Carolyn Hobdey is a multi-published author and leadership/culture change specialist known for naming the conversations workplaces avoid. She’s the voice behind The Midlife Mistress and author of All The Twats I Met Along The Way, De-Twat Your Life! and Redefining Selfish.

Episode Summary

Male allyship is usually framed as men supporting women. Carolyn flips the lens: what happens when men feel they can’t speak honestly at work, online, even at home, without being judged, mocked, or written off? Drawing on 25+ years in leadership, HR and transformation, she explores the growing mental load many men carry: the pressure to “say the right thing”, the fear of backlash, and the confusion of mixed messages around vulnerability and strength. Together, Jenny, Matt and Carolyn unpack why labels like “pick-me” can shut down important conversations, and how women can advocate for men without excusing harmful behaviour. The heart of this episode is simple (and powerful): curiosity, listening, and creating environments where humans can be nuanced—because culture only moves forward when everyone has a voice.

What You’ll Learn

• Why some men feel “there’s no safe way” to speak up, especially at work

• How the “pick-me” label can silence advocates (and what to do instead)

• The hidden cost of mixed messaging: “be vulnerable… but not like that”

• How to support men without amplifying harmful behaviour

• Why connection beats correction when culture is tense

• How leadership stereotypes still reward the wrong traits

• What “inclusive” looks like when men are included too

• A practical way to build healthier workplaces: Carolyn’s SIMPLE model

Guest Picks

• Book: The Five Dysfunctions of a Team — Patrick Lencioni

• Music: “Lost Without You” — Freya Ridings

• Quote: “Feminist is my second favourite F word.”

• Tool/Framework: The Chimp Paradox (mind management model)

• Also mentioned: Why Do So Many Incompetent Men Become Leaders? (And How to Fix It) — Tomas Chamorro-Premuzic

Connect with Carolyn

• Website: The Midlife Mistress https://www.carolynhobdey.com/about-carolyn-hobdey/

• All The Twats I Met Along The Way (book)

• De-Twat Your Life! (book)

• LinkedIn: Carolyn Hobdey https://www.linkedin.com/in/carolynhobdey/

About Leading BOLDLY

Leading BOLDLY is the podcast for SME leaders, founders, and entrepreneurs who want practical strategies and real conversations that build bold brands and strong teams—hosted by Jenny Jarvis and Matt Clutterham of Q Branch.

https://www.qbranch.consulting/

https://www.linkedin.com/in/jenny-jarvis/

https://www.linkedin.com/in/mattclutterham/