Our Rough Draft Season 1: Episode 13
When Jobs are Hard
⚠️ Trigger Warning
This episode discusses suicidal thoughts and experiences. If you or someone you know is struggling, you are not alone. Help is available—call or text 988 to reach the Suicide and Crisis Lifeline (available 24/7 in the U.S.). You can also visit 988lifeline.org for chat and resources.
In this honest and emotional episode, Denise and Tim open up about the hardest chapters of their working lives. Tim shares the story of a toxic boss and the dark spiral that followed his return from deployment—when asking for help was seen as weakness and survival meant finding a way out. Denise reflects on the realities of leadership in education, from heartbreaking losses to systemic dysfunction that left her questioning her worth and purpose. Together, they unpack what happens when your identity, vocation, and humanity collide with unhealthy work systems—and how connection, compassion, and truth-telling can bring you back to the light.
Show Notes.
What We Talk About
How work can shape (and sometimes shatter) your sense of self
The unseen struggles veterans face after returning home
The emotional toll of leadership in education
Why asking for help should never be viewed as weakness
The impact of fear-based and disconnected workplace cultures
Rediscovering purpose after loss and professional trauma
The role of humanity and honesty in healing
Quote of the Episode
"You told me to ask for help—and then said I showed weakness for doing it." — Tim Waters
Conversation Starters
Have you ever had a boss or job that made you question your worth? How did you find your way out?
What does it mean to bring your full humanity into your work—and what happens when it’s not welcomed?
How can we better support people—veterans, educators, or anyone—navigating burnout, trauma, or transition?
Resources & Mentions
Books & Reading
The Circle by Dave Eggers — A haunting look at corporate culture and the illusion of workplace perfection.
Ted Lasso (Apple TV+) — A reminder that empathy, humor, and humanity belong in leadership.
Articles & Research
“Veteran Suicide and the Role of Transition Stress” — National Center for Veterans Studies
“The Importance of Psychological Safety at Work” — Harvard Business Review
Tools & Practices
Practice SafeTALK —training programs that teach how to safely talk about suicide and offer help.
Reflection prompt: Write about a time you felt unseen or unsupported at work. What would you tell your past self now?
Connect & Reflect
We’d love to hear your story. Tag @theroughdraft and share what helped you through your hardest work season—or who showed up for you when you needed it most. Your story might help someone else feel less alone.
Mini Moment
Tim recalls gripping the steering wheel as his boss told him he’d “shown weakness” by asking for help—a moment that nearly broke him. Denise later shares her own breaking point: being told she wouldn’t have her contract renewed, not for performance, but simply for being who she was. Both stories reveal the cost of inhuman systems—and the courage it takes to keep showing up with heart.
Try This
This week, ask someone at work how they’re really doing—and listen without fixing.
Reflect on your boundaries: Where can you lead with more humanity, and where do you need more support yourself?