Belatedly Following Through

I left Amazon after 19 years at the end of last summer. When folks asked me why I couldn’t find any easy answer. I thought that I would eventually try to get down in words why I’d done it. It was one of the topics I had in mind when I set up this blog. But it’s been hard to get started. 8 months later my thoughts are still coalescing. And maybe I’m a little shy to talk about some of the reasons. My generation isn’t as quick as later ones to air every bit of wet laundry in our heads and there’s no big crisis to talk about. My problems are strictly first world problems. But I think it helps me to write out my thoughts and maybe others will find it interesting. I dunno. I’m worried that if I wait any longer it’ll go stale. Just be warned that this might be rather self-indulgent. I’m going to dive deep into what the time at Amazon felt like, where it fit in my life and how well it did, and how it got to feeling like it didn’t fit. It’s a story of the stories we tell ourselves about ourselves, the hypocrisy that’s so deep we hardly even notice it, and the lamest kinds of midlife crises. I have thoughts on closely related topics. These include the promise and peril of all the new LLM technology and the history and specifics of what feels to me like a cultural decline at Amazon. I’ve decided to only touch on those lightly here and to write about them more in the future if you ask nicely.

Why did I leave a healthy career at a giant, successful, innovative tech corporation where I had a fancy job title and what looked like a decent shot at an even fancier one? I guess the place to start is that I never really wanted that in the first place. When my lovely (future) wife and I moved ourselves to Seattle, we told all our friends we’d be there a couple years. Then we’d come back home to pick our lives back up. I didn’t dream of being a tech tycoon. I didn’t have any desire to leave my beautiful commonwealth. My dreams consisted of living authentically, working on the causes and projects that interested me, and making my own choices about how I spent my time. At 26, when I joined the company, I was a really idealistic and moralistic young adult. Like my parents, I’ve always been pretty judgmental, having strong ideas about what’s right and wrong. Being raised in a protestant church probably also reinforced the seriousness of morality and a calling to do good in the world. At some point in my upbringing, that got refocused into a rejection of attitudes and behaviors that my family and community around me accepted as normal.

As a nerdy kid I naturally gravitated towards other kids who felt different and got introduced to the punk and hardcore music I’ve cherished ever since. I was very open to what bands like Propagandhi and Earth Crisis had to say (some of which aged well and some of which didn’t) about human and animal rights and personal responsibility. I remember being assigned to read Jim Hightower’s “There’s Nothing In The Middle Of the Road But Yellow Stripes and Dead Armadillos” in high school and becoming very suspicious of corporations and centrism. Even growing up during the Simpsons’ golden age and their satirical take on all aspects of society probably steered me. I don’t know but maybe I was ready for all these influences to shape me into someone different because I didn’t really feel like I fit in at school or in church. I didn’t feel like all the things my parents encouraged me to do were a fit for me. That’s not necessarily because anyone was wrong or bad, just because of how I perceived the world and what felt good and what didn’t. And writing this down, it all sounds like completely normal teenage rebellion to me. What does strike me as different is that I’ve always felt like if things seem wrong to me that it’s my personal moral responsibility to work against them or to at least not participate. My observation is that a lot of people don’t really make that connection or find it easy to let themselves off the hook. I, on the other hand, have an easy time assigning and feeling bad about personal complicity. As I advanced through my teenage years I drifted away from the church I’d been raised in and eventually the religion that went with it. I drifted through high school graduation and into college. There I found peers that really accepted and valued me for the first time in many years. Then, like so many people my age, all the piled kindling in my heart was set ablaze by the political aftermath of 9/11 and the rush into the Iraq war. The square world had proven itself lacking in principles. More than ever I wanted authenticity and truth, an end to war, respect for human rights, care for the environment. I didn’t want to be part of the machine, making, advertising, and selling crap to each other at the cost of everything that really mattered. Going to work at what would become the biggest retailer in the world wouldn’t have been high on my list of dream jobs.

But I was mostly a dreamer without firm ideas for taking action on all these passions. And I had terrible interpersonal skills and social anxiety. It’s really hard for me to meet new people and to be vulnerable with them. I didn’t have a network, I didn’t know how to build a network of folks that were interested in the same things as I was. I’m not sure if I even fathomed that finding work aligned with my values was something I could do. It’s like I just didn’t know to look for those possibilities. And maybe I lacked the courage to even see paths that didn’t lead to obvious and relatively easy ways to get paid. I liked comfort and space to tinker. The kind of comfort I was familiar with required money. I discovered by my early 20s that I had a talent for programming computers and that people would pay me for it. The creative element of it, building little logic machines and watching them do stuff, appealed to me. I liked the aesthetics of logic well expressed in code. I had a vague desire to be part of building big impressive systems rather than what I’d been doing: dicking around with little corporate intranets and fixing people’s MS Access databases. As a social awkward, a giant organization is an easy place to get into and find a comfortable place in. When I graduated from college with a BS in computer science I applied anywhere that seemed even a little likely to result in paying work. I ended up working for the US Navy at a warfare laboratory. Somehow, despite my own personal convictions I ended up being part of the military industrial complex.

