The Sweet Spot
On software development, engineering leadership, machine learning and all things shiny.

Quarter Life Crisis

At 23 years old I decided to quit my first full time tech job and take a year off to figure out my life. Was it worth it?

I grew up on the stereotypical overachiever fast track. My dad was a Silicon Valley hardware engineer who got me into coding when I was in fifth grade, and my passions kept me scripting, coding and building web sites in middle school and high school. When I graduated from Berkeley with an EECS degree, it was pretty clear I was ready to dive headfirst into the industry.

I joined a fairly large company, filled with smart and friendly people. It was a pretty stable, comfortable place. My coworkers organized lots of social events and there was an obvious deep camaraderie between all.

I was the new grad hire on an older team1. I had a great manager and teammates I could learn a ton from. Totally an ideal place to launch a career.

Except… a year and a half in, I quit. I decided I’d leave the industry for a bit. I was happy at work, but I wasn’t OK.

You see, I had just gone through my first big breakup, one that reverberated deeper than I realized. When that relationship ended, I went through a period of deep soul-searching and realized that I needed some time away.

Around that time, some friends let me know that they were entering a yearlong internship at our Oakland church community. I decided that I’d join them that year. And so it went - I moved out of my comfy Emeryville apartment and into the cramped quarters of our East Oakland community center. It was going to be the start of one of the most transformative experiences of my life.

Photo of me in front of our urban garden

Instead of daily standups behind big glass vistas of the San Francisco skyline, I woke up to daily meditation and time spent in the urban community garden. Where I took for granted the amenities and services of our big glass skyscraper, I was now the one vacuuming, scrubbing and cleaning the facilities2. Instead of spending most of my day with high-earning tech workers, many days were spent chatting (and sometimes squabbling) with our unhoused friends who lived on the church steps.

I know it’s cliché, but having time to step out of the career hustle was so good for me. It was good for the young man that I was, who needed time to focus on himself and rebuild a grounded identity. It was good for me to spend among friends and trusted community. It was good for me to spend a season focusing my energies outward. It was good for my balance and sense of what was normal to see how folks way, way outside the tech bubble lived, especially in East Oakland as we served in the soup kitchen.

I think that if I had not taken that year off, I would have continued in the hustle - lost deep in the bubble that so many of us in tech ensconce ourselves with.

I fully understand that my time spent in East Oakland that year cannot fully be separated from conversations about gentrification and privilege. After all, I had the financial means to take a year off without worrying about debt. And a year later, I re-joined the industry, easily switching back into my privileged life in tech. To that end, the learning continues.

And yet, that year fundamentally transformed me - it gave me a perspective on life outside of the tech bubble. It gave me friendships that have lasted to this day and sweet memories (and uproarious stories) that will last a lifetime.

At 23 years old, I made a good decision to take a year off. I’d say it was worth it.

  1. My team’s average age was over 40 - I think about how rare this is now. 

  2. There was one particularly bad rainy day where the sewer main backed up that resulted in shenanigans we collectively dubbed “Chocolate Rain”. You don’t want to know. 

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