In the same week, I emailed one person to say Poughkeepsie was my preferred market and another to say Amanda and I were looking to move West.
Both were true.
We had just returned from Switzerland. Wahoo was full again with product work, hiring conversations, software updates, and questions about how we were building RGT. Apply was still moving in the margins. I was back in New York, but I was also looking at several different versions of what might come next.
The Hudson Valley version started with a direct note to the broker who had helped me before. I wanted to acquire a few properties and start building a rental portfolio. Poughkeepsie was the first choice. If something promising appeared in Newburgh, I would look there too.
This was not a theoretical interest in real estate. Amanda and I already knew what an old Poughkeepsie house could demand. We had spent years rehabbing a damaged Victorian there and then lived in it with friends and family during COVID. I knew the work could get messy. I still wanted to explore doing more of it.
The house had taught us all the obvious lessons the expensive way. Old buildings contain problems inside other problems. A small repair becomes a wall. The wall becomes wiring. The wiring becomes a conversation about whether anything in the room has been done correctly since 1890.
It was also one of the most satisfying things I had worked on.
Software can move fast because so much of it is invisible. A house refuses that abstraction. The floor is either level or it is not. The pipe leaks or it does not. Somebody has to carry the material into the building and make the thing work.
I liked that.
The rental idea was a way to turn the experience into something repeatable. Not a giant real-estate empire. A few properties in a market I understood. Buy carefully. Fix what needs fixing. Make places people actually want to live in. Learn whether the operating model works before getting carried away.
I was already a little carried away.
The West version arrived through an introduction a few days later. I wrote that after 13 years in New York City, Amanda and I were considering a move. I described my background in the simplest terms I could: product and technology at high-growth companies.
Moving West had its own logic. I had spent years flying back and forth for work. The companies, weather, outdoors, and pace all made a case. It would be a clean break and a new professional chapter.
It would also mean leaving New York, which has a way of sounding easier when you are not standing in it.
There was no grand plan tying these together. One direction was more houses in a place we already knew. The other was a possible new city and a new professional chapter. Meanwhile, the very practical file in Drive was temporary registration paperwork for my 1999 Chevy Tahoe.
That is probably the most accurate picture of the week. I was thinking about technology work, a rental portfolio, moving across the country, and whether the old truck had the right paperwork.
I do this a lot. I explore several futures at once and wait to see which one gets more real. It can look indecisive from the outside. To me it feels like building options.
The trick is knowing when an option deserves actual work and when it is only fun to think about.
Poughkeepsie deserved a note to the broker. The West deserved a conversation. Neither one deserved a moving truck yet.
New York still had a strong case. Friends. Running. Work. The density of people and ideas. The fact that you can leave one meeting, walk ten blocks, and accidentally find the next thing you care about.
That night I took one photo at Lincoln Center. New York was still home. I was not ready to pick one direction yet.
Poughkeepsie or West?
For now, neither. Keep looking.