Why I'm Quitting My Job and Leaving San Francisco

Two weeks ago I gave notice to my job that I would be leaving at the end of the year. On January 5th, I am moving to Chicago to focus on my solo projects and freelancing.

P.S. This post was originally published on December 12th, 2012.

Time for Change

Sometimes we find ourselves in an uncomfortable spot in life, needing to make a change even though the motivating forces are blurry. This happened to me a few months ago. It had become increasingly clear to me that my job wasn’t right for me. More specifically, it was the role that I played in the organization and how it was no longer providing me with the skill growth I was hoping to gain.

You see, I studied graphic design (and, laughably, music business before that) in Chicago. But before I studied graphic design, I had this intuitive sense of what made good software products and how one could use software to solve problems. I also had an uncanny knack for getting in touch with people who had no reason to talk to me. Becoming a designer was a small step to start building the hard skills I needed to be able to look at myself objectively, as if I was starting a business, and say “I want to work with that guy”.

The goal at the time, as a 19-year-old college sophomore, was to find a way to work for a technology startup in San Francisco. There was little else on my mind; I had to get to San Francisco and get my foot in the door. Nothing else felt like it would prepare me to someday start my own company more than to be “in the middle of it all”.

Right before my final year of college, I found a way to get in touch with Twilio. Not long after, the stars aligned and they had an opening for me. Almost exactly two years ago, I left Chicago and moved to San Francisco. Over the past two years I have played the role of a product manager, and I have enjoyed almost every moment. My time there has been truly great, and even though we have had our disagreements over process and other things like that, the company treated me extremely well. I gained everything from the job I was hoping to gain, plus some much needed clarity of purpose.

Cheating My Way In The Door

The problem is that I cheated. I snuck my way into a job at a great startup because I thought that was what I wanted. In my mind, the only thing that mattered was to be working at a startup. The role I sought out was product manager, mostly because my design and programming skills were too thin for someone to hire me to do either of those fulltime. I thought that would be okay. I could get my foot in the door and slowly move from a product manager role into a product designer role, which is the role I preferred.

Thus, as time went on, I continued to feel unfulfilled. My projects were exciting and I had autonomy, but I wasn’t playing the role that I needed to be playing. Too often I found myself not caring deeply enough about the output of the product because I didn’t have a direct hand in crafting the code. My input was always from standing behind the engineer, which if you are a builder, is a sad place to be while giving advice.

Toiling in Obscurity

So far, the best analogy for my situation is one based on another love of mine: standup comedy. Imagine that you are a young standup comedian. You have only been performing for a few months. However, you know that if you are going to make comedy into a career, then some day you need to move to Los Angeles to be in the thick of the scene.

One day, you take a job as a associate producer on a sitcom in Los Angeles. You think this is the break you needed to get your foot in the door. You’ll be able to do standup shows at night, and work as a producer during the day. Then a few months or so later, you’ll be able to quit your producer job and become a full-time standup comedian.

The problem with this situation is that you rarely find the time or energy to practice your craft at night. You never write new material and rarely evolve your existing act. You can’t quit the producer job because you need the money to survive in Los Angeles, but the job is the primary thing holding you back from progressing. You realize the only way for you to work as a comedian is to jump ship. You must toil away in obscurity while you hone your craft. Only then, once you accept that you can’t get past doing the long hours and hard work, can you really start to make progress.

Clarity of Purpose

It has become clearer than ever what I desire to accomplish in the next stage of my life. That is an important part of all of this. In the past, my actions felt like they were driven mostly by ego and the desire to be known in the startup community. If being out here has taught me anything, it is that none of that stuff matters (obviously). It is okay if I don’t fit in and if other people don’t understand my motivations.

My problem is that I also took a job that wasn’t exactly what I wanted to be doing so that I could be in San Francisco, instead of staying where I was and honing my craft. I wouldn’t change any decision I have made so far, but I do think it is worth evaluating those decisions over time. I have learned and grown immensely while working out here in San Francisco, but the time is right for me to move on.

One last thing…

Words could never express the thanks I owe Jeff Lawson, CEO of Twilio, for taking a chance on me two years ago. He gave me an opportunity nobody else had up until that point. I can only hope that I provided a fraction of the value to Twilio that he provided to me. To observe Jeff leading the company and product team was inspirational and hugely impactful on me.