My first harsh lesson from the job market

Lessons from a former founder on the job hunt

It was spring 2023 when I decided I to leave my startup. But I couldn’t just walk away. I was the owner and the sole employee. And there were still several long term income share agreements being managed through the company.

But I needed a change (and a bigger salary). So after letting the investors know, I gradually scaled back my day-to-day obligations at SharpestMinds. I began to automate everything I could and eliminate all but the necessary tasks to keep the company alive. The goal: get the company into maintenance mode and then focus on my next challenge, pivoting my career.

I wasn’t sure what that career would be, given my bespoke path as a generalist. But I felt confident that I could land a role as a senior software engineer.

Then, mere days after my decision, I read a job posting on HackerNews—an early stage startup looking for a founding engineer. It struck a chord. I was still busy with SharpestMinds, not ready for a full-time job, but I reached out anyway. I was confident and I was was honest. I would have to start part-time, but I would be perfect. It worked. Days later, I was meeting the founders for an interview. My first in seven years.

It went well.

The next step was a technical screen. They brought me into the office for two days to work on a real problem in their codebase (they paid me for it too—a very classy move). This was their first engineering hire, and they wanted to make sure it was the right one.

This is where my confidence finally took a hit.

I struggled through the technical screen. I spent more time reading documentation and trying to understand the code than I did building. In the end, I shipped a prototype, but it was underwhelming. The founders liked my attitude, my thought process, and my product sense, but I did not meet their technical requirements.

It was disappointing, but it was a valuable lesson. A wake up call that my technical chops weren’t at a senior level.

During my last few years at SharpestMinds, I had been coding less and less. Some of my skills had atrophied. But, beyond that, I had been working in the same codebase since I left academia. Using a semi-obscure framework (Meteor.js) that abstracted a way a lot of core concepts. And SharpestMinds never had to scale, or worry about optimizing performance or compute. My experience, at least my programming experience, wasn’t as impressive as I thought it was.

So with a slightly bruised ego, and an awareness of my weaknesses, I set out to change that.