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The year of occupational hell… and Hades

Note: I’ve tried to maintain close relationships between characters in their real life counterparts, but the romantic ones in Hades are obviously not romantic between coworkers. Still, they hint at some level of closeness, past or present. Also, if you haven’t played Hades, you should play it, but more important to this post, there are game spoilers.

In March 2024, I had worked on my technical writing team for almost two and a half years. I had just been promoted within my role. I had just launched a major initiative that people had been asking for… since before I started at that company. I was respected, well-paid, and had great coworkers, including a manager I may follow if they ever leave. Everyone in my personal life thought I was living the dream.

Why would I want to give that up?

There was one source of dissatisfaction: I constantly found myself worrying about whether I was doing enough work at my job, despite my manager’s reassurance that I was doing great. Other people were taking on more tickets than me, while I was organizing major projects that were less clearly measured by quantity of Jira tickets. And as much as I hate to say it, the technical writing market is becoming saturated, and AI eating the world isn’t helping. I feared a machine doing the most important parts of my writing, while my years of listening to SDLC framework books while running and playing Pokemon Go meant I had opinions about process, engineering operations, and where downstream teams like documentation, testing, and even support fit into the SDLC (topics that are often absent).

Meanwhile, the R&D operations team, a team with high turnover, was now empty and hiring, and a job posting was up. I should have been suspicious, especially after digging through the history of the past people in this role and their tenures. No one had reached the one-year mark in the past two years in this role. My company experiences enough regular changes that digging much farther back would be counterproductive.

The year before, I completed a mentorship program within my company where I was paired with a member of the executive team. We continued to stay in touch, and I ran the idea by him. He talked me through all my reasons to do it and all my reasons not to do it. Finally I realized: the worst the hiring team could do is say no.

So I applied and said it was okay for my manager to know about it. He was chill; he wouldn’t take it personally.

I interviewed with three people: my future manager (Hades), one of the engineering VPs (Nyx), and finally, the head of HR, who was involved because of this role’s high turnover. I expressed concern about the high turnover and how I didn’t want this experience to end with me leaving the company. Not because I didn’t want to job search again, but because I really didn’t want to leave. I also spent this time doing my own interviewing by contacting the predecessors in this role that I knew, both of whom left voluntarily. One of them said directly she wasn’t interested in talking about her time at the company but was happy to give general advice. The other accepted a Zoom call and gave me all the tea, which almost scared me off. But she reminded me, my experience could be different.

In hiring land, they said yes. We negotiated a rotation where I could return to my old team with no repercussions after about four months. As it turns out, saying no was far from the worst that could happen.


At the time my company had three large engineering teams, and since hiring was still in progress to fill out the rest of the operations team, I got my first choice. To be clear: I still deeply respect Nyx and all their engineering managers; in fact, if I were able to stick with them I may not be writing this.

In mid-April 2024 I was added to about a dozen Slack channels and started watching LinkedIn learning videos about agile project management and Jira administration. I settled in and started working on some of the projects that were left behind. My engineering teams were still building several new products, including one that had been in private beta for over a year.

At the time we lacked product leadership. As a result, a lot of the decisions I had to make should have been made by product, but we reached a point where we couldn’t put them off. But there was one initiative that couldn’t be put off. One new product offering had been communicated by the exec team as being available in August, less than four months from the time I started. And work had barely begun on it. In fact, I did some digging and discovered that working sessions were still happening as late as a month ago, but I couldn’t find any results to determine that work could begin.

There were other items entangled in this Stygian knot of risks and assumptions: another release associated with this same timeframe (that ended up not happening), an answer of “We need to investigate before having an answer” that someone took as “Yes”, so much more. Chaos, pure chaos.

My first job was to tame the chaos, and that’s exactly what I did. What I intended to be a one-off Friday afternoon meeting about two weeks after starting my new role turned into a 20-person meeting that people kept adding others too. Marketing wanted to know what was happening. Sales somehow got in on the call. Everyone wanted to know what the heck was going on, and I was there to make leadership talk to each other instead of hoping the rumor mill reached them.

