A Year of Whimsy

There was a moment late last year when the thought occurred to me: "I've lost my sense of whimsy."

I could name a dozen reasons why this crossed my mind. The dawning dread of thirty lurks on the horizon. I work for a newspaper that has endless chyrons running breaking news constantly from the view of my desk. I’ve gone around the sun enough times to see the rise, fall and renaissance of low rise jeans. Surely that’s enough to sour anyone’s mood. 

The majority of these symptoms for my mallaise boil down to one simple variable. Life is too serious. Bills have to be paid, doctors have to be visited, offices have to be returned to. Perhaps, among all these mind numbing tasks, essential to the basic functions of adult life, I began to take myself too seriously. The slippery slope of repeating the similar sequences over and over again had led to a perceived blandness in my day to day experience of life. 

And yet, life can be so much more through some basic and easy fixes. Or, maybe, a singular, basic, and for that matter, easy fix.

Thus, my decision to make 2026 my year of whimsy. 

It's sleek. It's sexy. Even the sound of the word is whimsical. The idea got me excited for what's to come. Grand visions of spur of the moment trips to far off places danced through my head. Walter Mitty and Anthony Bourdain and Ted Lasso come to mind. I'll pick up new hobbies and become a master of those newfound skills overnight, I’d think to myself. People will comment how much I've changed for the better. It will be ecstasy! 

But I know this isn't true. 

None of that is realistic. And besides, I still have a 401k that I refuse to liquidate on behalf of my delusions of grandeur. No, whimsy will have to come the old fashioned way: through spontaneity, open mindedness and sheer, unabashed commitment to 'the bit'. 

When I tell friends of my year of whimsy, most respond with some question along the lines of "And how do you plan to make your life more whimsical, Tom?" To which I state a glaring and unavoidable truth. "The least whimsical thing to do is come up with a plan. When I see an opportunity for whimsy, I will take it." You see, whimsy has no rules and therefore I will have no preconceived notions of how it should come about. Whimsy should come at you like a proposition by strangers for a threeway at a bar. It should be totally out of the blue and greeted with a quick up and down before shrugging your shoulders and saying "fuck it, yeah, why not?"

Most people nod their heads in agreement with me, commenting "You know, you’re right, that makes a lot of sense actually," and then the conversation inevitably moves on to halfhearted resolutions for the new year. 

But here's the thing. My year of whimsy isn't a resolution to be cast aside like a middle tier gym membership in the second week of February. My year of whimsy is a way of life, not to be half assed with the rest of life's monotony. It will require diligence and fortitude. It will require the bravery to take risks and question the little things throughout a given day. Most importantly, this way of life will constantly require the self reflection and self awareness to state "this isn't very whimsical of me," when the sad truth arrives. 

Ultimately, I hope for my year of whimsy to be a state of mind more than anything else. I hope for the opportunity to come early and often. I hope for whimsy to be natural and free and inspiring. And finally, I hope those around me are along for the ride. 

This past weekend, my wife Carly and I had to drive the length of Long Island from Montauk to Massapequa and then onto Westchester. In total, it takes about three and half hours with a bit of traffic. Upon our departure from Montauk, we drove up the hill out of town and toward the Hamptons. Suddenly, a literal fork in the road presented an opportunity. 

"Turn left," I said to Carly frantically, "take Old Montauk Highway." 

The turning lane quickly approached and we both craned our necks around to check the massive blindspots in the 2005 Ford Expedition we occupied. Clear of risks and danger of oncoming cars, we careened left at a questionable speed and onto Old Montauk Highway, whilst I cried "Whimsy!"  

The road ascended and plunged with the rolling terrain. Our stomachs dropped as if we were on a rollercoaster when we took a hill at 50mph. Dune grass and shrubs grew into the side of the road and occasionally hit the car on tight curves. The ocean melted into a clear blue sky and I wondered what it was like to take this tiny two lane road to Montauk back in the day when the state highway didn't yet exist. I imagined the old fishing town as it once was, without millionaires and billionaires walking amongst the working class folks of town. Carly told me stories of the fancy restaurants and pilates studios that were once humble fish shops and movie theaters. Remnants of the fishing village that was still remain, though you have to go out of your way to find them. Montauk had changed and this old road we were currently driving on was a reminder of those forgotten days. 

Old Montauk Highway is only about four miles long and takes eight or so minutes to traverse end to end, depending on how legally you drive. We drove past Gurney's (once a sleepy beachside hotel, now a five star resort) and the massive Hither Hills Campground (barren of the Mercedes campervans and RVs that populate its sites during the summer) and stopped at the entrance to (new) Montauk Highway. Our detour was successful. We waited for a Rivian to pass before turning onto the much flatter, wider and straighter road. 

"Always worth it," Carly muttered to herself and she pulled onto the highway and we commenced with our Long Island journey.