Let's make this a year of experimentation
Less white-knuckling, more fun!
Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.
Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.
Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #36. ✨
Let’s make this a year of experimentation
It’s been a long time since I rang in the new year wearing a plastic tiara from Walgreens, standing in a Wrigleyville McDonald’s patronized entirely by drunk people.
Celebration and revelry are time-honored ways to usher in transition, but as I’ve learned with age, so is contemplation. As
writes in Wintering: The Power of Rest and Retreat in Difficult Times, “The year will move on no matter what, but by paying attention to it, feeling its beat, and noticing the moments of transition—perhaps even taking time to think about what we want from the next phase in the year—we can get the measure of it.”New Year’s reflections take many forms, chief among them resolutions. When I imagine someone who’s resolute, I picture furrowed brows and a focused squint—a determined, thin-lipped countenance. They are firmly committed to starting something. Or they’ve decided, in no uncertain terms, to stop doing something else.
Those who consider open self-flagellation passé have adopted the language of intention. It’s the resolution’s younger sibling, wearing a more relaxed outfit, even though the intention-holder wants to make identical life adjustments.
But here’s the thing.
We don’t always get to choose the shape of our life transitions. And too often, the ones thrust upon us are grim and joyless.
So when we do get the chance to choose our own change-and-transition adventure—New Year’s being a prime example—why wouldn’t we prioritize ease? Lightheartedness? That distinctly fizzy quality of joy?
For those who appreciate New Year’s as a moment to invite chosen life changes, allow me to offer a third option: experimentation.
What comes to mind when you hear that word? An unshowered Bonnaroo attendee trying out a new drug? Someone taking the fuzzy handcuffs in his bedside table for their inaugural spin? A white-coated lab attendant mixing chemicals in a beaker, primed for a scientific breakthrough?
Why should they get to have all the fun?
Because that is the key, after all—one we’ve collectively lost sight of. Fun.
If your response is a quizzical head-tilt or eyebrow raise, you may have accidentally dropped “fun” from your vocabulary. You might be like Rachel Sugar, representing too many of us when she asked herself during a comedy show mid-pandemic:
What was fun? I can no longer remember. A comedian makes a bad joke about ketamine, and a different comedian makes a better joke about puppy mills, and in the distance, I can hear the strains of several competing dance-pop DJs. There seem to be a lot of people, or maybe it just looks that way, when everyone is sitting at least 6 feet apart. Am I having fun? I wonder. Is this what fun is?
When we’re not sure what happened to fun, experimentation can help us relocate it, like an AirTag pointing to a set of misplaced keys.
It’s a lighthearted way of approaching change, as well as a necessary skill in times of uncertainty. When we’re not sure what lies ahead—and really, do any of us, ever?—becoming adept at experimentation helps us stay nimble…and sane.
What is an experiment?
It’s easy to define what experiments are not: for one, they’re not panicked attempts to reach a desired outcome as quickly as possible. So let’s talk about what they are.
✅ Experiments test a hypothesis and offer a definitive result.
Does a new volunteer gig help you make friendly local connections? Does adding an extra vegetable to your dinner feel more satiating? Does checking your email less frequently lead to more serenity at work?
The answer might be “yes,” “no,” “sometimes,” or “more information required.”
✅ Experiments have end dates.
As opposed to resolutions, which you’re supposed to continue…forever. (Seems a little unrealistic.)
After a successful experiment, you can joyfully incorporate things into your life as ongoing habits or practices—or, if the experience sucked, let things fall by the wayside guilt-free.
✅ Ideally, experiments happen one at a time.
That’s so you can test the variable in question before your results get conflated with the next thing you want to try—especially if you’re testing multiple changes in one domain of life. (Side benefit: doing one thing at a time is great for your peace of mind.)
✅ Experiments ask us to detach from the outcome.
When you test a hypothesis, you’re asking a question and making space for the answer to appear; you’re not expecting, or hoping for, a specific result.
As a bonus, detaching from outcomes leaves us free to approach our experiments with a sense of playfulness (see above: unshowered Bonnaroo attendee, fuzzy handcuffs).
