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Leading with Playfulness: The secret to Confidence


Boldly Unbounded in Playfulness
Shenanigans that ensued during company headshots 😂


 

Hello, you Boldly Unbounded Soul ✨


Sitting on a Sicilian terrace overlooking the Med, I witnessed childlike play emerge among 120 people simultaneously.


The energy wasn't all that different from the childlike wonder of the imaginary food fight scene in Hook.



You see, we were doing a scavenger hunt during a company retreat.


Groups of team members were sprinting across the lawn—giggling and shouting like we did as kids—a race to the winner’s title. I could almost see what these adults were like as kids. All the worries of life and work urgencies melted away, exposing the power of play.



 


WHAT’S PLAYFULNESS?


We’re all familiar with play. It’s a staple of childhood for most. Mine was biking through the state park, playing pirates on the hammock in the backyard (our dogs 🐶 were our “enemies” we ran from with our yardstick swords—don’t worry, no dogs were harmed in the pirate play), riding horseback to explore the unknown, and playing Tomb Raider II on the computer.


What was yours? Bring yourself back to those moments. What do you notice in the body?

Maybe you feel pure bliss. Or a smile spreads across your face. Or even nostalgia arises, yearning to relive those moments.


But, what is playfulness?



  • humorous perspective in social situations

  • spontaneous, carefree view of life

  • loves to puzzle over problems and to come up with new, creative solutions

  • amused by oddities and have a preference for extraordinary things and people



 


WHY PLAYFULNESS WORKS


A plethora of research shows how important play is for children’s development. But, what about adults? Progressively, research has found play is just as important for adults, but its purpose is different. It’s not for development but for your overall well-being.


So, why do it? What are the benefits?



Improves coping with stress


Playfulness helps you cope with and adapt to stress better. It prevents you from using negative, avoidant, and escape-oriented strategies. And, it helps you cultivate resilience, acceptance, and positive reframing.



Boosts work performance, and reduces imposter syndrome


Playfulness changes how you perceive, value, and address situations, leading to better work performance and job satisfaction. It promotes finding original solutions to challenges, facing difficulties, and embracing failure. In other words, it embeds growth mindset into your way of being, a key trait of exceptional leadership.


And people who play show lower expressions in imposter syndrome. This is incredibly important for high-achieving people who struggle to celebrate their accomplishments. Why? Lightheartedness—a trait within playfulness—acts as an antidote. It allows you to adopt a playful worldview in serious situations. It empowers you to improvise and see life more like a playground than a battlefield.


Think of it like recess in school. Making up obstacle courses on the jungle gym and ‘competing’ to see who can finish it first. It’s not about who wins—though bragging rights were fun—it’s about the joy as you launch yourself onto monkey bars with imagined lava below, finding novel ways to finish the course first.




⚠️ Caveat: Biased, toxic cultures that value individualism and overwork are the root causes of imposter syndrome. Check out this tool—B.R.A.V.I.N.G. for an Organizational Measure of Trust—to assess your company’s culture of trust. You're in a toxic, likely biased, culture if there’s a risk of trust loss or no trust.


Promotes creativity and intrinsic motivation


When you play, you experience a more positive mood and intrinsic motivation, while experiencing less extrinsic motivation. This leads to higher ingenuity, specifically creating more novel ideas and ways of doing things.



Nurtures virtue


Virtue imbues the love of learning, curiosity, creativity for practicing wisdom, appreciation of beauty and excellence, gratitude, and hope. These traits make the day-to-day more fun, and they serve exceptional leadership. Imagine how your day would feel if you came from this place instead of knowing, focusing on gaps/mistakes, and cynicism.


🥼 Experiment: Recall a recent work situation. First, view it from a place of knowing/being right, gaps and mistakes, and cynicism. Then, view it from a place of virtue—what you can learn, wisdom you can tap into, gratitude, and hope for the future. What do you notice in your thoughts, physical body, and emotions?


