There are two additional activities that can help:
Games are a great way to practice acting with uncertainty, and experiencing “I made the best decision and still lost” in a low-stakes environment. Poker is not ideal, since you often don’t have all the information, even in hindsight, to know if you made the best play—look for games where you make choices, then have the random outcome / hidden information / simultaneous choice reveal. Any cooperative board game (eg Pandemic) is great for this, since they are specifically callibrated to not be always winnable, and they are simple enough to do hindsight analysis and know if you made the best possible choices (at least in the endgame).
Ask someone else “what would you do (or would have done) in this situation?” Especially for big decisions, an actual outside view is far better than attempting to take the outside view from within your own head.
There are two additional activities that can help:
Games are a great way to practice acting with uncertainty, and experiencing “I made the best decision and still lost” in a low-stakes environment. Poker is not ideal, since you often don’t have all the information, even in hindsight, to know if you made the best play—look for games where you make choices, then have the random outcome / hidden information / simultaneous choice reveal. Any cooperative board game (eg Pandemic) is great for this, since they are specifically callibrated to not be always winnable, and they are simple enough to do hindsight analysis and know if you made the best possible choices (at least in the endgame).
Ask someone else “what would you do (or would have done) in this situation?” Especially for big decisions, an actual outside view is far better than attempting to take the outside view from within your own head.
For a more in-depth discussion, you can listen to this podcast episode: https://lrcast.com/limited-resources-226-rotty-and-application-of-tools/
(ROTTY stands for Results Oriented Thinking—learning too much from the result of a decision without considering the counterfactuals)