Last year student of psychology here. Compulsive thought about past perceived mistakes (rumination) is an extremely common disadaptive behaviour that is highly correlated with present and future anxiety disorders and depression. That is not necessarily what the OP is talking about, but I fear it might be ambiguous enough that some readers might be lead down a risky path.
The main reason it is so dangerous is because repeated thought tends to bias thinking towards previous patterns, increase the intensity of fear (that makes complex thought more difficult) and cause exhaustion that leads to less productive analysis and higher incidence of mistakes, specially in complex topics.
The recommendation is usually simple: do not ruminate. As the OP suggests, schedule a period where you can think clearly about it instead of trying to do it continuously and, if you realize you are getting overwhelmed by exhaustion and/or emotion, make sure to stop so it doesn’t bias your thinking. Learning to do so is very hard for a lot of people, so they usually need to practice with outside help first.
As for the original topic, I would agree with the OP that being able to analyze a situation and take the right choice despite the common risk aversion biases is an important skill for enterpreneurs in new fields. However, it is also necessary to remember that it requires a high degree of field-specific knowledge (without it, adequate estimation of the risks is unlikely) and that the adequate amount of risk taking behaviour is field-dependent (for example, while learning a new topic being willing to risk being wrong continuously is the right choice, as it leads to faster learning, but the same is not true in finance within a highly established field. In the same vein, a person who uses a very risk adverse approach [and, as a result, is unable to take what the OP describes as difficult choices] is unlikely to prosper in the high risk high reward environment of startups).
The other factor he mentions, being able to adapt to new evidence even if it means your previous decisions were wrong is a very useful life skill, but I would focus more on “adapt to new evidence” and less on “even if it proofs you were wrong”. Weighting new evidence correctly and using it to properly re-evaluate a situation is really important when making decisions, but focusing on whether one was right or wrong is a waste of precious cognitive resources. Be willing to admit you were wrong if you were, but don’t conduct the analysis with a focus on proving or disproving the rightness of your previous actions, as it would bias your though either in favor (more frequently) or against (less frequently, but still happens) yourself. Focus on understanding instead. Once again, learning to do it alone is hard for a lot of people (in many senses, thought patterns are build by social interaction), so outside help is usually necessary.
Finally, being able to adequately conceptualize the current situation so a topic can be evaluated is an ability by itself. A lot of people are unable to take those “hard choices” not because they are hard, but because they are unable to apply the schemas they may have learned in business class or philosophical discussion in real life (or viceversa). That is a field of study I have not studied enough to be comfortable giving guidance on thought.
Last year student of psychology here. Compulsive thought about past perceived mistakes (rumination) is an extremely common disadaptive behaviour that is highly correlated with present and future anxiety disorders and depression. That is not necessarily what the OP is talking about, but I fear it might be ambiguous enough that some readers might be lead down a risky path.
The main reason it is so dangerous is because repeated thought tends to bias thinking towards previous patterns, increase the intensity of fear (that makes complex thought more difficult) and cause exhaustion that leads to less productive analysis and higher incidence of mistakes, specially in complex topics.
The recommendation is usually simple: do not ruminate. As the OP suggests, schedule a period where you can think clearly about it instead of trying to do it continuously and, if you realize you are getting overwhelmed by exhaustion and/or emotion, make sure to stop so it doesn’t bias your thinking. Learning to do so is very hard for a lot of people, so they usually need to practice with outside help first.
As for the original topic, I would agree with the OP that being able to analyze a situation and take the right choice despite the common risk aversion biases is an important skill for enterpreneurs in new fields. However, it is also necessary to remember that it requires a high degree of field-specific knowledge (without it, adequate estimation of the risks is unlikely) and that the adequate amount of risk taking behaviour is field-dependent (for example, while learning a new topic being willing to risk being wrong continuously is the right choice, as it leads to faster learning, but the same is not true in finance within a highly established field. In the same vein, a person who uses a very risk adverse approach [and, as a result, is unable to take what the OP describes as difficult choices] is unlikely to prosper in the high risk high reward environment of startups).
The other factor he mentions, being able to adapt to new evidence even if it means your previous decisions were wrong is a very useful life skill, but I would focus more on “adapt to new evidence” and less on “even if it proofs you were wrong”. Weighting new evidence correctly and using it to properly re-evaluate a situation is really important when making decisions, but focusing on whether one was right or wrong is a waste of precious cognitive resources. Be willing to admit you were wrong if you were, but don’t conduct the analysis with a focus on proving or disproving the rightness of your previous actions, as it would bias your though either in favor (more frequently) or against (less frequently, but still happens) yourself. Focus on understanding instead. Once again, learning to do it alone is hard for a lot of people (in many senses, thought patterns are build by social interaction), so outside help is usually necessary.
Finally, being able to adequately conceptualize the current situation so a topic can be evaluated is an ability by itself. A lot of people are unable to take those “hard choices” not because they are hard, but because they are unable to apply the schemas they may have learned in business class or philosophical discussion in real life (or viceversa). That is a field of study I have not studied enough to be comfortable giving guidance on thought.