This is the moment I’m most proud of in my year of occupational hell. It’s a shame that things go downhill from here.


After that, my first few months were mostly uneventful. I did help get the product’s development redefined so we could define what “on track” means, and we reached an availability date that everyone could agree on: end of January 2025. It would be hard work, we had to cut scope, and it would be the top priority of the engineering teams involved, but most importantly: it was possible. I was no longer holding my teams to a date that I didn’t believe was possible.

Between that and some of the progress made on some of my other initiatives, I had to start thinking about whether to return to my old team. They had hired a contractor to replace me during my rotation, who happened to be the person I replaced nearly three years earlier.

Everything was going well, so when I had to make the decision, I said I would stay. Everyone was happy… for now.


Receiving some amount of coaching is part of any job that you’re new to, and I welcomed any opportunity to grow in my new role. But after I decided to stay, the comments about my personality began, all from my manager.

“Why did you think that was a good question to ask?”

“Don’t you think an executive understands why the holidays will slow things down?”

“When you pose a comment like that, you should also come with a solution.”

My manager recommended using generative AI to generate scripts and sent over some LinkedIn learnings about communicating with executives.

Instead, I leaned on the other people in my role. The contractor on my team who was there when I started had departed since he wasn’t interested in the specifics of the role that a full-time hire would entail, but a new person started, who then referred a former co-worker to make us a team of three plus our manager. My two colleagues–let’s call them Achilles and Patrocolus–were and still are amazing. They’re experienced in operations and truly understand the ins and outs of program management. Both of them thought I was good at what I did despite being new at it and gave actionable and productive feedback when I asked for it.


By October, I was starting to wear out, even though one of those products was finally available. I was treading water, not seeing any big improvements, and I didn’t feel empowered to make decisions for fear that my manager would criticize me for it.

Then my manager came in with some news and reshuffling of work. Both of my colleagues had an initiative taken from them. One of them had something added to their plate to replace the thing that got taken away.

Me? The plate only got fuller, and I inherited a team that was already taking up all of Patrocolus’s time, yet my manager insisted should only take up only 20% of my time, even though I already spent over 20% of my time in meetings. Theoretically, this was an opportunity to learn about different engineering teams. The reality was much different.


Instead of writing my 23rd NaNoWriMo project last November during the final event that felt like a non-event, I started playing Hades. In case you’ve lived under a rock for the past five years, it’s a stunning dungeon crawler where you play as the demigod Zagreus and try to escape the grasp of the underworld. There are four levels, lots of monsters, bosses for each level, and ways to power yourself up, both for that particular run and for all future runs. Because of the randomness of any given run, no two runs are exactly the same.

One thing is certain: every run ends in death, even if you manage to escape the underworld.

There’s one thing to know about me. I’m laughably bad at playing combat games. I flail with my controller like doing so will help with my aim. I dash and slash in the general direction of any monster in the hopes that I’ll hit something.

Unlike at work, there’s no punishment for failing in Hades, so I picked up the game and started playing.

Sure enough, I failed fast and hard. For my first dozen or so runs, I couldn’t even reach the end of Tartarus and emerged from the pool of Styx before Megaera could have her way with me.

I kept trying. And trying. and trying. What was the worst that could happen, I’d die and have to try again? Maybe that was an opportunity in disguise.

Hades needled at me occasionally in the House of Hades, but during the runs I had the gods on my side offering advice, telling stories, and giving me boons and keepsakes. After many failed runs, I could finally start helping my friends out. I freed Sisyphus. I let Achilles visit Patroculus. I freed Orpheus and helped him start making music again. All with some help from Nyx, none of it from Hades.

Over time, being bad at the game became a strength. Because I was failing so hard and so quickly, I could plan ahead. I always chose the weapon that provided more night so I could power up the Mirror of Darkness, a gift from Nyx. I saw a lot of character dialogue earlier than I probably should have. I was able to power up the Mirror to max out everything I wanted to use before defeating Redacted.

I kept trying, and trying, and trying. Eventually I was able to clear Tartarus consistently. Then Asphodel, despite those damn magma traps. When I found myself talking to Theseus regularly, I knew the end would be a long hard road, but a path forward existed.

