Career cockroach: One Gen Xer talks about adaptability as a primary job skill🪳

When I was in high school in the early ’90s, I dreamed of having a big important 20th-century cool Boomer job… Maybe I’d be a magazine writer, or a newspaper columnist! Maybe an author! (You know, back when that was a viable career, and not just something influencers did to justify their platforms.)

Then the internet came along in the mid-90s, and it was immediately clear to me that this new thing was going to change everything. My first website in 1996 was a college class project about how digital publishing would democratize information and change the world. (Little did I know how bad it would get… clickbait, misinformation, deepfakes. Turns out maybe killing the gatekeepers wasn’t the best idea. Oops?)

I was editing a rave magazine (dream job!) in 2000 when and I first tried blogging, and push-button publishing truly felt like magic. Finally, writers didn’t need permission to publish! In the ultimate irony, my hard-earned first book deal didn’t change my life the way I thought it would… The blog I launched to market the book ended up making as much money in a month as the book made in its entire lifetime. Being an author was a career dead end, but being a blogger was just the beginning.

(Eventually, my book publisher bought ads from my website and all the magazines I’d been rejected by went out of business… clearly, my 20th century legacy media dreams were dead.)

As Offbeat Wed grew, one of its biggest revenue drivers was working with wedding vendors, helping literally thousands of small business owners promote their work on the site. Some vendors paid $1k for ads and then got $40k in client bookings. This was when Google search actually functioned, before the algorithm hellscape took over. It felt miraculous. Forget magazines or books: I had my blog

Despite being a very Gen X person running the site, most of Offbeat Wed’s readers were millennial. They used to tell me I was like a “grumpy big sister.”

To which my Gen X response was, of course, “WHATEVER.”

Adapt or die (or at least… go get a corporate job)

Then through the late 20-teens, things changed. Independently published blogs were replaced by massive social media platforms, which started to feel addictive and like a parasocial circle-jerk. Running a digital media company started to feel less like freedom and more like a miserable grind. I was burnt out and exhausted from 15 years of entrepreneurship and I wanted a change, so I took a job at a publishing platform managing anti–AI content campaigns.

And then… (plot twist!) last year my corporate job got re-orged out of existence, and I found myself with unexpected free time. Bored, I started playing around with AI… not for work, but for personal development and self-awareness. And then my brain broke. AI wasn’t just a productivity tool; it was a mirror, a coach, a brainstorming partner. It was so mind-blowing that I wrote a little guidebook about how other people could use AI in similar ways.

Huh… I had completely changed my mind!

Who says you can’t teach an old dog new tricks? I believe this is now called neuroplasticity. Just keep learning.

Then I had another realization: those wedding vendors I had worked with for decades could use these same deep-training AI techniques to refine their brands, make their businesses more inclusive, and free themselves from the burnout-inducing hustle grind that had nearly taken me out as a small biz owner. And so now, I’m an AI consultant for small businesses.

So I went from magazines to blogging to publishing and working with small businesses (ie wedding vendors) to working for a publishing platform fighting AI, back to working with small businesses but now I’m teaching them how to use AI in ways that feel deeply human and embodied?

My little cockroach feelers are wiggling because the only thing consistent here is a combination of technology, storytelling, and adaptability.

It’s this adaptive cockroaching that has been the name of the game for Gen X professionals. The jobs our parents had that we were educated for literally don’t exist any more. Every decade of our careers, we’ve had to mutate and evolve like cockroaches surviving a nuclear blast. And let me tell you: my real job skill, honed from my childhood as a latchkey kid left to my own devices, isn’t publishing, writing, or marketing. It’s adapting to whatever comes next.

So this year it’s building out an AI consulting business, but next year I might be a post-apocalyptic goat farmer (with heavily optimized operations procedues, obvi)… I’ll figure it out. WHATEVER.