2 - on not overthinking

making decisions when there are so many options and not enough time

Hello friends ✨ It’s almost June, and we’re almost halfway through 2021. Crazy, isn’t it? Things have opened up in SF. People are coming back. I can’t wait to see what post-vax summer looks like.

This month’s issues:

  • On not overthinking: a new heuristic I’m adopting for my life

  • What I’m up to: what I chose to do and how I arrived at it

  • Goals for June


On not overthinking

“Would your younger self be proud of you?” is a terrible question. “Would your 80-year-old self regret this decision?” is equally as bad. 

Both are frequently used in introspective exercises and decision-making frameworks, but they overlook the fact that your past and future selves are not you. The judgment of either self is meaningless to you right now. 

The trap most people fall into is overthinking their decisions, either too far into the past (does this decision fit my narrative?) or too far into the future (will this be something I want to do in 10 years?). I completely understand: I myself have always been an over-thinker. Before graduating college, I labored over the How to Pick a Career exercises. One year into the workforce, I worked on Designing Your Life, thinking I’d find the answer there. And when I switched jobs, I took a week off to reflect on my values, hired a decision coach, and took 1.5 months to come to a decision.

Nietzsche says that “you must be ready to burn yourself in your own flame; how could you rise anew if you have not first become ashes?” Not overthinking is something I embrace now.

I like what David said here: focus on moving forward and making as many 'probably correct actions' as possible

Doing is ultimately the best form of understanding. The key here is making as many of them as possible. But how can you do that when it seems as if one decision will lock you in a path for a while?

There are three ways to think about this:

  1. On a large enough timescale, you can make a lot of decisions.

People tend to focus on the decisions before them, not realizing that there are more decisions they can make in the future as long as they stay in the game of life. Very rarely are decisions catastrophic.

Moreover, I would have some green lines connect back to the black lines in the above picture. Several life paths that appear closed are actually still open. I’ve seen students who committed to one university over another, regretted it, and convinced the admission office to let them in again. I’ve known people who chose the untraditional path, decided that they wanted a more conventional life, and got the job because, not in spite of, their background. Most decisions are reversible.

Taking those together, as long as you live, you can continue making several decisions, and even come back to options you passed on before.

  1. Increasing your speed and intensity will allow you to make more decisions and gain better resolution on each of them.

Derek Sivers on learning a full semester of curriculum in three hours:

The standard pace is for chumps” — […] the system is designed so anyone can keep up. If you’re more driven than most people, you can do way more than anyone expects. And this principle applies to all of life, not just school.

Put yourself in a position where you can get to the next decision as quickly as possible. Are you setting a speed limit on something in your life just because that’s what most people do? (e.g. K-12 education). For example, there’s a notion that you have to spend 2 years at your first job out of college, and somehow those years will critically determine the rest of your life. This causes analysis paralysis since it makes the decision seem more critical than it is. You become more free when you know you can cut your losses as soon as you realize this is not what you want. Likewise, if it's a stepping stone to what you want, you can get there faster than you think.

Speed is correlated with intensity — to get to the next checkpoint quickly, you might need to work harder. We preach balance and moderation, but intensity is a part of what makes life worth living. I love Ava’s take on it:

Intensity is the pursuit of aliveness. […]

there are certain forms of knowledge that will be denied to you if you stay within the bounds. You could think of intensity as the pursuit of gnosis, of “transcendence arrived at through intuitive, interior means." It’s hard to deny that extreme results (whether it be athletic feats or works of art) generally require extreme focus, extreme commitment, and extreme personalities.

Decide to do something, and when you do it, pursue it with the max speed and intensity that you have. It will get you to the next decision point more quickly, and you will be more certain if you want to continue on your current course as well.

  1. You can choose to do a lot of things at once.

Serendipity often results from breadth. Hamming said in You and Your Research:

You can't always know exactly where to be, but you can keep active in places where something might happen. […]

I notice that if you have the door to your office closed, you get more work done today and tomorrow, and you are more productive than most. But 10 years later somehow you don't know quite know what problems are worth working on; all the hard work you do is sort of tangential in importance. He who works with the door open gets all kinds of interruptions, but he also occasionally gets clues as to what the world is and what might be important.

Choosing something does not mean closing yourself off from other possibilities. Focus on the thing you choose, but gain small exposure to things you find promising. That’s why I keep a list of things I want to build — even if I’m not working on X in the immediate future, I can keep tab on X by occasionally staying in touch with people in the field.

This inspiring read also tells you that you can in fact do a lot of things at once if you truly know how to prioritize. You can always do more than you give yourself credit for.

Does this mean that you shouldn’t live an examined life? No, in fact, journaling every day might be the key to avoid overthinking. People are paralyzed by seemingly big decisions because they are not sufficiently introspective. If you write down how you feel every day, a “big decision” might be as easy as another journal entry. But if you’ve never taken note on yourself before — it’s scary to see where to start because you don’t know yourself enough to know what decision is considered sufficiently good.

From Joan Didion on keeping a notebook:

I think we are well advised to keep on nodding terms with the people we used to be whether we find them attractive company or not. Otherwise they turn up unannounced and surprise us, come hammering on the mind’s door at 4 a.m. of a bad night and demand to know who deserted them, who betrayed them, who is going to make amends.

What should you do then, if you’ve never taken notes on yourself? The best time to do it was when you were born, and the second best time is now. Don’t remain idle, do something, and write down everything you experience along the way.

Really, most advice in life boils down to “just do it.” And when you do, keep in mind that most decisions are reversible, do it with all speed and intensity, take notes of your experience, and keep in touch with the world around you. With all that, you can keep moving forward and trust that most of your decisions are probably correct.


What I’m up to

In the previous newsletter, I was pondering what I should do next (what area, join a startup or start my own, etc.). Here is what I’ve arrived at:

What: Longevity.

Why: Looking across everything I want to build, longevity seems like highest leverage thing to work on. Not only because it reduces suffering, but also because it would enable more long-term thinking and human flourishing. I’m obsessed with the concept of the self and how longevity enables more lives otherwise unlived, and believe that people can find more purpose if they have more time.

How: I’m joining an exciting project to create more longevity startups. Details to be coming soon :)

My process:

  • I’ve loved biology since I was in high school, but didn’t have the courage to pursue it intensely (the advice at the time was that you have to either do a PhD or go to med school for a viable career with a bio major — and I wanted to do neither). Over the last year, I’ve become convinced that 1) biology is the next software in the coming decades, and 2) I can have a viable career here without a formal degree. That’s why I already knew that I want to stay in bio since I left my last job.

  • Do I want to enable people to do what they want, or do I want to work on the field directly? I don’t know yet, but it seems to make sense to start with the first one (hence why I was thinking about AWS for biotech in the previous newsletter).

  • Finally, longevity itself. I’ve been interested in the field for a while, but didn’t think I could work on it directly yet. That’s why I’ve explored a few adjacent options — mainly working on product/growth at biotech/healthtech startups. Twitter told me otherwise and connected me with people who helped me see that I can do something to make progress directly in this field.

Overall, I tried to do what I preach: not overthinking. I already knew that I want to work on longevity, and took the most promising opportunity I saw. I will apply myself with all speed and intensity in the next endeavor, and trust that it will work out in the end.


Goals for June

  • Writing every week: Related to doing a lot of things at once, I want to continue keeping in touch with my creative side through writing. I want to write not only for function, but also for form. I’ll be writing weekly notes here and reading more about how to write (especially from fictional writing perspectives — starting with this book). Send me any recommendations you have on how to practice writing beautiful prose!


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