Our Rough Draft Season 1: Episode 12
Best Jobs/Worst Jobs
This week, Denise and Tim talk about work — the best jobs, the worst jobs, and all the lessons in between. From Eddie Bauer to education, they reflect on the leaders who shaped them, the people who challenged them, and the experiences that revealed what makes work meaningful. It’s a conversation about joy, purpose, and the hope that keeps us showing up — even when it’s hard.
Show Notes.
What We Talk About
The culture at Eddie Bauer and how it set a lifelong standard for leadership
Mentors who modeled confidence, kindness, and integrity
When the “dream job” turns out to be the hardest one
Learning to lead without losing joy
Why hope and humanity belong in every workplace
Living your legacy through the work you do every day
Quote of the Episode
“Hope has to be a part of the plan — if it’s not hopeful, it’s dumb.” — Denise Waters
Conversation Starters
What made your favorite job feel meaningful?
Who taught you how to lead — by good example or bad?
Have you ever stayed in a job longer than you should have? Why?
How can you bring more hope and joy to your work this week?
Resources & Mentions
Films & Viewing
The Intern — A reminder that mentorship and meaning can happen at any stage of life.
Books & Reading
Dare to Lead by Brené Brown — Practical wisdom for leading with courage and empathy.
Radical Candor by Kim Scott — Balancing care with honest feedback at work.
Articles & Research
“Why Meaningful Work Matters” — Harvard Business Review
“The Secret to Loving Your Job (Even When It’s Hard)” — Psychology Today
Tools & Practices
Gratitude Check — List three people who helped shape who you are professionally. Reach out and thank one.
Reflection prompt: When have you felt most alive at work, and what made that moment possible?
Connect & Reflect
We’d love to hear your story. Tag @theroughdraft and share your best-and-worst job moments — what they taught you, who showed up for you, and how you’re finding meaning in your work today.
Mini Moment
Tim describes the kind of boss who makes you question your worth. Denise nods, remembering her own version of that story — the job she always wanted that nearly broke her heart. They laugh, they pause, and then agree: joy and hope don’t just survive the hard jobs — they’re what pull us through them.
Try This
Send a message to someone who believed in you early in your career.
Identify one small way to bring joy into your workday.
End your week by asking: What went right?