Why I Quit a $500K job at Amazon to work for myself

Daniel Vassallo

Feb 9

Last week I left my cushy job at Amazon after 8 years. Despite getting rewarded repeatedly with promotions, compensation, recognition, and praise, I wasn’t motivated enough to do another year.

I spent my entire time in AWS building tools for developers. I liked that field so much that I would have been satisfied working in it for the rest of my life.

I joined Amazon as an entry level developer. Within 3.5 years I had been promoted twice to a senior engineer, and I was practically guaranteed another promotion to principal engineer this year if I had stayed. My potential at the company was high, I was told.

My esteem within the company grew along the years and I was regarded an expert and a leader in my field. People looked up to me and respected me.

I made $75K in my first year and that gradually grew to $511K by my last year. I could have made another $1M if I stayed another couple of years.

My work–life balance was good too, despite Amazon’s reputation. I didn’t need to prove myself anymore, and I could get everything done in 40 hours a week. My team worked from home one day a week, and I rarely opened my laptop at night or weekends.

Also, the people I worked with were exceptional. I had three managers in total, and all were generous people with lots of empathy. I’m very grateful to everyone I worked with.

Everything was going well and getting better. But despite all this, my motivation to go to work each morning was decreasing — almost in an inverse trend to my career and income growth.

It would have been foolish of me to expect my motivation to start increasing if I got yet another promotion, or another compensation bump, or another big project. But there was something else that was trending down with my motivation. It was my freedom.

The Motivation Decline

For the first couple of years my motivation was off the charts. I was mostly working with another person on an internal tool, and there was very little scrutiny around it. It was a time where I had a lot of independence in choosing how to work and what to work on — at least relative to more recent years. It was just me and the other person improving this thing, talking to users, releasing updates, testing it, and everything else. Whatever we felt was important, we generally got to do. We did the best work we could for its own sake and we were mostly self-directed.

The last couple of years, however, were quite different. I was leading the most important project in the history of my department, with many stakeholders and complex goals. What I could do was always bounded by my ability to convince all the people involved that it was the best way to navigate our goals.

I was always going to be working on somebody else’s terms at Amazon. The terms were simple in the beginning (keep fixing the thing), but kept getting more complicated as the years passed by (maximize all goals; satisfy all stakeholders). Then there were other restrictions inherent to working in a large organization about how to do the work, what work to do, what goals to set, and what business was worth pursuing. This situation was squeezing me into doing things that I’d rather not do, and vice versa.

Finding New Motivation

What kind of work would I do if I had to do it forever? Not something that I did until I reached some milestone (an exit), but something that I would consider satisfactory if I continued to do it until I’m 80. What is out there that I could do that would make me excited waking up every day for the next 45 years that could also earn me enough money to cover my expenses? Is that too unambitious? I don’t think so. Because there are two types of drivers that get me out of bed in the morning.

One comes from the outside in the form of a carrot or a stick. For instance, I’m not automatically driven to do my tax returns every April, but I make sure I do because I don’t want to go to prison. Or I might not want to work on something I dislike, but I do so anyway because I may need to pay the bills, or want to buy a fancy car. These are the extrinsic motivators.

The other comes from within. This is what drives me to do things when there isn’t a carrot or a stick. Hobbies are one activity driven by this. But what I was looking for was something that I could do for a living that was also driven by this type of motivation: the intrinsic kind.

Back to the question of whether this is too unambitious. See, I realized that extrinsic motivation doesn’t last. Whenever I got promoted, it felt good for a week, and then it was as over. When I first hit $100K income, I would take a peek at my W2 for a few days admiring the six digits, but then it wore off. When I hit $200K, $300K, $400K, and $500K, it was the same thing. I would be delusional to think that earning $1M, or $10M would suddenly make it different. And I feel the same with every other extrinsic reward or material possession. Getting them feels good for a while, but this wears off quickly.

The things that don’t wear off are those that I’ve been doing since I was a kid, when nothing was forcing me to do them. Things such as writing code, selling my creations, charting my own path, calling it like I saw it. I know my strengths, and I know what motivates me, so why not do this all the time? I’m lucky to live in a time where I can do something independently in my area of expertise without requiring large amounts of capital or outside investors. So that’s what I’m doing.

What’s Next?

I’m going all in on independence, and I’m going to try to make a living with my own bare hands starting from nothing. I don’t expect to only do things that I like, but it will be on my terms. My target is to cover my family’s expenses before I run out of savings while doing something that intrinsically motivates me. What more would I ever want to be satisfied with my work?

If you liked this article, I’m going to be writing more about:

• How I’m setting up my new independent business.
• And obviously about the lifestyle business that I’m starting.

Now that I can use Twitter without being subject to Amazon’s social media policy, you can follow me there as I continue to document my journey.

Originally published at danielvassallo.com on February 9, 2019.