You ever feel like applying for jobs is a game you didn’t sign up to play? The rules are awful: stack your keywords, perfect your formatting, hope some mysterious algorithm doesn’t filter you out before a human even lays eyes on your resume. And then? Crickets. Ghosted. Like you never even existed.
I’ve been on both sides of this mess—as someone desperately applying for work and as someone who’s sifted through thousands of resumes. You know what’s wild? Both experiences suck.
There’s no joy in rejecting a sea of candidates you’ll never meet, just like there’s no joy in crafting the “perfect” cover letter only to get ignored. It’s dehumanizing for everyone involved. But when I realized just how broken the system is, I stopped playing the same way.
I stopped trying to out-resume everyone else. Instead, I started thinking, How do I make them see me as a person before they even look at my resume?
I did weird stuff.
Okay, maybe “weird” is the wrong word. I’d call it bold, creative, maybe even slightly unhinged. Like that time I wrote a cover letter joking about being late to work (don’t recommend it—worked for me, though). Or the time I made a Fiverr rap video just to stand out. Spoiler: the rap was terrible, but I got the interview.
But here’s what I learned: the wacky stuff isn’t the point. The point is to break through the noise. Not by being gimmicky—by being human.
You’d be amazed how far a genuine connection goes. A short message to someone on the team, not to pitch yourself but to say, “Hey, I love what you’ve done here.” A thoughtful comment about their podcast or an article they wrote. People notice that. They remember it.
I remember it.
There was this one guy who messaged me at 5:55 a.m. about an entry-level sales role at my company. He didn’t try to sell himself with some overly polished elevator pitch. Instead, he told me a story—how our product mattered to him, why he cared about what we were building, and how he saw himself fitting into the team. It was personal. It was real.
By 9 a.m., I’d already sent his name to HR.
It’s funny because if he’d just uploaded his resume and waited like everyone else, I probably never would’ve known his name. He’d be one of 500 other candidates lost in the pile. But instead, he cut through the noise. He wasn’t just another applicant. He was a person.
And that’s what I think we forget when we’re job hunting. We spend so much time trying to fit the mold, trying to follow the “right” steps, that we lose the thing that makes us stand out: ourselves.
Look, I know not everyone can—or should—make a rap video for their job application. That’s not what this is about. It’s about showing up differently. Asking the questions no one else is asking. Reaching out to the people no one else is messaging. Finding ways to connect that feel honest, not transactional.
It’s about reminding yourself—and them—that you’re more than just a resume.
You don’t need to game the system. You just need to sidestep it entirely. Forget about the hiring manager’s inbox, where a thousand other applications are sitting. Reach out to someone on the team who isn’t getting bombarded with messages. Learn about the company, the culture, the projects they’re excited about. Make it about them, not you.
And yeah, it’s risky. Maybe they won’t reply. Maybe you’ll feel like an idiot for trying. But what’s the alternative? Sending your soul into the void and waiting for a response that’ll never come? I’ll take the risk.
If you’re curious about how to stand out in a job hunt, I talk about this more in a video. It’s a little unpolished—kind of like this process—but maybe that’s the point.
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