I don’t think that reflects especially well on me. Don’t get me wrong, I don’t hate the military or believe there’s never a just time to use it. I hate wars of choice, jingoism, and war profiteering. Which is not to say that the Navy lab exemplified jingoism, more that it was a jingoistic time under an administration that helped set that tone. Neither would I call anything that happened there profiteering, though I would say that there was a lot of waste and weak contracts and a porous fence between the government and contractor side. It was more a weird fit for me given my ideals, and I felt very conflicted. That aside I’m proud of myself for getting that job. I had been chronically underemployed as I went through a rough patch of growing up. It’s not clear that would have improved. I was rough around the edges and didn’t really know what to do or how to do it. When I saw that ad for the Navy job fair it wasn’t a place I was eager to work. And I couldn’t have felt more out of place when I got there, more uncomfortable in my business clothes than most and much less interested in shaking hands and making small talk. My friends had tried to convince me to go do something fun instead. But I needed to work and making software got me paid better than any of the other things I knew how to do. When I got to the fair I sat in my car for a while holding my small stack of resumes. I think I remember walking in, checking out the scene and then walking back out to my car and nearly leaving. But I was just scraping by on the kindness of my friends and a little from my parents. I needed work. So I sucked in my breath, ground my teeth together, opened the car door, and walked in there to find someone to talk to. I walked out with a salaried position with the title Scientist. Regardless of how I felt about that job, it bent the course of my life upwards. It gave me security and structure that I sorely needed, at a time when it was not obvious which direction things were going to go. It’s not deep or original but very true that being willing to do stuff you don’t want to do is a key skill for getting to the bigger stuff that you do want.

I found that job miserable over the 4 years I had it. Having money was great but the job was 70 miles away from anywhere I was willing to live. I commuted an hour and a quarter in each direction every day down monotonous country roads. Every day I passed the site, now in the state highway median, where once stood the farmhouse in which John Wilkes Booth was shot to death. Culturally there were huge gulfs between me and almost all of the people I worked with. I found it a bad place to learn the skills I wanted. Very few of my peers seemed to have any clear idea of what they were supposed to be doing and there weren’t any strong incentives driving high quality or efficient outcomes. There were people there of the attitude that work was boring and nothing ever happened but it paid. There were people there I never saw do any work at all. One older gentleman sat at his desk every day in the same outdated dress shirt and trousers reading the newspaper, occasionally having discussions about the bible with people who stopped by his cubicle. The peculiarities of how software is built for navy systems meant that all the hardware, software, and practices were decades behind what was happening in the outside world. The effort required to change any process and perhaps lack of incentives to do so didn’t lead to any focused efforts to improve how things were done. The contractors were supposed to be writing all the software under the supervision of the civilians but it was never clear to me in what sense the department I worked in was supervising the contractors we worked with. The whole time I was there the focus was on getting the department to do more of the software engineering ourselves. Given that, it’s striking that most of the people I worked with didn’t have very much software engineering expertise. They were looking to me to tackle what felt like complex tasks, in one case adding a new hardware interface to our simulator system, a task that another civilian who’d been there for several years had taken on and not succeeded at, in another case a greenfield effort to port the main software system we worked on to open standard hardware and operating system and a new inter-component middleware. I want to stress that I was the new guy in my first salaried job. I wanted to be taught the craft, whatever they could teach me there. US government acquisition is its own complex trade that I could have learned but I was never pulled into that part of it. Instead I was left to my own devices to figure out what to do with the loose goals they gave me. There was little in the way of constructive feedback or mentorship. None of this should be taken as universal claims about the DoD acquisition world, or even about the department I worked in. I can’t claim I clearly understood what was happening around me at the advanced age of 25. It is, however, how I experienced it. I wanted out. I had my resume on the job sites within the first couple years I worked there (back then they were called things like monster.com and Yahoo hot jobs). It was slow going, I took a couple interviews over that time. They were random roles where I remember the interviewers having little idea what to do with me. The bulk of my industry experience was writing Ada and C programs that ran on microcomputers from the early 90s and never left warships and locked laboratories. Nothing stuck until Amazon cold called me in late winter 2006. They flew me out to Seattle, put me up for a night in the Grand Hyatt at Pacific Place, brought me into a conference room in the old Pacific Medical Center building on Beacon Hill and grilled me for 8 hours (including during lunch). They spit me out exhausted. A week later they gave me an offer to come onboard as an entry level software dev, an SDE1. I was so naive that I thought they were going to pay me less money than the Navy was paying me and I had a number in mind for how much of a pay cut I could accept. Fortunately that wasn’t the case. I was also naive and arrogant enough that I thought I had killed it at the interview. Thinking through it now I think signs actually point to me just barely making it through. But I had made it. For Catie and me it was an excuse to get out of our college town and go experience another part of America. We told our friends we’d be back soon. For me it was salvation from a job I really hated and didn’t believe in.

