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9 Hard Lessons You Learn as a Director at Amazon
What unexpected things happen when your scope increases, almost everything is ambiguous, and results (not effort) are all that matter.
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Welcome to the Scarlet Ink newsletter. I’m Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers and tactical leadership advice.
Free members can read some amount of each article, while paid members can read the full article. For some, part of the article is plenty! But if you’d like to read more, I’d love you to consider becoming a paid member!
My initial interest in early retirement started as I imagine the majority of the community discovers the idea. Sitting there at my work desk, I felt a sense of existential disappointment at the idea of working another 40 years.
I’m glad that I began my savings journey, and while I had detours along the way, the lessons I learned landed me in a pretty great place. I get to sit here in my home office with a coffee next to me, writing a lovely letter to thousands of people.
However, I don’t want to lose track of a vital lesson (yes, at least loosely related to this article).
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If you were to smooth out a graph of my average work satisfaction over time, it would be clear that as I progressed in my career, work began to be less unpleasant. The negative aspects decreased, and every year I was able to engage with more work that I honestly enjoyed.
When you look at senior employees who seem genuinely excited to be in the office, I used to wonder what was wrong with them. “They’ve made plenty of money. Why are they still in the office every day?”
I mean, I still think that to some extent. But there’s a kernel of wisdom here as well. Read any LinkedIn or Reddit post about work, and you’ll find a good number of junior employees filled with bitterness and cynicism. They rail at the stupidity of management, the incoming AI wave as defeating all hope of a better future, and the pointlessness of their daily tasks.
But I think the junior years of work are honestly pretty hard. You don’t understand why you’re doing things (sometimes people don’t bother telling you, or you just don’t understand). Your work is a small piece of a big jigsaw puzzle you quite possibly don’t see. And your work is rarely influential in the grand scheme of things, so you really are just a small cog in a big machine.
The opposite end of the career ladder is interesting. Because if things have gone well, you might now be directing hundreds of cogs. You’ll know exactly why you’re doing the work, and you frequently agree with it. You can see the bigger puzzle, and you can identify how you specifically helped put that puzzle together. Plus, you have significant autonomy over your specific contributions, and those frequently line up with your skills and interests.
So the job is better. And that’s probably a significant aspect of why many senior people with fat bank accounts continue to work. They are finally at the point in their career where they’re having fun. And while I didn’t like my job enough to stay, I can at least understand the idea. I think it’s worth sharing this knowledge with everyone because it’s healthy to see the light at the end of the tunnel. You, too, may enjoy your job someday. If you don’t already, that is.
Okie dokie, time to move on.
Sharing my experiences.
I wanted to write about what it was like to move into a senior leadership position at Amazon. It’s the type of thing that many people never get to experience.
Several times I’ve written narratives about what it feels like to be in those roles. Those articles turned into some of the more popular things I’ve written. So if you haven’t read them, take a gander.
