I think this is a discussion about what the best order is in which debiasing should occur.
Project management seems to be an implementation of debiasing strategies and they first teach you to make more accurate predictions and then later teach you how to prevent the sunk cost fallacy from not cancelling a failing project.
Because of this i think debiasing should occur in a kind of logical order, one that prevents someone from cancelling all projects due to a good grasp of sunk cost and a bad grasp of utility calculations.
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I get the feeling a large portion of this story can be classified as learned helplessness.
Several studies(google for cal newport) have shown that base talent has little effect on how good you can be at something, the real variable is deliberate practice, pushing the limits of what you can handle a tiny bit to slowly keep improving. ( obviously your swimming example does have harder limits imposed by the limits of your body, this does not seem to apply to fields outside of sports though and in sports like boxing there are different classes because of the differences in bodies)
When I learned about grade signalling I started making mistakes on purpose to lower my average (which was around 9.5 at the time). That was a terrible tactic in hindsight and it still causes selfdoubt on exams today.