Working for the Navy was all generic officeware, chipboard desks and padded cubicle walls, fluorescent lights, business casual, drop ceilings, the occasional framed photo of George W (offsite of course), often unclear goals, never any consequences for missing them, lots of minesweeper, a 70 mile commute mostly through farmland and forest. It’s washed out nearly to grayscale in my memory. Moving to Seattle and taking a job with Amazon is in bright, fully saturated colors. Seattle itself was exciting. It was a big city where my cultural and political attitudes were fairly normal for someone my age if not on the conservative side. We got there at a time when folks like us could still afford to live in the city. It was said that the Amazonians under 30 lived on Capitol Hill, the ones over 30 lived over the I90 bridge in Issaquah (we lived in West Seattle). Instead of driving 70 miles through interstate and country highway I was now riding my bike across the West Seattle bridge and up Beacon Hill every day. At work I was suddenly surrounded by people, mostly around my age or only a little older, mostly transplants like me, interested in similar things, with similar geeky interests, similarly skilled and deep in technical knowledge. We spoke the same language, knew the same landmarks. I was dropped into an engineering culture that continuously shipped software features at a breakneck pace dealing with customer volume and availability constraints that very few other companies do. It felt like a place run by engineers, not by bureaucrats, and it was intellectually stimulating and satisfying to be part of it. It had concrete ideals, written down, and well known by everyone that encoded how we wanted to operate daily, programming the company to move quickly towards big audacious sustainable value for customers and the business. Looking around it was easy to believe that those ideals were taken seriously and lived by. It was a company that didn’t make commercials, didn’t make many public statements, didn’t pay much attention to its stock price, just focused on making customers happy. I was a person who felt that we all had a moral obligation to drive less, consume less, eat seasonal local food, produced without the use of industrial fertilizers and pesticides. The founders of the company (I assumed) started with the goal of making all the money for all of time. Even so I felt that the focus on long term sustainable growth led me and the company to a similar headspace.

You can probably guess that the Koolaid eventually stopped tasting so good. It did. But despite anything else I have to say, there are great things that never changed over the 19 years I worked there. There was a lot to recommend it as a job. I was well compensated for my time. They made me feel valued; like I was doing good work and positively influencing the company and helping its customers. They were sensitive to my social anxiety and despite it I was promoted 3 times to positions where success required having a pretty wide influence. They always assessed my performance on the impact I was having for customers and not on whether I was giving a bunch of talks and leading a bunch of high profile meetings or speaking to high powered executives. Which was good because those are all activities that I would find extremely uncomfortable. I think I still had room to grow upwards in my career there. I wasn’t stuck. And best of all, I was around incredibly smart and driven people, real world class experts in distributed systems, scalability, and security among others, blazing new trails through uncharted territory. I never stopped learning and not just about technology but also about being a leader, how to be kind, how to think big and get a lot done, new ways of seeing human behavior and the world. I started to see a lot of things through the lens of the leadership skills I picked up at Amazon. It was not hard to stay. Later people would sometimes congratulate me for the length of my tenure and I’d wave it off. All I did was not leave. It wasn’t hard.

