Two Chicks With A Side Hustle

Let’s be real: writing cover letters can feel like a chore. Like folding laundry or pretending to like group texts. But if you’re firing off the same generic letter for every job, you might be ghosting yourself before the hiring manager even opens your resume.

So… should you customize your cover letter every time?

Short answer: Yep.
Longer answer: Yep—but it doesn’t have to be painful.

Here’s how to make it worth your while (without rewriting your soul every time).


1. Think of It Like a First Date

You wouldn’t use the same opening line on every person, right? (Okay, maybe you would—but let’s not.) Hiring managers can spot a copy-paste job from a mile away. A custom cover letter shows them you’re actually paying attention—and not just applying to everything that moves.


2. Use Their Language, Not Yours

Every company has a vibe. A voice. Read the job post like a detective. Are they looking for a “go-getter” or a “collaborative problem solver”? Are they corporate-smooth or startup-snarky? Match your tone to theirs—without losing your personality.

Pro tip: pull keywords from the job description. ATS systems (those bots that scan resumes) love a good match.


3. Address the Real Pain Point

Don’t just talk about what you want. Focus on what they need. If they’re hiring a remote customer service rep, they’re probably buried in support tickets. Say how you’ve handled that in the past—and how you’ll make their life easier.


4. Keep It Tight

Your cover letter isn’t a memoir. One page, max. Three short paragraphs:

  • Why you’re excited about the role
  • How your experience makes you the right fit
  • A quick, confident close (no begging!)

Bonus: customize the first sentence. If you start with “I’m excited to apply for the [Job Title] position at [Company Name],” congrats—you’ve already bored them.


5. Reuse Strategically

No one’s saying you have to start from scratch every time. Build a solid “base” letter you can tweak. Keep a few plug-and-play templates ready. Just make sure you actually tweak them. If you forget to swap out the company name, we can’t help you. (Well, we can, but your chances won’t be pretty.)


Final Word: Show Them You’re Worth the Click

Hiring managers aren’t reading every word—but they are skimming for signs of effort, personality, and fit. A tailored cover letter helps you stand out in a sea of sameness.

So yes, customize it. Show them you give a damn. And if writing’s not your thing—hey, that’s what we’re here for.

Need help creating a flexible cover letter template? Drop a comment or let us know—we’ve got you.

Happy Hunting!

~ Two Chicks…

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