I Want to Go Places and Ask Better Questions
My plan to independently report the stories cities reveal about how societies work—from Valencia and beyond.
Last weekend, I sent two emails.
One went to the roughly 100 people who bought lifetime memberships and have been with this newsletter through several iterations. The other went to free subscribers, who signed up anywhere between nearly five years ago and as recently as last week.
I broadly explained where I think this publication can go and asked readers who value that direction to help me give it more of my time.
Some of you responded almost immediately—with paid subscriptions, gift subscriptions, direct contributions, and incredibly generous messages.
Thank you.
Now I want to show you what I’m asking you to help build.
First and foremost, I don’t want to build a travel newsletter. That’s the last thing the world needs.
To further explain what I want to do it helps to understand where we’ve been.
When I started this newsletter, it centered on the Never Retire theme, bounded by the idea that traditional retirement is out of reach for so many people, including me. So it's better to not only acknowledge, but embrace this reality and structure life to accommodate it.
Then, my wife and I decided to move to Spain. So the newsletter naturally shifted to focus on that.
Once we arrived, it became about life in Spain.
The common thread is that this newsletter has always reflected what's happening in my life—both the theme and individual posts.
Now we're settled in Spain living the life I've spent several years anticipating and writing about.
I’m still going to Never Retire—but while we’ve arrived at the destination, it feels more like the beginning than the end.
So, from here, it only makes sense to give the newsletter a clearer focus for the foreseeable future.
Right now, a considerable chunk of my work away from this newsletter involves pitching stories to editors. Just the other day I had a pitch accepted—along the lines of what I discussed in a recent newsletter post—that should appear soon in Global Finance Magazine, where I’ve been doing a lot of work. I’ve included a link to my latest for them—about Chinese EV maker BYD’s European expansion—at the end of today’s post.
I just sent a pitch to another publication about an angle on overtourism that I don’t see discussed much in the news or the public debate. We’ll see what happens with that.
I identify a trend or spot something unusual or undercovered, develop an argument, and propose the commentary and reporting required to turn it into a story. Then—when the pitch is successful—I write it. While it can be frustrating, I genuinely like the challenge of this type of work, which sits mostly in finance.
I want to apply more of that same process to this newsletter.
In many ways, this direction makes almost too much sense given my history.
Nearly 25 years ago, I was formally studying cities and writing about them academically. I never really stopped studying them or thinking about how environments shape the way people live. At the same time, most of my professional writing—whether about investing, finance, or more popular topics—has always been strongest when I combine reporting with a point of view.
This brings those two parts of my work together.
Start with a question. Identify the place where that question becomes visible. Or start with the place and discover interesting questions to answer along the way.
Uncover trends, anomalies, and stories that don’t get any or enough attention, then go out and investigate them—through observation, local reporting, photography, research, and, when the story calls for it, conversations with the people who live with the issue every day.
I’ve already started doing this. But I feel like I’m only at the tip of the iceberg as my writing becomes increasingly a product of living in Europe, not merely being from the United States.
My recent posts about Valencia’s bicycle infrastructure didn’t come from sitting at my desk and deciding to write another argument in favor of bike lanes. They came from riding throughout the city, seeing where the infrastructure works and where it breaks down, following the politics surrounding it, and comparing Valencia’s progress with what I experienced in Barcelona and Paris.
The same applies to my writing about weak ties, public space, belonging, and the difference between urban inconvenience and urban vitality. The ideas come from research and three decades of thinking about cities, but also from walking out the front door and seeing how they operate in everyday life.
I want Valencia to remain the base for this work.
But I also want to expand the reporting ground.
Throughout Spain. Across Europe. And, eventually, much farther away.
Not to arrive in a city, walk around for three days, tell you where I ate, and move on to the next destination. There are already plenty of people doing some version of that—often very well.
I want to arrive with questions, or enter with blank slate and them come to the surface.
Here’s how people—locals, tourists, government officials—frame an issue, but here’s what’s behind their rhetoric and what it actually looks and feels like on the ground.
Here’s where and why a place seems to be doing everything right—or wrong—and how it can improve. And how can other places learn from these real-time and real-life experiments?
I want to do it in Europe, but eventually I want to considerably expand my scope.
For example, I can’t stop thinking about these videos I see of Americans living in China. They talk about the quality of life upgrade the way I do in relation to living in Valencia. But I can’t shake the pull of wanting to investigate exactly how your life could feel so much better in China, a country many Americans have been conditioned to believe is evil and a terrible place to live. Where do the rhetoric and reality meet—from both geopolitical and fine-grained local perspectives?
These aren’t firm itineraries or promises that I’ll be everywhere next year. They’re examples of the places and questions that increasingly occupy my mind—and of the direction I want this publication to take.
Travel will be part of it because changing environments sharpens your perspective.
But travel isn’t the product.
The reporting, observations, photographs, conversations, and essays that come out of it are the product.
Ideally, I’ll do this differently from the way a journalist typically approaches a place on assignment. I don’t want to fly in, collect a few quotes, confirm an argument, file a story, and leave.
I want to spend enough time somewhere to establish at least the beginnings of a routine.
The goal isn’t to arrive with a conclusion and use a city as scenery.
It’s to arrive with a question or arrive with very little and let the place complicate the answers to what I was curious about or didn’t even know was a thing in the first place.
Paid subscriptions help create the time and freedom required to plan and to work this way. To research before arriving, report while I’m there, and think and write after returning. To follow an idea beyond a single post and produce a body of work that connects what happens in one place with the choices people accept as inevitable somewhere else.
One-time contributions can help move individual projects forward, and I’m incredibly grateful for them. But ongoing monthly and annual subscriptions are what can make this reporting a consistent part of my work rather than something I have to fit around everything else. That continuing support is what gives an independent publication a foundation to plan from—not only for the next post, but for the next year.
This is where the newsletter’s various iterations come together.
The Never Retire idea was always about structuring a life that doesn’t require escaping from it. Moving to Spain was the biggest step my wife and I took toward building that life. Writing about Spain helped me understand what changing environments reveals—not only about the place you enter, but the one you left and the assumptions you carried from it.
Now I want to take that method farther.
Spain remains the base. Valencia continues to be home, where I’m observing, participating, and developing many of these ideas. But the publication can use other cities as reporting grounds for understanding how environments shape behavior, what societies believe they owe one another, what they think their governments owe them, and why one place accepts as unavoidable what another has already proven can be changed.
That’s what I’m asking readers to help me build—not a travel newsletter, but an independently reported publication that uses places to explore the systems and question the assumptions shaping everyday life.
Some of these reporting ambitions can happen relatively soon. Others will require more time, planning, and support.
But the goal is the same.
I don’t want to see more of the world simply for the sake of seeing it.
I want to return with better ways of understanding the one we already inhabit and often struggle to make sense of.




“Ask a better question.” As a lifetime subscriber, I find that approach true from “Never Retire” to following your writing on this new adventure—so do the systems you explore exist because they “answered” a particular question at a particular time—or are the “questions” themselves universal? But the answers depend on the system? ☕️