On Whimsy | Whiteboard

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Insight 17 | September 26, 2016

On Whimsy

by Alex Nichols
And I think that's what we're getting at with Whimsy: as we pursue joy in our lives, an already opaque thing by nature, we have to recognize that not everything in life is controlled through structured plans. In fact, some of the best things in life come through letting go of our expectations, and stumbling on something worthwhile.

Whimsy is an interesting word: It first appeared around the early 17th century as something to describe a trinket… something fleeting. And then it evolved until it reached it’s current definition of:

“playfully quaint or fanciful behavior or humor.”

…which I think is a fantastic definition. It makes me feel like a kid again just thinking about it. But I also think it fails to capture exactly what comes to mind when I hear this word. Instead I picture things like this: climbing mountains. hot air balloons. Walking across Niagara Falls. It’s these notions of pursuing experiences for the sake of the experiences themselves that draws me to their act. In fact, you might even say that each of these are… pointless.

And so, before going any further, I’d like to advocate for a new definition of the adjectival whimsy

Key Messages


Whimsy... redefined.


"Joy (in my sense) has indeed one characteristic, and one only, in common with them; the fact that anyone who has experienced it will want it again" - C.S. Lewis.

We’ve brought up Self Actualization a lot around Whiteboard recently. In these discussions, it’s interesting to me how many times we talk about self-actualization as the end goal, but really, when you think about it, self-actualization is but a measure of progress towards what we hope is… something else. And whether that something else is glory, or fame, or peace… I think it can ultimately be summed up in the word Joy.

I’m reading Surprised by Joy by C.S. Lewis where he makes the statement:

“(Joy) is here a technical term and must be sharply distinguished both form happiness and from pleasure. Joy (in my sense) has indeed one characteristic, and one only, in common with them; the fact that anyone who has experienced it will want it again.”

It’s so hard for us to nail down, but I think a lot of us would agree that at the end of the day, humanity seeks joy.

And so, if joy is this hard to define substance we’re all after, how does incorporating whimsy and spontaneity into our lives help us achieve it? I believe the answer lies in the opaque nature of whimsy itself. In fact, whimsy is really a paradox. And similar to asking “if you know you’re being spontaneous, are you actually being spontaneous.” But, I think that’s the whole point.


Are whimsy and structure really at odds?


There are benefits to acting spontaneously.
  1. Bucking trends of comfort. Either we’ve established good habits and we’ve plateaued, or we’ve established bad habits that need to be broken. I think this particular applies internally. By taking a mindset of whimsy and practicing spontaneity (trying new processes, exploring outside options), we create the space needed to review our own ways, good or bad.
  2. Challenging routes to joy. What does joy mean to our team? What does joy mean when visiting a site? When reviewing a brand? What does it mean to offer spontaneity and whimsey in a rather routine world?


What are the ingredients to a whimsical life full of spontaneous experiences?
Final Thoughts

I believe we have all the necessary ingredients to a joyful, whimsical culture. After six months at Whiteboard, I honestly believe I get to work with some of the most genuine individuals on the planet, and while at times, work can feel mundane, I believe whimsy is just around the corner.

Should we choose, we have the ingredients to access the other side of the coin of structure. If we’re willing to create the space and take the risk, I know we have a family of individuals willing to amplify this experience and share it with the world.

Chief of Staff

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