In this compelling episode of the Chasing Entropy Podcast, I sit down with none other than Thom Langford, EMEA CTO at Rapid7 and “twice-recovering CISO,” for an honest and often humorous deep-dive into the lived realities of cybersecurity professionals.

Finding Purpose in Security

Thom reflects on his unconventional path into cybersecurity, entering the field two decades into his tech career and quickly realizing he had found his “tribe.” From his early days wrangling VAX/VMS systems to leading security teams, his journey underscores the importance of mentorship, curiosity, and persistence.

Burnout, Mental Health & Imposter Syndrome

This episode doesn’t shy away from the emotional toll of cybersecurity. Both Thom and Dave speak candidly about the mental load that comes with defending digital infrastructure, from career burnout to imposter syndrome. Thom offers relatable stories including hiding in a bathroom stall to avoid public speaking—and shares how vulnerability, perspective, and humour became his coping tools.

Security Isn’t Funny, But It Can Be Fun

Thom’s approach to security education is rooted in humor and storytelling, which he argues improves information retention and builds connection. He shares insights from The Host Unknown Podcast and reminds us that just because security is serious doesn’t mean it has to be dry. Laughter, he says, is often the best way to tackle hard truths.

Reducing Friction, Building Better UX

A recurring theme is the need to reimagine user experience in cybersecurity. Thom advocates for intuitive, low-friction security that doesn’t require justification, just like locking your front door or putting on a seatbelt. When secure behaviours are second nature, we’ve truly succeeded.

Advice for Newcomers

To those entering the field, Thom’s message is clear: you don’t have to be technical to make a difference. Whether managing risk, policy, or compliance, every role matters. He also urges senior professionals to manage their calendars more assertively for sanity’s sake.

Where to Find Thom Langford

• 🎧 Host Unknown Podcast
• 📸 TomLangford.photography
• 📝 Blog at TomLangford.com
• 💼 LinkedIn

Catch the full episode to hear two seasoned CISOs pull back the curtain on the cybersecurity industry with wit, wisdom, and just the right amount of entropy.