In Praise of the Meandering Career

One of the biggest challenges people have when embarking on an unconventional path is disconnecting from extrinsic markers of success and listening to internal motivational cues. On the default path, you can spend an entire career playing other people’s games. At first, people on a pathless path try to fill the lack of extrinsic goals with new ones... See more

We should be chefs when it comes to career-path-carving (a.k.a. reason from first principles). This is because of the following: (1) it takes up a significant chunk of our lives, (2) it plays a big role in determining the quality of our lives, (3) it serves as our primary mode of impact-making, and (4) it also serves as our primary identity.

A chef ... See more

Moreover, our culture of specialization conflicts with something most of us intuitively recognize, but which career advisers are only beginning to understand: we each have multiple selves. … We have complex, multi-faceted experiences, interests, values and talents, which might mean that we could also find fulfillment as a web designer, or a communi... 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

I like to think of careers as less like ladders and more like lily pads. In retrospect, some hops might look as if they were on a path, while others might look like a digression. Some might prioritize work, others might prioritize life outside of work. But whatever you hop to next, know you’ll have the chance to hop again. Little in life is permane

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