Where will I be happy?
The Drift's advice column #2
Today we are presenting the February installment of Sophie Haigney’s new advice column. Send your submissions to letters@thedriftmag.com with “Advice” in the subject line.
Dear Sophie,
I am a freelancer. I have the great privilege of living pretty much anywhere. After almost five years in my current city, I’ve decided it’s time to move on, but I am paralyzed with indecision about where to go next. For my entire working life, I’ve been responsible for making decisions about where to go. I’ve never had a job, or a partner, to help me decide that. My family members live in cities I don’t think I can afford long-term, so that rules out moving to the same place as them. I used to value the freedom that came with my job and lifestyle, but now, I’m wishing I had more constraints in life, and by constraints, I mean responsibilities outside of myself. I want to find a new home where I can anchor myself in community and build a meaningful, civically engaged life. But as I consider my options (all in the western U.S.), I find myself trying to optimize and am coming up with no single answer. Where can I one day afford a house? Where can I afford health insurance? Where might I find a salaried job if I can’t find freelance work? Where is walkable? Where might be decent for dating? Where can I get outdoors easily? Where do I already have friends? Where is there a good arts scene? Where will the climate apocalypse be the least bad? The questions all amount to: Where will I be happy?
When presented with an almost endless amount of choices about where to move, I’m stuck. So, where should I go?
- Meg
Dear Meg,
Like you, I think all the time about where I should live. I talk about it with my friends, and suggest cheaper-than-New-York cities where we might eventually decamp and buy houses, or at least pay much lower rents. (This category encompasses almost any other city.) I talk a lot about Providence, for the future, and try to sell it conceptually to people I know; I am more resistant to but open-minded about Portland, Maine. This, despite no plans to move and many professional and personal reasons to stay. I imagine your dilemma resonates with a lot of downwardly mobile millennials. We might not have the level of flexibility you do, but many of us feel on the verge of being priced out of housing in our current cities. We are famously less likely than our parents to have both kids and partners by now, two things which gave previous generations some parameters for choosing a location. Many of us, like you, have the option to work remotely — and the dream of remote work is that it can be done from literally anywhere. Okay, but, as you ask: from where?
Optionality can quickly become its own kind of prison, as we have collectively learned from dating apps. Your craving for a constraint amid all this flexibility seems congruous with a broader cultural reckoning with the downsides of infinite choice. It seems as though both progressive and conservative cultural figures are constantly shouting: commit, commit, commit! In a viral Harvard commencement speech in 2018, Pete Davis said he left the school “believing that the most radical act we can take is to make a commitment to a particular thing,” whether “to a place, to a profession, to a cause, to a community, to a person.” David Brooks has been talking about commitment for years, including in another commencement speech in 2015, saying, “Your fulfillment in life will come by how well you end your freedom. By the time you hit your thirties, you will realize your primary mission in life is to be really good at making commitments.” A tall order!
None of this is really wrong; I do think people can get stuck in what Davis calls “infinite browsing mode,” and I agree that making hard choices is scary but rewarding. I’m not sure, however, that just saying “commit!” is as useful as people think it is, or that there are as many people contentedly playing the field into late adulthood as pundits seem to imagine. I think more people are confronting big choices, like where to live, in positions like the one you describe: ready to make a commitment, but uncertain about what the criteria for that choice should be. You proposed a lot of possible criteria in your question, and it sounds like you’ve considered and weighed and thought and re-thought about each of them. You even use the word “optimizing,” which is telling: you’ve been looking for an imagined perfect place that is climate-safe, has a good arts scene, has access to the outdoors, is walkable, and affordable. You know, I think, that such a place doesn’t really exist. The attempt to optimize for too many many different variables is leading you nowhere.
My suggestion is: move to the place where you know the most people you love. Of course, it should satisfy some of your other needs and desires. You should be able to afford housing and do the work you need to do. You should like “the vibe” of the city when you visit, in a basic sense. But your priority should be going toward people — whether this is a group of friends you could see yourself slotting into, or one very close friend with whom you could build a broader social world. I would move to this place even if it means going somewhere more expensive, or considering a geographic region you wouldn’t otherwise, or eschewing the arts scene or the outdoors. I once thought I could never live in a city where I couldn’t get outside easily. I was wrong, since I live in one now — a place I came to initially not because I really wanted to but because of an ex-boyfriend’s job. Now I’m here, and even though I do really miss access to the outdoors, and I spent a lot of time and money traveling to places where I can look at mountains, and sometimes this feels silly, it’s a trade-off I’m willing to make.
That is because I think the great advantage of living in cities — in apartments stacked on top of each other, at great expense, alienated from nature — is that we are surrounded by people. Ideally, we are surrounded by people we know and love, and through them, discover a more expansive world in which we might meet new people we come to know and love. Through them, we might meet a romantic interest, or someone to work with. We might go to the bar on a Friday, and then go back to the same bar the following Friday with the same people, plus a few new ones, and then do it over again. Over time, this life among people you know and love will take on its own momentum. You might feel, if not quite a sense of permanence, that you could at least see yourself doing this for now, for the foreseeable future. This is why I do not live in Portland, Maine, and am unlikely to ever live in Portland, Maine, even though it checks all the other boxes of a city in which I would ideally live.
Part of what I find frustrating about the general tenor of debates about commitment and choice-making is the way they focus so much on you, the individual, and what you must do. You need to find the right person to marry. You need to find the right career and stick to it. You need to decide. To the extent that these commitment-mongers acknowledge “community,” it tends to be either general or rooted in family. (For Brooks, the guiding principles are “family, God, craft and country.”) I think that considering your relationships with your friends when making a big choice like the one you’re facing can help place less weight on what you personally need to do to live the best life, and more on how you might make one in proximity to others. A million other choices will rear their heads when you’re in whichever city you choose, but many of them will be easier if you’re living near a group of people you love and trust. You can choose where to live based on where those people are, and I think that in fact you should.
If you enjoyed this installment, send Sophie your own question by writing to letters@thedriftmag.com with “Advice” in the subject line.




Yes! Proximity to others. Love your column! xxL