Why I Quit My Dream Job at Amazon

Almost three weeks ago, I quit my job as a Software Development Manager at Amazon, after four years there. I've always said that my true "dream job" would be working for myself: making my own decisions, mistakes, and direction... but working at a place like Amazon was the next best thing.

There are stories of people crying at their desks because of how brutal Amazon culture can be (tight timelines, incredibly high expectations, and ambitious projects that seem impossible at times). I'm not too proud to admit that I once broke down in tears in my office from the pressure. I had snapped at my manager from the stress, and he [privately and correctly] got after me for it. It was so out of my "calm, cool, and collected" nature that it made me question what the heck I was doing there, and I broke down. After that, I picked myself back up and pressed on for another couple of years. The volume of things I learned and the growth I experienced there is astonishing. I don't regret it for a second.

June 18th, 2021, however, was my last day there. I'm now working for... no one.

I'm now doing what I've wanted to do since I was 12 years old: start my own business, on my own terms, making my own mistakes, and hopefully building something that people love. It was only because of Amazon that this is possible, so I'm incredibly grateful every day.

How did Amazon make this possible? Luck and good timing, mostly. I joined in 2017, when the stock price was at around $800. I was granted enough shares and rode the stock wave enough to allow me to quit and give me about a year of runway doing my own thing. That gives me a year to build, launch, and start making enough to support me and my family... not much time at all, but this is a once-in-a-lifetime opportunity that I can't miss out on.

Officially, I'm on sabbatical due to health reasons (the stress at Amazon often caused my high blood pressure to spike), but I'm taking this opportunity to do what I have been unable to do working "nights and weekends" for the past 20 years on side-projects. By going "full time" on my own project, my hope is that I can extend that year-long runway long enough to turn it into two years, then three, then... we'll see.

Ideas are cheap, and building is the easy part, so I'm not shy about sharing my idea. I'll post next about how I settled on my current idea, why I think it'll succeed, and what my plan is. For now, though, this is how I ended up here, and I plan to #buildinpublic here and on Twitter as @PocketBryan as I go. I will also be posting video updates on my blog as I go.

Edit: I spent the day yesterday setting up a blog where I can post long-form updates and videos. I didn't like the idea of using something like Medium that throws up paywalls, and I wanted to have one place to link to my video updates, etc. I'll continue to post milestones and interesting updates here, but keep an eye on PocketBryan.com as well if you're interested in following along.

Edit 2: I just posted a quick update about what I'm building, why, and why I think it'll work this time (as well as a list of my many failures before now 😂): https://www.pocketbryan.com/2021/07/08/the-idea-invoicing-for-freelancers-and-why-i-think-it-will-work/#more-64

  1. 7

    Bryan - looking forward to following along. I left my full-time job about a year ago to start working on new projects. If I can ever be helpful, let me know!

  2. 3

    Did the same two years ago and started working on own thing. Launched it last week. Good luck for your solo journey ahead. Followed you on twitter.

    1. 2

      Congratulations on the launch!

  3. 3

    Same story here, same company. Putting in my time and hoping to try the same in a few years. I will be following closely. Thanks for sharing your story and congratulations!

    1. 1

      Hey, are you sure you have to wait a few years? If you don't enjoy your job, why not start sooner? Even if you're not ready to make the jump, you could try to do a little in your free time or try to negotiate to go 4 days a week.

    2. 1

      Awesome! It's a small world for sure. Hopefully some of what I share will come in handy!

  4. 2

    Way to go, Bryan! Your story is so inspiring. Mental health should go first and you did the right thing. Good luck on your new path. All we do at Keypup is about empowerment and freedom for developers. Let's chat on Twitter 👋

    1. 2

      Thank you so much! Looking forward to chatting more.

  5. 2

    Awesome man... No price on having good health. Will be following you.

    Good luck

    1. 3

      Very true. It was a wake-up call when I found myself in the ER about to have a heart attack. I know startup life is no cake-walk, but so far my stress levels have plummeted because I no longer get frustrated by the silly decisions others around me are making.

  6. 2

    Welcome - excited to see your progress!

    Best of wishes!

