What’s Next?

I’ve been thinking about what I want from a new gig.

• Lately too much of my time has been spent working alone, making things in a bubble, pitching ideas in isolation. It’s pretty lonely! How do I fix that?

• What I want is a co-conspirator and mentor again. Someone who kicks my ass and pushes my designs and prototypes, my nascent coding and writing skills. I want someone who can open my eyes, show me the way.

• It’s shocking how many bad jobs are out there. I don’t expect to build something that changes millions of lives but I’d like to contribute to a worthy cause and not join a company that happens to be a leader in the Dao-based multiplayer AI top-of-funnel consumer business market. I reckon that requires me to have the guts to say no to a lot of stuff, even if that’s a terrible idea for my financial health. But my parents always chased easy cash throughout my childhood and watching that taught me a valuable lesson: never follow the money.

• The problem with joining a big company is that you have no idea what the team dynamics are. Sometimes you can talk to the leads of that team but you really have no idea what working with them will feel like once the OKRs start flying around. Is the team healthy? Are they competent and reasonable? And, most importantly, are they funny?

• I don’t wanna jump around from team to team or company to company. I want to be on a problem for like 5 years straight. That’s a solid amount of time to learn how things get done.

• With big companies there’s more stability but you and your team can get lost in the yearly re-org. There’s more politics. Decisions are so much harder to make. But then there’s this opportunity to build something enormous and slap your name on it. You get to unfurl the curtain and reveal how this enormous software factory works, and that’s always exciting. Big companies also open doors by connecting you with so many people. Then again, they also attract middle managers like a family of hungry bears to a river.

• Yet small companies might not last long! Sure, you could take a chance on this tiny company but are they gonna be around next year? Do they make any money? Or is this company fueled by the delirious hopes of VC firms hoping to get something out of it soon?

• I realize the biggest threat to small businesses like, say, a freelance web design shop that I might start, is health insurance. I know, I know. Saying this is boring and stressful as all hell and not useful at all. But the healthcare system in America is a misnomer—there is no such thing. Instead of a healthcare system there is only a violent and colossal bureaucracy in its place. Every insurance company is a leech upon the body politic and everyone in between medicine and me is an accomplice. The dystopian healthcare system limits us all from our potential, limits our freedoms and life choices.

• Maybe I should go back to freelancing? Healthcare aside, there’s also weeks and months of anxiety and shame when nothing comes in. Plus, I don’t really have a huge network of folks I could buzz and start getting good work leads. Last time I did freelance work I had to say yes to a bunch of stuff that I wasn’t proud of, projects that will be forever buried.

• I wanna make websites like my essays all day long; big, rambly things that feel punk rock and aren’t just machines for generating clicks and eyeballs. But is there really a market for work like that? The big scrolly-like things for the NYT and its ilk feel like they’re going out of fashion. But maybe I can take those skills and apply them elsewhere?

• I’ve always worked best on teams of three or four people. Any more than that and you need managers and quarterly goals and all the horseshit that comes with large numbers of people. At a small scale, a team can be more nimble than a thousand mismanaged folks—they can work like a tiny little squadron behind enemy lines without the need for backup or artillery support.

• I love it when a team doesn’t have a backlog. When you’re in a room with a bunch of smart folks and they all can collectively decide what the next most important thing is right away. And then just do the darn thing.

• No more working weekends, no more working late at night. I did well with that at my last gig and hope to keep that up. Having that boundary is vital and anyone who says that you gotta work hard to play hard simply doesn’t know what good, valuable work looks like.

• I hate meetings. Most of the time they’re a complete waste of time. On small and nimble teams they’re brief enough but I’d like to work on projects that don’t require constant in-person chats because eventually you spend your entire day socializing and I dunno! I don’t like that! If I haven’t made anything at the end of the day or made any kind of progress at all then I feel stressed and terrible.

• I want to work on something exciting. Now, exciting for me is boring for a lot of other folks but what I mean is that there’s nothing more bleak than turning to someone in a fit of excitement and them giving you a bored look. Or, worse; having no one to show your stuff to. That kills me and makes me wanna walk right in the ocean. I want my excitement to be shared.

• I want to feel like I’m doing a lil mutiny everyday.

• What about returning to design systems work again? Eh. You have to spend half your time convincing folks that your job is worth doing. It’s exhausting being in a room talking about buttons for the thousandth time this week and when management suddenly changes their minds about how stuff should look then they expect you to do a shit ton of work in a hilariously short period of time. Design systems work is always under-staffed, under-appreciated, and tends to only be feasible at large companies where you’ll spend a lotta time in meetings explaining that you already have a design system and, no, you don’t need to build it again from scratch. Most people spend more time talking about what to call a design system than actually workin’ on the design system and god this all sounds exhausting to me. Perhaps I’m just not built for it.

• What about dedicated front-end work? Hmmmm. That kinda work has paid the bills in the past but if we’re being real honest here then I’m not a good developer. Good prototyper? Maybe! But when it comes to engineering high quality interfaces at scale then I don’t have the patience to learn how Typescript is doing this one goofy ass thing today and fiddling with a framework isn’t what I want to do. At least in my experience it becomes very repetitive work anyway.

• I want to push my design skills, ideally. I think I’m better at the graphic design of website-making and less so at the product side of things. That would usually push me into the role of a "growth designer" and dear lord what a depressing thing to slap onto your resume. I wanna make websites and write, not stare at graphs all day long and argue about how if we moved this one button here then sales would go up by 0.3% in the southern territories in Q2. All of that sounds pretty lame! Sorry!

• Another product design gig? I think so? I’m starting to improve my skills there. The problem, generally, is that to do great product design work you have to be very political. You have to push back on the original brief and gather consensus at the leadership level. But that’s super stressful, and is what almost killed me at my last gig. I’ll just obsess over what the CEO or CTO think about my buttons and that will give me shingles and make me want to cry over lunch.

• I worked at a huge converted factory in the Dogpatch district a few years ago. The building used to build ships and this company comes around a hundred years later and fills it with plants and neon signs and beautiful chairs. It was stunning. But it was impossible to think in a space like that; I could hear what someone was saying on the other side of the office.

• A company could spend $10 million on an office and it will still suck compared to what I can make with a few things from Ikea.

• So I want to work from home. Offices contain endless distractions and get inbetween me and the work. Plus, being able to run to the bakery and randomly pick up some bread in the middle of the work day is a Caligulan luxury I refuse to let go of.

• The one invaluable thing about office work is brainstorming. But you only need 1 day a week tops for that. Any more and you’re just wasting everyone’s time.

• So product design at a small company then? Fewer than a hundred employees? Somewhere without the politics, somewhere I can work remotely, somewhere I can work with smart and funny people on something that feels dazzling but isn’t a VC-funded dystopian nightmare.

• I want to build stuff that I can brag about. Small details that shine. Stuff you can blog about.