Because that was the beginning of the problem I was seeing with my new role: I like knowing that I have accomplished something. I want checklist items that I can put on a performance review or a future resume or just for my ego. I want to take pride in my work, and with the extra workload and stress, I had reached a point where I couldn’t do that.

On run 89 with a little help from god mode, I claimed victory from an intense battle with Hades and met Persephone for the first time. In this game as well as in my life by this point, no joy can last for too long. I emerged from the Pool of Styx once more, only to be greeted by the lazy Hypnos, who couldn’t believe that my cause of death was Redacted.

Then I got up, pet Cerberus, talked to the NPCs in the House, and walked out the door again.


I wish I started seeing results at my job as a result of persistence and a little bit of god mode. The opposite was the case.

The additional team I was assigned to featured Alecto and Tisiphone, an engineering manager and product manager who were at each other’s throats due to the stress of their situation. Development on one item had been stalled, a hard deadline for a client commitment was creeping closer, and the roadmap kept growing. And both of them looked to me for answers.

Patrocolus stayed on to help out with the release of one item that had been a source of contention for quite some time. The conflict between the two managers continued; I remembered how these two demanded so much of his time during the onsite in the early fall. I talked to both of them separately to figure what the hell was going on, and both of them blamed the other. Our retro sessions were unproductive because both of them were so stressed out and ready to take out their frustrations during those meetings. Here I was in the middle. I could make their process better, but I couldn’t fix the fundamental problem: the stress and ambitious roadmap that we were already behind on, that our new arrival Charon was waiting on.

You can change process, but all the good process in the world doesn’t change people or circumstances.


I had started playing Hades to escape work, but at some point, Hades the game started taking over my full evenings, to the point where I started setting alarms so I could go to bed at a reasonable time. But Hades was living rent-free in my head, belittling me occasionally before my runs, echoing feedback I received about who I am like I’m not good enough in my actual work. One thing became clear: I needed to get out for good.

I started updating my resume and cover letters in December to prepare for January job applications. There was little use in applying to jobs due to the holidays, after all. Hades told me before the holidays that I would be removed from Alecto and Tisiphone’s team because their manager Chaos had learned of the drama on that team and decided those problems were above my pay grade. The public reason was that they would be early adopters for some new processes we’d be trying as one engineering organization. I had finally cleared the occupational version of Tartarus, even though Hades needed to help.

I took two weeks off for the December holidays, partly because I hadn’t taken more than a couple of days off at a time since July for Go Fest and partly because I was on the verge of burnout. I spent a couple of days catsitting and doing nothing else, and spent the rest of the time going to Pokemon tournaments. It took days to think about something besides work all the time and feel relaxed in my surroundings.

January arrived. I returned to work on the sixth, spent my birthday alone because I had no energy to make plans, and then all hell broke loose.

Patrocolus was laid off the next day.

Patrocolus, the most experienced and (honestly) the best of us on the team. A few other layoffs happened in that wave, including, as I found out later, the product manager for the team that was making my life hell.

Besides the practical question of who would be taking over the work of Patrocolus, there was also the emotional impact: Patrocolus and Achilles were friends. We were a close-knit team of colleagues. I looked up to Patrocolus.

Achilles and I made a deal: If one of us got fired in the aftermath, the other would quit in solidarity. We both decided we would refuse to take on Patrocolus’ work if Hades asked us.

Hades dismissed Achilles after an emotional team meeting to ask me alone. I held strong, explaining that this was a very emotional time and I should be able to think about it in order to not make any rash decisions. This, it seemed, was an acceptable answer. We would have our scheduled one-on-one later in the week and we could talk more then after I had time to think about it.

But I knew what my answer would be.

If I got fired, I got fired. I had savings. I’d be fine, even for a long job search. At least I would finally escape the underworld.


Remember that advice to use generative AI to generate conversational scripts? For the first time ever, I took that advice, and was punished for my refusal by a formal writeup. I was told to pay attention while I was scribbling down notes of every single interaction, just in case I needed it for future reference.

