Have you ever thought of being an amateur as a good thing?

Many of us learned from an early age that our worth was tied to excelling at what we do and turning it into something productive. And many leaders carry the belief that they must be certain, skilled, and polished at all times.

But what if the exact opposite were true?

When we allow ourselves to dabble, to be amateurs, to be just okay at things, our brains literally become more adaptable and our nervous systems learn to stay grounded in the midst of risk, uncertainty, and vulnerability. Just as importantly, leaders who model dabbling create spaces where families, teams, and communities are safe to embrace curiosity and exploration. 

Resilient leadership requires us to meet high-stakes challenges with adaptability, grounded presence, and compassion. Intentional amateurship prepares us for life’s curveballs by building those skills in low-stakes settings.

Today’s guest returns to make the case for being a dabbler as a practice of freedom, resilience, and leadership. She shows us how choosing to play, experiment, and simply try expands our capacity for presence and courage.

Karen Walrond is an award-winning author, speaker, and leadership coach on a mission to create a kindness revolution.

Her books encourage readers to identify their values and inner light and use them to make the world brighter for others.  Audiences around the world have left her keynotes inspired with hope and a renewed determination to serve.  And her one-on-one leadership coaching sessions, workshops and retreats, rooted in the tenets of positive psychology coaching, have helped hundreds of clients unearth their gifts and past triumphs to lead with confidence, compassion and kindness.

Karen and her family split their time between Houston, Texas, USA and Bath, Somerset, UK.

 

 

Listen to the full episode to hear:

• The restorative power of doing something purely for the love of it
• How following her curiosity has shaped Karen’s career and how she protects her amateur pursuits
• How Karen’s dabbling adventures tapped into her seven attributes of intentional amateurism
• How intentional amateurship helps embed self-care, self-compassion, and self-transcendence into our lives
• How practicing being an amateur helps us bring curiosity, compassion, and resilience to our leadership
• Why the humbling experiences of dabbling are a vital reminder for leaders that they’re in it alongside their teams

 

Learn more about Karen Walrond:

• Website
• Instagram: @heychookooloonks
• Facebook: @chookooloonks
• Connect on LinkedIn
• The Make Light Journal on Substack
• In Defense of Dabbling: The Brilliance of Being a Total Amateur
• Radiant Rebellion: Reclaim Aging, Practice Joy, and Raise a Little Hell
• The Lightmaker’s Manifesto: How to Work for Change Without Losing Your Joy
• The Beauty of Different: Observations of a Confident Misfit

 

Learn more about Rebecca:

• rebeccaching.com
• Work With Rebecca
• The Unburdened Leader on Substack
• Sign up for the weekly Unburdened Leader Email

 

Resources:

• Cherished Belonging: The Healing Power of Love in Divided Times, Gregory Boyle
• Tattoos on the Heart: The Power of Boundless Compassion, Gregory Boyle
• George Michael, Mary J. Blige – As
• Conclave
• Homeboy Industries

 

Favorite Moments

“An amateur is someone who does something purely for the love of it.”

“Dabbling is how you find the thing you love.”

“We’ve forgotten how to be interesting.”

“Your job doesn’t make you interesting.”

“I wonder what would happen if…”

“I will never take a dime for this.”

“The point is just to show up.”

“Hobbies are not silly — they are how we take care of our souls.”

“Kindness is a power move.”

“Humility is remembering: we are in this together.”

Conversation Highlights

00:00 — In Defense of Dabbling

Karen introduces her new book and reframes “amateur” as something powerful: doing something purely for the love of it, not for mastery, money, or productivity.

02:00 — Why We’ve Lost the Ability to Play

They unpack how hustle culture and performance pressure have conditioned us to believe everything we do must be monetized or mastered, leaving little room for joy.

07:00 — The Case for Intentional Amateurism

Karen explains how intentionally practicing something you’re not good at can be as restorative as meditation or yoga—and often more accessible.

The “I Wonder If…” Mindset

09:00 — Curiosity as a Life Strategy

Karen shares how her entire career—from law to parenting—was built on curiosity, not certainty. Following “I wonder if…” becomes a powerful driver for growth.

When Passion Becomes Work

10:00 — Why Monetizing Everything Backfires

Karen shares how turning photography into a paid job stripped the joy from it—and why she intentionally keeps some passions protected from productivity.

Dabbling Adventures & Self-Discovery

13:00 — What Trying New Things Reveals About You

From pottery to surfing to piano, Karen reflects on how dabbling exposes your patterns—perfectionism, frustration, resilience, and joy.

16:00 — Failure Without Stakes

Astrophotography didn’t work out—and that was the point. Dabbling creates low-stakes environments to practice failure, curiosity, and self-compassion.

The Hardest Part: Starting

21:00 — When Your Brain Fights You

They explore the resistance that comes up (“this is a waste of time”) and why the goal isn’t perfection—it’s simply returning to the practice.

23:00 — The Power of Showing Up (Even for 3 Minutes)

Karen reframes success: it’s not mastery—it’s coming back, even briefly, with self-compassion.

Why This Matters for Leaders

26:00 — Practicing the Muscles That Leadership Requires

Dabbling builds curiosity, humility, resilience, and connection—qualities that directly translate into better leadership.

30:00 — The Fear of Looking Stupid

They unpack how fear of judgment prevents people from trying new things—and how low-stakes play builds real-world resilience.

Humility, Connection & Leadership

36:00 — What Humility Really Means

Humility isn’t weakness—it’s remembering you’re not above others. It’s a grounded awareness of shared humanity.

38:00 — Leadership as “In This Together”

Karen reframes leadership as service and interconnectedness, not status or authority.

Wonder, Awe & Perspective

41:00 — Why Wonder Matters More Than We Think

Whether it’s gardening, pottery, or the stars, dabbling can reconnect us to something bigger than ourselves—and quiet the noise of modern life.

The Bigger Message Behind the Book

47:00 — Why Dabbling Is Actually Subversive

What seems like a “nice hobby” is actually a radical rejection of hustle culture and productivity obsession.

49:00 — This Is Not Optional Self-Care

Karen reframes hobbies as essential practices for self-care, self-compassion, and sustaining energy in a demanding world.

Karen’s Philosophy on Life & Leadership

50:00 — The Three Anchors

Karen shares her guiding principles:

• Self-compassion
• Kindness
• Love

When she leads with these, everything else aligns.

Closing Reflection

Karen reminds us that:

Dabbling isn’t about being good.

It’s about being human again.

In a world obsessed with output, optimization, and expertise—

choosing to do something purely for joy is quietly radical.

It builds:

• resilience
• humility
• curiosity
• connection

And ultimately…

it brings you back to yourself.

💌 Let’s Keep the Conversation Going

What’s something you used to love… that you stopped doing because you weren’t “good enough” at it?

And what would it look like to pick it back up—just for the joy of it? 💛