I’m genuinely surprised by the response to my first newsletter and post on LinkedIn. I thought maybe I’d hear from a few friends. Instead, thousands of people have seen it, and hundreds have engaged with it. Welcome aboard to everyone who subscribed. I hope you find value or entertainment in what I have to say.

As promised, here’s the first update. You can read the backstory here.

A Fantasy Metro Map for Portland (Maine)

I recently spent three weeks in Montreal. Visiting in mid-March is probably not advisable as it sits between the charming snowy winter and the lush green summer, in that middle period when snowbanks melt, leaving behind cigarettes, trash, and dog poop. You can sometimes taste salt in the air when a bus passes, kicking up a winter’s worth of ice prevention. Montreal in March is like a bear emerging from hibernation—a bit ragged and raw, but undeniably impressive.

It’s a vibrant city with great neighborhoods, friendly people, and a great metro system. I developed a transit crush for the Montreal metro. Each weekend, Renee and I would buy the unlimited weekend pass and plan our weekend around the various routes and stations.

There’s a kind of magic to cities with real transit systems. Subways and trains invite curiosity. Each stop feels like stepping into a new micro-culture, a shift in energy, style, and sometimes even language. Without the distraction of driving, you notice more. You see, feel, and smell the city—for better or worse.

Part of what fuels that sense of wonder is the maps. I’ve gushed about them before, writing that “maps are a portal to a future memory.” But I’d never tried making one, so I challenged myself to design a subway map for my hometown, Portland, Maine.

I designed a system that I thought would serve the city’s needs, but also included fun elements, like stops at the beach. Along the way, I wrestled with questions like: Why does my map look so weird? What’s a reasonable distance for someone to walk? How do you pick a name that captures a neighborhood?

What did I learn from the experience?

• I probably don’t have a future as a cartographer
• Representing complex information is a challenge
• There’s a thriving community of transit map enthusiasts and even a website that encourages people to create and share maps for their city. I love this. We should all be imagining/designing our future.
• Somewhere inside of me is a desire to work on landscape-scale projects

Tinkering with AI

AI is everywhere now. I’ve used AI daily for a few years, mostly in trivial ways. Like a lot of people, I feel conflicted. I can envision a dark future, where a portion of humanity’s sense of purpose is outsourced. I can also see a world where AI helps us build meaningful things, like AI for nature, which I wrote about recently.

I put aside my inner Wendell Berry for a day and decided to build something. Specifically, I wanted to try out Replit, trending for its AI-assisted “vibe coding”. For the less technical (hi Mom), Replit lets you chat with an AI that builds software for you—no coding required.

My first project was in response to a text from a friend at 9 pm on Wednesday.

We’re in a fantasy surf league together (don’t ask), and he wanted access to historical surf data that’s tough to find online. I’ve done some web scraping before, so I knew the approach. This time, I decided to try it with Replit and AI. The result was impressive (and totally overkill). With some coaxing, it spun up a complete front-end and a web crawler that pulled thousands of data rows into a downloadable CSV (whoa).

While the surf project was ridiculous, it resembles the kind of AI use I’m drawn to—building small tools that solve real problems, with AI augmenting my thinking rather than replacing it.

That said, it’s not all roses. I was struck by how much power the AI agent had inside my codebase. It had free rein to make changes, which feels a little alarming if you don’t fully understand what it’s doing.

Later that same day, I built a script to write event summaries for my Maine Outdoor newsletter. I used to enjoy writing them, especially in the early days—but after 80 issues, it’s started to feel formulaic. I’m torn. Does using AI here free up creative energy, or is it just me being lazy? I’m still figuring that out.

A Poem about the Global Economy

I wasn’t planning on it, but in the spirit of creating freely, I wrote a poem in response to tariffs and market trends. It came out pretty dark, but in a deadpan sort of way, which I like.

—

• I had coffee with my good friend James. I blurted out idea after idea, most of them technical. Then, I paused and said, “I also want to try to make clam chowder.” We both laughed.
• When feeling down, I often go to Beau Miles’ YouTube channel. His videos are playful and soulful in a way that speaks to me. I’ll always reserve a seat for him on my spiritual board of advisors.

The internet tells me things are going badly today
I saw a Tweet with a lot of red charts
Red is how we know the economy is doing poorly
The word we’ve created to describe the purpose of humans

The president, slightly red himself
Decided others weren’t playing the game fairly
The rules of which his forefathers defined
Loosely enough to shift without guilt

I check my phone for red
And find it coloring multiple accounts
Which is stressful
Because I traded years of my life to fill them

So I could convert those numbers into real things
Like flying in a machine powered by dinosaur juice
To work remotely from a country
where my numbers are somehow worth more

And I can eat healthy lunches
Of things grown from the ground
And occasionally the meat of less important beings
For the price of writing good emails and asking timely questions

I tuck away some of my numbers in a special space
Designed by the same institution now turning them red
Shielding them from those who might need them
Or the greedy hand of an inefficient system
Depending on the opinions of those I don’t ask

I’m told my numbers will multiply like rabbits
That 8% annual compounding will lead to abundance
At a future point where it’s acceptable to rest

And trade past time for current goods
That come from places where people don’t seem to know
About the machine that turns numbers into more numbers

Where the future is also uncertain,
But the stress comes from hunger
From timing crops to the rainy season,
Rather than timing the dip

—--

Writing poetry feels good. It matches how I experience the world—through vignettes and small connective moments. It’s abstract enough that my inner critic stays quiet during the process. I’ll keep exploring poetry, short stories, and fiction alongside my unexpectedly successful LinkedIn thought boi pieces.

Maps as a Catalyst

I could probably devote this entire month to creating maps and not run out of ideas because gawd damn I love maps.

I want to spend more time making web maps, but I’m still pretty new to the tech. So I picked a simple practice project: a tool that splits Maine into small squares and shows where I’ve had outdoor adventures. Two things excited me:

1. Taking time to reminisce on where I’ve been
2. Finding the “blank spots” for future adventures

I gave it a name and style that reflects my interests in both tech and the outdoors. It’s inspired by GitHub commit charts, which show how often developers contribute to a codebase ( a point of pride for many developers). The project is a playful nudge to spend more time outside, away from screens.

The app’s pretty simple. One view lets me “claim” the squares I’ve visited, and another shows a public version of the map. I’m surprised by how much of the state I haven’t explored and am compelled to visit some of those empty spaces.

https://git-outside-max.replit.app/

The grid-and-claim concept could extend to collective action projects, like outdoor cleanups. I’m thinking of cloning this project and using it as a crowdsourced trash pickup tool for Earth Day. People could open the map and claim an empty square, like a remix of common “adopt a mile” programs. A simple map with a compelling tagline like “Turn Portland Green” could be powerful.

This map expresses a bigger idea of using technology to inspire action. Over the past decade, I’ve worked with over 100 companies on branding, websites, and digital products. I’m learning to recognize what lights me up and what leaves me cold (sorry crypto, sorry fintech, sorry cybersecurity). For me, it’s less about the application (technology) and more about the application (the problem it solves).

I’m drawn to technology with a tight IRL connection, which I wrote about recently in my conditions for good work. I want to build things that shape physical places and communities in positive, tangible ways.

Everything Else

Here are a few observations from the past week that don’t fall neatly into the sections above.

• I met an entrepreneur at a non-profit event this week who told me his philosophy is to “be drawn, not driven”. I like that.
• A Walk is a Tool and a Platform - A wonderful essay and presentation about using walking as a platform for creativity.
• “The more complex the product or process, the wider the field for the trained hoodwinker.” A great line from a lesser-known Aldo Leopold essay titled Land Use and Democracy