Let me tell you, I used to hate writing cover letters. Like, full-on staring at a blank Google Doc at 11 PM with a half-empty Dunkin’ cup sweating on my desk, wondering if anyone actually reads these things. (Spoiler: They do. And the wrong approach cost me a job I really wanted back in 2018. Oof.)
Here’s the thing: I treated cover letters like a formal obligation — robotic paragraphs stuffed with “I’m a team player” and “I’m excited to apply” clichés. Then my buddy Jared, who hires for his startup, told me over beers, “Dude, your resume tells me what you did. Your cover letter? That’s where I decide if I like you.” Lightbulb moment.
The turning point? I started treating cover letters like Tinder bios for jobs. Not the cringey “I like long walks” kind, but the version where you actually show personality. Like that time I mentioned rebuilding my ’97 Jeep Cherokee in my garage (true story) when applying for a project manager role. The hiring manager later told me it stood out because it proved I could troubleshoot chaos. Who knew?
Here’s what worked for me — no fluff:
- Ditch the “To Whom It May Concern” if you can. I’ll stalk LinkedIn for 10 minutes to find the hiring manager’s name. No luck? “Hey [Team Name]” feels less stiff.
- First sentence = mic drop. My go-to: “I didn’t think my obsession with spreadsheets would ever be useful until…” or “The first time I [relevant story], I knew I wanted to…”
- Connect dots THEY care about. Example: Instead of “I managed social media,” try, “I grew a DIY Instagram page to 10K followers using Canva and dad jokes — let’s talk engagement strategies.”
- End with a question. My last line’s usually something like, “Can I brainstorm how my Jeep-tinkering grit could solve [specific challenge they mentioned in the job post]?” Makes replying easier.
Oh — and the rookie mistake I still cringe at? Sending the same generic letter to 20 jobs. Tailoring sucks, but guess what? Spending 15 minutes tweaking each one got me 3x more interviews. (Coffee helps. So does a Google Doc template with swappable bullet points.)
You’re probably thinking, “But what if I’m not quirky?” Relax. Authenticity > quirkiness. My friend landed a corporate finance gig by writing about teaching her kid to budget with Monopoly money. It’s about showing why you care, not performing stand-up.
Wrap-up? Do this: Write like you’re explaining to a friend why you’re weirdly perfect for the job. Then delete the stuff that sounds like a dictionary wrote it. Hit send before the self-doubt creeps in.
And if you get stuck? Picture me in sweatpants, hopped up on cold brew, cheering you on from my couch. You’ve got this.