#214 | How to Cultivate Happiness at Work & Life

Is joy at work actually a real thing? I used to think it was right up there with unicorns…until I sat down with Jen Whitmer. Our conversation on How to Cultivate Happiness at Work & Life felt especially timely as the year winds down and as “Joy to the World” starts playing on a loop everywhere (looking at you, CVS in October).

Joy at work isn’t something you wait for it’s something you build. Jen shared how expecting your workplace to magically become joyful usually leads straight to frustration, and her own story proves just how much influence we actually have over our experience from making standardized testing fun in schools to navigating a truly toxic job shift. One of the ways she lives this out is through play. Not in a forced-fun way, but in small, intentional moments that shake up the routine. Even something as simple as setting a five-minute timer in your next meeting to say, “let’s play with this idea,” can open up new energy, creativity, and connection.

One of my favorite things Jenn said was “roots always grow in the dark.” Just like plants build their strongest foundation underground, away from the light, some of our deepest growth often happens in seasons we never would’ve chosen. Those darker, messy, in-between stretches are where real strength gets built, and seeing them as part of the process instead of a setback can completely shift how we move through hard seasons.

Jenn also highlighted the power of honest and helpful feedback. Honesty alone isn’t enough feedback works best when it’s specific, actionable, and focused on behaviors rather than personal traits. This approach requires vulnerability from both giver and receiver, creating a space where people feel supported and motivated to improve. By being clear and constructive, “clear is kind,” we build trust, strengthen relationships, and cultivate a culture of growth. Your team will thank you for feedback they can actually use.

Ultimately, cultivating joy at work and in life isn’t about waiting for perfect conditions or magical moments. It’s about taking small, intentional steps: playing with ideas, giving feedback that matters, and leaning into the growth that comes from life’s darker, in-between moments. As Jenn’s insights remind us, joy is something we create, nurture, and share. So whether it’s a five-minute burst of play in a meeting, a thoughtful piece of feedback, or simply noticing the small things that bring you purpose, each choice adds up. Let’s make joy contagious at work, at home, and everywhere in between.

Timestamps:

09:08 Finding Joy at Work

14:37 Honest and Helpful Feedback

23:08 Navigating Layoffs and Low Morale

26:48 Joy is Workplace Rebellion

31:53 Purpose: Impact Beyond Yourself

37:07 The Joy Ratio Explained

42:39 Childlike vs. Childish Through Play

45:31 Using Timers for Motivation

47:20 Play Circuits

56:59 Creating Joyful Workplaces

Links:

Jenn’s NEW Book

Joyosity Explorer Map

Joyosity Podcast

Joyosity Works Playbook

Jade Simmons

Vanessa Van Edwards

Leo Chan – Lego Serious Play Expert

Magic Lessons with Elizabeth Gilbert podcast

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