They say the three biggest decisions in life are: who you're with (partner), what you do (career), and where you live.
I don’t have any of them figured out.
So I decided to write about each—the only way I know to make sense of my busy head—starting with the one that's been on my mind the most: Where to live1.
It’s a strange thing. To not feel I belong in the place I was born.
I keep explaining to people how little I like southern Ontario, how nobody takes care of it anymore, I'm starting to sound like a badly broken record.
I’m not saying I believe in past lives or anything, but if I did have a past life, I certainly didn’t live in some cookie-cutter suburb appended to a big city, surviving off its buzz like a parasite2.
But, if not my hometown, I'm left wondering: Where to live?
Choosing a place to live is perhaps the most consequential life decision I will make, maybe only after who I marry. Too consequential to be casual about3.
The expanse of options at my fingertips, all the places I could live, feels both condemning and liberating.
The stakes are high enough to give a sense of vertigo.
*
Last January in Austin, Texas, I met a guy at my Airbnb in roughly the same situation: young, graduated from college, remote job, travelling around. Loves his family but wants a life of his own. Not sure where to plant roots. When to commit.
"I'm waiting, for something or someone to come along," he said, over big bowls of lentil soup at a local Turkish restaurant. "Tie me down, I guess. Tie me to something... I don't think I can choose myself."
Deep down, I think we want to be bound to things. Bound to people, bound to right and wrong, bound to places. Tied down, in exactly the right way.
Yet if I were to paint my early twenties, assuming I could paint, which I can't, it would be a broad landscape—this open, untrammeled plain, stretching wide in either direction. Long wheatgrass slumping lazily in the wind, as far as the eye can see. Mountains hazy in the distance.
Standing there, one can see, almost taste, all the different paths. All the possibilities. All the lives that could be lived. But instead of moving forward, they’re frozen.
What if I chose wrong?
It would be titled "The Dizziness of Freedom"4.
*
Since my head is filled almost entirely with unknowns, I want to explain what I do know.
I know I want to move out. Establish myself. Become "independent"5. Sink into a community. Hike the same sun-strewn trails, attend church on Sundays, find my favorite locally roasted coffee. Live by the seasons. See the rhythms of a routine turn ritual. Save money, take risks, make things. Eventually, build a home and start a family. I've grown tired of travel and temporary living.
I know place matters. Moods inhabit places and influence those who dwell in them. Some surroundings speak of enchantment, others discourage it. The wrong city can corrode a decade of self-development.
I know I am sensitive to my surroundings. In the steel streets of Toronto, or my family’s lakeside cottage in the countryside, or my canvas tent in a quiet meadow, I am somewhat of a different person. Each place draws out certain traits. Others, it demands. I can't will myself into slowness, but I can curate an environment that cultivates slack instead of speed, perpetuates ease instead of urgency6.
I know home is less a place than a state of being. Home, really, is when the urge to leave just... stops7. It’s the exact opposite of restlessness. But eventually, the state of being becomes intertwined with the place and the two become inseparable.
I know to choose a place I must think about what I want to do and experience, down to the day-to-day mundane motions. What sounds will I hear at night? Sirens or cicadas? Where must I go to find community and where must I retreat to sit in solitude? How much do I care about morning sunlight? Watching thunderstorms? Privacy? How many steps do I want between my desk and the outdoors? Between my bed and a forest? Places can encourage some habits I would never do otherwise. Similarly, they can make other habits slightly more difficult, enough to drop them entirely.
I know a big part of choosing where to live is being conscious and clear-eyed about the inevitable tradeoffs. There’s no perfect place. Just a set of trade-offs I'm more willing to make. What are must-haves? What am I okay giving up for something else I want more? Living off-grid in Newfoundland this summer, surrounded by tall trees and the muted roar of the Atlantic, is lovely for the remoteness, the stillness, the closeness to nature. Saying good morning to grazing moose or the Scottish blackface sheep in the pasture. But there are crummy, inconvenient parts too8. The brutal bug bites, weak wifi, and primitive plumbing. The continual labor, just to avoid being overgrown by plants or overtaken by animals. Travelling an hour to get groceries while worrying about the load of clothes I left at the laundromat.
