This is the seventh in a weekly series on my DC sabbatical (Sep 1 → Nov 30, 2026). Catch up on earlier posts if you missed them, and join my mailing list for future posts.
Most mornings this week started on the stoop outside the rowhome I am living in, coffee and book in tow. Neighbors walk past on their way to the bus stop. Dogs stop to inspect the bushes. People nod, say good morning, and acknowledge each other as part of the same community. And while I am sitting there, I am also keeping an eye on the street, which makes the block a little safer for everyone.
It is a small thing, but it is one of the biggest benefits of density. When people live close together, they get endless natural chances to run into each other. Transit does the same thing. It takes people from completely different walks of life and puts them in the same metal container for twenty minutes. Without denser neighborhoods and good transit, we will keep drifting further apart, and the further apart we get, the more anxious we become about talking to each other at all.
That anxiety has been on my mind, because talking to strangers is a skill I really want to get better at. I think most of us want this to some degree. It is no fun going through life pretending not to see every person you pass on the street. I do feel a difference between DC and Cincinnati here, and there is more of a barrier to striking up a conversation with someone on the sidewalk. But this week handed me plenty of chances to practice.
On Thursday night I went to the kickoff of DC Abundance, a new organization bringing together policymakers, think tank folks, and advocates to simplify government and make it easier to build infrastructure, fund schools, and push science forward. Derek Thompson, co-author of Abundance, shared his thinking and took questions from a packed crowd. Happy hours like this are usually my thing. I am a social guy and I love meeting new people. But there is still a barrier to entry when you walk into a room where you know basically nobody. Luckily, Jerome was in town from Baltimore, so I had a buddy, and as the night went on I found myself meeting more and more new people.
One of the best of those conversations was with Allister, who now serves on the DC State Board of Education. We talked about abundance, but also about ambition, mindfulness, and wanting to make our cities better. Allister was born and raised in DC’s Chinatown and has watched his neighborhood change dramatically over his lifetime, becoming less and less affordable along the way. He pointed out that DC now spends around $52,000 per student per year while results keep getting worse, and that a striking amount of the district’s money goes to lawsuits. That sounded familiar. Back in week three at the STB’s Passenger Rail Advisory Committee meeting, I heard about transit agencies now paying for $300 to $500 million insurance policies to protect themselves from predatory lawsuits. It seems to be a problem across industries.
The second came from a Hinge date. No, I am not counting my date as a stranger. I mean the folks at the table next to us, Betty and Christian, who we ended up chatting with. When my date had to head out to another commitment, I stayed and talked with them for the rest of the evening. They had met each other at the DNC, where Christian leads the graphic design team. Their energy was contagious, and I hope to see them again.
Saturday started with a run with my friend India, which was lovely, if very hilly. Then came a unique event that I had stumbled across on Partiful: an “Anthony Bourdain Meet Cute.” The idea was simple. Bring a snack to a local park and meet strangers. At this point in my DC journey, I could not have asked for a better event. I spent the hour beforehand reading in Malcolm X Park, which was incredibly peaceful with the water feature running. Then hundreds of people showed up, and I had a great time meeting new folks and hopefully a few new friends. It goes to show how much people are craving connection, even when they are stressed about how they are perceived in this crazy world.
Don’t worry, I did some train stuff this week too. I spoke with someone who will likely become AAO’s new pro bono counsel, which would be a huge help for a volunteer organization growing as fast as ours. I also called my uncle Andrew, who has been finding success with his startup, to get his take on how to pitch an idea well. I look forward to getting more of his advice, and hopefully finding some pitching success of my own.
Speaking of the pitch, I kept sharpening the national plan this week, focusing on how AAO can prove the return on investment of doing this work across a national network. The tricky part is that the payoff is speculative. Even if we execute our advocacy perfectly, a single politician can still undo it all (looking at you, John Kasich of 2010). But I think the message is still strong. We have seen a powerful national advocacy push for passenger rail, and we have identified the gap in the statehouses. What we have never had is an unstoppable, diverse, energetic movement in statehouses across the country. If you are interested in seeing the pitch, let me know!
Thanks to an intro from Jerome, I also met with Eric Lundy from TransitCenter. We talked through my plan, and I learned more about what TransitCenter is working toward. Their focus is more on public transit than passenger rail, but they will be a great ally as this work moves forward.
On Wednesday we held our October board meeting, where I unveiled my proposed plan for AAO’s organizational redesign, the product of weeks of work and brainstorming. The team was excited about many of the changes and had good ideas for making it even better. I am also still working on board development and engagement. On a volunteer board, getting everyone on the same call consistently is genuinely hard, and attendance was lighter this month. That has me reflecting on my own leadership, and on how I can accommodate everyone’s needs while making sure people feel inspired and excited to show up and drive the organization forward.
On Thursday I had calls with my mentors Becky and Alex. We talked through what is next, the pitch, and AAO’s organizational design. Both have a tremendous amount of experience, and I feel so lucky to learn from their journeys, both in their careers and personally. I hope I can avoid some of the pains they have already been through, and I will certainly be harnessing their insight.
Mindfulness was a big part of my week too. I finished The Power of Now by Eckhart Tolle, which I found profound and still approachable. I especially enjoyed how often he draws ties between the teachings of Jesus and the teachings of Buddhism. It reminded me of another favorite of mine, The Book of Joy, a series of conversations between the late Archbishop Desmond Tutu and the Dalai Lama. I recommend that one to everybody. I have been trying to find time every day to unplug, step away from my mind, and just be, and this book gave me new strategies and more questions to ponder.
One of the strangers I met this week spent three months at a silent Buddhist monastery in Taiwan in his twenties. When I asked about his biggest takeaway, he said it came from asking himself why he was there. He had become the quietest person in the monastery, the most thorough with his chores, and the strictest in his lifestyle. But he was not the happiest. That stuck with me: working through the tasks of mindfulness just to check the box is not the point. I know I am not yet at the place where I can simply be, but I hope I get there, and this sabbatical is helping.
I am also nearly done with Railroaded by Richard White. The corruption behind the transcontinental railroads is astounding, though not surprising. What upset me more was how often people succeeded simply by being the bigger bully, and how realistic that still feels today. In my time on the Hill, I have noticed that nearly everyone I meet is some level of jaded. I hope I never fully give up on my belief in the goodness of the world. I suspect my strategies will need to evolve as I meet more people, balancing my ethics with what it takes to reach the goals I have in mind. But my goals will always be about improving my community, helping other people, and holding myself to my own standards. With my support system of friends and mentors, I am confident I can stick to that.
Against the three goals from my first post, this week leaned personal, and I think that is exactly what it needed to be. I came to DC hoping to build new relationships with passionate people, and this week I practiced the skill that makes that possible, walking up to people I did not know and saying hello.
For All Aboard Ohio, the redesign is finally in front of the full board, we are close to adding pro bono legal support, and I am thinking hard about how to keep a volunteer board energized as we grow.
For the national network, the pitch keeps getting sharper, and I have new allies and advisors helping me make the case.
Next up is TransportationCamp in New York with Hayden on October 24, and then I’m speaking at the High Speed Rail Alliance conference in Chicago on November 13. In the meantime, you can find me on the stoop most mornings. If you’re ever walking by, say hi!