Reply to: Humans are not automatically strategic 

AnnaSalamon writes:

[Why] do many people go through long training programs “to make money” without spending a few hours doing salary comparisons ahead of time?  Why do many who type for hours a day remain two-finger typists, without bothering with a typing tutor program?  Why do people spend their Saturdays “enjoying themselves” without bothering to track which of their habitual leisure activities are *actually* enjoyable?  Why do even unusually numerate people fear illness, car accidents, and bogeymen, and take safety measures, but not bother to look up statistics on the relative risks?

I wanted to give a practical approach to avoiding these errors. So, I came up with the following two lists. To use these properly, write down your answers; written language is a better idea encoding tool than short-term memory, in my experience, and being able to compare your notes to your actual thinking sometime later is useful.

Goal Accuracy Checking

1. What do you think is your current goal?
2. How would you feel once you achieve this goal?
3. Why is this useful to you and others, and how does it relate to your strengths?
4. Why will you fail completely at achieving this goal?
5. What can you do not to fail as badly?

Reasoning behind these question choices:

1. If you have no aim, you are by definition aimless. By asking for current goals rather than long-term goals, we can specify context-specific actions and choices which would allow better execution. For instance, my goal could be “to be a better writer” or “to think more rationally”. More specific and time-limited goals seem to work better here, specifically if they can be broken down into sub-goals.
2. An analogous choice here would be pleasure or reward maximization in the future. Generally speaking, it does not seem to be the case that we are motivated by wanting to feel worse in the future. So if your goal allows you to feel better about yourself, or to improve the material conditions of your immediate community—that seems to be a good indicator that it is worthwhile. I would like to hear what people think about this, though, as some goals might show their self-destructive tendencies based on the feelings they induce when they are finished. An example: creating your own business and working 18 hours every day might feel “good” insofar as it allows you to feel productive and that you are doing something meaningful and useful for humanity; you might miss a few weddings and socializing with friends and family meanwhile, which are time-limited and oftentimes more personally meaningful pursuits in the human experience than creating a 10 times more efficient rocket engine, etc.
3. My attempt at doing some utilitarianism. The why here is important because if your intentions are harmful in nature you will know straight away by writing them out. This also allows for goal-utility comparison. I might want to be a world-class guitar player, but I have never played guitar, and my family is starving. To seek a guitar-playing career for the next 10 years might not necessarily be the best course of action, even if it produces a higher sense of “good feeling” as in (2). Moreover, aligning with the skills you already possess will allow you to have more leverage in your pursuits—you would not ask Mozart to code the new version of Windows.
4. Writing why something will fail outright allows for a more rational approach to decision-making. Estimating probability of success of sub-steps to be really useful here. For example, the odds of “making it” as a freelance guitarist are around 0.000002% [1], and the average pay is around $27.58 an hour in the US [2]. If we have identified in the previous steps an immediate need, for instance a debt in increase of $10000; being able to see multiple paths forward from our relative strengths, and seeing where the common pitfalls are, allows for better decision-making and choices along the way. An analogy here is that once we know what the map looks like, coursing through its rough terrain is easier, so long as we keep checking the map for pitfalls. 
5. Finally, what action can we take to execute? This framework is very similar to the SMART framework [3] in that it asks for specific, measurable, actionable, relevant and time-based action. But it differs in that it considers the short and long-term consequences of the process. It checks opportunity cost, personal relevance and attainability all at once. 

Probability Reality Checks

1. What do you fear now, and why? 
2. How probable is it? Visualize it.
3. What can you timely do about it?

Reasoning:

1. Fearing some things makes sense from a survival standpoint. Deprogramming the part of your brain that is in charge of avoiding snakes might not be useful if you live in a forest full of them.
2. If the probability is high, then moving to step 3 quicker is warranted; our brains do this often with the fight or flight response. Visualization is essential here, as humans are not too adept at understanding big numbers, it appears to be easier to see what 0.0001% means when it is drawn on a picture, for example.
3. Oftentimes pondering endlessly about a problem leads to rumination, so having an actionable set of steps to take helps to counteract that. Use a timer if needed, and keep the time horizon specific and actionable.

As we all know, there are plenty of factors impeding rational decision-making in everyday life. We typically fall prey to our emotions or to common cognitive biases. In addition to learning about these, it is useful to write out the automatic thought process and to respond to it with rational responses on paper—an approach typically used by CBT. 

Do you have any other recommendations? Please don't hesitate to post them in the comments, I am genuinely interested to see what works best for you, and will add more lists as seen fit. 

Sources:

https://tsmcollege.edu.sg/why-being-a-sustainable-musician-is-so-much-more-important-than-being-a-successful-musician/ [1]

https://www.careerexplorer.com/careers/musician/salary/ [2]

https://www.google.com/search?channel=crow5&client=firefox-b-d&q=SMART+goals [3]