It is worth keeping in mind that how to defeat X is not well-defined. The usual method for circumventing the planning fallacy is to use whatever the final cost was last time. What about cases where there isn't a body of evidence for the costs? Rationality is just such a case; while we have many well-defined biases, we have few methods for overcoming them.
As a consequence, I determine whether to workaround or defeat X primarily based on how frequently I expect it to come up. The cost of X I find less relevant for two reasons: one, I have a preference against being mugged by Pascal's Wager into spending all my effort on low-likelihood events; two, high cost cases often have a well developed System 2 methodology to resolve them.
A benefit is that frequent cases benefit more easily from spaced repetition and habit forming. In this way, I hope to develop a body of past cases to refer to when trying to plan for how long defeating future X will take.
Examples of frequent cases: exercise, amazon purchases, reading articles. Examples of rare cases: job benefits, housing costs, vehicle purchases.
Lately, I’ve been musing on the nature of self-improvement in general. When I notice that something I’ve been doing-- be it mental or physical, the next immediate chain of thought is “Okay, how do I improve my life now, knowing this phenomena exists?” In doing so, I’ve recently realized that this is missing a crucial distinction that can lead to more confusion later down the road.
This important divide is the question of optimizing around, or powering through. So before figuring out what actions I should be taking, it seems important to ask myself, “What am I trying to optimize for?” If the negative biases and habits I manage to identify are rocks, then the question is whether or not the best plan of action is to plan around these rocks, or crush them entirely. This is far from a clear-cut division, however. It appears that breaking bad habits--powering through is going to be more costly in terms of resources spent. Additionally, a successful plan for overcoming these errors will probably have a mix of these, especially if ridding oneself of the tendency entirely is the goal.
For an example of how these two are often blurred, take the planning fallacy:
One strategy may be to overestimate times when planning, pushing through the “it feels wrong” feeling to develop a better sense of how long things take. To augment this, there are also planning techniques, like Murphyjitsu designed to get you considering “hidden factors”. It’s far from clear how much actions that compensate for biases by countering their effects actually reduce the bias entirely, especially if the helpful action also becomes second nature.
But overall, I think this is an important distinction to keep in mind, because I’ll often be stuck asking myself “Should I work around X, or should I actively try to defeat X?”
Does anyone have experience trying to go specifically in one way or the other to counter their biases?