    1. 1

      Thanks! I realized yesterday that probably not every little update belongs here (might be too much noise for people not interested in that level of detail), so I set up a blog for those who would like to follow along as I learn and share more frequently: https://www.pocketbryan.com

      1. 1

        Sweet - signed up!

        (great blog design btw! what tech stack did you use?)

        1. 1

          Thanks! I was going for quick and easy, since I wanted to spend most of my time on the actual SaaS, ha ha.

          It's just Wordpress running on Dreamhost using the Iceberg theme that I spent way too much time customizing and tweaking 😬

          1. 1

            Haha - well it payed off!

  7. 1

    Im ex Amazon too. Love your post man! Can totally relate. Why build alone? I can help you out part time. We should connect!

  8. 1

    Hi Bryan, I used to think, naively, that anybody who could code could build a profitable project. This really motivated me to pick up coding last year.

    But reading your article has been very educational, and makes me think a bit differently about the whole thing now.

    Looking forward to seeing your progress :D I've subscribed to your newsletter and followed you on Twitter.

  9. 1

    Love your story! Took the same leap as you earlier this year :) I was also in my dream role at my dream company. It takes a lot to make the decision but I hope you're riding the wave okay!

    1. 1

      Thank you! I wake up every morning excited and feeling so lucky to be able to even have this opportunity. So far, so good!

  10. 1

    Best of luck - Bryan ! Just out of curiosity, are you married / did you get your family onboard with this plan ? I guess with a family to feed the decision to strike out on your own becomes much harder (irrespective of the cash you've). Also, were there friends / well wishers who dissuaded you ? I think its often far harder to reject advise from people who only mean well and looking for your best interest !

    1. 1

      Great question! I'm married with five kids, between the ages of 8 and 17. My wife is amazing, and although she doesn't quite understand my drive to start a company (she's probably grown tired of hearing about my "ideas" over the years), she is incredibly supportive and trusting. We sat down and talked through the budget, what we could afford to do (and for how long), and what we would do about things like health insurance. We're both very risk-averse, so it was an important conversation to have up front and be very open about the risks (and opportunities).

      As far as others go, I'm keeping it quiet for now. Most people I know don't even know I've left Amazon. I'm not lying about it (I'll happily talk about it if asked), but I'm not broadcasting it. I've found that most people just don't get why us Indie Hackers are motivated to do what we do, so until I'm more successful and can point to real revenue numbers, etc, I'm just going to keep it to myself (in my personal circles, anyway). As for sharing with strangers/friends on the Internet, ironically, I'm not holding back!

  11. 1

    Congrats on the big move Bryan

  12. 1

    Same, specifically on July 2nd since I wanted that sweet extra month of health insurance :)

    1. 1

      Nice :) I thought about doing that, bit every additional day felt like a week. What are you working on now?

      1. 1

        Rest and home improvement projects for now! Going to Facebook next in 3 months as an E4 engineer.

  13. 1

    Let me know if I can help you in anything, good luck!

  14. 1

    Wow I can't wait for further updates! Excited to watch your journey

  15. 1

    Hey Bryan - sounds like we have similar ideas about freelancers :)
    Feel free to check out my app http://remotime.net/ for some ideas.
    I'm still only dedicated in the evenings, so I'm sure you can improve on what I've done in no time ;)

    1. 1

      Cool! I feel like there's so much opportunity in this space. It's great to find a like-minded person like you here. Looking forward to chatting more!

  16. 1

    Congrats on freeing yourself.

    I'll follow your journey on Twitter (https://twitter.com/dsebastien)

    I did the same two years ago, and am clearly not looking back. I've had small wins, and those feel immensely more rewarding than an high-paying job can ever be. The feeling of freedom is great, and you're now free to be as creative as you wish to.


    1. 1

      It’s definitely encouraging to hear about so many other people that have successfully made the leap before me

  17. 1

    Hey @PocketBryan 👋

    Have you read “Sprint — How to Solve Big Problems and Test New Ideas in Just Five Days” by Jake Knapp?

    Could save you months.


    — Mateo

    1. 1

      I haven’t but I’ll take a look

  18. 1

    There's nothing quite as invigorating as quitting your full-time job 🎉

    Just had the chance to read your article about your previous products and the new product strategy. After quitting my own full-time job, it took me twelve months to get to the mindset and clarity that you currently possess. From my perspective, it looks like you're already on a great path, well done.

