“Only young once ;)”
That was how I ended an email about whether I should take a third job.
I had already started the second one. Peek was the day job. AdaptiveBlue was additional systems work. The new offer came from a tiny startup, maybe three people, that wanted help preparing a site for massive growth.
I wanted to run with it.
The money mattered, but not in the abstract. Somebody close to me wanted to spend more time building a clothing business and less time doing work that drained her. If I could take on enough extra work, there might be room for her to make a serious push at it.
People around us were supportive and worried in equal measure. The concern was obvious: three jobs sounds like a reliable way to burn out, become miserable, and make everybody around you miserable too.
My answer was not especially sophisticated. If I crashed and burned, I could start over.
That was very much how I thought at twenty-five. Work was not only income or a career ladder. It was a way to see what I could handle, learn a new business, and create options for the people around me. The downside felt temporary. The chance to build something felt immediate.
The apartment was starting to reflect it. We had painted an entire wall in the home office with whiteboard paint. It made the place feel more workable, which was useful because I kept finding more work to put on it.
There was a lot of optimism in that setup and a real warning inside it. I liked hard problems. I liked being useful. I also had almost no instinct for leaving capacity unused.
Three jobs was excessive. I knew that. I still wanted the third one.