If your real passion lies outside of the office, then climbing the corporate ladder would be falling prey to inertia. Instead, the better path would be reducing your expenses by moving to a cheaper city and living more modestly. With lower costs, you could switch to part-time and pursue your passions.
Isn’t that the higher-level game you're really optimizing for?
Excellent throughout. My big "system" insight is that many tech businesses with 10-100 employees waste a tremendous amount of time on coordination, and their output could be exceeded by one good engineer (me.) I will test this in the coming months and years. A few people have made this work successfully, and when I look at some who've failed, their mistakes are clear.
I very much do not want to climb any corporate ladders, and if I ever do so, it will only be for the money... which will lead to depression, weight gain, etc. I want to build cool shit, and see people use it. If my contribution to that is so diluted it might as well not exist, I won't be having any fun.
This year, I am allocating more time to fitness and exercise, with the North Star of being fit for adventure travel in Latin America.
I will continue what I began last year, where I create side projects and leave them up, instead of declaring them a failure and taking them down. In furtherance of this I will learn easier ways to deploy and host web apps, and select suitable architectures early in a project. An RDMS and a full EC2-like operating system running a web server is simply not necessary for a great deal of web apps. This is the lower-level insight that will make me succeed. I'll be able to build and test more ideas faster.
The part of this post where he writes about getting into "flow state" for a task that you should not do is very insightful. I've done this in the past on side projects that were doomed from the start. At another level, you could try to make a relationship work, or a city work, but what you really need to do is make a big change.