When last I wrote, it was still summer vacation for me, with school about to start up again at Four Corners after the Labor Day weekend. I was facing down that regular turning of the year with a mixture of resignation and unrest—in my mind, I’d always promised myself if I spent more than 5 years moonlighting as a school employee, I was screwing myself over. Here I was: not quite at 5 years of working within the school district yet, but at the beginning of my 6th school year as an Educational Assistant. I hadn’t hit my silent deadline, but it was looming right in front of me.

But the start of the year came, and as much as I’d looked for work over the summer and dreaded this return to the norm more than usual, it was easy to get back in the groove. The staff at Four Corners is a pretty solid crew, so much better than what was the norm elsewhere. Before, most of the employees in my same position were ladies 30+ years older than me in a sort of semi-retired limbo, with a lot of bad attitudes all around.

At Four Corners, I finally had peers around my own age, a better balance of male & female, and almost everyone on the same wavelength. It’s hard to describe what that wavelength is… a sort of good-natured cynicism—black-humored, wise-assed, foul-mouthed, but still genuine & supportive. Just my style.

So I sighed internally and resolved to make my peace with another year of doing work that is, yes, important and rewarding and different every day, but for not enough money to live on and with no path for advancement outside of picking up a teacher’s degree. Is it any wonder that in the absence of anything constructive happening in my career, I so regularly threw myself into the deep end of my hobbies instead?

All of that to say, I was looking to shout down my inner doubts and reach a point of forced contentedness rather than make a change. Maybe it was something about that effort that made it all come together. Call it latent desperation: so subliminal I didn’t even realize it was happening.

But with my savings in the toilet, a couple money scares and more than my share of lingering and looming financial doom, I’d cope by trolling through my regular rounds for online job-hunting. Just enough so I could tell myself I hadn’t given up, mostly Craigslist and a few corporate pages I’ve got bookmarked, waiting for my lucky day. Careful to not be looking at any education jobs.

Thus it was that I took a look at the Portland subreddit, since I’d noticed after posting to advertise Ready, Set, Game events there that they had a monthly job-seeker thread stickied to the top of the page. Plenty of local outfits listed their openings there; I’d seen that Simple had someone regularly posting for their hiring, as I’d applied with them before. I didn’t see them this time, in that September thread, but I saw another company: Squarespace.

For context, this is a Squarespace site. Even now, these words sit in memory on a Squarespace server somewhere, in a room in New York I’d imagine, where they’re headquartered. Or as I should say: where we’re headquartered. Because while I’m still working in Portland, it’s for the very recently-opened Portland branch of Squarespace, Inc.

It all happened crazy-fast. I’d been a user for ages—I heard a promotion on This American Life way back in 2009—and I figured the company would be a good fit. It was working online support, and I’d done similar work for a friend’s company two summers earlier. I applied in September, not even two weeks after school had started, and only 10 days later I’d interviewed for & accepted a job offer to start the first week of October. Head-spinning stuff!

And what a turn-around it’s been already. Taking home almost twice as much in pay was certainly a nice step up. Let’s be real: I was making shit money before, but even so. I’d gotten used to making nothing, though not quite living on nothing. Hence money scares, debt, etc. But to skyrocket to double what I was used to, well… let’s just say I no longer have stress nightmares. I’m not exhausted all the time from laying awake worrying. And you no longer can track the figure in my bank account by my following my mood & sense of self-worth.

That’s the baseline for a positive change. On top of all that: holy shit I’m doing something where my background feels at least somewhat relevant. I didn’t go to college for this thing, no, but it’s honestly not that far from formal public relations, which I at least got familiar with. And four years of learning how to communicate comes in damn handy plowing through emails.

Ah yes, the job itself: online customer support. Doesn’t sound glamorous, but in all frankness I love problem-solving. I’ve always envied people in tech support positions at least for the fact that when they worked to solve problems, those problems could usually be solved. Working with troubled kids is all about problem-solving too, but these kids ain’t gonna be “solved” anytime this decade, for the most part.

If we’re counting, then, that’s two big improvements: pay and position. And then there’s the company and team. At Four Corners, as I said the team was solid. I had some concerns about our latest administrator (the most recent in a chain of principals who rarely lasted more than a school year), but everybody else in the building was a total keeper. They made that job worth coming back for: all reliable, supportive, and a fucking good time to hang out with.

That part has stayed true here in my new job, I’m happy to say. They’re a touch less cynical—I mean, come on, they’re not public school employees, so of course they’re less cynical. So I miss a bit of the old “we’re all in this fucked shit together” vibe. And on the upside, while Squarespace is indeed a venture-capital funded startup, that’s a hell of a lot more stable than tax-funded school district. Reynolds (a district I grew up in, so this is not just from a place of worker bitterness) laid me off three years in a row at the height of the recession, only to rehire me & a raft of other laid-off EAs every fall. Whether those moves were cost-cutting, poor planning, the ebb and flow of tax money, I’ll never really know. But I’m thrilled to no longer be subject to those particular whims.

It’s only about a month on from my start date from Squarespace, but already it feels like home. I get to work downtown, use my discounted TriMet pass to avoid a stressful commute, and I’m jazzed to see the folks at the office every day. Lots & lots of overlapping spheres of interest, experience, and perspective, but without sacrificing the spectrum of diversity. (Other than age, maybe—everybody there trends totally young, but again: startup, right?) I enjoyed the hell out of my colleagues at Four Corners, but I sincerely doubt I would have ever been running D&D games in a conference room there after hours. Which I now am, haha! And I’m already putting the perk of unlimited free websites to use…

So I’m looking forward to settling into this particular groove for the foreseeable future. Already I know that the opportunities here are great. Staying within this company for the next 10 years or more is something I can absolutely see happening. And if that’s not the longterm plan, then halle-fucking-lujah, I’ll be able to take a more transferable skillset away from this than I ever could’ve gathered in public schools. That was, above all, my greatest fear: getting specialized enough in the field that I’d find my options trapped by a cage of my own making.

My Journalism degree still sits mostly unused, but who knows? By any measure, this is more of a step in that direction than just about anything that’s happened in the last 5 years. I’m excited to see where this takes me, and looking forward to sharing more about that in the weeks & months to come.