After Across the Sky, Keller moved across the country to New York City. Thinking about what music to use as his calling card in a new environment, he "made a list of tracks that were the most authentic" and ended up adding one new track to compile Gathering Leaves, which earned him a deal with Alula Records. Then, with new cellist Meena Cho, with whom Keller had a monthly gig at legendary Greenwich Village nightspot Caffe Vivaldi, he made Santiago's Dream, which better integrated his acoustic music with electronics, telling the story of Keller’s move across the country through the eyes of Santiago, the main character in Paulo Coelho’s beloved novella The Alchemist. Meanwhile he had started composing for dance, so when Cho moved back to Chicago, Keller let go of performing and returned his focus to composing and recording, though retaining his focus on acoustic music.
In fact, his next album, 2009's In Absentia, had not a single electronic sound or effect on it. "Because of the very personal nature of that music," Keller explains, "it was very important to me that it be very pure, so it had to be acoustic. It had to be very real and raw and human." Created in response to his father-in-law's unsolved disappearance, In Absentia is a deeply moving album of emotional gravity. Never has the "chamber music" part of Diliberto's characterization of Keller's music been more apt: Keller and his ensemble of strings, English horn, piano, and light percussion lead us through an emotional journey that plays out almost like a film score, with its vivid depictions of various emotional states – "Reflection," "Exhilaration," "Struggle" – at the core of which is the stunning simplicity of "Absence."
Another album soundtracking a significant personal experience followed, of which Keller says, "The Day I Met Myself is the one album in my catalog that I had to make. I had this experience in 1999 – and there were no drugs involved this time – hiking in Wildcat Canyon [in California]. There was a lot of drama going on in my personal life. It was August, and it was warmer than normal in the Bay Area, very cloudy, and there was a huge brush fire in Yosemite, not too far from Berkeley. I thought about turning around, going back, and choosing a different day. But instead, I went farther out into that canyon than I had ever gone and found myself in this very remote part of the park. Being completely alone – I didn't see another soul all day – spending that many hours alone with my own thoughts, I was able to process a lot of what had been going on for me at the time. By the end of the day, the smoke [from the brush fire] had cleared and I felt that in myself the smoke had cleared as well; I had worked out something in my life and felt better about where things were."
"Because of the lingering smoke in the air, there was the most amazing sunset, bright orange, very surreal. So I took that as a metaphor: sometimes in your life things aren't going well, but you've just got to stick with it and eventually things will get better – eventually there will be a beautiful sunset at the end."