Ep 38: How To Handle Difficult People at Work

What if the only way you could escape your toxic work environment was being hit by a bus—not to die, but just to get a break?

Shocking as it sounds, that’s the level of desperation bestselling author and executive coach Diana Lowe once felt, and she’s not alone. In this riveting episode of "Jen Mess with Tess," Tess Brigham pulls back the curtain on the hidden emotional toll of modern workplaces and the true meaning behind being “hard to handle.”

Join Tess Brigham as she sits down with Diana Lowe—author of "Hard to Handle"—for a raw, honest conversation about surviving abusive bosses, how ‘difficult’ is just a matter of perspective, and why clinical depression became a turning point for radical career reinvention. Together, they untangle how we can learn to live in the mess of work (and life) and find purpose where others might only see crisis.

Key highlights include:

• Diana Lowe
• ’s journey from enduring toxic workplaces in finance, to becoming a champion of emotional intelligence and intentional leadership—even when her own breaking point was a diagnosis of clinical depression.
• Surprising ways we internalize abusive work environments and why so many suffer in silence, secretly hoping for an unexpected event to rescue them.
• The real story behind "Hard to Handle": Why every villain has another side, the value of seeing the strengths in ‘difficult’ coworkers, and why we’re all someone’s ‘Chuck’ at work.
• Generational shifts in the workplace, from tattoos and dress codes (bras at board meetings?) to new norms around mental health—and how leaders can adapt.
• The truth about DEI (Diversity, Equity & Inclusion) in organizations: why emotional intelligence—self and other-awareness—is the missing foundation, and how unconscious biases persist, even with the best intentions.

If you’ve ever felt misunderstood at work, frustrated with your boss, or questioned your place in the corporate ladder—this episode will not only validate your experience but give you practical wisdom on how to lead (and live) with more awareness and empathy.

Episode Overview

• 00:00:00 – Tess Brigham introduces Diana Lowe and her unconventional career path
• 00:01:04 – Diana Lowe on surviving bad bosses and finding mission in adversity
• 00:03:05 – Recognizing abuse and the moment depression forced a life change
• 00:06:31 – The origins and real meaning behind “Hard to Handle”
• 00:08:25 – Why ‘difficult’ is always in the eye of the beholder
• 00:12:01 – The case study format of the book and lessons from corporate life
• 00:22:18 – Growth, vulnerability, and choosing whether to stay or go in tough situations
• 00:25:14 – Generational differences: mental health, tattoos, and the bra at work debate
• 00:34:45 – Feedback, personal growth, and the art of building people up
• 00:37:39 – DEI, emotional intelligence, and the nuances of real inclusion
• 00:51:07 – How to connect with Diana Lowe and explore her upcoming projects
• 00:53:04 – Closing thoughts: learning to live in the mess

Don’t miss this episode’s honest, no-fluff take on surviving—and thriving—in the workplace chaos.

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