Why Job Hunting Feels Like Facing Paul Skenes with a Whiffle Ball Bat

You have no idea how many times I tried to get ChatGPT to fix the fact that the guy’s hands are backwards. I gave up, eventually.

Looking for a job in 2025 feels a lot like being a hitter in baseball. Except the pitcher is an Applicant Tracking System, the umpire is AI, and you’re constantly trying to guess where the strike zone is on any given day.

Every day, you walk up to the plate (aka the job board), resume in hand, and take your best swing. Fastball? Maybe. Curveball? Probably. Ghosted by the bullpen catcher? Oh yeah, you can count on that.

Like baseball, job hunting is a game of failure. Something I tell my Little Leaguers (and I’ve said the same to Middle School players and High School players) is that there are a lot of guys in Cooperstown who hit .300 — which means they failed at the plate 70% of the time. Meanwhile, on LinkedIn, if you get one email back out of 100 applications, you’re basically Ken Griffey Jr.

You're told to tailor your resume. Cool. So now you’re choke-gripping your bat, changing your stance, and squinting at AI-generated job descriptions like they’re sliders outside the zone. You want me to have 10 years of experience in a tool that launched last spring? OK. At the same time, you’re looking at job descriptions going “well, I can do that… I don’t want to, but I can” like a second baseman who is looking at either a roster spot in the outfield or another year riding the pine.

And don’t even get me started on Applicant Tracking Systems. It's like stepping into the box and being told the strike zone changes every pitch. Oh, you used Arial instead of Calibri? Strike one. Didn’t format your CV the way our system likes to ingest it? Strike one. Your previous title doesn’t match up with our job title database? Strike three - get your butt back on the bench.

But here’s the deal: just like in baseball, all it takes is one clean hit. One company that sees your value. One recruiter who actually reads past the first line of your cover letter. One hiring manager who realizes you're not just swinging — you know how to hit. One GM who sees you and thinks you’re worth a shot.

So keep stepping up to the plate. Keep swinging. And if you ever feel like bunting out of pure frustration, just remember: even Babe Ruth struck out 1,330 times.