_Yeehaw!

In March, without quite planning it, eight posts arranged themselves into something beautiful: a complete roadmap for how AI adoption actually works. (It was definitely in my head, cool how it all came out in the end!)

The throughline is this: it starts with YOU before it starts with your organization. Your individual fluency (and your team’s individual fluency!) has to come first. Only then does organizational adoption have a chance. Skipping the individual journey is a recipe for wondering why nobody is using AI while you watch your peers fly ahead. 

Next month, we’re shifting gears. I've been running workshops with real transit leaders across North America, and the stories coming out of those rooms are too good to keep to myself (imagine $15k saved in less than a week). In April I'll be writing about what I'm seeing when people like you actually walk this path. (By the way, do you want to listen to them tell their stories in a podcast? YES 🤩  NO 😴 )

But first — here's your March Roundup!

The 5 Phases of AI (And Why You Can't Skip Ahead) is the piece that crystallized everything March was building toward. There's a very real future where you walk into your office, open a chat, and ask "what's my most dangerous bus route?" — and AI looks across your CAD/AVL data, your incident reports, your customer complaints, and gives you a real answer in minutes. That's Phase 5. But the path there has an order of operations, and the line between individual leadership and organizational leadership is everything. 

⚡ How to Turn the 💡 On is your organizational playbook for AI adoption that actually works. I introduce the AI Task Force: a small, cross-departmental, cross-level group of your most eager experimenters who meet regularly and spread adoption by modeling it themselves. I call them the electric current — when leadership and staff connect their circuits, the lights turn on.

These are the posts about building individual AI fluency — Phases 1 through 3 of the AI Journey.

My Favorite Threesome makes the case for using multiple AI tools instead of committing to just one. Claude is the cofounder, Gemini is the PhD student, ChatGPT is the bro. The Magic of Deep Research is the practical deep-dive into the tool that surprises people most in my workshops. The Most Comfortable Interview Ever teaches you a six-word prompt that works immediately. It's basically Oprah, except nobody's watching and you can do it in your pajamas. 

Meanwhile, The Art of Transit is the philosophical heart of the month. Every agency has two kinds of work: science and art. AI is getting very good at the science. Which means the most valuable thing about you is what you can sense. And if all of that sounds too serious — No Insight Today, Just Cake is your reminder that play is what makes people want to keep learning in the first place. 

Once enough individuals have built their fluency, your organization is ready for Phases 4 and 5. But there's a reason this section comes second. URGENT is the shortest piece I've written this month and the one that needed the fewest words. What separates agencies that survive from those that don't? Ridership per public dollar spent. AI is the unlock. If you haven't read How to Turn the 💡 On and The 5 Phases yet, start there — they're the playbook for the great leap forward.

I'm hitting the road this month. If you're at any of these, come say hi — or better yet, come learn.

April 15 — Toronto, ON: Practical AI: A Hands-On Workshop for Transportation Leaders at OTE 2026, in partnership with the Ontario Public Transit Association. Three hours, bring your laptop, leave with real skills and a completed analysis you built from scratch. If you're in Ontario, this one's for you. $95 — register here.

April 23 — Virtual: Practical AI for Transit Applications webinar with CALACT.

April 27–29 — Dallas, TX: Two sessions, including a 3-hour deep-dive workshop training, at the TACAA (Texas Association of Community Action Agencies) annual conference.

April 30 – May 1 — Lubbock, TX: And VERY exciting to me: running another 3-hour AI workshop for the new way to select transit technology. Even MORE exciting, I’ll be leading the closing session for Texas’s transit leaders outlining the road forward of the workforce in the AI era. If you’re in or near Texas, you can’t miss this (or the big party at the football stadium).

We've tripled since I started this in late January. It’s still just me doing all this (although I’ve started hiring!). But I know there are a lot more people who will gain value than the 150 of you reading this. 

If one piece above made you go “huh” and think of someone,  please forward this to them. Just one person. That's how we shatter more glass ceilings.

I’ll see you in Ontario. Or Texas. Or Montreal. Or Mexico City. Or online… or on the subscriber list! 😄

TransitGPT is where I share practical AI insights for transit leaders. Subscribe if this resonates or forward to a colleague who needs it. And hit reply — I read everything.

Go shatter your glass ceiling.