felt like choosing my identity”, and a maybe a general thing of not taking my obvious known mistakes seriously enough, and maybe something else.

I’m going to have a firm rule for the next six months: I’m allowing myself to still try to acquire skills, but this always to be in the context of a project in which I am building something: