Stay grounded to take flight
Finding your place in the world doesn't require travel plans
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 #14. ✨
☀️ How was your week?
I spent lots of quality time with my dad and brother. Before my dad flew back home to the Mid-Atlantic, we all visited Vashon Island on Strawberry Festival weekend, stopping at a lavender farm and a cidery along the way. We savored Neapolitan pizza in downtown Tacoma, strolled along Commencement Bay on a sunny afternoon, and grilled out on my back patio. It was the Platonic ideal of a summer staycation, complete with two of my very favorite humans. My heart, it is full!
With summer in full swing, travel’s on my mind. Not coincidentally, it’s the topic that inspired this week’s dispatch.
If you’re interested in another perspective on the subject, I highly recommend this piece by
. It dissects the various costs of travel when you live with a muscle disease, weighed against the benefits of making a journey that’s certain to be deeply impactful—all with a dose of wry humor sprinkled in.On to today’s letter!
Stay grounded to take flight
“The peak of a mountain is only as strong as its base. You've got to be grounded if you want to soar.” –Brad Stulberg
During my mom’s time in home hospice care, there was nowhere else I wanted to be. Judging by my reading list, you might have jumped to a different conclusion.
Housebound with her that Chicago winter, I tore through Scott Keyes’ book Take More Vacations, which makes a compelling argument for rethinking the default, planning-centric approach to picking a travel destination. I followed it up with Hidden Travel: The Secret to Extraordinary Trips, a thoughtful tome by Steve Brock on interacting differently, more meaningfully, with our surroundings.
Even with my feet resolutely planted, I suppose it was inevitable—during a time of anticipatory grief, of endings—to yearn for the lightness and novelty that travel promises.
In recent years, my mom returned—like clockwork—to the beaches of Anguilla as winter gave way to spring.
Family history was one draw; my grandparents began their own regular visits forty years ago. I took my first steps in Anguilla, on a trip that also included a jumble of aunts, uncles, and baby cousins.
After numerous years away, my mom eventually started returning—and she invited me along. By that time, I was in early adulthood, and I always found a convenient reason to decline.
At first, my paltry salary was to blame; I didn’t feel comfortable springing for the airfare. Then, as I found my career footing, I couldn’t imagine taking enough time off work to justify the multiple-planes-plus-a-ferry journey. That journey only grew longer when I moved out west.
As with everything else, I thought I’d have more time. Someday, I always thought, I’d say yes to her invitation, and spend quality time together in the place she loved most.
In her last months, I tried to avoid centering my regrets in our conversations. But I couldn’t help but express my profound sadness that I’d never rejoined her in Anguilla.
To my surprise, she understood. “You’re a redhead. You can barely spend five minutes in the sun. It didn’t really make sense for you,” she shrugged.
She turned my attention toward the future, toward a different set of islands. She asked if I’d ever heard of the Hebrides, an archipelago off the west coast of Scotland—the country we’d visited together during my first trip abroad as a six-month-old.
Serenely, almost dreamily, she described the pictures she’d admired in a travel magazine, all mossy-hilled and salt-crusted and windswept. “I’d love if you could spend some time exploring the world,” she said, “and find your own place somewhere out there.”
After returning to Washington, I figured that before too long, I’d do just that: use my suddenly plan-free schedule to visit one (two, three…) of the destinations I’d been dreaming about. Maybe Budapest, or the Tokaj region of Hungary—home to a branch of my family tree. Chilean Patagonia, or Buenos Aires. A second visit to Istanbul, to refresh the Turkish grammar and vocabulary I’d studied in college. The Alaska cruise my mom and I had considered taking together.
Once I decided to create this newsletter—which would mean contending with memories as tender as bruises—my urge to flee grew stronger.
But without a trip penciled into the calendar, without the seductive distraction of research and planning and itinerary-building, I found myself out of excuses to avoid writing.
Back when photography was my main creative outlet, my way of crystallizing experiences into memories, travel was its perfect complement. I spent countless weekends flying and driving to new destinations. The more I explored, the more I practiced capturing novel surroundings on film, the more my photography improved.
Writing is different. It improves the more I stay put, the more I’m enmeshed in routine. Quiet surroundings enhance my capacity for the deep work of exploring internal landscapes.
Being grounded with my thoughts, I began to realize, might be more fulfilling than flying away from them.
About a week before my mom’s final hospitalization, I walked up to my makeshift desk at her house, mug of steaming coffee in hand. I was prepared for another weekday spent bouncing between client meetings, work emails, and caregiving duties.
On my desk, I found seven pages of her handwriting—she’d stayed up the previous night to write something down for me. Among other blessings she wanted to pass along, she’d copied the full text of “A Mother’s Prayer,” by Rabbi Rami Shapiro.
She’d never been religious, but battling cancer had made her reflective, more spiritual, and curious about her roots. She developed a meaningful relationship with the hospice rabbi after an encounter one Shabbat in the hospital. Writing “Jewish” on her intake form had led to a special delivery of challah and grape juice on Friday night, which—as a non-practicing Jew—left her bemused but also clearly delighted, as she recounted the story.
In reading the prayer, I was struck by this line: “May my child grow to discover her unique place in the world, and may she find the courage to take it.”
That unique place might be a corner of the world I’ve yet to visit—maybe one of the Hebrides islands. I plan on going there someday, and bringing her memory with me.
But it just might be here at home, lost in thought at my little writing desk, my mom’s handwritten prayer keeping me company.
💬 What do you think?
I’m curious to hear from you. How do you stay grounded while you’re on the road? Have you made any new discoveries about yourself closer to home?
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
Maddie, this beautiful piece brought me tears. Keep writing, young person! Oh, and I posted it on Twitter, so new followers can see it.
These wise words + Baby Maddie in Scotland = maybe my favorite post of yours so far! There truly is nothing better than staying put at home sometimes. But, we should definitely travel together to Budapest/Tokaj region or perhaps Hebrides at some point!