Despite all that good stuff I still had the gall to feel like I wasn’t doing what I was meant to be doing. Especially early on I saw working there as a short term arrangement. Since it was lucrative we’d stay there a bit and then take the money and go do other stuff. I remember hiking back down a mountain with Catie once in the mid to late 2000s (maybe Pilchuk?) and saying something like “What’s the point of selling my time to make all this money if we don’t end up with more freedom to go do other stuff?”. I remember another time drinking one too many Arrogant Bastards out somewhere with our Amazon friends and Catie pulling me aside to encourage me to stop talking to them about hating my job so much. I did a lot of talking, a lot of dreaming. I remember once at Friday beers in the office a manager trying to improve my outlook on the societal good we were doing with AWS, protein folding and all that. I was more dramatic back then. But like I said it was comfortable and easy to stay even despite all my shit talking. A few years went by where we enjoyed our time growing into full-fledged adults, we married, and had our first kid. My career at Amazon picked up some momentum. Time started to accelerate and years flew by in a sleep-deprived fog. One day we opened our eyes and realized it had been seven years and we hadn’t gone back home like we’d planned. We had to decide whether to commit to making Seattle our home or keep our word and go back. It wasn’t easy but we decided on the latter so our kids could be around more of their family. You can’t really go back home but we tried our best. I thought that would be the end of my Amazon career but they valued me enough to offer to keep me as a full remote worker even though that wasn’t at all a thing there in the early 2010s. So I stayed and kept my big city job while moving to a smaller city without a ton of jobs of the same caliber. Then just a few months after moving we had our second kid. With her plus the continuing momentum in my career, several more years flew by in a haze.

Then one day in 2020 everyone quarantined themselves and hardly anyone was driving and I spent well over a year constantly anxious about my health and my family’s health and the health of our nation and world as political fires caught and burnt hot (or maybe I never stopped being anxious). It was quiet and the birds were chirping. The sun was shining. The breeze was gentle. Every day between video calls I’d walk around in my yard watching the plants grow. It was a time for reflection and it led to a bit of a midlife crisis for me. I became obsessed with the time I have left and its shortness. I didn’t feel like I was spending it the way I should. I decided that I would take five years to, I shit you not, grow my long-time gardening hobby into a new career as a market farmer. That’s someone who grows vegetables on limited land close to a city and does some combination of selling direct to restaurants and consumers and setting up a shack at the farmers markets. The five years would let me develop the knowledge and infrastructure I needed and to grow our savings to get us closer to financial independence. Part of that infrastructure was moving somewhere with at least a couple acres. I simply had to be closer to nature, somewhere quiet with a distant horizon. The plan to be a farmer didn’t survive the coming five years. It was obviously just a desire to escape the life I’d built and if I wanted to leave myself the possibility of making positive contributions to things that matter, the 20+ years of experience as a software dev give me way more leverage than a brand new market farmer. Starting over in your late 40s is hard. I don’t know that I’ll ever have the energy for that. So that was gone but the idea that my best-by date was sometime in the next five years stayed.

A lot happened in those years. My profile continued growing, having been promoted to principal engineer in 2018. I helped build stuff that I’m very proud of and also had some painful failures. During the pandemic years and until the time I left it got a lot more stressful at Amazon and a lot harder to accomplish anything. The culture had shifted and not in a great way. And various things the company did wore some of the luster off of my image of it. I think those things started before the pandemic but they accelerated and got worse after. From late 2021 through the end of 2023 I helped guide a project that promised to radically reduce the cost of executing security efforts and maybe all infrastructure safety efforts. It was an area I’d spent a lot of time thinking about. I had big ideas I wanted to try. A lot of funding was put together to take a swing at it and it turned into a drawn out horror show of a project. I struggled to get managers involved to see the cliffs they had to avoid, that in fact they were insisting on heading directly into, to get them to see the doors they should avoid closing, and just to get them to pull in the same direction rather than fighting each other. I had peers on the project hearing me out, listening to my concerns, assuring me they were on it and then acting in a way that made it clear they weren’t. Once we spent 3 days offsite with a dozen people in order to hammer out a launch plan that everyone could align on. We spent 8 hours a day meeting and going to lunches and dinners together. We left with agreements in place and within the next few days one of the teams involved refused to do any of the work they’d signed up to do. Folks were making decisions for all the wrong reasons, for clout and short term gains, rather than to deliver long term value to customers. And it felt like they were trying to manage my perceptions and feelings more than they were trying to address my critiques. I kept making sure my managers were aware of what was happening, I kept talking to all the main folks involved. I tried to choose my battles, give up on certain things I wanted just to get everyone to agree. I kept on falling for people making commitments to me and then not keeping them. The worst thing about it is that teams were being destroyed by all this mayhem as well. A bunch of engineers could see as well as I could that they weren’t being asked to deliver the right things. They could also see that compared to other teams their work environment was chaotic and grim. I tried. I feel like I didn’t get the support I needed but it also left me feeling like an asshole for not doing more and for not being able to right the ship. Ultimately a shocking number of people either left or were managed out. We did also manage to deliver, way too late, but really nice actually. The customer response was good and it let us deprecate multiple tools that customers hated. But the delay hurt and burnt a lot of trust with partners. By the time we launched the marketplace was a lot murkier than it had been when we thought we were going to launch. Had we launched earlier and maintained that trust it would have been a lot easier to march forward quickly into even bolder ideas and bigger promises. I think those long-term prospects got a lot harder as a result of how it went down. The whole thing made me feel like an asshole.

