20 DAYS AGO • 3 MIN READ

One of the cringiest things I’ve ever done…

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Sloppy Copy

Shared every Thursday to marketers, solopreneurs, and business owners. (I'm Cass, btw — your cool new copywriter friend with ideas for your website, sales copy, emails, and other fun content things.)


One of the cringiest things I’ve ever done…

…is posting on LinkedIn.

(At least, that’s how it felt when I started.)

To me, LinkedIn was “boring.” “Performative.” “Self-indulgent.” “Cringe.”

Plus, all my connections were people I knew IRL — not people who chose to follow my business account. I was afraid I’d look stupid, fail, or annoy everybody I knew into hating me.

But I did it anyway… and now I’ve:

  • Had multiple posts go viral
  • Learned a TON about my clients, my trade, and how to grow
  • Gained 1,400+ followers in just a few months
  • Got more confident being authentic online and experimenting with content
  • Built relationships — dare I say, friendships? — with great people

(And none of my connections hate me, AFAIK.)


Why pushing through the cringe is *always* worth it

The biggest question I’ve gotten since starting to post on LinkedIn is: “How did you stop feeling self-conscious about it?"

The truth: I didn’t. I just got used to the feeling, and did the thing anyway. Because:

  • The best content is vulnerable, authentic, and personal. And if I’m not willing to do that, I’m not going to reap the rewards that come with it.
  • The most successful people also feel self-conscious, cringey, or out of their depth when they start
  • Most people are too afraid to even try — so you’re already a step ahead just by going for it
  • The most judgmental people are the ones who are watching from the sidelines
  • Nobody cares how you come across as much as you do

I still feel awkward about it sometimes (especially when it gets brought up IRL). But it gets better with every post.


How to get comfortable getting vulnerable

In business and in marketing, you’re going to fail, get vulnerable, and learn through your experiences. This is good — because it's a sign that you're performing at your full potential.

But I’d be lying if I said that stuff was easy. So here’s how to get used to it:

1.) Start small.

You don’t need to spill your life story in your first post. Share something light but real — like a mistake you learned from, a small win, or a belief you’ve changed your mind about. The more you practice, the easier it gets to open up.

2.) Reframe vulnerability as usefulness.

It’s not about oversharing for the sake of it — it’s about helping. If your story saves someone else a headache, or helps them feel less alone, then you’ve already done your job.

3.) Focus on consistency, not perfection.

Your first “cringe” post won’t define you. What matters is showing up again and again. Vulnerability compounds — every post makes you a little braver and builds a little more trust with your audience.

At worst, you’ll cringe a little and laugh at yourself.

But at best, you’ll connect with people who really get you, relate to you, and want to soak up more of your content. Those are the types of audience relationships that lead to real, long-term results.

Odds are, you’ve already experienced some of this stuff — and I want to hear what you’ve learned from it.

Hit reply or shoot me a DM to tell me about it.


C’mon, dude: I sent hundreds of ugly emails

The marketing version of ESPN’s legendary “C’mon, man” segment

One of my clients uses an especially clunky email marketing platform. In our meeting this week, they mentioned that all the emails I’ve been building and sending — for the last 11 months — have a white background and white text when viewed on mobile.

I sent myself test emails every dang time. I could’ve sworn I tested the mobile formats. But… apparently not.

Learn from my mistake: Always test your formatting from your phone. Not just for websites. For emails too.

(I realize this might be an obvious piece of advice. But I’ve been doing this for 7+ years and still managed to screw it up. Soooo, better safe than sorry.)


👋 I’m Cassidy — copywriter, content strategist, and founder of Content by Cass.

And also your super-chill friend who says hi, shares her most embarrassing moments, and cheers you on every Thursday.

Follow me on LinkedIn for unfiltered, slightly jaded nonsense and insights

Check out my services if you need a content or copywriting partner

Book a free chat to say hi, learn more, and bounce ideas around

PO Box 1749-208 Big Bear Lake, CA 92315
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Sloppy Copy

Shared every Thursday to marketers, solopreneurs, and business owners. (I'm Cass, btw — your cool new copywriter friend with ideas for your website, sales copy, emails, and other fun content things.)