A major fallacy I believe to exist around risk-taking is the discounting of leverage which comes with it. Risks get you in a danger zone which also means you have much better tools at your disposal. People can't perform good assessments of their decision when they don't think of the leverage a risk gives them.

Your performance with the leverage will be much better as compared to otherwise. Dropping out of college can be a risk for someone but is also a source of leverage in terms of time and energy for people working on something important. This risk taking fallacy can prevent you from being in good places sometimes. Other times you may not know what to do with all the leverage and just perform the same way you did earlier.

The only good way to approach risk-taking in this context is to have immense self-awareness in terms of your skill. That's the only way you will know what kind of leverage you need and what it adds up to when you have it. Know how much you want to stretch. The formula for risk thus comes down to this :

$Magnitude = Skill * Leverage$

Magnitude being the size of the goal (a lot good risks have large ambitions behind them). Skill being your personal skill and leverage being the leverage created when you take a decision which involves uncertainty and possibility of failure. A good risk would be where the left and right hand sides are close to equal. If they're easy to equate, maybe you're not stretching enough, if they're too tough, you're really messing up. Try to increase one of these to get a decent ratio (maybe 3:2) because you can leave some room to your circumstances and factors which top-up along the journey. Your network, luck, upbringing, environment.etc contribute to this. That's why we kept a buffer point up. All of them may not align but smart people can stretch enough with the ones that do. Quite useful.