Moments, Not Years

The Case for Playing at Work

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 Links Mentioned: Mary Hendra's podcast, Lead with a Dash of Play: https://maryhendra.com/podcast/ [https://maryhendra.com/podcast/] Playful by Cas Holman: https://casholman.com/book [https://casholman.com/book] IDEO Play Lab: https://www.ideo.com [https://www.ideo.com] LEGO Serious Play: https://www.lego.com/en-us/themes/serious-play [https://www.lego.com/en-us/themes/serious-play]

Moments, Not Years

What does it take to start choosing your life instead of just pushing through it? In this episode I talk with Ariela Picciotto — one of my closest friends — about a path that never really went to plan. She left New York years ago to be closer to the people she loves, traded a planned move to London for an unplanned life in Paris, and eventually followed her curiosity out of the corporate world and into coaching. There was a breaking point along the way: the day she got the offer she'd been chasing, her body finally gave out and she landed in the ER. We talk about what that taught her — about finite time, the choices we make with it, thinking about life in seasons, and what happens when you stop measuring your years and start measuring your moments. About Ariela Picciotto: Ariela Picciotto is a leadership and career coach with 15 years of GTM leadership experience mostly in tech scale-ups, including as General Manager at ClassPass, where she launched and scaled France and Southern Europe into one of the top five markets globally. After building a career that looked impressive on paper, she found herself asking: I built this, I chose it, so why does it no longer feel like me? Those are the questions her clients carry too, and the ones she now helps them answer. She works with senior women in tech who have built successful careers and yet feel unfulfilled, stuck, or quietly wondering if this is still it. Through coaching that combines strategic career thinking with embodied leadership and inner authority, she helps them get clear on who they are becoming so their next move actually fits. She holds an MBA from Columbia Business School and a Certificate in Professional Coaching from New Ventures West, and coaches in English, French, Italian, and Spanish. Connect with Ariela: * Website: https://www.arielapicciotto.com/ * LinkedIn: https://www.linkedin.com/in/arielapicciotto/ Connect with me: * quitmyjobpod@gmail.com [quitmyjobpod@gmail.com] * Instagram: @quitmyjobpod * Substack: https://maricellaherrera.substack.com/ [https://maricellaherrera.substack.com/] Show Notes: 00:00 Offer Day ER Wakeup 00:10 Podcast Premise Intro 00:52 Behind on Episodes 03:24 Meet Ariella 06:26 Childhood Dream Jobs 07:08 Choosing Business Path 09:40 Consulting Reality Check 11:22 Ballet Studio Role 14:34 Leaving New York 17:32 Family Time Math 20:13 ClassPass Breakthrough 23:22 Burnout and Reorg 25:30 Getting a Coach 26:41 Stress Sends Her to ER 27:52 Healing Before Day One 29:02 Why Coaching Called Her 33:26 Coaching as a Business 35:31 Rejecting Hustle Culture 38:44 Going All In on Coaching 41:29 Redefining Success 48:55 Balancing Ambition and Play 53:13 Advice to Her Past Self

Slightly Scandalous, Completely Badass

Michelle Stanek has been dancing since she was four years old. She drew a ballerina in a second-grade coloring assignment when they asked what she wanted to be when she grew up. Decades later, she is a professional pole artist, world-touring performer, national champion, and now — inventor. The path there was anything but straight. A toxic dance director who made her cry in the car at 16. A grad degree in art history. A job she loved and lost in the 2009 economy. A random Tuesday afternoon pole class a coworker dragged her to. And then — millions of views, workshops in Japan, Russia, Australia, Iceland, and a competition performance in 2012 that people still show their moms and aunts when they want to explain what pole dancing actually is. In this conversation we get into what it really takes to make art your career (hint: the "find something you love and it never feels like work" line is, in her words, bullshit). We talk about teaching philosophy, neuroplasticity, going deeper instead of harder, and the difference between being a sellout and just trying to pay your rent. We also talk about the Stanek Spinner — the pole accessory she's been prototyping and bringing to market — and what it means to make a physical art form accessible to more bodies. Michelle is one of those people who makes you think and laugh at the same time. This one runs long because I couldn't bring myself to cut it. About Michelle Stanek: Michelle Stanek is a NYC-based pole dancer, boy mom, part-time art fair producer, and newly-self-appointed entrepreneur whose motto is "I'll figure it out." Connect with Michelle: * Instagram: @michellestanek [https://www.instagram.com/michellestanek/] * 2012 USPDF performance: https://www.youtube.com/watch?v=Ih2yztRNTFg [https://www.youtube.com/watch?v=Ih2yztRNTFg] * Michelle on the Stanek Spinner at Pole Theatre Canada June 2025: https://www.youtube.com/watch?v=CPwq1-pdA38 [https://www.youtube.com/watch?v=CPwq1-pdA38] Connect with me: * quitmyjobpod@gmail.com [quitmyjobpod@gmail.com] * Instagram: @quitmyjobpod * Substack: https://maricellaherrera.substack.com/ [https://maricellaherrera.substack.com/] Show Notes: 00:00 - Work You Love Myth 00:23 - Show Mission Intro 00:54 - Life Updates and Substack 03:02 - Editing vs AI Debate 05:46 - Meet Michelle Stanek 09:34 - Childhood Dance Dreams 10:35 - Quitting Ballet at 16 14:05 - College and Real Job Track 16:11 - First Pole Class Spark 18:29 - Layoff to Pole Career 21:55 - Gig Economy and Income Streams 25:47 - Pole Grit and Empowerment 28:18 - Competing and Going Viral 32:02 - Why That Performance Hit 34:24 - Imposter Syndrome After Winning 37:43 - Cancer Fueled Mantra 38:56 - Winning Then World Tours 40:36 - Art Business Not Sport 41:41 - Aging And Sustainable Income 43:08 - Money Passion And Pressure 49:13 - Beyond Basic Teaching 52:07 - Building Self Directed Students 57:24 - Inventing The Spinner Platform 01:03:57 - Prototypes Patents And Process 01:05:46 - Daily Progress Mindset 01:10:01 - Advice To Younger Self 01:11:47 - Closing

You Know Your Values, Now What?