I know a place must be courted before it is committed to. Reality is dense with information, nuance. I can ruminate or read about a city endlessly, but I won't know if we're compatible until we spend some time together. Ideally in an intense, low-cost, easy-to-reverse way (like a week in an Airbnb). A "good vibe" is the subconscious processing a million bits of data all at once and delivering it up as an inarticulable yet certain signal: "yes, this is good."
Finally, I know fate—the used bookstore brimming with 18th-century classics, the retired carpenter who happens to live down the road, the coffee shop encounter that turns into a lifelong love—is so intertwined with place, they're impossible to separate.
*
I feel more pulled toward East or West Coast sensibilities. The ruggedness and grit. The appreciation for the outdoors, fresh air, Patagonia sweaters. But to pack up and move, thousands of kilometers from my friends and family, start fresh, requires a desperate confidence I seem to lack.
Still I think all the quiet yearning for rustic cottages in the countryside, warm and soft afternoon strolls through a meadow, laying down in the grass, should not be taken lightly. We take it far too lightly9.
If there is one primary belief I want to get into my skull, it is that
(here I inhale)
YOU DON'T NEED TO BE THE PINTEREST OBSERVER
YOU CAN BE THE COTTAGE DWELLER
You can just find a place and make it beautiful.
*
An ideal, to me, is to live on the outskirts of a small town. One with a quaint, 19th-century main street. Red-bricked with wrought-iron lampposts and Victorian architecture. Big flower baskets in the Summer and pumpkins in the Fall. Stuck in a sleepier, simpler time. A place big enough to create community, but small enough to cultivate real relationships. Bump into friendly faces on the street. Know people by name.
Build or renovate a New England style home on a grassy, sunlit piece of land. Far enough for a sense of seclusion. But close enough to walk to the local bakery, meet for coffee. Plant a thousand roses, grow vegetables, raise chickens. Learn to timber frame. Get lost in the woods. Sing in the rain.
I think small towns straddle my desire to live in the middle of nowhere with my need for human connection.
For years, I reserved this dream for retirement. But one day I realized: If you know what you want, why wait?
Yet I’m not sure this is the next step. If life has taught me anything, it never works out as planned. Nor do I want it to.
Even my small town ideal is likely to crumble and crack beneath the blunt force of reality.
But I’m glad I didn’t get everything I wanted. Most things I was utterly and unbearably convinced about, would’ve been terrible for me.
Heartbreaks, left to time, almost always turn to miracles. I still sweat looking at all the close calls.
Like many — dare I say, most — people in their 20s, I'm seeking a sense of belonging. That sense of familiarity, which lives unspoken in the heart much more than articulated in the mind.
To cultivate belonging is to be invested in things that cannot be replaced by anything else. Like a favorite sweater or a lakeside path you’ve walked a thousand times.
Utterly unique in the emotional landscape they engender.
*
In the end, all I can do is ask beautiful questions. Questions that shape my life as much by their asking than having them answered. Then, sit with them. Wait and hope10.
In the end, so it goes with all these "weighty" choices, life will decide for me. A place will choose me, more than I will choose it. I'll just be left trying to make sense of it all11.
And in the end, I know the place matters less than my commitment to it. What I do when I get there. Being embodied in how I live, regardless of where I am.
The decision to dwell poetically is wholly divorced from the place itself. It's an act of constancy, the best kind of courage.
The magic is in falling in. Burning the bridges. Sinking the boats.
Some things in life you only get if you're all in.
There will come a time when I have to commit. Despite all the other potential options. Just commit. And resolutely believe what I choose is the best and only option that fits me.
Only the choices that are somewhat irreversible, like mailing a letter or getting married or buying land, can be truly romantic.
