To be frank, I question the value of compressing information of this generality, even as a roadmap. For example, "Networking" can easily be expanded into several books (e.g., Dale Carnegie) and "Educating oneself in career-related skills" has almost zero intersection when quantified over all possible careers. If Eliezer had made a "things to know to be a rationalist" post instead of breaking it down into The Sequences, I doubt anyone would have had much use for it.
Maybe you could focus on a particular topic, compile a list of relevant resources you have uncovered, and ask LW for further opinions? In fact, people have done this.
Well, I somewhat agree. A list like this definitely isn't very useful all by itself. The utility I imagine is in figuring out where the gaps in your knowledge are, and what you need to do better. If my goal is to live life as well as possible, I don't just want to read a bunch of sequences; I also want to figure out which sequences I should read.
You say that you question the value of compressed information like this as a roadmap. Do you think that a different type of roadmap may be more useful, or that a roadmap may not be useful at all?
If Eliezer had made a "things to know to be a rationalist" post instead of breaking it down into The Sequences, I doubt anyone would have had much use for it.
On the other hand, you tend to need an outline which graduates up to this level of vagueness at some point before writing large, in-depth works.
Seconded. Another question to ask: would you really expect this list, even if complete, to contain any new or useful information?
A list I collected a couple summers ago, inspired by Josh Kauffman's list and another list I'm unable to track down at the moment. Clearly incomplete, too specific in some areas and too sparse in others, and some questions are probably leading. Not sure whether there is value here since I've never really used it since compiling it, but the idea of a list to make sure there aren't gaps seems useful.
Pick up a journal, set aside a few hours, and spend time answering questions in an area you haven't considered in a while. Make it fun: treat yourself to a nice lunch or go somewhere special while you answer questions. Thinking, especially about large topics, is hard work.
Global Heuristics
Keep in mind that in any given area of your life, you are unlikely to be at the optimum; for instance, unless you think you are already traveling too much, you should be traveling more. If you had to change a little bit, which direction should it be in?
Pay attention to opportunity costs. Even if something is desirable, you might be giving up something even better. Trade offs have to be made and optimizing locally may not produce global optima. At the same time, question your assumptions about trade-offs. Is there any way to acheive all goal simultaneously?
Pay attention to fungible goods, considering alternate ways to achieve the same goals in a cheaper way. For instance, rather than justifying an extra bedroom by saying your mother could stay in it when she visits, consider cheaper and nearly as good solutions like paying for her hotel room or giving her your room. Remember that money is not the only way to measure costs. Economize between money, time, attention, good will, energy, and other goods.
Avoid framing choices as "whether or not" (as in "I'm trying to decide whether or not to break up with my boyfriend"). Empirically, framing a situation this narrowly tends towards poor decisions (see Decisive by Chip Heath and Dan Heath). Thinking of just one more option can cast light on what's important to you and what's feasible in general.
Work
Relationships
1. Am I aware of my needs and wants and communicate them clearly?
2. Am I on good terms with past lovers or spouses?
Home
Body
Continued
Tools
Social Interaction
Personal Finance
Hobbies and leisure
Identity and strategy
To health, add, "Be aware of and have plans to mitigate common risk factors in your daily life (seatbelt while driving, etc.)".
To health, add, "Maintain a balanced and stable mental state (seek counseling if necessary)".
Hobbies could probably be relisted as, "Fun: Find ways to ensure you're enjoying yourself (hobbies, etc.)".
To interpersonal, add, "If interested in doing so, pursue sexual relationships and/or spawning activities".
You are engaging in the rudiments of goal factoring. I suggest using workflowy for the simple tree structure it provides if you don't already use a text editor with such functionality. Using trees, you can drill down from long term goals to short term goals. Doing such provides a wonderful method both of organizing lists of things you need to do, and increased motivation due to seeing how sub-tasks directly relate to the things you really want.
This week's southbay meetup is covering this topic.
Insurance: If not already mandated by the state you are living in, buy insurance against catastrophic risk, that is any liability you are unable to pay without a major hit in your quality of life. This includes health insurance, liability insurance, disability insurance, legal expenses insurance if you are self-employed, rentor's insurance if your possesions are particularly valuable and life insurance if you have dependent children. If possible, buy insurance with co-payment as this reduces the premium massively. Again, anything that you can pay for without serious reduction in quality of life or that is a near-certain expense is meaningless to insure.
Also, insurance offers nice information and services. Liability insurance deals with mitigation and litigation for you, home owner's insurance informs you through the premium of particual risks of placing your home. They may even deal with the headache of finding and ordering people to repair your home.
Some would argue that cryonics should be added to health (and hence that in the needed-but-already-suggested 'insurance' section, life insurance should be included for cryonics as well as for e.g children) .
As an experiment, this seems like the sort of thing that the cloud outlining tool Workflowy would be useful for -- I'd be interested to see LWers start to fill in the various bullets down to whatever nesting level they're interested in.
https://workflowy.com/shared/0356fc36-a7b5-d275-6a8e-aaa79e2bea44/
I've prepopulated it with the contents of the post (but not the comments.)
Press Control-? for a list of keyboard shortcuts.
To the health section I would add mobility. Most of us are destroying our bodies by sitting 8+ hours a day. You have to find a way to balance it out.
Hobbies could probably be relisted as "Fun: Find ways to ensure you're enjoying yourself (hobbies, etc.)".
I came up with an idea today: I think it would be useful to have a list of everything that a typical person ought to do. After all, there is quite a lot of stuff that a typical person ought to do; how else is a person supposed to remember it all?
Here's what I've come up with so far:
Health
Money
Altruism
Interpersonal interaction
Recreation
Responsibilities
Productivity
Skills
Anyone have any suggestions for additions or improvements?
edit 1: some suggestions by Rain and aelephant