Flunking Retirement
GenX in the jaws between Medicare and AI
Last week, one of my first tech career mentors reached out to me. I would have never spent two decades as a technical curriculum developer, were it not for them. We had an hour-long catch-up call. They have spent their last 14 years directing technical training for a very large, specialty manufacturing firm. They had 40 staff reporting to them when they were laid off last summer. Which is a very large headcount, for the “tech trainer” industry-niche.
Several hundred job applications later, they have had two callbacks, one interview, and nothing close to a job offer.
I am 59. One year older than they are.
Two years ago, my own tech career ended with a phone call. That call was followed by instructions to box and send back the laptop setting on my dining room table, where I typically worked. Which is how every job change I have made for 25 years has been consummated: wipe the old box, box it, ship it, unbox the new box, and load it with whatever tools I would be learning to explain next.
There was no new box this time.
As a technical trainer and curriculum developer, I spent 25 years on a non-stop learning curve, from tool to tool and tech to tech. Watching for patterns. Noticing metaphors. Relying on both to tell stories, to guide folks over the learning hump.
Then came AI. Now, there is no need to learn digital tools. We can tell a chatbot to produce what we want, and hope it gets it right. No skill required. Which is handy, as a recent MIT study shows how AI use causes rapid “cognitive decline.”1
Have you ever photocopied a copy of a copy, of a copy … ?
In 1995, I built my first website using Notepad and cURL (Filezilla came later). It was for a partner at my law firm. I wanted out of Family Law. My liver couldn’t take watching families explode for a living.
If I could grind my way through law school and the bar exam, I was not going to be stopped by cryptic man pages, vague error codes, and strange encoding formats, nor hours of twiddling Apache web server configs.
A man page, short for manual page, is a form of software documentation found on Unix and Unix-like operating systems.
I worked my last full-time desk job in the late 1900s.
During the late nineties, the ability to spell HTML could land you a job in web tech. After a one-two step through two short desk-bound roles, in Portland, I was hired by an early application server company, based in an office park outside of Boston. Application servers are web servers that rewrite static web pages by injecting them with relevant data. They gave birth to Amazon and the internet as we now know it. You’re using one right now.
I wanted out of Family Law.
My liver couldn’t take watching families explode for a living.
I would visit that office park exactly once before Allaire was acquired by my next employer, Macromedia, whose office park I never visited at all.
It was not until Macromedia was acquired by Adobe that I would physically visit my direct manager’s personal office, exactly once. That said, she and successors flew me everywhere else. I flew all over, leading live training events for web coders worldwide, during the first and second internet booms.2
My husband told folks I worked for the CIA.
Some of these events were for a handful of techs, others for hundreds. I had no fear of an audience. My high-school honed theatrical skills, and my law-school honed research, writing, and advocacy skills, all came in handy.
I learned that airports, hotel rooms, taxi cabs, and computer training labs look remarkably similar worldwide. Except for the power outlets. Check those carefully, or your gadgets may fry.
There is no doubt Adobe’s upper management loathed me (impersonally, of course). During my first week working for them, I, a lowly tech trainer, was shipped out, business class, to spend all of five days teaching in Hong Kong.
I learned that airports, hotel rooms, taxi cabs, and computer training labs look remarkably similar worldwide. Except for the power outlets. Check those carefully, or your gadgets may fry.
For the next ten years, it did not matter where I wanted to live, so long as an airport was close by.
My husband and I could have been digital nomads. We thought of it. Talked of it. Dreamed a bit. We bought a starter home instead, and upgraded twice over the years. Nomads kept visiting us, instead. Portland was weird that way.
A digital nomad is a person who travels freely while working remotely using information and communications technology such as the Internet.
Eventually, though, I stopped traveling for work. All of those hotel and airline expense reports put a target on my back. Plus, this was the tech industry. Upper management quite literally exists to cut travel costs, labor costs, and any other costs, beyond their bonus.
Online learning hit us first, as a viable curse. I switched to designing, writing, and recording online training content, instead.
A reference to the Sufi poet Rumi in a job solicitation—headhunters used to stalk people like me—caused me to pivot from web tech to so-called “big data.” A set of tools and technologies that exist because the industry goal is for your every app or web click, and your every action taken with a GPS device or RFID widget, to be tracked and stored for analysis.
Forever.
The bigger implications of my work have never been lost on me.
Over the next ten years, spread across three startups and one little consultancy, I produced dozens of online courses about differing flavors of data management. My work product involved hundreds of video hours, and thousands of (beautiful, information-dense, visually rich) slides and workbook pages.
When Michael and I moved our lives from Oregon to Montana, I told my boss as an afterthought. Laptops work the same way, anywhere.
My phone rang, just as I was stepping into the shower. I would have ignored it, but the screen said “Kevin.”
Kevin was my manager. I had worked for him at our prior employer, too. The timing was odd. He rarely called. He trusted me to roadmap my own work and get it done, on time, on budget, and on point. Weeks could pass with nothing passing between us but a few texts. It was a thin company, as such things go, with about 110 people on staff, around the world. We kept busy.
“This is a bad news call, isn’t it, Kev?”
AI had done a triple whammy on this little, big data management startup that paid us, killing off our financing, canceling an acquisition, and lapping our formerly cutting-edge product. So, the founders laid off nearly everyone in North America. America is expensive compared to India.
Code and data flow freely over (most) borders3. I had taken advantage of this fact for ten years, building online training often consumed overseas. In 2023, this same free flowing data took advantage of me, in return. Between AI, and cheap overseas tech workers—whose food and housing costs may well be one-fifth of my own—my job role no longer stood a chance.
It is ironic that Apple’s founder—the tech industry saint, Steve Jobs—died young. Killing jobs is the core purpose of the tech industry. Jobs elimination has been the purpose of automation since the first water wheel was set to spin.
