This is a linkpost for https://utilitymonster.substack.com/p/digging-from-the-pitfalls-of-rationality
I think you (and people in similar situations) would benefit more by studying psychology than abstract rationality and decision theory. You are a human, with a particular emotional experience of the world. As such, you deserve your own sympathy and understanding.
To elaborate on that just a little: the human brain uses massively parallel processing, and is relatively limited in using serial algorithms. So a fifty-item list of criteria is great for an algorithm that makes decisions, but intractable for a human brain. Intuition (parallel processing) and logic must be used to check and balance each other.
Second, emotions and value judgments are intrinsic to human brain operation. Humans are terribly vulnerable to confirmation bias, because the associative nature of thinking makes it easy to think of ways to find evidence for our current representation/thought/hypothesis, and not evidence against it.
Unfortunately, I don't know of a good rationalist's guide to psychology.
TLDR: I was bold. I became more insecure. That made me sad.
I had the master plan. 1. Solve moral philosophy. 2. Solve rationality. 3. Understand the biggest causes in the world. 4. Become a hybrid of Scott Alexander / Tim Urban / Nathan Fielder to maximize my positive impact.
And I did step 1. It took 210-820 hours[1], many sloppy rough drafts, and reframing my goal to: Reflect on my values until I decide it’s a bad use of my time to try to reduce my moral uncertainty. But I did it!
Then came step 2. It started okay. But I didn’t settle for okay. I was going to maximize my happiness.
What do I picture…?
Reading How To Measure Anything inspired me to ask myself, “What do I picture when I think of happiness?” And for every answer (e.g., “sleeping well”), I’d ask myself, “What do I picture when I think of sleeping well?” The goal was to break every question down until I came up with measurable metrics. I didn’t get to that point, deciding to stop after breaking down my desires into 30-ish pages of goals. Choosing what to do between these hundreds of goals was overwhelming. So I made a 50-ish item summary of that list. But I still felt like a mess.
So (after three months of De Quervains tenosynovitis), I made a new, more organized list. Based on that list, I decided to make a list on what to learn about decision-making. After organizing that list, I decided to study decision theory. I hoped it would teach me the fundamentals of decision-making. But it didn’t provide me much value. I got fed up with asking myself abstract questions and plunged into learning data science. I coded 4 hours a day every day until I finished my course.
On the surface, I was more productive. But under the surface, I gradually got worse. I felt like I went back to the person I was two years ago. The person who was too scared to take an unconventional path. The person who just wanted to pass the test, even if my only reward was a green checkmark.
The pleasure of green checkmarks is fleeting. For whatever reason (feeling my lack of productivity will lead me to be perceived as a loser?), I’ve become more insecure. Sometimes this leads to attention-seeking behavior. But for the most part, I’ve shied away. I’ve tried to avoid talking about myself at home. And I’ve gone to fewer social events. When I’m really down, I tell myself that I’ve fucked up my career, and I’m a 32-year-old virgin with no close friends. All despite my enormous privilege and desire to make a positive impact.
That’s debatably true.[2] But a negative attitude won’t help me.
Starting To Dig
I’ve had moments of courage where I’ve made bold plans and asked myself tough questions. But when I fail to sustain that courage, I end up in the pitfalls of rationality. I don’t want to be there anymore.
The estimate refers to time I spent thinking about morality from April 2021 - October 2022. I noticed I estimated 100 hours in this April 2022 post. I can’t remember how I made that estimate. In retrospect, I’d guess it was an underestimate.
I’ve fucked up my career is the negative way of putting I haven’t been employed for 3 years. I am a virgin. When I don’t feel insecure, I don’t think there’s anything wrong with that. I’m being negative when I say I have no close friends. I don’t want to write in much detail about my relationships with others on the internet. Lastly, maybe I’m privileged. My dad’s a lawyer, and that’s helped me financially. I prefer to call myself fortunate since privileged seems to carry a negative connotation. Not that I’ve thought much about which of those terms to use.