other people want you to have a purpose

I am existing in a period of my life right now that does not have a lot of stated direction. I mean, perhaps that is not entirely true — perhaps the stated direction is not commit to any long-term stated direction, at least for now. Put another way, I have no intentions currently of doing anything besides optimizing for short-term, one-off “stuffs” — with the idea being that one day I will wake up and have more clarity on what is right for the long-term.

In re-reading that paragraph, I do not believe I am passing the authenticity bar. I want to rephrase some things, but I am leaving the above in so you can see not just the outputs but also how I get through the idea maze of untangling the thoughts inside my brain. And by “so you can see,” I really, more accurately mean, so I can actually see (as I am the primary/intended reader of this blog).

So what I mean by the above is NOT that I am doing nothing to strengthen the long-term. In fact, I would say most everything I am doing and spending my energy on is 100% optimized for the long-term. I am focusing on the health of my brain, heart, and body. And I am being intentional about that — to a degree that I am proud of and believe is the right thing for me to be doing. I also feel lucky and grateful that I am in a position where I can afford (or at least I think I can afford) to not worry about having to work at this moment.

And so, to get back to the point I tried to start with, while I am optimizing for the long-term, part of my “optimization” is in saying no to most all things (a thing that I wish I learned earlier on in my life — more on this in a moment) and actively, intentionally not making any new long-term commitments (outside of the health stuff I mentioned earlier).

I find there to be lots of pressure (or better put, at least an amount of pressure more intense than what I am seeing on my day-to-day) — mainly from the external world, but inevitably that trickles into my inner monologue of sorts, to HAVE AN IDENTITY TIED TO A LONGER TERM THING. And perhaps this is mainly in my head — and now on the page here — but I feel that pressure in a way I have really only felt two other times in my life.

The first was during senior year of high school and the second was during senior year of college. In both of these instances, we will get to the details in a moment, I felt this same flow of “what should I be doing with my life?” But more perhaps more importantly, and more interestingly to me, I found myself being ~okay, not sustainably forever okay, but ~okay in the immediate term satisfying that answer with something simple like: ‘I do not know yet, but I will figure that out when the time is right’. I would say, if pressed hard, I would not be able to answer precisely when the time is right — but I would say that I am not just doing nothing in the immediate term. I am taking steps, albeit not always straight line steps (as is true with most things, like chess, taking the direct/straight path is rarely the most effective one), towards clarity. So I would be ~satisfied with my answer, albeit a bit nervous but mainly satisfied.

But people — OTHER PEOPLE — people that I would tell about my current state, would be almost…upset? Maybe the wrong word. Frustrated? Still maybe the wrong word. Confused? Closer…Basically, my answer was incompatible with their expectations.

During senior year of college – I would give this answer and people would be so curious and eager to know. They would love to know where I am going to be spending my time after college.

In the moment, I interpreted this reaction with cynicism. I default assumed the reason they so badly wanted to know was because they wanted to be ranking me on their internal social and economic status leaderboard that they implicitly keep in their heads. They wanted to rank themselves against me. So that their identity could go to bed at night knowing more precisely where they sit. They have this leaderboard idea in their heads, and they have these ladders that feed into them. They perceive high status to be categories of life with well defined ladders. Where you go become a consultant, then work in private equity, then go to business school, then go back to private equity, and then make your way into startup land, and re-climb the adjacent ladder. I never appreciated the ladder way of life — ironically a bit here, I always thought about things more laterally. At every stage, you do not have to keep climbing. You can move horizontally across the economy into various things that you enjoy doing (or not enjoy doing). So I met this ladder way of life with frustration — I never got it. That was my reaction back in high school and college.

And to some degree, I still think that to be true but I think my reaction now goes more to a systems level critique.

Like now I get it. But I still would never treat life that way.

It’s more that our system — at least one of the systems I currently or at least recently participated in which revolves around the “modern tech economy here in the US” — does not really comply with this notion that you can exist with “no clear purpose.” The purpose of “working on my health or whatever” does not satisfy people’s needs.

They get insecure about their own identity because they look at me, as they are standing on their windy latter, and they are hoping to see me on my own ladder or something but in reality they see me just chilling out or exploring in another direction.

They have been trained to think that regimented purpose tied to some sort of corporation is BETTER than having nothing like that in place. The system drives that forward — but it has a huge misunderstanding of speed and how the single biggest risk I face today is choosing the wrong next thing to work on.

Choosing the wrong next thing, making the wrong bet, is the most costly thing I could possibly do wrong — because if I invest energy in the wrong direction, I may end up with absolutely nothing and needing to start over. Now this is not an appropriately nuanced take, and I rather not get into the idea that optionality is such a good thing debate right now (but the TLDR of my opinion is that optionality in your career is a bit overrated in that I think careers are defined by taking bets, having opinions, and over a long enough time period, being right. Optimizing for optionality at all times is a hedge, and will not get results that I care about). But for right now, not committing to a long term certainly is a play at optionality. Certainly is a bet that giving myself sufficient space/distance right now is the single best way to help maximize my likelihood of choosing the *right next thing*.

And my hope is to avoid that mistake — I will only work on things that I love, not just things that I like (or especially not things that I hate).

And this alone I believe to be a relatively new thing for me. I mean I always had some level of having a no bullshit bar in my life. But the difference between working on something you absolutely genuinely love and something you even really like I now believe to be astronomical. In such a way that we as humans I think tend to underestimate the impact of scale and just how big of a difference great versus good really makes. I used to get even marginally excited by good opportunities coming into my life. Now, and this is something I am training myself on at least a bit, I try not to really care about the marginal good. I want the marginal great. This delta – between loving and liking – is so big and important to me. Whenever I underestimate this delta, I have regrets. A great place where this happens is in hiring or finding teammates. The difference between an exceptional teammate and an okay one is astronomical. I have made the mistake so many times on settling, mainly because I was insecure and tired, and I can tell you getting the fit to feel more like how a glove should fit, is so worth the time (time and time again I learn and underestimate this lesson).

Another place is with meetings. My default over the years has been meeting new people — over and over again I find myself filling my calendar with random meetings. I am not against randomness. And I am always genuinely down to help people out with things. But I no longer have a passion or interest in filling my calendar with 14 meetings a day to infinity. It is not energizing or fun to me to keep at that pursuit — largely because most of the meetings are not memorable and are a drain on my ability to do GREAT work during the day. They take me out of my flow state.

A lot of this is downstream of my personal self confidence. It is funny how much really stems from that. My capacity to say yes to meetings is a reflection on how I respect my own time and my own self-worth. Now I am not saying have no meetings ever, though that may be a better default. I am saying really consider what clears your bar — what is your opportunity cost.

You do not have to maniacal about this — I mean you definitely could be (and some people are). It does not mean never have fun. It does not mean never do things that are low expected value (though again you could).

It does mean — and again this is a note to me beyond others really — to not fall for the trap in thinking that doing a bunch of good not great stuff is going to really make a meaningful difference in your life (rather than add stress and anxiety). If something is not GREAT, consider shedding it, delaying it, or doing the worst possible version of it until you want or need to or can make it great.

This applies in many contexts. This could be argued in the opposite framing, too, saying that sometimes you just need to get started.

The message I hope to have summarized for you above, though, is just thinking that in careers, and in thinking about how I spend my time, I am totally comfortable compromising making a decision today for making a way better decision x amount of time from now. Even if that does not fully comply with how the rest of the world wants me to fit into their ladder schema.