The Grey Areas Podcast with Kelsey Donlon
The Grey Areas Podcast with Kelsey Donlon is ready to disrupt corporate America! This is a space for candid conversations and deep dives into the complexities of the workplace. The mission: to empower women with transparent, inspiring narratives and challenge the status quo in corporate culture.
Grey Areas is a safe, non-judgemental digital platform, podcast and community that inspires and empowers women to navigate the grey areas in the workplace. So what does that mean? Well, the ‘grey area’ is an ill-defined situation…or in other words, it’s murky AF. Kelsey is here to help make this vague situation, much clearer. This community and podcast will hold corporations, executives and Human Resources accountable by leveraging legal education, transparency, and shared stories to drive change.
Each episode will tackle aspects of the grey area; managing anxiety in the workplace, tension between coworkers or managers, understanding employer boundaries, working with HR in an appropriate and effective way, navigating job loss, and so much more. So tune in, to hear Kelsey and her guests share a wealth of information and to be part of a safe space for people who have a hard time navigating the toxic workplace.
Let’s navigate grey areas, together!
The Grey Areas Podcast with Kelsey Donlon
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: makelinkedinweird.com
LinkedIn: Jillian Richardson
Kelsey's Links For You:
Website
Grey Areas Instagram
Kelsey's Instagram
LinkedIn
TikTok