While it definitely started before the pandemic, the emotional toil of being a principal engineer also wore on me more in the years after. This was probably because of my continuing growth in scope. I did more and more talking as the years went on, more and more advising, consulting, reviewing, in bigger and bigger groups. Folks tended to never appreciate how little context folks like me operated on. I’d walk in, read the doc, start giving my reactions to what I’d read. I’m someone who is conflict averse and who finds it very easy to argue both sides of almost any decision. I agonized over whether I was giving the right advice or being reasonable at all. I agonized over whether I was being constructive or coming down too hard on people’s ideas. People I worked with regularly would tell me in one on ones that I was nicer to them than other senior folks. My yearly performance reviews consistently said I was good at being approachable and earning trust with people. It wasn’t enough to beat those feelings down. I also never felt like I was doing enough to push my own ideas through or to clear blockers to make efforts successful. I’ve learned that I’m just not an executor, I’m a dreamer and planner and so I kept finding myself at the limit of what I knew how to do. Or worse, I would have solid ideas about things that could definitely move the ball forward, just that they were things I didn’t feel comfortable doing; stuff like giving talks, taking the argument to leaders I didn’t know well, making new contacts, pushing back in unpopular ways. I’ve learned since that this is common for introverts. Introverts and extroverts are stronger together. Introverts deeply understand problems and make plans and extroverts take bold action.

The broken glass grind of 2022 and 2023 destroyed whatever ambition I had left. I really started wishing I could just run away. Especially as we got into 2023 I started talking about maybe leaving after this milestone or leaving after that milestone. At least two of those came and went. The rise of the AI hype cycle through the last 3 years of my career poured cement over my already collapsed excitement. I’m deeply ambivalent about the technology. I see the huge potential. I also see huge risks that few in positions of power seem to be doing much to prepare us for. While Amazon is hardly one of the worst offenders here, the endless industry-wide hype dimmed my view of my industry and those leaders in positions that I was theoretically aspiring to rise to myself. I felt a growing disconnect between myself and the community around me. Perhaps I could have done a lot of good by being a voice of reason but honestly I didn’t have the energy left. I think things have escalated pretty rapidly in the 8 months since I left but it was pretty obvious then that there was a lot of pain coming, a lot of bad ideas to shut down, a lot of teams that had to be redirected to solving problems that their customers actually have, a lot of agent created chaos to mitigate. None of this is a judgement on Amazon’s decision making and there are a lot of smart people working hard to get through these transitions. I just had no passion for being part of it.

In the closing days of 2023 I was re-orged into a different team. These were folks I had worked with for a long time but who I hadn’t collaborated directly with for years. That part of the larger org had grown rapidly so I was in the fine position of being deeply familiar with much of what they were working on but also being a new face. I could look like a genius because I already had ideas for how to solve some of the challenges they faced. I felt broken after all the drama and the new role served to rehabilitate me somewhat. I had a legit good year and a half where I influenced a bunch of different efforts, started up some mechanisms to get the local PEs engaged with a wider array of the teams and projects in their space. I successfully got a project started to model aspects of the business that had not been properly modeled before. It would unlock a ton of automation to scale security and operational workflows that were either awkward or simply impossible before. It still felt like I was going through the motions and that the clock was winding down. I showed up and said what needed to be said, I did things that seemed like the right things for my role and level. I also spent a lot of time in-between not doing much in particular. I found myself feeling like I was fooling people. They were always thanking me for taking time out of my business schedule to work with them. I would think that they just thought I was really busy because they didn’t know what else I was working on. They assumed it was a lot of stuff. I figured that one day they would all get together and talk it through and realize I wasn’t really working on anything. I’ve already listed stuff I did during this time so objectively I don’t think this is true. But oftentimes it felt true. I was kind of working in bursts. I had ideas of things I could do but just couldn’t build up the motivation to do more than the first couple of steps. The thought kept cycling in the back of my head that it was time to pick a date and go. If not now then when? I’d had the idea five years previously that I was going to leave mid-decade. The persistent motivational challenges I was facing and an especially hard project reinforced the rightness of the plan. At the end I’d told myself so many times that I was going to leave that it became impossible to stay. It was like school in the late spring with all the colors and sunshine out the window and summer fun just around the corner. So finally I pulled the trigger and with almost no ceremony I slid out of the company that I’d been a part of for over 19 years. And once I gave my notice I suddenly couldn’t exactly remember why I was doing it. But in the broad strokes this is basically it.