Blogging since 1998. By David Wertheimer

Month: December 2025

The Year in Cities 2025

Many of the newsletters I read are publishing “best of 2025” wrap-ups where they rattle off the posts that either got the most attention or made their authors most proud. Which is nice and all, but I saw that content already. I guess the digital cadence means it’s better to do the newsletter version of a clip show than just not hit send for a week?

Here at the Ideapad, where there’s never been a post schedule, one thing that hits like clockwork is the Year in Cities recap. Herewith, the twenty-first edition. All the places I went and spent the night. A procession of weddings and ballparks, pretty much.

As with last year, the commitment to sleeping over eliminates some of the nuance: we went from Pittsburgh back to New York by way of Baltimore, because baseball. And that Kentucky stay was over the river from Cincinnati, a pedestrian bridge away from a Reds game, which was the point of our visit. But we’ll stick with the system, which allowed us spend a night in Kentucky, after all.

Repeat visits are noted with an asterisk.

New York *
Coral Gables, FL
Chicago, IL *
Palm Beach Gardens, FL *
Cleveland, OH *
Detroit, MI
Newport, KY
Pittsburgh, PA
Edgartown, MA *
Montecito, CA

On economics

I took a microeconomics class my first semester of college as an undergraduate. It was part of the core curriculum requirements. I found it incredibly boring. My distaste for it was part of the motivation for me to declare a major in English instead of something pre-business.

More than a decade later, I took a macroeconomics class, midway through my graduate coursework in business school. I found it fascinating and took to it easily. I enjoyed it so much that I went to my professor and asked him if it was too late to switch careers.

My professor leveled with me, and said that most professional economists pursue master’s and doctorate degrees straight out of undergrad, and my desire to pivot after nearly a decade in digital media was probably not the best course of action. So I stuck with the internet, but I never lost my taste for macroeconomics. I’ve kept up with the sector over the years, and I still think about whether I’d be good as an economist, or in a similar field, where I am trying to understand broader trends and figure out the near future (not unlike my many years in UX).

So when I discovered the Narcissist Forecasting Contest a few years ago, I was an instant yes. Adam Braff, who owns a data consultancy, runs a fun annual game that poses 25 probabilistic questions about the year ahead, predicted by 150 or so professional and armchair analysts. It’s equal parts macroeconomics, social science, political science and gut feelings.

This is the tenth year of the contest and the fourth year I’ve played. My first year, I was in over my head, but my second year I improbably finished in eleventh place. That was enough to make me a participant for life, and also a little confused—who was I to be any good at this?

I fell back to the middle of the pack in 2024, but in 2025 I combined research, contemplation, existing knowledge, and (mostly) my gut. Unexpectedly, I began seeing my name in the top ten of the standings every time Braff wrote about the contest. I had a near spit-take when my name showed up in his August update because I was in the lead—and then I held on to win the forecast as of late last night.

I have had fun morning reflecting on winning. I am irrationally proud of my victory. I’m also wondering again if I can do anything with the latent observational and predictive skills the forecast has awakened. Should I try my hand on Polymarket? Check in with my macro professor?

I actually took the time to talk to Braff about forecasting as a career angle; he works in big data, so it’s a parallel pursuit for him, too. I’ll probably stay the course with my professional life for now. But it’s fun to consider that my hunch in 2004 was a pretty good one.

Ideapad © 1998–2026 David Wertheimer. All rights reserved.