What always stands out about startup reflections like these is how utterly undefined, freeform, and rapidly evolving the roles can be. The old fire hose saying

What always stands out about startup reflections like these is how utterly undefined, freeform, and rapidly evolving the roles can be. The old fire hose saying is true, but it’s not just that you’re drinking from a fire hose, it’s that you often don’t know what’s coming out of the hose next. One minute deep technical decisions, the next minute helping to establish hiring philosophy, and cashflow and growth always on a background thread. After a few years of this I think my experience is not uncommon. If you exit and through whatever circumstance (success or failure), come back inside an F500 company, you realize that trial by fire has force fed you a vast amount of new skills without even realizing it. On one hand, the realization is really empowering, the realization you feel comfortable taking on various high impact tasks without much thought that you could have never jumped right into before. On the other hand, it can feel limiting, because F500 companies tend not to encourage even the most talented technical people to cross roles and help define company wide hiring practices. It’s an invaluable education, but I don’t know if MBA is quite the correct ananlogy, not sure what a better comparison is.