Career Misconceptions of a Dreamer

It was always confusing to me what people were supposed to do with their careers. Nobody explained it well, and I wasn’t aware of the right questions.

So I had a hard time getting my career started properly. My transition out of college was turbulent. I was carried in silly directions by problematic beliefs:

  • If I have a “normal” job (9-5), I’ll end up as a cog, with a boring life.
  • Therefore, I have to be the boss / director / owner / founder.
  • I’m great at school, so I’ll succeed at everything fast.

Up until age 17, I was learning a lot of basic skills and the plan was “do well in school.” This plan went well, but the next part was naturally “make your own plan,” and I didn’t realize I was failing to do so. Finally, I hit an inflection point around age 23.

A year out of college, I was lost and increasingly humbled by the effects of not having a career / life plan. I eventually made some dramatic changes to get my personal growth back on track in a positive direction—specifically, moving to SF and getting a job in tech.

At the time, I didn’t have a unifying framework to describe these first career steps. My motivations were intuitive. Although I wrote a lot of blog posts trying to make sense of it all, the fact is I was iterating away from my low point rather than toward a well-defined high point. I had a few maps and compasses, but none of them were a complete framework that explained everything clearly.

I’m still figuring out what my life’s high point will look like, but I have recently developed a better understanding of how to climb the career mountain. I see a triangular compass of essential assets to develop: skills, strategy, marketing. And now, I see the development of these assets as a worthwhile journey in which I can enjoy and find meaning day by day.

Skills are the most obvious category. Welding, driving, using Google…these are the tactical abilities that allow us to get work done. I mistakenly used to think that being a quick learner could substitute for many other skills. I now appreciate the vast gulfs separating levels of exposure, experience, expertise, and mastery (even more than when I thought of this last year).

Strategy obtains, employs, and outsources skills. I mistakenly used to think a good strategy would be extremely crisp and detailed. I now see that strategy doesn’t always need to manifest fully at the outset. It’s OK (and sometimes essential) to move in a vague direction at first. But the bones of a great strategy become increasingly clear over time, and they will stretch far into the future.

Marketing speaks to the moral, human, external component, in contrast with the selfish metallic concepts of skill and strategy. Marketing looks at the body of work produced by your strategy and the meaning of this work in the eyes of others. I mistakenly used to undervalue empathy and wouldn’t have given marketing its own (well-deserved) category. Does the rest of the world know, and how do they judge you?

You train to get skills. You plan to have a strategy. You market to create a story and niche positioning within the universe. High quality progress in these things is critical to having an impactful career and a meaningful life. They transcend any particular job, stick with you, and happen to also be prerequisites to any substantial or meaningful endeavor.

Here’s a litmus test for my younger self: do you agree with this framework, and understand it fully? If not, you really should stop dreaming and “just go get a decent job.”


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