A few years ago my business collapsed and a quarter-life crisis ensued. In the anguish and self-inquiry that followed, I arrived at a kindergarten-grade epiphany about life and purpose: What I want in life… is to have a good life. I want to flourish.
Then came the obvious question: What does it take to flourish? After several more months with a journal before me and a ballpoint in hand, I had it figured out. Or something like that. I had: a hierarchical list of ten personal values whittled down from forty quarterfinalists, a loose sketch of principles for life and work, and a sprawling list of hobbies and interests. I considered how I might take this apparent roadmap and cram it into a life of flourishing. I was overbooked. I couldn’t imagine keeping track of it all.
Out of all of the values and principles and the heaps of ambition, I wondered where the real leverage was. In trying to design a good life, was it better to home in on even fewer values? Select fewer principles and fewer hobbies? How could I flourish in the fewest possible moves? More contemplation and compression followed, and the resulting conclusion was that ‘a good life’ comes almost entirely down to working through and answering three questions as assiduously and thoughtfully as possible. Three questions which result in three decisions that rub off on nearly every other important decision in life—for good or for bad—through second- and third-order effects:
Who should I spend my life with?
Where should I spend my life?
What should I spend my time on?
Though each question can be explored along several dimensions,1 it is the primary dimension that matters most by an order of magnitude. The primary dimensions of these questions are: Who should I marry? Where should I live? What should I do for work? The more time I spent considering the nature and implications of these questions, the more urgent and underrated the questions seemed. You get all three right, you flourish. You get any of them wrong and you’re swimming up current, big time.
There is something almost patronizingly obvious (or perhaps satirical seeming) about pointing out the importance of who you marry, where you live, and what you do. But it must not be so obvious, because the answers to these questions are often taken for granted or left to chance. And we were never taught how to address and explore them in school. And nobody ever told me: you don’t need to worry about much in life, just focus on getting these three things right and keeping them right and you’ll be fine. As a consequence, few of us thoughtfully prioritize finding a truly compatible partner (or seeking to understand how to be a wonderful partner for another); very few of us spend a few months, let alone a whole year, deliberately choosing where we’ll spend our lives; and very many of us fall into a career and then build a life around it, rather than the other way around.
I’ve already shared some thoughts related to the question of what, and I’ve spent the past few months developing an extensive ‘problem selection’ process to tease out the question further. I plan to cover different aspects of the question of who in an essay soon. Here, I’ll examine the question of where.
“Where should I spend my life?” It is a question most often addressed indirectly. The most common answers to the question seem to be: where I grew up, anywhere but where I grew up, where my partner grew up, where I went to school, where I took a job, I heard Austin is cool. It is quite often a decision one cannot recall ever having specifically made, or a decision that was made long ago under circumstances that barely resemble current ones. It is rarely a decision made after considering, researching, visiting, and deliberately trialing several viable contenders—after contemplating how different places intersect with hobbies, interests, needs, desires, ambitions, and hopes. So, while most people would agree that where you live really matters, most people also assume that where they live is good enough, and that good enough truly is good enough.
Or, perhaps the thought just never occurs to most people—the thought of saving up, then carving out a block of one’s life to intentionally decide where to live. But why shouldn’t it? Yolo, right? How many things affect the quality of your life more than the place you live?2 Would more people spend more time on this problem of place, if they had been instructed how to choose wisely, or if they believed it was possible to truly choose? Because if it’s a top priority it’s almost always possible to choose, and it really can be done for roughly the same cost as staying in one place. And it is totally worthwhile, even if you end up back where you started.
Where you live does matter. You can live in a place where you don’t lock your doors when you leave, or a place where you are unfailingly conditioned to use knob locks, chain locks, and deadbolts. You can have access to beautiful, remote, open natural spaces within minutes or within hours or within half a day’s drive of where you live. You can live in an echo chamber, or you can live in a cultural hotbed, or you can live in something in-between. You can live in a place that adds financial pressure to your life, or relieves it. You can live in a food desert, or in a place where fresh produce is abundant and small-scale farming is supported. You can live where neighbors have block parties, or you can live in solitude. You can live within walking, driving, or flying distance of the family and friends who matter most to you. You can live in a place that makes you feel like a place doesn’t really impact your overall well-being, or you can live in a place where you pinch yourself everyday, because you can’t believe you get to live in that place. Countless choices create infinite possible futures. Your environment shapes you completely, and when you live in a place that fuels you, rather than a place that slowly, imperceptibly drains you, you become more alive.
And yet, it’s common never to fully perceive this or own the opportunity to explore the question: where should I set up my life?
I’ve thought about where a lot over the past few years. When I began contemplating the three questions and taking them very seriously, the biggest gap of the three in my life was the matter of place. I lived in Los Angeles, which was great for so many things and great in so many ways—but it was hours from the remote alpine meadows and streams and air that made me feel the most alive. My wife felt the same way. So we began researching cities and towns and regions and even countries, looking for places that met a criteria that aligned with our values and interests and the vision we were developing for our life. We narrowed it down to fifteen contenders ranging from big cities to small towns,3 then spent seven months driving across eight states, immersing ourselves in each place. At every stage, in every place, we considered trade-offs and we imagined different possible lives. We narrowed it down to three finalists, then returned to each of those finalists for roughly two months. Then we selected a home. Bend, Oregon. Now we live there, and everyday we both say something like: I can’t believe how great it is here.
Before I began searching for a new home, I had spent far more time comparing online reviews of $20 products than I had spent comparing cities where I could live a good life. Growing up, my Dad called this ‘majoring in minors’—a miscalculation of priorities. But nobody ever mentioned ‘majoring in majors,’ and nobody mentioned what the real ‘majors’ even were.
The real majors are: who, where, and what. Out of the millions of decisions that one makes in a lifetime, there are many that don’t matter and quite a few that do, but there are just three major decisions that count for almost everything: who you spend your life with, where you spend it, and what you do with your time. Each of these three areas of your life should be given an excruciating amount of consideration—as though they’re the only three decisions you’ll ever get to make, because in some indirect sense, they are.
Note: I recognize that a common objection to the ideas above is that the ability to decide these things is inherently privileged. Particularly the idea that anyone can have complete control over where they live and what they do. I will readily admit that there are all kinds of exceptions, but by and large I respectfully disagree. I think that most people can find a way to initiate the things they truly want in life. Actions express priorities. And the inertia that causes people to describe things as impossible is often really just fear: of the unknown, of disruption, of instability.
Thanks to Michael Dean and
for feedback on this essay.ie. the question of who can apply to who your friends are, who your best friends are, who you form a life partnership with, who you associate with at work, how much time you spend with family, etc.
Only one, I would argue: Who you spend your life with.
Ashland, Bend, Portland, Seattle, Bellingham, Boise, Ketchum, Missoula, Kalispell, Bozeman, Steamboat Springs, Denver, Durango, Santa Fe, Sedona.
This just came up on my feed. It is phenomenal and thought provoking. Brilliant.
Matt - you’ve nailed it. Superb essay and a simple outline for people to break out of the norm. Break the inertia-love it!