“There will be a contest with prizes,” said the flyer.

​I almost crumpled it up and threw it away — that’s how strong my reaction was.​

I had received the flyer in the mail for Trivial Pursuits, the one-day workshop that my calligraphy guild, the Friends of Calligraphy, organizes as its annual gift to the membership.​

Trivial Pursuits is really a buffet of six different workshops, presented by member volunteers, that participants rotate to over the course of the day.​

It’s always fun + sensory-overload, in equal measures.

And because this is a calligraphy guild, naturally we take advantage of any opportunity to put our lettering skills to use!​

So instructions on the flyer to register for the workshop said the following:​

“You are encouraged to send your registration in a funny, non-funny, gorgeous or whatever envelope. Decorated envelopes will be displayed at the workshop. There will be a contest with prizes. Do what pleases you.”

These kinds of things—contests, competitions, where the goal is to create something amazing that will be judged—used to paralyze me in the past. I’d end up not even participating at all out of perfectionist paralysis! 😖

​Now, I approach it as an opportunity to play!When my family went to the beach for the Thanksgiving holiday, I brought a stack of envelopes, some Pigma Micron markers, and my travel watercolors with me, and figured I’d improvise.

​Let my inner 4-year-old take the reins and have fun!

​Let it be crappy!

​Don’t worry about the contest part—just have fun!

​Here’s a snapshot of what emerged.

My envelope for the contest (the pen is covering up the address, for privacy :))


I have no expectations of winning any prizes, and I’m looking forward to seeing the amazing creations I know will be there, that will surely blow my mind.
But here’s the thing: LIFE is not a competition; it’s a PARTY! You get to be you, I get to be me, and we all get to shine together.

​When we can approach everything this way, not only can we relax and have a lot more fun, but it actually lets us do our best work, too! (Funny how that works…)

​So yes, I’m sending in my envelope, and it will be judged for the contest, but I didn’t make it for that.

​I made it for the joy of creating. Pure and simple.

​Creative sandbox playtime.

​Which is what all of us need more of in order to access our best work.

​Lessons for Leaders

If you lead a team, how is my envelope story relevant to you?

​Well, if one of your goals is to foster a Culture of Creativity and innovation, be very careful when it comes to competition.​

While competition can motivate some people to do their best, in others it can trigger the kind of perfectionist paralysis that used to shut me down (and that I still have to watch out for!)​

If you run competitive events, how might you also leave lots of space for team members to be able to take risks without worrying about being judged or criticized?​

Innovation thrives in an environment of constant experimentation and iteration, “think quantity, not quality,” and “what if..?” (these, btw, are two of my 10 Creative Sandbox Way™ guideposts).

​When people feel like everything they produce has to be amazing, they are liable to just stop producing.​

Competitions might seem like a fun way to spark better results, but beware of the backlash!

​And make sure you have a more comprehensive strategy if you want to unlock the creative genius just waiting to be released inside your people.

Need some help catalyzing, cultivating, and sustaining a Culture of Creativity in your team or organization? Let’s connect! 

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