How Artificial Intelligence Helped Me Rethink My Job Search at 50+ — And Reignite My Confidence
After months of frustration, ChatGPT gave me something unexpected: a clearer, more confident version of myself.
Six months.
That's how long I'd been searching for a new job (and I know others who’ve been sarching much longer) — applying, interviewing, polishing my resume, sending off dozens (if not hundreds) of applications into the void. And as someone over 50, I already knew the road wouldn’t be easy. I had a long, successful career behind me, but somehow that seemed to work against me as often as it worked for me.
At first, I leaned into what I thought was conventional wisdom: Keep the resume straightforward. Limit it to one page if possible. Play it safe. But safe wasn’t working. Worse, the longer the search dragged on, the more it chipped away at my confidence. Was my experience irrelevant now? Had the world really moved on without me?
In a moment of frustration (and a little desperation), I decided to try something new: ChatGPT. I’d been hearing about it everywhere — how it could write articles, summarize documents, and even help with professional tasks just as other AI tools were instrumental in producing my award-nominated dramatic audio series HINDSIGHT: THE DAY BEFORE.
Could it help me rethink my resume too? I figured I had nothing to lose.
Seeing Myself Through a New Lens
The first thing I did was upload my old, "safe" resume to ChatGPT and ask it to modernize it — not rewrite who I was, but help present my experience in a way that today’s employers would find clear, compelling, and aligned with what the market expects.
What I got back was… eye-opening.
ChatGPT didn’t just update the formatting or throw around corporate buzzwords (although there are plenty of those). It surfaced skills and accomplishments I hadn’t thought to highlight. It drew connections between different phases of my career that I hadn't consciously made. It rewrote my experience in a way that sounded — for the first time in a long time — powerful.
It wasn’t just that the AI was technically good at summarizing. It was that it was objective. Where I had downplayed certain achievements ("everyone’s done that, right?"), ChatGPT framed them as significant contributions. Where I saw disconnected roles, it saw a story of adaptability and growth. It took my raw materials — years of hard work, lessons learned, successes (and yes, setbacks too) — and shaped them into a narrative that made me proud.
After months of feeling invisible in the job market, that was an incredible ego boost. I wasn’t washed up. I wasn’t out of touch. I just hadn’t been telling my story the right way - which is a tough admission for a storyteller to make, let me tell you.
A Resume That Finally Felt Like Me
Using ChatGPT, I ended up with a one-page resume that felt crisp, modern, and — most importantly — authentic. It still sounded like me, but a me that could stand tall in today’s competitive market. A me that wasn’t apologizing for being experienced, but showcasing it as an advantage.
It also gave me permission to stop playing small. Instead of burying my leadership experience, project successes, and cross-functional skills in the fine print, the new resume put them right where they belonged: up front and center.
That shift wasn’t just cosmetic — it changed how I approached the whole search. I found myself writing cover letters with a little more swagger. Walking into interviews with a little more energy. And yes, applying for roles I might have hesitated to reach for six months earlier.
Lessons Learned
Am I saying ChatGPT is magic? No. You still need to bring your own voice, your own career history, your own understanding of what you want next. The tool is just that — a tool. But what it can offer, especially for those of us who’ve been in the workforce a while, is a fresh pair of eyes. A reminder that your experience does matter — sometimes you just need help framing it for a new audience.
Looking back, I realize my old resume wasn’t wrong. It was just stale. It was a museum exhibit when what I needed was a living, breathing introduction.
Today, I'm still searching — but with a lot more hope, a lot more energy, and a resume that makes me excited to talk about what I bring to the table.
If you're over 50 and feeling stuck, I can’t recommend it enough: give yourself permission to rethink your story. Whether it’s with a career coach, a trusted friend, or even an AI assistant, sometimes a little objectivity is all you need to remember just how much you have to offer.
Mark Haynes has decades of experience at the intersection of communications, marketing, design, and technology. He’s ridden the wave of many tech revolutions (including VHS winning over Beta) and can probably help you and your company surf the one that’s right in front of us - artificial intelligence. Reach out if you need a hand! Visit markhaynes.com for more info!