How do I improve at being strategic?

In my experience, the number one obstacle to strategic thinking is that people tend to confuse their impulses to virtue signaling with their actual goals. People tend to be very strategic about actual terminal goals: that is, things they genuinely desire, in the same way as one might desire ice cream when hungry, or air while drowning.

So my go-to tactic for helping someone to be more strategic is to test their desire: can they actually experience the in-the-torso feelings that are strongly correlated with desire and pleasure, when thinking about the goal?

If not, they probably do not have a terminal outcome that is actually desired, and instead are being confused by their brain's attempt to signal virtue, solve a perceived problem, or reduce cognitive dissonance.

(By "signal virtue", btw, I don't just mean conspicuous displays of morality, but also things like following in parents' footsteps or trying to live up to the expectations of others, trying to justify one's existence or purpose, and rather a wide variety of other weird things brains do to promote or maintain perceived self-worth and/or social standing.)

Anyway, when humans appear (in my biased sample of experiences) to not be being consciously strategic, it is generally because they are being unconsciously strategic about achieving an entirely different goal than the one they believe they're trying to achieve. And the goal they consciously believe they're seeking is in fact the result of their brain's strategic planning, rather than the input to another round of such planning.

The ultimate goal of such things is usually "to be a good, worthy, lovable person who visibly cares about the right things according to the value system(s) I have internalized".

Such goals, however, seem to run on different hardware than practical, desire-based goals. And if the non-desire-based goal is based on an idea that one "should" be a particular way, then it becomes virtually impossible to trigger the desire-based machinery at all.

(Because it is very hard to feel desire for something you believe you're already supposed to have done, had, or been.)

So.... if you want to be practically strategic, the very first step is to make sure you know what you want and why you want it. If the real goal cannot be defined in terms of a concrete observable outcome in external reality, that you can actually physically feel some form of pleasure at the idea of attaining (vs. merely feeling an anxious need to have), there is little point in going forward with any strategic planning, because strategic planning and social signalling tend to be mutually incompatible.

(Because our "desire to signal" wants to make our signalling-driven desires appear "honest", i.e. that they're not being done in order to signal.)

This makes it difficult to notice at first glance when we're doing so, so the desire test (aka the "mmmm" test", as in, "can you think about this in a way that makes you sound like you're enjoying yourself?") is a hack to work around this potential for self-deception. Our signaling desires seem to be injected on a different subsystem of the brain (maybe by rewarding certain directions of thought directly?) than the one that is used to pursue tangible desires like food or mates.

Food and mates make our mouths water or bellies rumble. Rest and safety make us go "ahhh" and relax. All of these pleasurable feelings arise from tangible goals, and motivate us to actually pursue them.

This one insight is, in my experience, worth a thousand abstract treatises on planning or decision-making. If you try to apply such ideas while actually pursuing a goal to virtue-signal, resolve cognitive dissonance, or fight something that seems "wrong", you're virtually guaranteed to use them in ways that will subtly sabotage any real action. (See, for example, all the vaccine distribution issues stemming from virtue signaling -- we are not immune to doing this sort of thing just because we label ourselves rationalists.)

Try to figure out what is causally upstream of what you care about. Recurse.

The first step that Anna points out is "Ask ourselves what we're trying to achieve" or in other words, know your goal. Since you have a desire to be more strategic you probably already have a goal in mind and realized that being more strategic would be an effective subgoal. From the rest of your post I think you've substantially worked on some of the other steps as well.

If you're struggling fulfilling the rest of the steps Anna laid out my recommendation is to just do things which may work towards achieving your goal that are very outside your comfort zone. That will pull you out of your pre-existing habits and get you to start evaluating different strategies instead of continuing to follow the strategy you've already worked yourself into.

If you're a procrastinator, start working on something that's a long term goal immediately for at least a few hours without breaks even if you start to think it might not be effective. If you think it's not effective that may be because of akrasia taking over once you actually start working on it.

If you are fearful of offending people go to an online or in person marketplace and start low-balling people with ridiculous offers and continually press them to make a deal favorable to you. Make the situation uncomfortable enough and you'll realize you have the ability to deal with the social awkwardness when you're trying to work towards your goal.

This is Anna's step e and I encourage working on this step because from your post it seems like you've already put good work into everything that comes before it.

My bad if this is more of tactics rather than the strategy tips you were looking for.

On the first level being strategic means to have explicit goals and think about what the best way to achieve those goals are. Review your goals and spending explitict time to think about them either by talking with other people or by reflecting about them and the means of achieving in writing. That will bring you further then most people. 

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