Changing Jobs, Changing Dreams

I’ve decided to change jobs again. This will be my sixth in the last 7 years. I’m far from the only person switching jobs right now, and superficially the decision was obvious. My wife and I recently had our first child, so a guarantee of being able to work from home will give me the flexibility to help more around the house, and spend more time with my son. And It’s near impossible to turn down a pay increase of 60% – a dramatic, if not unheard-of amount. But, this transition required me to reconcile with the nature of the new company, and the nature of the work environment; I had to abandon the vision I held for what my work could look like and what the impact could be.

Four months into the pandemic, the board informed us that we were to be liquidated.

A few years ago, I was working at a large Media Company. My wife and I lived in a cozy apartment in an old neighborhood of a beautiful and monstrous metropolis. Each morning I would dress well (if casually), shave, style my hair, and head to the office. The commute was a fifteen minute walk and a 30 minute train ride. Just long enough to release any tension from work, and maybe get in some reading. The office was in a beautiful modern building, had an open plan (with good noise management) and a breathtaking view. The people who worked there were sharp and pleasant. I loved the environment and was learning a lot.

It had its blemishes; the work wasn’t always challenging, and I didn’t see a way to advance beyond my position as an individual contributor. But, my work and home life were well separated and balanced, and I was proud to support some of the best publications in the world.

Life pushed me away from the Media Company. The industry was struggling. Like many of its peers, the company’s strategy failed to stem the tide. At the same time, my wife began agitating to return to leave the metropolis. It was time to start the family we had been talking about for years, and it would be more pleasant in the company of grandparents, aunts, and uncles. In a fortuitous coincidence, I was offered a leadership position with a former employer. This Ed-Tech company had stabilized and now had the ambition to grow beyond its small number of clients. I accepted, and we packed up our apartment and moved from the metropolis to a modest city in a modest part of the United States. Upon arrival, I set my sights on building a team in my new hometown.

For the next 18 months, instead of growing a team, I worked out of my apartment; no peer feedback, and little contact with our overworked CEO. COVID exacerbated the isolation and the uncertainty of working at a small company struggling to gain traction. Often, it would be weeks between contact with anyone else at the company. I tried to focus on the work in front of me. I scouted out office locations, and did what I could to prepare the product for the expansion that would never come.

Four months into the pandemic, the board informed us that we were to be liquidated.

Finding another job during the early months of the pandemic wasn’t an attractive prospect, but it was a chance to change things up. I wanted stability, a place where I could grow. I wanted to feel like a part of something bigger, something important. Aft

I became convinced that the ideology of and relationships between the various stakeholders would not allow for fundamental change.

The new job was as an individual contributor working on a critical piece of infrastructure, at a Fortune 100 company that had – remarkably for a small-to-medium-sized American city – offices near a public transportation hub. The title was a step backwards, but as I said in the interview, I was “looking to get my foot in the door and quickly advance to an Architecture or Director position”.

Six months later, I’d done just that, and I was miserable.

No single factor or incident led to my dissatisfaction. Rather, there was a steady drumbeat of novel frustrations. Each system, process, and client relationship seemed unrelated to it’s siblings, and so myriad details had to be memorized. Tools, techniques and infrastructure were dated, and attempts to modernize were quickly met with multiple levels of resistance. Relationships between organizations and between neighboring teams were so fraught that misusing a single word could lead to weeks of fallout. Every time I tasted satisfaction from learning something or making a significant contribution, there was a slew of aggravations and disappointments that would sour it. When I described my daily frustrations family and friends were baffled that I hadn’t left already.

The promotion certainly delayed my exit. I wanted to show gratitude to my director for giving me the opportunity, and there were aspects of the position that yielded professional growth. The position entailed a new level of exposure and responsibility. Navigating the complex bureaucratic and political terrain was a novel challenge. The slow pace of work and intense bureaucracy handicapped progress, but if the program could be improved, I would be in an ideal position to guide that change. Making a positive impact on a critical piece of infrastructure would be something to be proud of.

Hope that these changes could be imminent kept me going for a long time. Our processes could be cleaned up, or even radically altered. We could adopt modern tools and techniques. The incentive structure could be adjusted to improve the relationships between the various stakeholders. Indeed, there were multiple ongoing initiatives purporting to do just that. However, time dragged on, and each effort was bogged down or warped to fit someone’s political objective. My optimism turned to pessimism; I asked myself “Why are we doing all this extra work over the Christmas break, just so that Organization X can put pressure on Organization Y?”, and “Is the client just taking our ideas straight to the competitor?”. I became convinced that the ideology of and relationships between the various stakeholders would not allow for fundamental change. New practices could be adopted, but gravity would pull everything back to stasis.