I drafted a resignation letter and sat on it over the weekend in order to overcome my own impulsiveness. That resignation letter is still in my work inbox’s drafts. I talked to Chaos the following Monday in the hope of getting some insight as Hades’ manager. Chaos not only got a good laugh about my being written up but gave me an honest overview of what was actually going on at the company, which made me realize: how much of this did Hades already know? It had to be a nonzero amount.

My best mentor through my entire tenure in this role should have been my manager. Instead, my manager emerged as Hades, while all the supporting characters emerged as the assistance and comic relief.

The Pact of Punishment was live, but this time I wasn’t in control of the Pact.


Once again, I turned to the game. I had bonds to forge with the rest of the characters, after all. Even Chaos, as difficult as it was to forge a bond with them, a statement that rings true for the real life counterpart in this tale. Hypnos was my final holdout, not because of the difficulty of the bond, but because I loved the idea of their laziness and the advice they gave. “Have you tried jumping out of the way?” “Have you tried not dying?” “Can you get their autograph for me?” Much like the manager who tried to backseat drive me two weeks into my new focus when I was still trying to figure out what the hell I was doing and had everything lifted from under my feet two weeks after that. Yes, of course I was bitter. And their counterpart on another engineering team, who would say they would do something and then not do it for days because of some urgent issue.

Part of program management is forging friendly relationships with coworkers, even though you’re not rewarded for it in the same way as you are when forging bonds with NPCs in video games. I don’t get to hand a nectar to a coworker and earn a heart. My coworkers don’t give me keepsakes, but they do occasionally give me extra dialogue.

When I finally escaped Hades for the ninth time and Persephone escorted me back to the House of Hades, I was shocked. Why was I dying when we were always near the Styx? How much did Persephone know that they weren’t letting on? That turns out to be their story to tell.


My final role in the year of hell is as release manager, the main item that Hades demanded that I take over during the great riff.

The final arc of the storyline introduces some new characters to our adventure. Skelly provided me with the knowledge of the tooling needed to get these releases out the door, but with everything that went wrong, I was constantly nagging Skelly for updates on what I needed him to do and relying on them for updates.

Sisyphus, the product manager, had a ridiculous backlog of product features to get out the door. Thanatos, the other engineering VP, who took over the product I was now managing releases for but was impossible to get in touch with because he was pulled in a thousand different directions. Hypnos the first was almost impossible to get in touch with, being slow to respond to Slack messages and unwilling to offer engineering advice. Hypnos the second was less directly involved with my work, but he was constantly overwhelmed with competing priorities and never could make my work number one unless it was absolutely necessary (and even then, only after a fire elsewhere had been put out). I wasn’t alone in feeling this way; especially for Hypnos the first, Sisyphus was also having a hard time working with them. And it was our job to wrangle the release process that was Lernie and its multiple heads.

Whenever I felt overwhelmed, which was most of the time, I occasionally used my powers for good for other teams. On every return to the underworld, I’d talk to the NPCs, pet Cerberus (the most important part), and try to improve the Jira automation and processes for my old manager’s teams. Persephone had a vision and understood the pain points, and we worked well together. Cerberus became my source of comfort during peak hell.

There were good people. Sisyphus was my friend in trauma; we may be trauma bonded now. They’re no longer the product manager but they’re still at the company. When I took a week off, they said, “Well, now we’re doomed.” Dusa led the QA efforts, proactively reporting issues and encouraging their team members to do the same during the testing cycle, and I went to bat for them and their team to get issues triaged and determine if those issues were release blockers. When we had to perform a full re-release, Asterius used their knowledge of all the items in the re-release to be a fellow loudmouth when I couldn’t find the fucks to speak up, and together we hacked away at Theseus. With their help, we cleared Elysium.

But the releases kept going wrong, primarily for reasons within engineering outside of my domain. Yes, testing could take longer, but the buck started with planning. We even had to completely redo one of our releases because there were so many screwups. I spent almost every evening after work rotting in front of my computer watching old VGC videos on Youtube and occasionally playing games while trying to apply to jobs, trying to move my body but failing at it. I still remember my neurologist, who I see once a year on average, asking me in March if I was depressed. Not a question he typically asks. That one hit different.


