Swimming Upstream as a Career Choice

In the beginning of my career I was a programmer. The colleagues I worked with at the time went on to become system administrators, data analysts, and full stack engineers. Me? I went the other direction. And so began a career of constantly swimming upstream.

Despite establishing a toehold in technology, it was the users that always drew me. To this day, I'd rather discuss user flows, customer acquisition, or UX intuitiveness over APIs or data platforms. Don't get me wrong - I have exclusively led platform teams in those pursuits for more than five years. I can hold my own in deeply technical meetings. The difference is the level of inherent joy the two types of discussions bring me. (Thankfully, I have had the pleasure and luck of working with some really awesome developers who made it fun and interesting. Without them, it would have been harder to stay motivated.)

In a previous role, I was asked to assist with creating a new group within the org. I worked hand-in-hand with the person who went on to become the VP of the group to establish processes, identify the target users, and work with executives to define the overall KPIs. However, once the group was established, I was asked to take on a role that would have been even more technical than roles I'd held in the past. It would have been a lateral move, but would have made me feel even more like a fish out of water.

It caused a bit of an internal crisis. I had the faith of the VP and other execs, but it filled me with dread. I listened to my gut and talked with the VP about stepping away. The exchange went something like this:

VP: But I know you can do this! You've just to want it.

Me: Yeah, I could also be an astrophysicist if I wanted to...

It's that key word, "want." I have chased roles in organizations that would allow for growth. The problem was, every growth opportunity kept going deeper into tech. Left to its organic flow, my career would continue to be technical. I'd be more in the world of 1s and 0s and less involved with behavioral science and visual cues. What I want is a more creative role, or at least more adjacent to creative pursuits.

A few years ago, I switched back to freelancing because it allowed me a greater degree of autonomy on choosing work. And though I love freelancing and consulting, there's still something to be said for full-time work. I still keep my eyes peeled, confident that there's a perfect role out there for me: one where I can put many years of product management knowledge to work, while working even more closely with designers. Preferably on a cool product. Preferably while working from home. And preferably with less swimming upstream.

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Agile Manifesto in Life