Play Bigger In Your Career Without Taking Outsized Risk

I took a walk near my mom’s house and stumbled upon this amazing playground. It's clearly designed by someone in touch with their inner child and/or prodigious amounts of mind-altering substances.

IMG_0786 3.JPG
IMG_0785 3.jpg
IMG_0783 3.JPG

It was the best kind of sensory explosion. Giant fish tunnels, double-headed slides, and that delightfully bouncy flooring that could only be the product of recycled tires and magic.

When I was a kid, a playground consisted of an outdoor litterbox (a.k.a. sandbox), a dented metal slide that would burn off even the most devoted layers of skin, and a horizontal iron bar stuck in the middle of a gravel pit (no joke: we appropriately dubbed it the “one bar”). Those were our tools. It was our job to make them fun. 

When I see playgrounds today, I view them through the eyes of my 7-year-old self. My inner 7-year-old was pretty excited about the giant fish tunnel, but what set this playground apart were the musical instruments. I’d never seen such an array, and I was mesmerized. 

I walked toward it, then stopped, then started, then doubled-back, then paused, then drew forward only to retreat. I continued on my walk.

I live for tiny pockets of daily joy like this, but the chorus of voices in my head won out. They reminded me how silly I’d look as a grown human on a playground and chastised me for quitting piano lessons and what if people are watching and don’t play unless you can play something well and you’re out here to exercise not goof off (also germs because this is a playground after all, but that’s a different post).

No one else was there. Who cared if I banged out a few wrong notes or played utter nonsense? Yet, annoyingly, I cared. 

So I did what any self-respecting adult would do: I went to get my mom. You see, my mom has never met a song she didn’t like or an occasion unworthy of a performance. She also knows the importance of play. 

When I asked, “Hey, Mom, do you want to bang on some instruments at this playground I found?” she replied, “When can we leave?”

Had my mom not agreed to go, it’s safe to say that I’d never have gone back to that park. I let my self-consciousness and fear of how I would look to others prevent me from enjoying myself. Missed opportunity.

Maybe you're less daunted than I am about playgrounds, but consider how often we shame ourselves into not doing something we really want to do, big or small. Shame is a strong word, but it’s appropriate. Yes, the same word we often associate with deep, dark transgressions also shows up in our careers with alarming frequency. 

The same forces that hold us back on small inconsequential decisions loom just as large when it comes to big career moves. That self-consciousness I felt on the playground took me back to those times in my career that I felt intimidated or not smart enough or like my voice didn't matter. I played small because I didn't trust what would happen if I went for it. I hid whole parts of my personality because I assumed they wouldn't be accepted.

Think of the last time you felt shame at work, or even slightly foolish in front of others. It’s the searing remembrance of that feeling—and the lengths we’ll go through to avoid it—that so often keeps us aligned to the status quo, reluctant to show up fully, and handcuffed to unfulfilling career choices.

And with the increasingly high-stakes pressure to appear perfect, it’s easy to understand how even the smallest mistakes trigger outsized shame. 

Yet when we allow space to play, we immediately lower the stakes.

Play is the enemy of shame. When we truly play, self-consciousness and comparison don't exist. We're caught up in the moment. Free of judgment from ourselves and others. We don't consider what the person next to us is doing; we're entirely consumed by the beauty of possibility, where it could lead, and what we'll create next. 


“The Chief Enemy Of Your Career Is Good Sense”—Pablo Picasso, kind of*

My mom approached the instruments as I wished I would have: starting out tentatively with “Happy Birthday” on the xylophone, then increasing in volume, commitment, and complexity as she gained confidence. 

She sashayed over to the chimes to play what she claimed were excerpts from Tchaikovsky’s The Nutcracker Suite. (“Did you recognize that?!” she asked excitedly. I did not.)

“This is so cool!” she’d repeat as she moved between instruments. 

