Jillian Richardson on Making LinkedIn Weird: Thought Leadership Without the Cringe

Welcome back to The Grey Areas Podcast! If you’ve ever felt like you have nothing to say on Linkedin or worse, that you’ll get fired for saying the wrong thing, this episode is your permission slip to show up anyway (and make it weird).

We’re joined by the endlessly brilliant and hilarious Jillian Richardson, a ghostwriter, writing coach, and the mind behind the viral “Make LinkedIn Weird” movement. Jillian breaks down how to turn your thoughts into compelling content, why ghostwriting is basically therapy, and how to build a platform without losing your personality, or your mind.We unpack thought leadership for 2025, explore what it means to post with authenticity, and dig into what it really looks like to write from your values, not just your resume.

Highlights include:

• 1:57 – Why perfectionism and fear of visibility are the biggest blocks for founders trying to write online.
• 5:10 – The difference between writing as yourself vs. ghostwriting for someone still finding their voice.
• 8:33 – Why trying to “sound smart” is the biggest mistake leaders make in their writing.
• 17:26 – What to say when you feel like you have nothing to say: Jillian’s go-to prompts and exercises.
• 22:09 – Behind the viral “Be Weirder on LinkedIn” post and the creation of her Make LinkedIn Weird course.
• 41:22 – When content feels “too weird”: How Jillian balances intuition and audience readiness.
• 45:29 – Cubicle Confession: Advice for a mid-level manager scared of posting online, navigating the tension between boldness and career safety using the “Envy/Disgust” Matrix.

Whether you’re ghostwriting for a CEO, building your own platform, or just trying to post without cringing, Jillian will help you bring your full self to the feed—and have fun doing it.

Jillian’s Links:
Website
LinkedIn