Resume Stuff: Do I Need to Keep 20+ Years of Experience Lowkey?

As my job search goes on longer, my resume keeps getting shorter.

Turning into the Steve Buscemi “How do you do, fellow kids?” meme is firmly in my top five greatest fears. Right up there with my long-standing fear of confined spaces (claustrophobia), my not-so-long-standing fear of forgetting to cancel my 30-day free trial of LinkedIn Premium on time, and rollercoasters, specifically ones operated by unsupervised teens.

And now, as I job search in my mid-40s (because, some stuff happened), I find myself staring at version number 38 of my resume wondering if I’m giving off the exact same trying-too-hard-to-fit-in energy as that hoodie-wearing, skateboard-toting Buscemi.

Experience is supposed to help. At least, that’s what I thought. At one point, I started to wonder if saying I had 20+ years of experience in the summary of my resume or cover letter was more cringe* than helpful.

A career coach and a free resume review service both agreed with that thinking. They each gave me the same advice: don’t lead with the number of years, and go lighter on early career roles.

Before I took their advice, I decided to do some of my own research. And we all know how well that usually goes when guys who look like me start “doing their own research” online. Don’t worry, this time the stakes weren’t the health and well-being of humanity. It’s just my career on the line.

In said research, I came across a 2024 survey by ResumeBuilder that found 42% of hiring managers admit to factoring in a candidate’s age when reviewing resumes. And how do they figure that out? 82% look at years of experience. 79% check for graduation dates. So even though you likely never have to say how old you are during this process, your resume will definitely say it for you.

And if it doesn’t? Your email address will. Well, my email address does. It’s just my name. No numbers, no underscores, no middle initial. Just my first dot last name at gmail dot com, a quiet little signal that I’ve had this account since Gmail’s early days when it required an invite. Might as well just send recruiters a pic of me wearing ankle socks.

In that same survey, 26% of hiring managers said you should absolutely list all your relevant experience. Even if it spans decades. Even if it includes the part of your career when, at 24, you were cold-emailing the people behind fan sites and MySpace fan accounts for acts like Mariah Carey, Evanescence, and 3 Doors Down, asking them to hype a new video exclusively streaming on your client Yahoo Music’s site. That sentence is quite possibly the most 2005 sentence written since, well, 2005.

True story: that outreach helped Mariah break a video view record, back when streaming a music video or any video, for that matter wasn’t just a regular thing we all did. I remember it being a big deal for her, an even bigger deal for Yahoo, and it was a wonderful career win for me. And it’s nowhere to be found on my resume.

I haven’t rewritten history. But I have stopped leading with it. “20+ years of experience” doesn’t show up at the top of my resume or anywhere in my cover letters anymore.

I am also considering removing the years I was in college. But I haven’t yet. Mostly because without them, I can’t bring up the fun fact that I was in the same Northeastern University freshman class as the Napster guy, Shawn Fanning. You do remember Napster, right? Right? On second thought, maybe I should drop the years.

I also followed the career coach and resume review service’s advice and trimmed some of my early jobs. Now it’s a bulleted list under a section titled “Early Career Roles.” It’s just the organization, title, and years. That’s it. All of those late hours and weekends in the office reduced to one line at the very bottom of my resume.

Have any of these changes helped?

I don’t know. And for better or worse, these changes I’m making don’t seem to be aimed at winning over a hiring manager, an HR person, or any actual person. It appears to be all about trying to get past our new AI overlords, reviewing resumes and deciding our fate in mere seconds.

Let’s go with a Gen X dad joke here and call it age against the machine. And for me right now, the machine is winning. Nearly undefeated.

So I’ve started rethinking how I present what I’ve done.

What I’ve learned — or what I’m still learning — is that your experience isn’t always the problem. It’s how it’s perceived. And if the goal is to get a conversation, sometimes it helps to just TL;DR it and save the rest for when we meet up IRL**.

TL;DR and IRL? I’m absolutely overcompensating with the young people talk to redeem myself slightly after the ick-worthy “age against the machine” line earlier. And please, please don’t let these previous sentences throw me into the Buscemi-with-a-skateboard zone!

So if you're reading this (first, thank you for making it all the way to the end) and you've figured out how to age-proof your resume without feeling like you’re erasing yourself, honestly, I’d love to hear from you. I’m looking forward to staying in touch and learning more about what you’ve done to hide — or not hide — your age and experience. Hit me up at the previously mentioned email address that is now old enough to legally drink: tim.hammill@gmail.com.

More stuff to come!
–Tim

*I asked ChatGPT to create a Gen Z persona to confirm I was using lowkey and cringe correctly. If that previous sentence alone doesn’t convince hiring managers I’m adaptable, it should at least prove I’m open to feedback and capable of collaborating with colleagues under 25, even if they’re not actual humans.

**Ditto for TL;DR and IRL.

Other Stuff Happening

Something I learned while writing this post: In 2024, Colorado passed the Job Application Fairness Act, which bans employers from requesting age, birth date, or graduation dates on initial job applications. The act is intended to help candidates who were getting screened out for having too much experience. Thank you, Colorado. You’ve already given us the Denver omelet, Crocs, the demon horse statue who lives inside the conspiracy theory airport, and now, age discrimination reform.

Tip: Networking is rough. Especially for an introvert like me (I see a Some Stuff Happened post about this in our future). But it’s more important than ever during times like these. Part of networking is reaching out to people you haven’t talked to in a while. Maybe even a decade ago. It’s possible they’ve changed email addresses, but probably not. Just look at my Gmail address. Reach out, say hi, refresh their memory on how they might know you. Keep your message brief and your expectations low. They might just surprise you and write back. And just like that, you’ve grown your network by reconnecting with someone you already knew.

Substacks on Substacks on Substacks: Want timely job search and career advice from actual experts — not a dude who just wrote about MySpace and Napster, quoted the same survey twice and called it “his own research”?

Check out Job Search Guide by Jan Tegze and The Job Hopper by Alison Doyle & Jen Luckwaldt. I also just discovered Laid 0ff, a weekly interview series with smart and cool people who were laid off.

And lastly, — not job-search related, just excellent writing — check out The Will Leitch Newsletter. Will founded the late great sports site Deadspin in… 2005. (Man, 2005 is really having a moment in this post.) His newest novel, Lloyd McNeil’s Last Ride, is out now. I picked up a copy at an event at Book Soup last night and got to have a nice chat with Will. Second time meeting him, actually — the first was also at Book Soup, 17 years ago.