Her performance culminated in a rollicking rendition of a profane impolite little ditty she “learned in college” about a drunk mouse challenging a cat to a bar room brawl. She ended her accompanying riff on the tom-toms with a wide grin and a curtsy.

I, on the other hand, let my “good sense” get in the way of being myself—on that day and many others.

How many times do you talk yourself out of big, exciting career idea with your rational brain? You get super excited about a direction, but talk yourself out of it because you don’t know yet how and when it’s going to happen. 

What if, instead of dismissing your idea out-of-hand, you decided to play around with how it might work? What would be the steps if it turned out exactly as you envisioned? What would be the easiest, coolest, smoothest way to the outcome? What would be the way you'd do it differently than those before you? Who would help you? You know, have FUN with it and figure out the answer in the process.

If the answer doesn't come immediately, that's cool. You're just playing around. You can play again tomorrow.


When "Happy Birthday" Takes a Dark Turn

This may or may not be my mom playing Tchaikovsky on the chimes.

This may or may not be my mom playing Tchaikovsky on the chimes.

I asked my mom if I could videotape her now refined version of “Happy Birthday” to send to a friend.

The tune starts out well enough but a sudden, unexpected key change leads into a more macabre rendition. Then there’s a wrong note followed by her delighted, “Oops!” Undaunted, she ends with an exaggerated trill before turning to the camera with a shrug and a smirk.

My mom was fully engaged in play. If I were to ask her why she didn’t care about the wrong notes, she'd probably say something like, “That makes it more memorable,” and she’s totally right. She was having fun, exploring, and experimenting.

The right notes weren't the point. I didn't ask to record because I was expecting a musical masterpiece. I asked her to create it because it's hi-larious and how can you not smile when you get a video of someone's mom playing a rainbow xylophone in honor of your birthday?

It’s my favorite Happy Birthday wish ever, and the rolls of video outtakes will keep my brother and me entertained for years to come. All because my mom was focused on the bigger song and not the individual notes.

Next time you’re hiding, playing small, or simply afraid to take the next step, ask yourself what would it look like if you just had fun with it. No pressure to get to the end result immediately, create a masterpiece, or revolutionize your organization. Just put it out there and see where it takes you. 

A missed note here or there is just a blip in a long and storied career. And so many of those blips become enduring lessons, humorous anecdotes, and critical inflection points. 

Or as my mom would say, "Oops!"


“Every child is an artist. The problem is to remain an artist once they grow up.” – Pablo Picasso

Who invented the idea that our careers and the pursuit of bettering ourselves needed to be a drag? We live in an amazing time where we can create any career we want, so why do so many of us settle for something of someone else’s humorless design?

Somewhere along the line, we replace our childlike sense of curiosity and imagination with fear and self-consciousness. 

We let our rational brains talk ourselves out of the promise and majesty of what we imagine we could be.

We don't engage fully in where we are at that moment because we actually kind of know how much we're capable of and what might happen if we bring our whole selves to the situation. 

Think about what's holding you back in your career and life. Then approach it as undaunted and excited as you'd be as your 7-year-old self crawling through a fish tunnel leading to a double-headed slide. 

I'd rather you try and fail while being your amazingly authentic self than succeed as someone you're not.


*Original quote by Pablo Picasso is, “The chief enemy of creativity is good sense.”

Scroll down to comment and share.

Headshot Web site.jpg

Author Bio: 

Before becoming a coach, Caroline spent 20 years in management consulting and financial services. She's made it her mission to help people grow, contribute, and get wherever they want to go.

Caroline wants women to recognize how much power they truly have to define their careers. The life and career you want really is possible once you have the roadmap. Take the first step by downloading her free guide.

She’s also a tennis fanatic, aspiring Minimalist, FIRE (Financial Independence and Retire Early) enthusiast, and Aloha Spirit seeker 🤙. She loves to share stories from her unconventional life and career focused on freedom, creativity, fun, health, family, and community. If she can do it, you can, too.

If you want to hear more about my twisty-turny career journey, here's my story.