About once a year I nearly get fired. This is not a virtue, but consider my calculus:
I highly value risk-taking, believing it is the only way to initiate any real progress in business and in life. Here is how it usually turns out:
90% of the time, nothing good or bad happens. Null program. I go back to the drawing board and find a new way to pursue my goal.
5% of the time, it goes really badly. Like nearly getting fired bad. Or substantially pissing someone I love off bad. I recover through humility, diplomacy, and patience, skills that must be cultivated to succeed at risk-taking.
However, the remaining 5% of the time the outcome is so awesome that it makes the other 5% worth the pain.
Risk-taking is a skill one can develop. It takes practice. It requires getting used to discomfort.
Note that we are talking about strategic, calculated risks, not recklessness. It is okay for emotions to drive the risks, but they still require careful consideration.
I encourage my interns to take risks during their tenure with me. Usually they don’t achieve the confidence to during the time I have with them, but I try to plant the seed.