The prospect of leaving the most important project I’ve ever worked on – and so soon after joining – provoked a sense of guilt. Given the difficulty of hiring a replacement, my departure would make operations more difficult for a prolonged period. My Director advocated that I receive the promotion, and they could face backlash. The program had already seen significant attrition; piling on seems cruel, and potentially harmful. But my primary responsibilities are to my family and myself.

Financial and environmental factors made the final decision to leave unavoidable. Even after promotion, my salary was anchored to the level depressed of the early COVID job market. Vacillation on WFM flexibility, effectively granting WFM to vaccine refusers, and secret attendance lists for the vaccinated, destroyed any faith I might have had that the corporation would be concerned about my well-being. The final straw was a bungling of my parental leave, and a denied request for flexible working arrangements, so I could be home and care for my newborn and wife while she recovered from delivery.

As I approached the end of my rope, a long-time friend joined a white-hot Web3 startup, and began recruiting me.

This miserable thought has led to a new desire: escape.

The decision should have been obvious. The salary increase was dramatic. The informal and fast-moving environment is more in line with my preferred mode of work. A flexible schedule will make it easier to be around my son in his early months and years. My hang-ups were ideological and political.

The ethical issues surrounding crypto and Web3 have been well articulated elsewhere. I’m broadly in agreement with the leftist critics of Web3. The opportunities made possible by a globally shared computing environment are largely outweighed by the ideology that permeates the entire pursuit. However, taking a step back and assessing the alternatives, the difference between the Web3 company and the wider market seems petty.

In bleak moments, I despair at the apparent futility of finding meaningful, well-paying work within the field I’ve devoted my professional life to. The lucrative trends can be convincingly framed in less than appealing terms: the expansion of corporate control through surveillance capitalism, destruction of labor power through automation & “Uber for x”, repackaging debt (most of Fintech), and the financialization of … well, everything. Rather than being materially distinct from the rest of the industry, Web3 fits neatly within it.

This miserable thought has led to a new desire: escape. The modest success of my career thus-far has allowed me to trap myself within obligation and expectation. As Tyler Durden said “The things you own end up owning you.’’, and like The Narrator I’ve begun to entertain fantasies of escaping a system that leaves me feeling dissatisfied and alienated. Unlike The Narrator, my fantasy doesn’t involve violent revolution. Instead, it’s the mundane dream of a tech industry ”exit”.

Part of the offer from the Web3 Startup included a sizable share of equity. After the latest round of funding, this stake is worth a bit more than my house. If the company is successful enough to get acquired, it could be worth more than I could plausibly earn in a decade or two of work. Full retirement might not be possible, but I could have space to pursue another, possibly more fulfilling, type of work. Maybe I could go back to school, find a new niche, or spend more time writing. At the very least I could take some time off to relax and enjoy time with my family.

For now, I just accept that vocation is not enough.

Leaving The Corporation for the Web3 Startup marked a personal rupture in the way that other job changes didn’t. It’s a surrender of what my work can be, what it can mean, and even look like.

Before I joined the Media Company, I just wanted to “sling code and get paid”. I subsequently developed the ambition of ascending into a new strata: Director, Vice President, even CTO. A corner office, a nice suit, crushing responsibility, and a cheesy smile in a corporate head-shot all seemed pretty good. When I got the promotion at The Corporation, it felt like I was moving along that path. But as time moved on, the prospect of staying put and climbing from within became unpalatable. Excelling would mean assuming some of the less savory behaviors, attitudes, and perspectives of the organization I was hoping to lead. The person I would become in that process was not appealing.

I thought that the position at The Corporation, despite all of the drawbacks, would be fulfilling because the system we worked on mattered. It was not. The lodestar of “meaningful work” was cold and distant, providing little relief from the torrent of frustration. Abandoning a program that plays a vital role in the functioning of American society, for one that does not, is something I’ve yet to fully reconcile. For now, I just accept that vocation is not enough.

Even the relatively modest goal of commuting to a nice office to work with engaging colleagues is receding. Before the pandemic, living in a modest city limited opportunities to pursue that goal. Now, even the the largest cities are seeing more durable work from home trends. Right now, many of the best opportunities are permanent remote jobs. I don’t see this trend reversing. Rather than continuing to rage against the coming of Solaria, I’m resigned to making the most of it. The extravagance of getting dressed, commuting to an office, and working side-by-side with peers has been, at least temporarily, rendered from my life.

Perhaps this is dressed up cynicism. Maybe I’ve just wasted 2000 words rationalizing the same crass self-interest that I’d criticize in others. But, if I’m not willing to commit to my ideals, why split hairs and miss the opportunity to spend more time with my family? Why have a more enjoyable work environment? Why not spend more time with friends and family? Why pass up the small chance that I could to reorient my life? It isn’t worth giving all that up to hold on to a dream that doesn’t make sense any more, and maybe never did.

Changing Jobs, Changing Dreams

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