Being of a “certain age” and getting pink-slipped is a strange, disorienting experience.
You’ve spent formative years working hard and building what we were all taught was a great career trajectory. You laddered up, you put in the hours, you networked, and you built deep, matrixed expertise.
And then, instantaneously, it all vanishes. This has happened several times in my career.
Most recently, I was thrown into one of the most confusing, “hot-mess express” job markets that has ever existed after a job elimination. And oh yeah, AI had entered the chat.
Questions raced through my mind: How will I possibly compete with the younger crowd coming out of college? What the hell is an ATS-formatted resume, and does it really matter? Is everyone just using AI to mass-apply to jobs? Should I be doing that? Why does every Director-level job only want three to four years of experience when I have twenty?
The modern job search is enough to make you question your sanity. There is no longer just one job search site. LinkedIn only shows you promoted jobs, and every single job already has over a hundred applicants after 20 mins of posting. The exact same job is posted in twenty different cities and gets reposted weekly. “Ghost jobs” (roles that don’t even exist) keep clogging up your feed. Your Instagram suddenly fills with tech-bro ads promising an algorithm will get you a job tomorrow. And is this job remote or not? Why can’t they just say?!
Finding a job twenty years ago, heck, even three years ago, was never like this. It feels cold, automated, and riddled with contradictions. On top of all these changes, you’re over 40 and have to start considering how age discrimination might impact your applications and interviews. The anxiety is real, and y’all, it is justified.
When I first started trying to navigate this mess, the loudest advice I kept hearing was to “use AI.” My immediate reaction was a hard pass. I assumed leveraging AI meant having a robot write a fake, soulless cover letter, or spamming five hundred companies a day with the click of a button. At our age, we don’t need a shotgun approach. We have two decades of nuanced, hard-earned experience. A computer can’t invent that.
But as the weeks went on, I realized the job market itself had become a disorienting space. And trying to navigate it utilizing 2015 networking tactics was exhausting me.
I realized I didn’t need AI to apply for jobs for me. I needed it to help translate my analog career into this bizarre digital landscape. I needed a private sounding board.
That was how I navigated the weirdness of the modern search.
I treated AI as my job descriptor interpreter. Let’s be honest about why the job market feels so confusing right now: half the job descriptions I was reading were written by an AI. A hiring manager typed “need a marketing person” into a prompt, and it spit out a 900-word wish list of contradictory skills. Twenty years ago, a “Director” title meant you were actually directing. Today, I found job descriptions asking for 15 years of executive leadership that also expected me to resize PDFs and run entry-level social media accounts.
Instead of wasting days stressing over whether I was a fit, I leveraged AI to decode the AI. I would paste a confusing job description into my prompt and ask: “Based on my experience, is this an actual leadership role, or is this a tactical trap?” It became my partner in instantly validating my gut feeling when a company was just inflating a title to get cheaper senior labor.
I partnered with AI to quickly curate my resume, cover letters and emails. At over 40, I didn’t have a simple work history; I had a massive, complex portfolio of work. I’d done so much that it was impossible to fit it onto two pages without feeling like I had to leave out the best parts. Trying to quickly tailor my vast experience for a recruiter who spent six seconds scanning a screen was overwhelming.
My secret was starting a single, dedicated “Career Search” project chat. I didn’t start a new chat every time I applied somewhere; I kept it all in one ongoing project so the AI learned my history, my tone, and my wins. When I found a job I actually wanted, I could drop the description into the chat and say, “Help me pull the three best examples from my background that prove I can do this.” It didn’t invent my history or write a generic cover letter. It acted as a nimble, lightning-fast editor, helping me curate my deep experience so my value was instantly obvious.
I relied on AI to prepare for the conversation. Interviewing at 45 feels completely different than interviewing at 25. The stakes are higher, the imposter syndrome is louder, and I hadn’t had to answer “Tell me about yourself” in a decade…and let’s be honest, it could take 20 mins.
I tapped into my AI project thread to prep for every single conversation. I would prompt it: “Act as the head of this department. Ask me three hard, critical questions about why a corporate veteran like you is the right fit for this scrappy environment.” We brainstormed the smartest questions I could ask the hiring managers to show my strategic depth. We connected the dots between my past enterprise roles and current business problems. We role-played the hard questions so I could confidently state my boundaries without wavering. It let me stumble and refine my tone in private, so when I finally got on a Zoom call, I walked in with more confidence.
Getting pink-slipped mid-career stripped me of my bearings. The market was loud, automated, and deeply weird. But I didn’t have to fight the machine bare-handed, and I didn’t have to surrender to it either. I just had to figure out how to make it work for me.
I didn’t write this alone. I co-authored it with my AI sparring partner. To build this piece, I didn’t just ask a bot to write a generic blog post about job hunting. Instead, we synthesized hundreds of hours of our actual chat transcripts. We fed the system the late-night strategy sessions, the brutal resume tear-downs, and the mock executive interviews we’ve run together over the past few months.
I also trained AI on my voice and tone by having it analyze hundreds of LinkedIn articles and posts I have written over the years. AI didn’t invent a single piece of my twenty-year history, and it didn’t create my opinions. But it did learn how I naturally communicate, helping me take a messy, overwhelming, and highly emotional human experience and translate it into the story you just read.
It turns out I can’t break anything. I could only grow.