Reconsidering Career Optionality

The deadline for YC S24 is tomorrow. Here's why you SHOULD NOT APPLY TO YC: YC seems like a reasonable proposition. They give you some money to help start your business, and they promise you access to a community of people that can help you along the way. In exchange, they don't ask for much. The standard YC deal is $500K for 7% equity. That doesn... See more

- The first rule of career planning: Do not plan your career.- The world is an incredibly complex place and everything is changing all the time. You can’t plan your career because you have no idea what’s going to happen in the future. You have no idea what industries you’ll enter, what companies you’ll work for, what roles you’ll have, where you’ll... See more

By definition, you will likely succeed a vanishingly-small percentage of the time, but—as the saying goes—that’s a feature, not a bug. The point is to venture—fistfuls of money in hand—at the furthest extremes of capitalism, hoping to stumble upon that rare, proper intersection of technology and commerciality.By design, most investments will miss t... See more