Lake Minneola to Lake Wobegon and Back

In July 2022, I wrote “Thoughts on Leaving California” about my move back to Florida after twenty years in the Golden State; I followed it a year later with “A Year Back in Florida”, which ended with “I’ll check back in after another year.” I’ve been doing that annually ever since, although the date has kind of crept up; this year I’m over a month late.

I wrote 2024’s check-in during a 16-month stretch of unemployment. While part of that was a deliberate break, most of it wasn’t. That check-in was kind of angry. Last year’s check-in got even angrier, even though I’d gotten a fun contract that ended up running over a year. Much of the anger stemmed from the country’s steadily degenerating sociopolitics; more than a little came from a sense of being trapped by geography.

So how am I feeling now, four years in, unemployed in a terrible job market, less than a decade from traditional retirement age when it seems increasingly likely we’re heading into a recession—at best—within the next few years?

The market for remote technical writing jobs, at this moment, needs to improve to be dreadful. If I rule out jobs that involve babysitting LLMs—and jobs that directly tie into the federal government, an organization I’m less than enthused about at the moment—I’ve found a total of twelve to apply to in the last month. That’s enough to receive unemployment benefits in California, but not in Florida, which makes it as hard as possible to get the meager amount they offer.

On the flip side, I returned to travel starting last year, making a summer trip to Pittsburgh by train. This year, I returned to both Silicon Valley to see friends and to Lawrence, Kansas, for the amazing Ad Astra “Repeat Offenders” workshop.

And, in a few weeks, I’m going to Maryland to see Garrison Keillor.

“Wait,” you might be thinking, “you’re traveling that far for a show with the Prairie Home Companion dude who was fired for sexual misconduct? Seriously?” Okay, the truth: my 81-year-old mom is using the Garrison Keillor show as an excuse to make one last trip to her home town of Baltimore, and I’m going with her.

Yes, she is still a Keillor fan, listening to his short weekly podcast and getting his newsletters; we’ve talked about the misconduct allegations in the past, and yes, I think she’s performing a “they were only allegations and they weren’t really that bad, were they” rationalization, the way many people make excuses for people whose work has meant a lot to them over the years. (Also see: J.K. Rowling, Neil Gaiman.) I used to enjoy Prairie Home, but left to my own devices, I wouldn’t buy a ticket even if the #MeToo aspect wasn’t present. His post-PHC work is a touch crankier and definitely less poignant. (And on Substack, because of course it is.)

But, as I said, this is less about Keillor than it is about making a trip back to Baltimore that mom has been talking about taking for years. While she’s had chronic health issues for all her life, they didn’t get in her way until this decade. (She might quibble with that assessment, but we took annual trips around the country.) But a case of shingles, of all things, about five years ago left her with a neuralgia behind one ear that makes it painful to wear glasses or hearing aids just at the time both her hearing and vision are getting markedly worse. And a couple of years ago, the summer of her 80th birthday, we both caught Covid, and it made her lifelong respiratory issues considerably worse; a cough has become chronic, and her already too-low weight has been steadily dropping, a dilemma compounded by a litany of dietary restrictions and stubbornly untreatable digestive issues.

I know I’ve been to Baltimore before with her, but honestly, I can’t remember when that trip happened; it couldn’t have been more recent than the 1990s. It’s not an area I feel a connection to, but it’s an area she’s deeply connected to. Since I moved in with her in 2022, her reminisces of childhood in Baltimore and southern Maryland, where she had an aunt she stayed with in summers, have become near-daily conversation.

This year, I came to the dismaying realization that my mother is deeply sad about her life. About the prickly relationship she had with her own mother; about the sense of isolation since we moved in the 1980s from relatively cosmopolitan Sarasota to backwater Hernando County—first to Spring Hill, a sprawling unincorporated community of tract houses, then out here to Ridge Manor, a rural unincorporated community destined to be overrun by tract houses in the next few years. And the isolation took a sharp turn for the worse post-pandemic. (I wish I’d pushed her to restart an annual Christmas party she used to hold for friends and neighbors, which I suspect helped with connections more than she admits to herself. She would point out, though, that several of the people she used to invite have moved away themselves in the last few years.)

This is a sadness I’m, bluntly, bad at helping with. I’m too reserved, not good at giving comfort (these are issues I know I should unpack myself sometime), and get impatient when we rehash evergreen complaints, from Florida’s endless construction to the sorry state of the American healthcare system. But it’s also that this side of her is mostly new to me. Before I moved in with her, I would have described my mother as generally happy; I’m not sure how much of that was me naïvely missing the forest for the trees, and how much of it is a new, late-in-life melancholia.

The Baltimore trip will be a challenge in a dozen different ways, from the complications her health conditions may make while traveling to the fact that our lovely neurotic cat, Maisie, will be left alone for a full week. A neighbor will be coming over to feed her, clean litter boxes, etc., but Maisie literally refuses to be seen by any human other than my mother and myself. I am hoping we won’t come back to a house full of shredded furniture and dried puddles of cat vomit, but I am not placing any bets. Regardless, my mom needs this trip, and I’m happy to do it with her.

I’ve come to another dismaying revelation, though, this one about myself. I’m going to return to that unanswered question about how I feel now, unemployed in a terrible job market, etc., etc.

And the answer is: kind of…good, I think?

I don’t want to make any grand pronouncements about being done with tech; in some ways, I love technology as much as I ever have. But to say I’m disenchanted with the industry currently would be a grand understatement. My biggest frustration is I don’t know what else I can fall back on. My biggest advantage is that I have time to figure it out.

I’m dusting off my copy of What Color Is Your Parachute?, a career advice book whose first edition is as old as I am. (Figuratively dusting off; I have the last edition from 2022 as an ebook, purchased during my 2024 interregnum.) It’s a quirky book, premised on the notion that you first need to figure out your dream job, then target employers and convince them to hire you. I haven’t gone through it in at least a quarter-century, and the truth is I never truly followed it. The closest I came was circling back to a company that had approached me about technical writing, though, and I don’t think it’s a coincidence that doing that led to the best jobs I’ve had.

In the meantime, I’m going to keep writing. I may get better about posting to this blog more regularly; 2025 was the most active I’ve been in years and it was still only 15 posts, and this post makes 11 in 2026. I’ve started following David Sparks’ advice in his Productivity Field Guide, which upon reflection seems a spiritual cousin to Parachute: instead of focusing on “how do you become more productive” or “how do you get a job”, they both focus on “who do you want to be?”

It’s a good question. It feels ironic that I’m starting to ask it more seriously again as I approach a traditional retirement age—but, in a different light, maybe that’s a great time to ask.