Prove me wrong.
It is ironic that Apple’s founder—the tech industry saint, Steve Jobs—died young. Killing jobs is the core purpose of the tech industry.
Since that phone call, I have had several more, talking with colleagues who, like me, are in their mid-to-late fifties. Many have been laid off. Many have sent out hundreds of job applications with near-zero responses, much less a new job. Much less one remotely close to their skill and experience level.
No one hunts for long-experienced tech workers anymore. Tech bros have chopped our whole layer from the cake. GenX careers are in hard decline, or finished, because of AI. We are now seen as slow, expensive, and insufficiently hungry, else we would have already clawed our way into the C-Suite.
Our bad?
Folks like me made the mistake of doing our jobs well, but in the tech industry. An industry whose executives wield dashboards full of targets (er, “metrics”) painted on the backs of their staff. In tech, a job well done is just a model to be automated out from under whomever did it.
In tech, a job well done is just a model
to be automated out from under whomever did it.
I willingly used generative AI exactly once.
In late 2022, as a self-motivated learning experience, I asked ChatGPT 3.5 to draft a training content outline for my company’s product. The result was as superficially convincing as it was remarkably wrong.
ChatGPT flat-out made shit up about what our product could do, yet presented its result with confidence and style. The Sales and Engineering teams would have screamed if they saw it. Marketing would have loved it.
Regardless, crap that it was, I could see that careers would be ending, soon, for anyone who made their living building things with graphics, words, or code. Because “now there is an app for that,” even if only a fool could trust it.
On a purely personal level, this honestly could have been fine by me. I got into tech early. While I never got the money-sprays some other colleagues received, I did okay. I bought property and steadily invested. I enjoyed practicing my craft as a instructor, technical writer, and videographer. I did good work, and lots of it.
I can check my privileges, alongside my good choices.
I began thinking of early retirement. This felt daring. It also felt like a gift to myself, for having set aside my literary dreams thirty years before. Truth be told, had I not been laid off, I was planning to quit within a year.
It was obvious AI would soon be slicing joy away from my work.
Using skills you have honed over the years can be a flat-out, full-speed joy, even if the underlying product is fungible. Over many (many) training content projects, I became a pro-level explainer. I developed a strong, flow-state ability to visualize complex processes, guide the learning eye from topic to topic, guide the curious hand from point to point, and assess what knowledge got across, or not.
I did not expect to end my working life knowing enough of nine programming languages to be mildly dangerous, within a reasonably wide range of coding and data management paradigms. I grasp and express tech well. All this, plus ninja-grade PowerPoint chops, strong illustration and animation skills, and a bit more than merely decent video editing and production abilities … made for some fun.
While I have never felt like an artist, I have most certainly been an artisan.
Since that phone call, I have retired twice, briefly. The first time I grew quickly bored. I had not made solid plans to keep making things the way I had enjoyed making for so many years. So, I went back to work, for a year, making a set of training courses about the Montana Constitution. Then, I retired again.
I would have happily continued this second retirement. It began just this past summer. But, Washington, DC, loves to play football with the health of those who elect them, while the medical, insurance, pharmaceutical, and hospital construction industries line their silken pockets.
I would have happily continued this second retirement. It began just this past summer. But, Washington, DC, loves to play football with the health of those who elect them …
Over the past two months, my husband and I learned that, by both age and location, we are dead-center targets for the highest medical insurance hikes of any demographic.4
We are turning 60. We live in a rural state. Our medical premiums were set to rise 421% from $759/month to $3200/month on January 1st. Medicare is five years away, if it survives that long. Even if we cut back to bare-bones coverage, we would still end up paying $2000/month, a 263% price hike, year over year, and that for the kind of insurance that quickly breaks if you actually use it.
This is not affordable. Inflation is not under control. Something about the whole medical and insurance industry needs to change, and soon.
All this said, a bit of a Christmas miracle came our way, this year.
For decades, I have done volunteer tech work for a variety of civic organizations. I have been a “social media manager” since long before that term was coined.
A few weeks ago, while sitting in the office of our Episcopal Diocese, helping their Admin staff with some fiddly web updates, I learned they had decided to hire someone to manage their website, newsletter, event registrations, and several other ongoing data management needs.
Even churches need to be online, these days.
The job is part-time. The pay is the lowest I have made since college. But, unlike tech bros and politicos, churches look out for people. The fully-covered medical benefits this church job provides—for both my husband and I—are better than anything the tech bros ever gave me.
“MIT Study Finds Artificial Intelligence Use Reprograms the Brain, Leading to Cognitive Decline,” Nicolas Hulscher, MPH
Hong Kong (x3), Istanbul, Buenos Aires, New Delhi (x3), Tokyo, Bangalore, Barcelona, Milan, Rotterdam, Sydney, Wellington, Ottawa, Mexico City, Munich, LA (x11), SF (many), San Jose (many), DC (many), Seattle (many), Houston, Boston, New Orleans, Omaha, Detroit, Chicago, Disneyland, Disney World, and Vegas baby, Vegas. And, no doubt a few more I have forgotten, like the nuclear waste facility in eastern Washington and weapons testing base in the Mojave.
“Internet Censorship: A Map of Internet Censorship and Restrictions,” Paul Bischoff
https://www.comparitech.com/blog/vpn-privacy/internet-censorship-map/
“Older Adults Face Tough Decisions as Affordable Care Act Tax Credits Expire",” Miriam Cross, AARP
https://www.aarp.org/advocacy/aca-subsidies-affect-real-people/
“Mapping the Uneven Burden of Rising ACA Marketplace Premium Payments due to Enhanced Tax Credit Expiration,” Justin Lo, et al.
I love reading your thoughts, Leo. Thank you for sharing your gift to do so.