Alana Winter spent 25 years building a national video distribution business before realizing she'd built something successful without ever asking herself what she actually valued. In this episode, Alana and Maricella talk about being raised by a serial entrepreneur dad who taught her to control her destiny, the moment the business became a grind and she didn't know who she was without it, and the three-year process of figuring out her own core values, and how she helps leaders do the same in a much shorter time frame. They get into the difference between needs, values, and your why (and why most people confuse all three), what she means by "the how matters less than the what," and her story about the bathroom attendant at the Beacon Theater that made me tear up. About Alana Winter: Alana Winter is an executive coach, facilitator, and serial entrepreneur who helps leaders navigate the moments when outward success no longer matches their inner truth. After building and running businesses for more than 25 years, including a nationwide video distribution company and the internationally covered Stiletto Spy School and MI6 Academy, Alana found herself in the disorienting space that comes after a major chapter ends. That experience led her into a deep exploration of identity, core values, and what it really means to build a life and business from the inside out. Today, Alana works with founders, CEOs, executive teams, and leadership groups around the world, helping them clarify their values, communicate more honestly, make better decisions, and lead with greater self-awareness. Her work blends psychology, lived entrepreneurial experience, and a highly intuitive ability to see the patterns beneath the surface. She holds a B.A. in psychology from Wesleyan University and has worked with thousands of leaders through EO, YPO, WPO, Chief, and private executive coaching engagements. Her work has been featured by NPR, The Today Show, The Wall Street Journal, Psychology Today, and other major media outlets. Show Notes: (00:00) - Nothing To Do Identity (00:21) - Show Intro And Premise (00:52) - Purpose Values Episode Setup (02:05) - Meet Alana Winter (04:54) - Childhood Dreams Icebreaker (06:19) - Raised To Be Entrepreneur (07:37) - Building Video Distribution (13:10) - Meaning Fades Business Grind (16:16) - Betrayal And Embezzlement (23:09) - Burnout Signs And Body (25:57) - After the Exit Void (28:09) - Meaning Over Opportunity (30:33) - Purpose Work for Kids (33:34) - Three Year Values Quest (38:15) - Values Needs Why Framework (44:20) - Living Values Anywhere (47:16) - Clarity Becomes a Calling (50:06) - Advice for the Goo Phase (52:18) - Podcast Closing

The Proof Is in the Pictures

What if figuring out who you want to be doesn't start with imagining your future self — it starts with looking at your past one? In this minisode, Maricella walks through a deceptively simple exercise: scrolling through last year's photos to find the one where you look exactly how you want to feel. What she found was more layered, and more useful, than she expected. From a trip to Greece to a random Tuesday alone in her apartment, this episode gets into how the feeling behind a photo, the memory it holds, and the moment you're in right now are three completely different things. Plus what nostalgia actually is scientifically, why play keeps showing up as the answer, and how to use your past self as an emotional anchor for the person you're becoming. Show Notes: (00:00) Intro (00:38) No Resolutions (01:42) Why Feelings Make For Bad Goals (03:03) Future Self and Manifesting (06:02) The Photos Exercise (07:57) Three Layers in Every Photo (09:54) Greece Trip and Disconnection (12:38) Cat Costume Joy and Buckets (15:22) Oven Broke but I Persisted (18:40) The Through Line Is Play (21:37) Nostalgia and Self Continuity (24:59) Closing the Gap to Future You (26:47) Try It and Final Goodbye (27:59) Outro Subscribe and Connect Takeaways: * Go through your photos from the past year and find the one where you look exactly how you want to feel. How you feel right now looking at it is data too. * Every photo has three layers: how you look in it, how you feel seeing it now, and how you felt when it was taken. They're not always the same thing. * Play isn't just about fun. The moments that light you up are telling you something about what you need more of. * Nostalgia isn't only backward-looking. Research suggests it's your brain connecting past you to present you in order to push you toward future you. * You don't have to picture an abstract future self. Start with a real past feeling and use it as the anchor. Links: * Em on the Brain (Emily McDonald) — Planet Em podcast on Spotify [https://open.spotify.com/show/1KV6h0wWN1Jh9t6qUPYIuQ] / Apple Podcasts [https://podcasts.apple.com/us/podcast/emonthebrain/id1852295289] * Emily McDonald on What Now? with Trevor Noah — "Can You Rewire Your Brain?" [https://open.spotify.com/episode/3mADIFfy4ByVVYItLY0JHn] * What a Broken Oven Taught Me About Myself — Substack [https://maricellaherrera.substack.com/p/what-a-broken-oven-taught-me-about] Find Maricella: * Substack: https://maricellaherrera.substack.com/ * Instagram: @quitmyjobpod [https://www.instagram.com/quitmyjobpod/] * quitmyjobpod.com