To be truly whimsical, go to Coney Island and do things on a whim.
Hi! I’m Tiffany, a tech and culture journalist and author of the Cyber Celibate newsletter. Having spent most of my career researching the frontier of technology for places like Wired, Vox, and MIT Technology Review, I’m currently working on reclaiming my relationship with technology by quitting a piece of tech each month and documenting my experience for Back Market’s Tech Journal. This will involve experimenting with more retro devices; changing how I consume technology day-to-day; and showing what happens when you lean into the Slow Tech revolution. For my first venture, I swapped my iPhone for a camcorder on a field trip I planned for my friends.

When my friend Sabrina asks to hang out, she doesn’t ask if I’m free. She asks me if I want to play.
Recently, the term “play” seems to have attached itself to the term “whimsy”. Instead of representing what it literally means —doing things “on a whim”— whimsy has come to be a catchall term for embracing your inner child, wearing fun colors, and creating your own set of vocabulary. While I object to the whole marketing subculture emerging from the resemanticization of this phrase, I do appreciate how it:
promotes tactile activities, which then gets me off my phone
encourages a release of inhibitions, which puts me in touch with my intuition
pushes me to explore things on my own, outside of the algorithm
reminds me that things are never really that deep
I wanted to reconnect with what whimsy actually means in a technological context. What does living whimsically actually feel like? How can we balance being in the moment with our 21st century-need to document everything? So, naturally, I took my friends on a field trip, and brought a camcorder with me.
Why a field trip? Because nothing hits quite like a nap on the bus ride back.
Remember how, after a long day of play, your body gives into the gentle bumps of a bus ride? The beauty of a good old-fashioned school trip, to me, was all about the structure. Noon-1: aquarium. 1-2: rollercoasters. 3-5: frolic by the beach. Different textures of entertainment were mandated, unlike the monotonous ritual of doom-scrolling-based rotting we seem to exclusively partake in these days. For the sake of their sanity, our teachers would try all sorts of ways to tire us out. The corporate world would call this timeboxing, but I’m here to remind you that a little scheduled fun never hurts.
To really dial up the nostalgia factor of this excursion, I dug deep into my memory and jotted down a few must-haves on this trip:
Capri Sun drinks
Worksheets
Packed lunches
Buddy systems
There were eight of us on this trip. On the day of, I confiscated everyone’s phone and assigned a line leader. Without our main means of communication, it was important we kept everyone together the low-tech way. It really helped when we walked past someone handing out neon-yellow T-shirts with the number of an injury law firm boldly screen printed across — right next to Coney Island’s historic almost-100-year old wooden rollercoaster, The Cyclone. A clever way to build hype, perhaps?
I documented the day the way our parents filmed our childhoods.
Divorced from the smooth, seamless experience of whipping out a camera (FYI: I am using a blue Minolta MN200NV Camcorder) on an iPhone, turning on my camcorder involved an endearing jingle, a few seconds of warming up, and tinkering with manual settings.
This delay, while trivial at face value, made all the difference. It forced me to think twice before filming something. It made me reconsider whether a moment, happening organically and spontaneously, was worth interrupting. It also, somewhat counterintuitively, captured moments that more… earnestly: people were looking in the camera instead of posing “candidly,” talking to the camera, and narrating everything. Over time, the jingle became something of a Pavlovian cue.
The footage was shaky. The zoom was fast (and unwieldy, at first). But all that helped bottle up the unserious, *whimsical* essence of the day. The trip wasn’t meant to be a manicured display of fun for social media. It was just an excuse for my friends and I to get outside on what may have been the nicest day of summer, get drenched on water rides, and fill up on empty calories after indulging ourselves in sugar. Embracing your inner child isn’t always performative!
We love whimsy because it’s uncomplicated
I think the appeal of the whimsy movement lies, partially, in how simple it makes life seem. There was a time where all we cared about was when our next playdate was or how many chocolates we could sneak into our mouths when mum wasn’t looking. Unburdened by existential fears and concerns about perception, we embodied hedonism in the most uncomplicated way.
In the truest sense of the term, doing things on a whim (in other words, going with your gut) lets us temporarily escape all the invisible structures of influence we live in. We let go of what’s expected of us, and we’re pushed to trust our intuitions. This means we’re free to live life beyond what the algorithm wants us to want.