In Hades, Zagreus agrees to continue his escape attempts for security purposes. After all, if it’s that easy to escape, then the underworld isn’t as secure as it is perceived to be. Every time he succeeds, he is taken by the Styx.

In May, after about sixty job applications and only one response with horrid Glassdoor reviews that wanted me to take a personality assessment first (I said no), I received the news of a lifetime, and from Hades of all people.

This role had evolved into something I had not signed up, and there was no expiration date to the current stress. and there could be an opportunity for me to move back to my old team. Was I interested?

Not to put too fine a point on it, but this was asking if I like to breathe. If I like not being fucking miserable all the time.

My general philosophy of work is that every job has some level of crap that you put up with. As long as the majority of the crap is the kind of thing you’d have to put up with at any job and the most frustrating parts aren’t specific to that role and company, then I can deal with it. At my last company, I was still writing software documentation in Word a year into the role when every other product line at that company was using a modern docs as code approach, and I needed to learn docs as code if I wanted to be a good candidate almost anywhere else in the future. So I jumped to my current company during the Great Resignation.

In my first role at my current company, I was only worried about doing enough quantifiable work. To be honest, I would worry about that in any company. Some people like churning out small tickets, and a couple of my coworkers are like that. I like when my thoughts incubate and hatch, when I can plan out large projects and processes and dig deep into those items that require deep knowledge of a topic. And I was doing fine. The funny thing is, I went looking for good writing samples for job applications and couldn’t find too many suitable ones because I was working on bigger teamwide projects.

Now, I worried about everything. My work life had turned to hell. My first role in this year of hell used my strengths, but the role eventually placed a harsh spotlight on my weaknesses for everyone to see while placing a shadow over my strengths. Everything felt like pointing fingers and there was no expiration date for the stress. And because I relied on other people so much, working more wouldn’t solve the problem. I was stuck in that room in Styx where you know you haven’t found the satyr sack yet but you have to keep fighting and whacking away at those huge rats anyway and you still have at least one more room to go through, and who knows, maybe you’re unlucky enough to have to go through all five rooms. (Fortunately this has happened to me only once.) Every obstacle had to be hit once to eliminate the damage shield before I could actually make any headway. I had a time limit for each level. Every boss was harder than before.

All I could do was stare at walls and try not to have a mini-breakdown every day.

So I was honest. Yes, I said, I would take that opportunity if one arose. Hades couldn’t promise that it would happen, but they would let me know if it was possible.


I waited, and waited, and spied on people’s calendars to figure out who was leaving. Was someone retiring? Quitting? Was Persephone leaving?

It turned out none of those were true. One person on that team was interested in exploring other roles at the company, including my role, and I wasn’t happy in my current role, so the opportunity for us to swap roles opened up.

Melinoë had the right to do her due diligence, and it was my moral duty to be honest. I wanted her to know what she was getting into, even though she wouldn’t be taking over the area that had been making my life absolute hell over the past few months. (That honor would go to Hades, who thought the role should take only an hour a day.) She talked to other people she would be working with, including Achilles, Hades, and even Chaos.

Ultimately, she agreed to the swap. I spent the rest of May getting her up to speed on the underworld and the projects she would be working on, while reacquainting myself with my old team. At the beginning of June, the swap was complete. I had finally escaped the underworld for good.

May all her escape attempts be successful.


Weeks later, I know I’ve made the right choice. In April, after the Atlanta regionals I spent half my break replaying work conversations (real and potential) in my head, actively dreading the return to work. As it turned out, I had reason to do so: I was supposed to be relieved of the one large task that was making my life hell, but an extraordinary circumstance meant I took it back, reclaiming it through the taming of Theseus until my permanent escape a few weeks later.

I went to New Orleans for NAIC in June and took the rest of the week off after returning. The only thought that went through my head the Sunday before returning to work was “Aw, vacation’s over.” No dread, no tears. Just acknowledgement.

That’s all I could ever ask for.

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