I’ve said numerous times that I’d never charge people for advice on how to move abroad.
I still mean it.
I think too many people move abroad and suddenly become relocation consultants—putting together visa applications, scheduling appointments, and hunting for apartments for other people. They’re opportunists at best, grifters at worst.
They use fear, distortion of the reality on the ground in a place like Spain, and flat-out misinformation to charge people to do things they can do themselves or outsource to actual professionals. I moved to Spain nearly two years ago. That doesn’t qualify me to act as your facilitator or pseudo gestor.
What I do get—from readers, friends, and people referred to me—are questions about the decision behind the mechanics: Would I like this city? Does what I say I want match the way life there actually works? What am I overlooking?
Until now, I’ve answered informally when I had the time. Those questions recur often enough—and expose a real enough gap—that I think it makes sense to formalize the part I’m actually qualified to do.
So today, I’m opening three spots for something different: a paid, private, written second opinion on the thinking behind a move abroad.
This is for people who are seriously considering a move or have already seriously considered a move, researched it, and begun constructing a plan—but want somebody independent to examine whether the place they’ve chosen, the money and work supporting it, their expectations, and the life they say they want actually fit together.
You’ll begin with a short application. If I think I can give you $550 worth of value—and you decide to proceed—you’ll complete a detailed written questionnaire. I’ll use your answers to produce a private written assessment explaining what holds up, what I question, where you might be contradicting yourself, and what you should investigate before deciding.
I won’t merely identify a contradiction and move on. Where useful, I’ll use concrete examples from my own move, decades of living in cities, and nearly two years of writing about life abroad to explain what that tension could look and feel like in ordinary life.
There’s no phone or video call. I won’t select your visa, find you an apartment, explain how to register in government systems, or provide legal, immigration, tax, investment, housing, healthcare, or administrative guidance.
You do the research and build the plan. I interrogate the argument behind it.
If this already sounds like what you need, you can stop here and complete the short application. You won’t pay anything now. I’ll review it and tell you within three business days whether I think I can help.
For everybody else—or anybody understandably wondering why this isn’t a reversal of what I’ve previously said—here’s the longer explanation.
People considering a move abroad tend to encounter two sides of the same mess.
On one side, there are Facebook Groups, YouTube videos, checklists, masterclasses, and thousands of comments from thousands of random people. We take in all of that generalized information—some of it useful, much of it senseless nonsense, and some of it produced by people creating problems so they can offer their two cents or sell a solution.
Then, we aggregate all of this into themes and can easily convince ourselves that we’ve received a targeted assessment of our own move. That we’ve developed a good sense of what it will actually be like to leave the place we’ve called home and build a life in a new country.
On the other side, there are relocation consultants willing to execute parts of the move for you—often while funneling you toward other “experts” through referral arrangements.
Both can provide information or assistance. Neither necessarily examines whether the life you’re imagining can actually take shape in the place you’ve chosen.
That’s the gap I’m attempting to fill.
I know that gap exists because I experienced it myself. While preparing to move, I absorbed much of the same online noise, anxiety, and bullshit everybody else encounters. Some of it influenced me even when my own research, experience, and instincts pointed in another direction.
At the same time, I was doing the deeper work of examining our motivations, money, routines, expectations, and relationship to place. That process helped me separate the things that actually mattered from the fears and assumptions I had picked up online.
I think I can help other people make that distinction before they move.
So I have changed my mind about one narrow thing. I now believe I can ethically charge for a second opinion on a plan somebody has already researched and developed—without taking ownership of the move away from them.
I’m not putting a $550 price tag on a casual question I might once have answered in an email. The paid work is absorbing a detailed account of somebody’s life and plan, interrogating it, and producing a substantive assessment built around that person’s particular circumstances.
That isn’t the same as charging somebody to outsource their move. In fact, it requires the opposite.
You have to do the work before I can be useful. The detailed questionnaire is part of that work. Answering it honestly should help put your move into sharper perspective before I write a word of the assessment.
I’ve spent most of my adult life noticing things about places that most people overlook.
Shortly after moving to San Francisco in 1999, I enrolled in San Francisco State University’s Urban Studies program. I later studied Planning, Policy & Design in a graduate program at the University of California-Irvine. Between 2002 and 2008, I conducted independent research, presented it at conferences, and published it—including in peer-reviewed academic journals.
More than anything, my time in academia made me fall more deeply in love with cities and develop greater self-awareness around the relationship between place and daily life.
Most people don’t spend much time considering that relationship. But—as we prepared to move to Spain and ultimately did nearly two years ago—I realized it’s among the most important things to understand before starting again in another country.
The mechanics matter. So does questioning your impetus, motivations, aspirations, and readiness for the uncertainty, temporary loss of competence, disrupted routines, distance from people, and ordinary emotional friction that comes with moving abroad.
