Lost in Career Transition? Why Play Might Be the Missing Piece.

If you’re in a career transition, you might feel a mix of uncertainty, excitement, and quite frankly, kinda stuck. Maybe you're questioning if you're on the right path or wondering, “What am I doing with my life?”

You’re not alone. Career shifts can bring up self-doubt, fear, and a whole lot of overthinking.

Most of us have been taught that there’s a “right way” to approach a career change—find the perfect job title, stick to your existing skills, and follow a linear path.

But what if, instead of putting all the pressure on finding the perfect next step, we also made room for more curiosity, play, and experimentation in the process?

Today, I’m going to share why integrating play, curiosity, and experimentation might just be the missing piece in your career journey.

Prefer the video version? Click below!

The Story of J.K. Rowling

There’s a story I love of a woman who lived in London and dreamed of being a writer.

She wrote whenever she could—sometimes in cafes, sometimes while her baby slept beside her.

As she wrote, she experienced some of the hardest transitions of her life—she lost her mother, moved to a new country, got married, had her first kid, and then went through a difficult divorce.

Finally, she sent her manuscript to publisher after publisher.

And after all her hard work, she got a letter saying, “Sorry, you’re not good enough. This isn’t gonna sell.”

Then she got another rejection.

And another. And another. Until she got about twelve in total.

Think of how you’d feel if you were in her shoes. What would you do? Would you give up? Or would you keep trying?

She chose to keep writing—playing with different character arcs, reworking plotlines, and staying open to inspiration.

The cool thing is that most of you actually know this woman. Her name was J.K. Rowling. And that manuscript? It became the famous Harry Potter series so many of us know and love.

Oprah’s Story

And she’s not alone.

Oprah was fired from her first TV job and told she wasn’t fit for television. Instead of accepting it, she experimented. She tried different roles—first in radio, then as a news anchor, then as a talk show host.

She tested different styles of interviewing, figuring out what felt right—what played to her strengths. And through that process, she found her voice.

And the rest is history.

Success Is Rarely a Straight Line

Some of the most successful people we admire didn’t follow a straight path.

They experimented, adapted, and built resilience along the way.

J.K. Rowling’s years of writing weren’t just about crafting a story—they were about processing grief, developing perseverance, and discovering the deeper themes that mattered to her: love, loss, and courage.

Oprah didn’t just shift career paths—she learned to trust her voice, develop emotional intelligence, and refine the unique way she connected with people. Her willingness to experiment—first in radio, then as a news anchor, and eventually as a talk show host—allowed her to refine her unique gift: creating space for authentic, transformative conversations.

Through play, both of them rewired their minds for greater adaptability, creativity, and problem-solving.

Career Transitions Are More Than Just a Job Change

Both J.K. Rowling and Oprah faced major career transitions—but neither of them just waited for the perfect opportunity. They treated their journey like an experiment.

That’s the power of play. It’s an active process that allows us to break out of overthinking, try things, and uncover unexpected opportunities.

And that’s exactly what we’re going to talk about today.

Why Play Matters in Career Transition

As a Certified Career Management and High-Performance Coach, I’ve worked with dozens of professionals in transition—and I can tell you firsthand:

Play isn’t just for kids. It’s one of the most underrated tools for career clarity and reinvention.

You see, career transition can happen on two levels:

• An internal shift (a gut feeling that something needs to change)

• An external shift (a layoff, promotion, or major life event)

The problem is that when people find themselves in a career transition, they often focus only on the traditional outer work—updating resumes, networking, applying for jobs.

And while these are crucial steps, they can feel directionless if we’re not also engaging in the inner work—like gaining clarity, strengthening resilience, and overcoming self-doubt.

That’s where play and exploration come in. Not to replace those structured steps, but to help make them more aligned and effective.

Inner and outer work go hand-in-hand. Without inner clarity, external actions feel scattered. Without external action, inner clarity never turns into real change.

But this is also where most people get stuck. They either overthink and never take action… or they take action without really knowing what they want.

That’s where play comes in. It helps bridge the gap between the inner and outer worlds—giving you a way to explore new possibilities without all the pressure of needing to get something just right.

Why Play Is the Missing Piece

Play isn’t just about fun—it’s a tool for self-discovery. It’s how we test possibilities, build confidence, and rewire our brains to handle uncertainty and challenge with ease.

Think about how kids learn. A toddler doesn’t try to walk, fall down, and then say, “You know what? Walking isn’t for me.” They keep playing with movement until they figure it out.

What if we approached career transitions the same way?

Action Step: Reignite Learning Through Play

So here’s your invitation: Pick one playful next step to explore.

• 🎨 Take a pottery or paint class

• Volunteer for a cause you care about

• 🎤 Try improv

• 🤝 Shadow someone in a field you’re curious about

• Go surfing

• Cook a dish from a different culture

• ✍️ Start a blog or write a LinkedIn post about something that interests you

• Take photos of things that inspire you

• Join a new social or networking group

For me, that looked like baking challah bread for the first time the other week. And while that has nothing to do with my career, the experience itself was a reminder that trying something new rewires our brains to embrace uncertainty—and that’s exactly what we need in career transitions.

These playful, low-pressure activities create a safe zone for exploration, helping you uncover skills, interests, and strengths you didn’t even know you had.

Turning Career Change Into an Adventure

A career change doesn’t have to be daunting. It takes action, yes—but when you bring in play, curiosity, and the willingness to experiment alongside that action, the process becomes less overwhelming and more of an adventure.

It’s about rewiring your brain and body to handle uncertainty, take risks, and connect with your heart’s intuitive guidance. And that’s exactly what we need during career transitions.

Your Turn

What’s one playful experiment you’re going to try this week? Something just for the joy of it. Something that sparks curiosity, excitement, or even a little bit of fear.

I’d love to hear what you’re exploring!

If you enjoyed this, you’ll love my next piece where I share 9 self-discovery questions to help you navigate the inner side of career transition.

Sending you love.