Even as inaction can be a risk, deciding which actions to take in one's career involves choosing between different bets. I've developed a rubric for judging specific risks that I've taken. Assessing these experiences together, we can identify useful commonalities for anyone navigating the path to Staff Engineer and beyond. 

I'll describe my career progression -- and regressions! -- as well the context that I've used to figure out what to work on and whom to work with. From this historical perspective, I'll distill a framework which you can utilize in your own work, as well as when mentoring others who are earlier on their paths. We will use this lens to ask what motivates us, what our goals are and where, as they say, "do you see yourself in five years?" By the end, we will have drafted an inventory of bets, their associated risks, how failure manifests in each case, and thus what we can do to avoid failure and hedge against risk, on the path to Staff Engineer.