CAREFUL 2019 Revision.png


  1. Whirlpool

  2. Everybody Wins

  3. Careful in the Future

  4. Simple Twist of Fate

  5. Go First

  6. White Leather

  7. Rabbit, Run

  8. I Didn’t Save You

  9. Weaponized

All songs: James O’Brien except “Simple Twist of Fate” (Bob Dylan)

Performed/Recorded: James O’Brien

Mixed/Mastered: James O’Brien and Matt Girard (Transference Audio)



I did not think I would travel this way again. 


The afternoon of April 14, 2018, just after the United States flew explosives into targets across parts of Syria, a new song leapt to mind. “Everybody Wins” was recorded, mixed, mastered, and released by April 15. 

At the time, it seemed as if that was that.


Back in the winter of 2018, a guy I know who makes a living as a songwriter chopped away part of his guitar-playing finger in a snowblower’s auger. His presence in my world, he’s been in it, to one degree or another, since the mid 1990s, is a significant part of how I got into this whole songwriting thing. I was upset. I walked around thinking about it for a while. He went on tour with a guitar player (or a band, one or another) after the accident, hand still healing. 

Listening to him sing one afternoon, a recording on YouTube, my mind jumped at me with new lines over the music of the song he was performing. I wrote out “Careful in the Future” pretty much all at once, in about an hour, maybe a little less or a little more. I recorded it at home, figuring here we go, maybe put this out as a single like “Everybody Wins,” and I’ll stick-on a cover song to go with it.

I recorded Dylan’s “Simple Twist of Fate,” which I’d been holding onto since learning it during a little spell of open-stage visits Karaugh and I were making, back in Boston, back around 2010 or so. We’d go into this little Scottish bar and listen to some folks play, and play a couple songs ourselves. I liked the way "Simple Twist" felt in my head, and through my hands, so I recorded it right after “Careful” and that, it seemed, was that. 


Except maybe two songs made a single and three would make an EP, more of a piece.

All these thoughts about mortality, I had this one chorus in my head and I wrote it down and wrote a song around it and it was awful. As I wrestled with the wreck of it, I realized the chords were really the chords of an older song — one I’d written back in the early 2000s. I remembered it all and recorded it: “White Leather”. Once the blockage was cleared, I found the rest of the new song to go with the troubled chorus that started the whole thing. "Go First” was done and I recorded that one, right away.


So, now I had four new recordings, plus “Everybody Wins” — the single from April. I was writing an album.


When I recorded Life Underwater and Church of the Kitchen Sink, the process went pretty much like this: demo a batch of songs. Repeat. Pick some of those songs out of the batch, record them, mix them, sequence them. The albums were born from the material available. Listening back to those two works, they sound, to me, like somewhat coherent collections, but the through-lines get thin.

Sitting in the apartment, earlier this year, 2018, with five new songs, I realized they actually fit together in a certain way, making up approximately half of what I knew could be an eight- or nine-song whole. Here’s how it happened, in the sequence that it occurred.

“Whirlpool”: I’d been listening to Paul Simon; I think it was one of his more recent albums, either So Beautiful or So What or maybe Stranger to Stranger — both being highly worth your time — and his voice just took over and I switched off Apple TV and wrote the song and recorded “Whirlpool”. To my ear, I can hear the simple and direct phrasing, of which Simon is a master, thinking of late-career songs such as “The Afterlife” and “Wristband”. I also understood that this new song of mine needed to be the first track of the new album, and then the sequencing clarified: “Whirlpool” then “Everybody Wins” followed by “Careful” and “Simple”. End of side one. Yes, I think of albums in terms of sides. Old man that I am. Side two was always going to be “Go First” and then “White Leather”. I’d need two or three more songs to finish what I’d started. I decided the approach had to be this — write them in sequence, each song responding to what came before it. And so it went.

“Rabbit, Run”: The criminal-in-a-desert vibes of “White Leather” got me thinking about another song from back in the day, a favorite of mine, “Cold Blood” (it’s on A Bothersome Injuries Forty, Vol. 2). And that got me playing around with similar chords, and then the pattern of “Rabbit, Run” appeared, and I’m not sure why the Updike title became the hook and chorus, but it did. The words fell into place based on the specific feeling that the music created. I’m not certain how often I’ve written a song based on the vibe of the music — if I remember it right, I’ve typically grabbed some chords to support a lyric. “Rabbit, Run” liberated me on this point. It springs from the kind of sounds — echoey and dark — that became the setting and the miniature world that I wanted to build throughout Careful in the Future.

“I Didn’t Save You”: It was pouring in Manhattan on my way home from downtown and I was stuck in the rain without an umbrella. You dodge from awning to awning in such a situation, or at least I did, that day. Crossing Amsterdam, the first line of the song materialized in my mind and I held onto it, no longer looking for shelter and running through the water, into my building and up, getting the whole thing out as quick as I could. When I sang it, that day, I thought of the way Morrissey sings, and Sinatra. I worked on the approach to achieve a kind of phrasing and breath-control that opened up within the spare space of the words and chords. Across the whole of the album, I explored reverb and delay and deep, dark, cave-echo tones that sang back to me as I performed them. “I Didn’t Save You” represents those elements.

“Weaponized”: I thought that I was done with Careful in the Future when I was done with “I Didn’t Save You”. It made for a short little album, but you could hear that the end of that song served as the end of a sequence. Yet, despite that, the phrase “we’re weaponized” came to me at some point in mid-May. It might have been around the time of the shooting at Santa Fe High School. I was also on a tear, listening to Leonard Cohen albums. The idea of one more song, one that would round out Careful. seemed right, a way to bring the album back to the external world, out of the dimly lit corners of dream and interior to which “Rabbit, Run” and “I Didn’t Save You” took it … and so “Weaponized.” Almost right away, I believe, it seemed to me that the song would serve as a follow-up to “Colorado”, which I wrote in the months following the shooting at Columbine High School, back in 1999. And so it is, and so here we are, still singing about the same horrors, nineteen years on. I hope this one is the last one of its kind that I ever need to write.

James O’Brien — Life Underwater Music

(15 August 2018)