    Genuinely wish you all the best with this! Spend as little time building the product as possible.

    1. 1

      Thank you! It’s taken me a lot of failures to get to this point, so you’ve learned faster than I have 😂

  19. 1

    Read the latest article on your blog and gave you a follow on Twitter - good luck and looking forward to your progress !

  20. 1

    You were at Amazon for 4 years AND rode the share price rocket, and you only have a year of runway?!

    I could probably retire on what you earned 😂

    1. 1

      We’ll, let’s just say I enjoyed the extra income 😂 I now have a nice house, a great pool, a fun car, and a year of runway… not trying to brag — just pointing out that you’re right. I could have had more runway if I saved more of it.

  21. 1

    Good decision without a doubt. Sounds to me like you had the ideal length and type of journey. The business experience you got there pretty much guarantees your success in anything you pursue for the rest of your life and it's highly unlikely any of your future professional endeavors will compare in difficulty.

    You don't have to run your business the same way but since you've worked with the highest quality people in the world, you at least know how they would handle X.

    As for the product....I think you made a really wise and practical choice. The TAM is huge and you can take advantage of the learnings from other similar successful products.

    To market the business, I would keep it simple and use this to launch your company.

    Congrats, you're going to kill it.

    1. 1

      Thank you! I’m a fan of Noah Kagan and somehow never saw that doc before. Thanks!

      1. 1

        So am I....Noah's casual and laid back communication style can seem a bit flippant if you're not paying attention to what he's saying versus how he says it. But there is no mistaking the fact that he is an original gangster.

  22. 1

    Being healthy is what matters the most!
    It's awesome that you took the leap as an Indie Hacker!
    I know that feeling of finally realizing you are putting your all in tight deadlines and for what?

    I realized that early this year and officially made the leap about two months ago to go Indie full-time! It's been liberating

    Good luck!

    1. 1

      Awesome! I'll be following along!

      1. 1

        sweet! likewise! I'll be following you!
        thanks for the follow

  23. 1

    Bryan, so excited for you. Read your blog and loved your recap of your old projects. Good luck on the new adventure :)

    1. 1

      Thank you so much! It's hard putting the failures and embarrassing stuff out there, but I know I'm not the only one at least. Hopefully it will help someone else :)

  24. 1

    Who knows how many chances life will give you to escape the rat race.

    I wish you good luck because you'll need it.

    I had 7 month for that. Not a great place to be. But it worth it .

    Nobody wants you succeed. Not your friends, nor your ex colleagues. Even folks here afraid that you'll get it. Crash that fucking planet ha-ha, you can do it.

    Follow you in Twitter ;)

    1. 2

      Very true. I'm honestly surprised that anyone cares at all. The culture here at Indie Hackers of rooting for each other and helping each other out is awesome!

      1. 2

        I disagree that everyone wants you to fail. Nobody wants you to fail and the truth is who cares. Anytime you come across anything negative, it's not hard to ignore it or block it out. You don't have a boss so you can ignore whoever you want with no consequences.

  25. 1

    Congrats on making the jump! I decided to decline to join AWS after interning there because I sensed some of what you experienced. After seeing other interns crack under the pressure and quit, I knew it wasn't for me and have been working at startups since.

    Good luck on your journey!

    1. 2

      I always tell people that everything at Amazon is at least 2x. Twice the experience (in the same amount of time), twice the scope and impact of projects at other companies, twice the pay (thanks to the stock price), and twice the stress! I don't regret it, but it sure was taxing.

      1. 1

        That shouldn't be a surprise to anyone because how else could they be where they are.....it's the same exact environment everywhere. Microsoft, Oracle, all of the top tech companies that reach that size use the same formula. Look at how many people quit those companies at 12:01AM when their stocks become vested or whatever it's called. Consumer products might be different but enterprise products and services is rough stuff.

  26. 1

    You got this.
    Welcome to the indie world.

    I wish you quick health recovery.

    1. 1

      Thank you! This is why I love the Indie Hackers community.

  27. 1

    Good luck Bryan. I'll be following your journey on Twitter.

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