In January of this year, I found myself at a crossroads of slow-burn crises.
(This is really, really long. You have been warned.)
I spent the back half of 2022 building the backend for a preseed ecommerce startup. I'm still very proud of what I accomplished technically under very constrained conditions, but the project was an emotionally and mentally draining disaster. One of the founders lied about the amount of funding they had received, telling us it was double what was actually on hand. The other founder mostly spun bullshit about how much he loved to "build" while doing nothing other than dropping the occasional clueless Slack message and bragging about his other startup, the $100 billion web3 juggernaut (as of this writing, that company's website returns a Cloudflare error).
The closest thing there was to a CTO was one of the founder's friends, a guy who loudly exclaimed "YAGNI!" at things like maintaining an issue tracker or writing unit tests. It was eventually found that he was doing almost no work and left the rest of us to clean up his mess.
It was fucking miserable.
I've spent over a decade now bouncing around the world of startups, and that's on top of a previous life working in more enterprise-y IT environments. I still love the actual work, but the past few years have felt like a slow squeeze as I work on projects that keep getting worse and worse. The current tech industry is fucking awful, and it sometimes feels impossible to do actual good work in it.
I've also been on a long journey, maybe one that's lasted my whole life, of figuring out why something always felt... off. I think I intuitively knew, at least from around the start of puberty, that I was something other than a cishet man. I spent my 20s and a decent chunk of my 30s wrestling with that, trying to iron myself out, seeing my inability to fit into that box as a personal failing, yet continuously coming back to these feelings. It was a conflict inside me that felt like having poor vision, desperate to find the prescription to clarify it. In the past few years, especially through COVID, I've finally been moving closer to figuring it out, but it's been a long and halting road.
Then one cold January morning, my smoke detector started beeping. Like a complete dumbass, I tried to reach it with one leg on my bed and the other leg on a rolling office chair. Then, dear reader, I ate shit spectacularly. If you had seen me fall, I'm sure you would have assumed I had broken a limb. My legs and arms flailed in mid-air trying to catch myself before I landed with a thud on the floor.
When I got up, I hurt like hell, and I ached for days after. But something about the brush with mortality made me act with renewed purpose.
I can't remember exactly when my egg first cracked. It may have been before or after I fell, but it was definitely around then. I do remember the specifics, sitting up in my bed at night with the TV on, deciding to finally engage head-on with the idea that had been dancing around in my head for years, maybe decades: Am I trans? When I finally gave myself the permission to really consider it, I was flooded with euphoria, like a light had turned on, filling the piece of me that had always felt like it was missing.
These events and all of the ones before leading up to them instilled in me a new drive. So many of the things I've felt in the past that sent me through periods depression, anxiety, and social withdrawal turned out to be... mostly dysphoria. It's not like dysphoria isn't still a major presence in my life, because it definitely is. But the inchoate cloud of negativity that once felt like it ruled my life is gone. When I have difficult emotions now, I can pinpoint them and figure out how to handle them appropriately.
This year has been about figuring out how to take this new understanding of myself and build a happier, healthier life; seek out stability, fulfillment, and meaningful work; stop just jumping from one disaster to the next. I've done some of the game history and preservation work of which I'm proudest, namely the videos and expanding the bots out to as many platforms as possible to ensure their survival. I eventually swooped in to briefly take over as CTO at the startup I worked on last year just to make sure the product that I worked so hard on actually shipped. (It did, and landed with a thud.)
And I also ate a lot more shit spectacularly (metaphorically speaking).
The only paying work I've done since May is a brief freelancing stint at the kind of awful consulting shop that thinks copy/pasting old versions of jQuery into the repo counts as JavaScript package management. Since then, I've been applying to mostly permanent jobs and interviewing regularly, but we all know the current market is a giant mess of bullshit.
I've gotten through a full round of interviews with two places.
The first is Internet Archive, which has been my dream job for many years now. I had an amazing experience interviewing with them and made really special connections with some folks there. But after the third interview right after Labor Day, they went dark for a really long time. When I checked in, I was told that there was another delay unrelated to me, so I would need to wait a while longer.
In the meantime, I continued interviewing at other places and somehow bumbled through three interviews with a... just fucking awful company that had been around for a long time, but had gone downhill since being acquired by private equity ghouls a few years back. The two engineers I interviewed with were MAGA chud dudes, who you may be surprised to find were also dogshit engineers.
And yet somehow, this week, I got an offer from them. It was an extremely low offer for a senior software engineer, but a decent chunk of change nonetheless.
I used having an offer on the table to come back to Archive and ask for a more forthcoming update than I was previously provided. I received a very kind and transparent response: They were almost done with the issues causing the delay before. They loved me and wanted to hire me, but there was someone else that they were going to offer the currently open position to first. Then they wanted to find headcount to hire me, but that would take at least another month.
It was bittersweet. Working at Archive has been a dream for so long, but it always felt like a thing that was out of reach. To get this close yet remain so far away hurts. A lot. I know that the Archive occasionally gets extremely impressive talent, so I don't necessarily have any damage to my ego. The other candidate may very well have equivalent engineering experience to me plus an MLIS on top. But I know now that it's possible. There are people there who would love to hire me. And yet.
I turned down the other offer. I don't think there's any circumstances under which I would take it. I've taken the past few days to reflect and figure things out.
I'm going to be honest: I am in an absolute dogshit position financially. I've maxed out my credit cards, and now I've stopped paying them. I've figured out how to string out my remaining savings to last a few more months, but I need to bring income in ASAP.
So where am I going from here?
The first part is that after interviewing fairly well with the Archive and elsewhere (and I do have some other places where initial interviews have been positive), I've finally gotten to a place where I feel pretty good about myself as an engineer. It seems silly after having done this work for such a long time to still struggle with the Ol' Imposter Syndrome, but it's taken a long time to get over it. I'm finally feeling better about myself lately in that regard, and it feels possible again to maybe find work with real purpose.
I've also found that my strategy for the past couple months of focusing exclusively on sending out as many job applications as possible isn't necessarily the best one. It may get me interviews and even offers, but it doesn't matter if they're at places where I don't want to work. I want to apply to jobs in a smarter, more targeted manner.
I finally decided that I'm just not going to bother trying to grind out LeetCode or any of that other bullshit. Every time I try to do that, I get bored, and besides that, I just don't respect it as an evaluation method for engineers. Instead I'm going to spin up some other projects that have been on my mind lately. The first is going to be Babby's First NES Annotated Disassembly. I'll be open sourcing that once I have enough to share. Then I have some other ideas in the works that I'm cooking up as well. I feel that these are a good use of my time to demonstrate my skills, keep myself sharp, and potentially raise my profile.
(I would desperately love to put more time into my video and history projects, but right now it's just hard to imagine how I would fit those into my life. If you're waiting for PlayStation Experiment 2, it's coming. I have parts of it done. I just don't have the capacity to pull together a project like that right now.)
I'm going to also put some more energy into nailing down some solid freelancing work. I'm probably going to aggressively market myself in that regard a bit more on here and other platforms very soon.
I'm also likely to pass around the Ko-Fi once again. I'm really hoping to just cover AWS bills for the bots and some of my other personal infrastructure. It's more than you might think: around $160/month right now (RDS + NAT Gateways are sneakily expensive).
I remain optimistic that my future is bright. For the all external bullshit I've dealt with this year, I am the most at peace with myself I've ever been.