Enhances your well-being




 


5 WAYS TO PLAY MORE EVERY DAY


So, are you convinced? Are you already picturing a more playful approach to your life and leadership? Let’s look at 5 ways to invite more playfulness into your day.



Meet Your Play Personality


While playfulness has common traits, it’s still unique to you. We each have our own play personality. Dr. Brown identified eight primary play personality types, based on thousands of interviews and observations. Most people have one primary play personality type and 1-2 secondary types.


  1. The Collector finds play by having an interesting collection of objects or experiences.

  2. The Competitor accesses play by participating in a competitive game with specific rules. The goal? To win.

  3. The Creator/Artist’s play comes from the joy of making things.

  4. The Director plays by planning. They love making things happen.

  5. The Explorer plays by exploring the world to inspire imagination.

  6. The Joker is the OG player—and one of the most extreme—seeking play through foolishness.

  7. The Kinesthete plays through movement.

  8. The Storyteller finds the joy of play through imagination.


I love to play! I’m the Storyteller, with touches of Explorer, Joker, Creator, and Kinesthete. What’s yours? Discover your primary play personality with this quiz.


Pro Tip: This is an AMAZING activity for your team! Invite your team to discover their play personality and lead different types of play on the team. It can inspire new ideas, cultivate team cohesion, and boost trust.


Laughter Circles for Instant Play


Laughter brings people together in a way that boosts physical and emotional changes in the body. It boosts endorphins, strengthens the immune system, relaxes the body, and diffuses anger. It also safeguards you from stress, protects your heart, and lowers pain. The biggest perk? It’s quick, easy, and free!


How do you get started?

  • Find a mirror and laugh into it. What will start as a fake laugh will turn into a real one. That’s it!

  • Hold a laughter circle. This is a common activity in India, and a favorite for my father-in-law. Do it with your friends, family, or team at the beginning of a work meeting, in-person or fully remote.




Experiment with Movement


Try different kinds of exercise—running, swimming, lifting, surf skating, yoga, pilates, scuba, surf, rollerskating, climbing, martial arts, obstacle courses… There are hundreds of ways to move. With each new one, you’ll learn more about how your body works and which ones are the most fun for you.


Speaking of fun, turn that exercise into play. If you dread it, don’t do it, unless it’s connected to goals worth struggling for.



Connect The Dots


We’re shaped by our experiences—and the more diverse your experiences—the more you’ll see the interconnectedness of our world. This will help you zoom out for big-picture thinking, understand complex systems, and reframe problems from different perspectives to discover new solutions. These are key aspects of exceptional leadership.


So, how can you connect the dots through play?


Find an activity that feels like play. A pottery class. Improv. Dance. Beach volleyball. Board games. Geocaching. Theatre. TV series.


Look for parallels in leadership.


In my last role leading Talent Operations and Enablement, we mapped Ted Lasso’s Total Football strategy to our team design. It was fun and strategic. It facilitated change that deepened trust, supported each team member’s energizers and strengths, and brought us closer together. It also amplified their exposure and skill development across the People function. And it made people laugh.




Go on An Adventure & Explore The Unknown


Exploration gifts us with the feeling that anything is possible. It leads to knowledge and a deeper understanding of the world around us. It inspires us and sparks innovation. It is the foundation of human success.


So find your next adventure. It could be…

  • A video game (My recommendation: Uncharted 4)

  • Geocaching for real-life ‘treasure’ hunting

  • Watching a documentary

  • Exploring a new hobby or learning a new skill

  • Travelling near and afar

  • Going for a hike

  • Doing an observation walk—journal or draw your observations as you go



 


TO LIVE WOULD BE AN AWFULLY BIG ADVENTURE


We can’t end today without one last mention of Hook, a staple for the imagination of a 90s kid. And a reminder to play as an adult. From the final words from Hook…


Granny Wendy: So... your adventures are over. Peter: Oh, no. To live... to live would be an awfully big adventure.



See you next week ✨


Rachel's sign off





 


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