From Fear to Fun: Breaking Free of Perfectionism

May 13, 2025
From Fear to Fun: Breaking Free of Perfectionism
Dale Sidebottom

I once ran a play session with a group of kids where one boy refused to join in. When I gently asked why, he shrugged and said, “I don’t want to stuff it up.”

That moment stuck with me because I’ve seen it in adults, too—teachers, parents, and even leaders who hold back, afraid to mess up and afraid of what it means if they do.

Perfectionism tells us mistakes are dangerous. Play reminds us they’re just part of learning.

This week, we’re exploring ways playful, low-pressure activities help release the fear of failure and reconnect us to what matters most: trying, laughing, creating, and growing. Let’s make space for a little more mess and a lot more joy!

Daily Mission Cards

Today's mission is to write a letter to yourself. Not to plan or improve. Just to notice and name something you're proud of.

Why this matters: Perfectionism is rooted in control—the need to manage every detail and protect against judgment. But writing to yourself with compassion interrupts that cycle. It shifts the focus from control to care.

No performance. No outcome. Only honesty and kindness.

Want more playful ways to practice this mindset? Grab your Kindness and Happiness Mission Cards and explore gentle, joyful activities that help reframe perfection into progress!

Empathy Uno

Perfectionism thrives in silence: in the pressure to appear okay and to avoid saying the wrong thing. But empathy thrives in connection, and connection begins with play.

Empathy Uno gives players a space to drop the mask and be heard. Each card unlocks a moment to share personal stories, emotions, and experiences in a safe and supportive way.

What makes this game powerful is its vulnerability. There’s no pressure to get it “right.” Just a doorway to self-awareness, compassion, and growth.

Download this game and let the conversations bring you or your students closer to each other and yourself!

Anxiety, Counsellor Taking Charge of Anxiety – The 4 Step System with Damian Murdoch

Perfectionism and anxiety go hand in hand. If you've ever lost sleep before a presentation, avoided social events out of fear, or felt like you're constantly running on stress, this 35-minute webinar is for you.

Damian Murdoch has been there. Now, he's sharing the 4-Step System that helped him reclaim his life and how it can do the same for you. Damian's approach gives you clear tools to understand how anxiety works in your body and mind, what to do when it strikes, and how to build long-term control.

Save this webinar and let go of the pressure. Learn to breathe again!

Spreading Joy in Cann River

Hitting the road to Cann River P–12 College was the perfect start to our week. We ran FunShops for every student from Prep to Year 12, and the energy was electric.

We focused on building peer connection, self-love, and everyday gratitude through play, and these students dove right in with heart and enthusiasm. The kindness they showed each other was next-level.

Huge thanks to the Cann River community for embracing us so warmly. We’re excited to see how the seeds we planted last week grow within your school culture.

Join us on this global journey of joy and connection! If you want to bring The School of Play to your community, fill out the form here

Don’t Miss: Dale Sidebottom Lighting Up the Stage at NPEI 2025’s Opening Keynote

Mark your calendars for July 17 because something playfully powerful is about to happen...

I'm thrilled to deliver the opening keynote at the 2025 National Physical Education Institute in Asheville, North Carolina!

The amazing folks at NC SHAPE have pulled together a line-up of true game changers from around the world, and I'm honoured to kick things off with energy, laughter, and a whole lot of purpose.

Where: UNC Asheville – Sherrill Centre
When: July 17–18, 2025

If you're passionate about transforming education through play, connection, and wellbeing... this is your moment.

Register now to secure your spot!

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