- Redefining Retirement
- Posts
- Gen X: The Unexpected Winners of the AI Revolution
Gen X: The Unexpected Winners of the AI Revolution
How the OGs of internet adaptation are perfectly positioned to profit from artificial intelligence

I was blown away back in '97 when my work computer got the internet.
I'd stay after hours just exploring.
Having all that information at your fingertips felt like a superpower. If you remember life before the mid-90s, learning anything meant trudging to the library or knowing someone with the knowledge you needed.
That internet "superpower" changed everything for me. Guitar tablature sites got me playing music again (leading to two albums and 100+ live shows). Online learning showed this former C student that I was actually an A student when studying stuff I actually gave a shit about. Most importantly, it revealed I didn't have to settle for the "get a job, wait for retirement" story we'd been sold.
Fast forward to today: That same revolutionary feeling is hitting me with AI. But this time, we Gen Xers have a massive advantage that most people are missing.
Here's what companies are figuring out…
AI without experience is just expensive autocomplete.
The Numbers Don't Lie:
77% of executives say their biggest AI challenge is finding people who combine technical skills with domain expertise (McKinsey)
Jobs that require AI specialist skills carry up to a 25% wage premium in some markets. For example, job ads for US sales managers that require AI specialist skills offer wages that are on average 43% higher than job ads for sales managers that do not require AI skills. (PWC report)
Last Thursday, I watched an AI training session where the trainer completed in-depth market research in couple hours that would've taken weeks just a year ago. But here's the kicker - the questions he asked weren't ones a newbie would even think of. They came from years of marketing experience.
Think about it: Who's more valuable?
A 20-year veteran using AI to supercharge two decades of real-world experience
Or a 20-year-old using AI to learn about your industry from scratch
The Internet Liberation 2.0 Just like the internet liberated us from small-town thinking and geographical constraints, AI is freeing us from the "too old to adapt" narrative. It's not replacing us - it's amplifying everything we've learned over our careers.
My path from mechanical draftsman to media buyer, freelancer, singer-songwriter, and digital entrepreneur wasn't despite technology - it was because of it. AI is offering the same opportunity, just at hyperspeed.
What used to take hours or days literally takes minutes now. Pair this with our hard-earned skills, experience, and curiosity, and we can write our own tickets.
The Critical Shift The most valuable person in the AI era isn't the one with the most technical knowledge - it's the one who can ask the better questions. And after decades in the trenches, guess who's got the best questions?
You're sitting on a goldmine.
Time to get out that digital pick and ax and start mining.
Action Plan
Here's Your Action Plan:
Subscribe to keep reading
This article is free — but it’s for Gen X solopreneurs, creators, and side-hustlers serious about figuring out what’s next. Subscribe for the weekly mixtape of newsletter tips and simple AI systems to help you stay relevant, make some cash, and build lifestyle-first work you’ll never want to quit. You in?
Reply