When I began thinking about my career, way back when, I had very specific ideas. I was going to study journalism, but not become a newspaper reporter. I’d take a few extra classes in layout and design, and land a cushy job writing features, or doing layout for a glossy magazine. I had my eye on something edgy for a while, but shifted to more high-brow pursuits when it came time to actually look for a job.

In reality, this is not how my career started at all, nor have I ever worked for a...