As you might know, my main freelance work is writing about finance.
Most city writers aren’t finance writers. Most finance writers don’t think seriously about cities.
A city writer might understand why a neighborhood works but not whether your work and money can sustain your life there. A finance writer might determine whether your spreadsheet works while completely missing what those numbers will buy you in day-to-day life.
And most move-abroad content never connects either side to the self-awareness required to understand what you’re really asking another country to change.
When I examine a plan, I’m not merely asking whether somebody can afford the rent or obtain a visa.
I’m asking whether the ordinary days they describe resemble life in the city they’ve selected. Whether their work schedule will allow them to experience what attracted them there. Whether they say they want density and community but dislike noise, smaller apartments, and encountering other people. Whether they want to leave American work culture while remaining economically and psychologically organized around it.
And whether they’re choosing an environment that fits them—or expecting geography to fix something that will follow them anywhere.
I won’t leave those tensions at the level of abstraction. I’ll show you what I mean with real-life examples. I’ll also tell you when I think the mindset you’re bringing to the move will make ordinary friction harder than it needs to be.
That might be uncomfortable. A useful second opinion shouldn’t exist merely to reassure you.
The point is to make your imagined move feel more like an ordinary Tuesday before you uproot your life to find out.
I also read and interrogate arguments for a living.
Your plan to move abroad is an argument:
This is the life I have. This is the life I want. This is what isn’t working. This is the place I believe will work better—and this is why.
I can read that argument and see where the evidence supports it, where the pieces line up, where you’re contradicting yourself, and where you might be making an enormous leap without realizing it.
You’re effectively bringing me a draft of a major life decision. I’m giving you editorial notes.
Ask me whether you’d like Los Angeles—as people sometimes do—and I’m not going to immediately answer yes or no. I’m going to ask where you’ve lived, whether you like driving, what you can afford, how much space you think you need, what you do on an ordinary weekday, and whether you want to encounter other people without planning it.
Los Angeles doesn’t produce one experience. The relationship between the person and the place—between the person and the neighborhood they choose in that sprawling mess—does.
The same logic applies to places I consider better, such as Valencia, Paris, Rome, Toronto, or wherever you’re thinking about building a life.
More importantly, I used this same way of thinking to pressure-test our move long before we made it—and I continue using it as we live it.
My wife and I didn’t pick Valencia because it appeared on a best-places list—best-places lists are bullshit—or because we like drinking wine in a plaza. We spent time traveling, thinking, talking, and writing about what we wanted our ordinary days—not our vacations—to look like.
The logistical preparation mattered and remains ongoing. But the more important preparation was understanding what the move could change, what it couldn’t, what we were giving up, and why the physical and cultural environment we chose fit the people we already were and wanted to continue being.
Spain didn’t make the move work.
Knowing ourselves—and knowing how to read a place—gave it a pretty damn good chance.
Our experience isn’t proof that Spain or any other place will fit you. It’s evidence that I’ve used this way of thinking when the decision involved my own money, relationships, routines, work, and life.
None of this qualifies me to submit your visa application or tell you where to live.
It qualifies me to examine whether the life you say you want resembles the life you’re actually preparing to build.
I sell nothing after that. I receive no referral fees, represent no relocation company, and have no financial interest in whether you ultimately move.
In many ways, this is the most concrete application yet of what this newsletter has become.
I write about how cities, money, work, culture, and psychology combine to shape everyday life. A Written Second Opinion applies that same way of seeing to one person’s actual decision.
A Written Second Opinion
You begin with a short application describing the move you’re considering, the preparation you’ve already completed, and what you want me to examine.
The first step is an application, not payment. I’ll review it and respond within three business days.
If I don’t believe my perspective can give you $550 worth of value, I’ll tell you. You won’t pay anything.
If I think I can help:
The fee is US$550, paid through a secure Stripe link.
You’ll complete a detailed written questionnaire.
I’ll send you a private written assessment—generally between 1,000 and 1,500 words—within seven business days.
I’ll explain what appears well considered, what I question, which parts of your plan may conflict, and what I think you should investigate before deciding.
You may send one follow-up email containing up to three clarifying questions.
This does not include a call, ongoing access to me, emotional coaching, or legal, immigration, tax, investment, housing, healthcare, or administrative guidance.
I’m beginning with three people because each assessment will require substantial work. I believe I can add real value to the thinking behind a decision this consequential—and that I’ll enjoy doing the work—but I want to build it carefully before offering more.
If you want somebody to select a country, find you an apartment, choose a visa, or walk you through the bureaucracy, this isn’t for you.
If you’ve already done meaningful research and want somebody to challenge whether your proposed move fits your money, work, habits, experience, expectations, and idea of a good life, I might be able to help.
I won’t make the decision for you. I’ll tell you what I see in the case you’ve made for it.