This isn't an essay about where to live, really. That's less important. It's an essay about living, wherever I am.
Besides, I maintain a deep faith, lower and more true than all my anxieties, that I'll end up where I'm supposed to be.
*
I grow tired of the world of words and plans and ideas. All these abstractions that pull me from life.
Sunlight is streaming in strong through the shutters, with that particular searing heat that follows a heavy summer rain. The cabin smells of cedar and spruce, dampness now married to gravity. Gulls cry from the sea.
July has waned, but the golden days of August still wait.
I wonder whether it will rain again tomorrow.
Yours,
If you want to help support my writing (and get behind-the-scenes access), the best way is to become a patron:
Also, thank you to everyone who has been generous enough to buy me a coffee. (I spent all of it on books about Christian mystics and the Desert Fathers.)
👋 what i’ve been up to:
Putting a steel roof and siding the walls on the cabin. Building a yurt. Foraging for wild blueberries. Hiking to lighthouses. Swimming in the icy Atlantic till my feet numb. New adventures on the high seas with old fishermen.
I’m sorry I didn’t write you last week. My summer has afforded less time for indoors and typing and screens. More doing and living and building. My thinking has slowed down and I want everything I share to be exceptional.
✍️ quote i’m pondering:
Author Cormac McCarthy on reframing bad luck:
“You never know what worse luck your bad luck has saved you from.”
📸 photos i took:
Summer in Newfoundland.
What I expect will be the most interesting and helpful won't be the specifics, but rather the similarity in the process for each.
Although I did meet a German man in Thailand who had two different monks in the same region tell him that he used to live in that area in a former life, and he loved to meditate in this specific forest alcove near a waterfall.
I've heard a few rules of thumb—"stay close to home near family," or "drop everything and move to where most of your friends are," or worse “just go travel”—but, to me, they're too overtly prescriptive to be decisive.
Kierkegaard: "Anxiety is the dizziness of freedom."
"Independent" because we are all so unbearably dependent on our fellow humans, it's not even funny.
I've heard some argue that home is within. One should strive to feel at home inside themselves. Then, they carry that with them wherever they go.
While this is close enough to be convincing, it's an underappreciation of place and an overestimation of our resiliency. It's a subtle act of ego to think we can transcend the influence of our environment, with enough stoic maxims or atomic habits.
Naguib Mahfouz: “Home is not where you are born; home is where all your attempts to escape cease.”
It’s a dangerous game to leave your perception of places, or lifestyles, to the hands of others without firsthand experience. People, especially on social media, tend to glorify the highlights but leave out the bad bits. Not out of bad will, but generally acceptable social conduct.
This line from Thoreau haunts me: “The mass of men lead lives of quiet desperation.”
Alexandre Dumas: "... until the day God will deign to reveal the future to man, all human wisdom is contained in these two words, 'Wait and Hope.”
Rilke: "Be patient towards all that is unresolved in your heart and try to love the questions themselves like locked rooms, like books written in a foreign tongue... Live the questions for now. Perhaps then you will gradually, without noticing it, live your way into the answer, one distant day in the future."
We ask God for guidance, but He never answers. Not right away. Not when we want Him to. Instead the response is: "Decide yourself. Go ahead."
I think God works more through the path of “not here”, than “here”. He knows man can only really learn the hard way—through trial and error, lived experience. True wisdom cannot be found in the world of mere words.
One thing Tim Keller and Thomas Merton taught me: when God does answer, we're not aware of it until much later. The answer arises in an embodied form, without us noticing. We live it, live our way into it, more than hear it.
"In the end, all I can do is ask beautiful questions." Mission accomplished with this piece Tommy. I've moved 36 times in my life, many of those with a family in tow, and I have loved many of those places, but when it's time to go, it's time to go. I like your idea that while living fully places will choose you.
First time reader. This was such a wonderful essay. It absolutely was so much more than decided where to live. Thanks so much for sharing this with all of us.