What I’m experimenting with in 2024
Not coincidentally, my own first experiments of the year involve leaning into uncertainty: dabbling in new skills, embracing a beginner’s mindset, and inviting spontaneity.
Here’s what I’ll be trying on for size:
✳️ Learning the basics of Figma and Webflow.
I learned to write HTML, CSS and JavaScript three years ago, intending for that knowledge to provide a foundation for learning web design and development software (the aforementioned Figma and Webflow). Life got in the way, but as
argues, late is so much better than never.✳️ Itinerary-light travel to new places.
I’ve booked trips to two new destinations: British Columbia’s Sunshine Coast, and the Isle of Skye in Scotland. (I shared the context for that second trip here.)
I’ll remain intentionally hands-off with those itineraries to make room for surprise and discovery—those shimmering, magical qualities that get bludgeoned to a pulp by overplanning.
✳️ Committing to fewer pre-scheduled obligations.
Dialing back on calendar commitments has already made room for last-minute get-togethers and fun projects that bubbled up in the moment (like baking Christmas cookies to ship out to friends). More of that, please!
For fans of inside baseball, here are two newsletter-specific experiments I’m starting this month:
✳️ Lowering subscription prices—and paywalls.
I turned on paid subscriptions when I published my first essay. It was an experiment whose results astounded me: readers that I’ve never met now support this newsletter with dollars as well as eyeballs.
So, that first phase of the paid-subscription experiment? A resounding, heart-swelling success. My next experiment: lowering annual subscription rates to $30, to make support more accessible for current and future paid subscribers.
It’s a change that makes sense to me: $30, after all, is the price of an annual magazine subscription, or a hardcover book—a price we all pay regularly for writing we like.
Another experiment will involve paywalls, or the lack thereof.
Last year, I published a paywalled newsletter at the end of each month. But as 2023 progressed, and more readers joined this space, I felt wistful that I wasn’t sharing these letters with everyone.
When a soft-but-persistent inner voice asks us to consider a change—well, we should listen. Experimentation, after all, is a tool we can use even when things are going well.
Most paid subscribers sign up primarily to support my work, not access paywalled content. (As
put it, “In other words, I have patrons, not customers.” Yup!) So I’ll play with leaving future essays free—with an occasional peek behind the scenes for paid subscribers—and see how that feels.✳️ A gentler publishing cadence.
In 2024, I’ll write as much as I did in 2023—but it’s possible I might publish a bit less.
There’s a lot I’ve loved about committing to a weekly publishing cadence:
It shook me loose from perfectionism, which used to prevent me from sharing my work at all.
It asked me to select topics that felt urgent.
It nudged me to find something to say when I fretted I’d run out of words.
It pushed me, gently, to question limiting beliefs. Yes, I might have jury duty one week, or experience an unforeseen plumbing disaster the next (current status), but it turns out I can still write a banger amidst expected and unexpected constraints.
And yet: my best and favorite essays of 2023 were written and rewritten over the course of weeks, rather than days.
Having time to put a draft down, pick it back up with fresh eyes, and incorporate outside feedback from trusted friends and editors led to work that resonated more strongly with you, dear reader.
Lately, I’ve been thinking about what
wrote here:The quickest way to fence ourselves in and shut ourselves down creatively is by expecting and requiring everything we make to be “useful” or “productive” in some way. It’s a very unfair expectation to put on our creative practice! A creative practice must, by absolute necessity, make room for learning and practicing things that produce material of no immediate “value.” We have to allow ourselves to experiment and engage in activities that are about process, not product.
In 2024, I’ll try leaving myself more room to experiment with writing that leads me down new and interesting paths—ones that aren’t required to be immediately productive, but that ultimately benefit you as a reader. That means giving myself permission to play faster and looser with my publishing cadence when the work asks for more time.
If you’ve made it this far, I’d love to know:
💬 Your turn!
I’m curious about your approach to the new year. What will you be experimenting with in 2024?
Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.
Warmly,
Maddie
Your turn, my friends! What will *you* be experimenting with in 2024?
Of all the new year's related posts I've read, I haven't seen anyone talk about experimentation. I absolutely love this!