July 7, 2026

The Case for Playing at Work

Show Notes

What if the part of you that doesn't take everything so seriously is actually your biggest professional strength? This week I sit down with Mary Hendra, a chief of staff, coach, and consultant who once froze when a branding expert told her, "Your brand is play." She thought it was the reason she wasn't getting promoted. It turned out to be the thing that made her a better leader. We get into why play belongs at work, how it builds presence, creativity, and the ability to let go when something isn't working, and why the smallest, quietest gestures often matter most.

We also go a lot of places I didn't expect. Mary tells me about the tugboats she loved as a kid and the metaphor she still carries from them, the semester she spent living in the Soviet Union because her sixteen-year-old heart refused to believe the people there were evil, and one gloriously disastrous team-building escape room. It's a conversation about community, about being a loud introvert who had to work at connection, and about giving yourself ten honest minutes to play so you can show up as yourself for everyone else.

About Mary Hendra:

Mary Hendra, host of the Lead with a Dash of Play podcast, fosters curiosity, compassion and play as both a mission-driven executive and solopreneur herself. Her career portfolio has ranged from leadership in County government to high school teaching, from co-leading a non-profit to guiding a tech-start-up through an accelerator. She currently serves as Education Director for Making Gay History and as Chief of Staff at a tech wellness start-up. Redefining “play” for the modern, busy adult, her workshops and cohort programs foster self-reflection and build clarity for individuals and teams, so that they can move forward with grace. Her book, Lead with a Dash of Play, is expected in 2027.

Show Notes:

00:00 Why I almost didn't make it to this episode

06:15 Tugboats, and the small things that move the big ones

09:30 Living in the Soviet Union, and what civic society takes for granted

22:00 Where the interest in play actually started

23:30 "Your brand is play," and why it stung

25:00 Play as a leadership skill we sideline

29:30 What play teaches us about letting go

36:00 Small ways to bring play in, starting with how you name your meetings

40:00 A spectacular play fail (the escape room)

46:15 One invitation to play

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