Painful But Worth It.

What if someone told you could live exactly how you wanted to? You wouldn’t have to go to work doing something you hated, or that violated some essential operating principle you once carried around in your child heart. What if you could — from your waking moment until you shut your eyes to sleep — make the hours of your day most closely resemble an ideal you create yourself?

Name it, says the genie, and it will be so. Well what is it?

It’s a question I think about a lot. Think isn’t the right word. I’m always pushing the malleable hours of my life toward some better version of themselves. This sounds really empowering as I read it right now. Wow this guy has got it together!

The truth is that I am constantly in error, falling short, heading in a direction I thought was right but isn’t quite. Going hard for awhile and then making, if not a U-Turn, a hard right.

But still, the ideal. To imagine something better and to steer in that direction, knowing you’ll miss it but hoping you’ll get closer. What a privilege it is to even imagine a life better than the one you’re living.

That’s what I’m asking you to do. Imagine.

You can stop reading now and get started. I think it would be a really great way for you to spend a Sunday morning. It will change your whole week. All the actionable tasks that come at you like descending Tetris pieces you can slot in in a slightly different way if you want to, a way that moves you toward an ideal you’ve created yourself.

You don’t even have to act on it if you don’t want. Just to imagine is enough for now.

But if you do take action — oh man! It can be painful. In fact I think the pain is inevitable. Because the world doesn’t really want to change. It wants to maintain course. Want isn’t the right word. The world (feel free to swap out world for life society culture) doesn’t know what it wants. It’s just moving along like it always has, nudged this direction by the individual and collective wills of everyone who came before you. Like a slow but an enormous ship — one that's really, really hard to turn, even slightly. Maybe it’s headed for an iceberg, maybe not. Either way, hard to sway.

The more you want something the more painful it is not to get it. So one solution is to want that thing less (wisdom there, take note). Corollary wisdom is to ask yourself why you want the thing so bad.

Both good exercises, but maybe save those ones for later. This week is for the dreamer.

When you try to implement a change in your circumstances, you will probably fail, but you will learn something, and also, even though you can’t see it in the moment, you will have succeeded — there is no doubt in this — in bringing that imagined, hoped for, elusive ideal a little closer.

Let me tell you why I putting these words to you. I wouldn’t do it if I hadn't put them to myself first.

I spent the last 8 weeks releasing a song. That sounds ridiculous to say. It’s like saying I spent 8 weeks starting a car. Don’t you just start the car and go? Release the song and get back to your life?

The answer is yes, but then no will listen to the song you worked on for so long. There are few things in this world you can be more sure of than the instant death of unmarketed art.

If one of the biggest challenges facing any artist dreamer dancer writer ship-nudger is the getting of any attention for your efforts whatsoever, much of the life of the indie creative in 2025 has come to resemble the self-checkout line. You will scan your own groceries thank you please. And if you are making something that can be transmitted digitally (and god help you if you’re not), the only thing that stands between you and some modicum of positive notoriety is your ability to effectively arrange the pixels on someone else’s phone in a way that makes them continue to watch you do it.

So the last 8 weeks I spent mostly manning my own marketing department, a field of human endeavor I find both tasteful and difficult. Maybe you can relate.

Nonetheless I did research on best practices for releasing music in 2025. I looked at all the beautiful children glowing in the prime of their effortless twenties and took from them what I could. I made, as much as could be done with my limited resources and time, the effort my own.

To that end I made some thirty or so SFVs (which is industry speak for Short Form Videos, but you can call them by their christian names, TikToks). Every other week, on Tuesday, I released some larger piece of content, be it a lyric video, and official video, an acoustic video. I worked hard on these things and even kind of enjoyed the effort, as I am one of those suspicious people who enjoy effort for its own sake.

Was the release a success?

Hard to say.

Some numbers moved.

You ask: did they move a little or a lot?

I answer: compared to what?

They moved a medium amount is probably the best answer.

Not enough, never enough, is the correct growth-mindest way to look at it. You can always do better. But the mental health mindset, the human being mindset is, they moved exactly the right amount.

But that’s not what I wanted to talk about anyway. The numbers. If you’re still reading you understand firsthand the futility of tethering your self-worth to your number of monthly listeners on Spotify. And I’m pleased to announce, I don’t. Fuck the numbers, I’m in the meaning business.

I am trying to make the world, insofar as I am able, resemble the personal ideal I have set before it.

So the question to ask is, according to said imagined ideal, did I spent my professional time in a manner the brought it closer to reality? Was posting a video on TikTok every other day really the way I want to spend my life?

No, of course not.

BUT

I am willing to do something I don’t love if it bears fruit worth eating.

The important thing is, I didn’t hate making the videos. They’re a challenge in their way. A game if you will. A little game to see if you can put something in the world that keeps someone’s attention, someone who will swipe away at their first nanosecond of disinterest. A tough game, sure, but still just a game. Don’t take it too seriously is my advice.

But what are these videos in service to? Because they were expensive, in terms of the time I spent making them, time I could spend working on the kind of art I feel I am called to make.

A critical question, because, starting Tuesday, I’m releasing my next song, and am about to do it all over again. A little different this time, learning what I have, but still eight weeks and a lot of late nights and early mornings punching the clock in the lonely self-promo department.

Editor’s note: The new song is called This Love and it would mean a lot to me if you would presave it on Spotify or wherever you listen to music, so you can listen to it on Tuesday when it comes out. Read a little more about it here.

Back to the ideal. The question I put to you I put to me.

My personal ideal is to have a career where I regularly create and host events where people gather together in a physical space to share something artful, something that makes us all feel more human. That is my life’s purpose. Everything I do is in service to that ideal.

I am willing to spend a lot of time on my phone if it means I convince you to get in your car and come to an event I believe will be worthy of you. I love being together with other creative people, or people who love art, and in my world, that setting tends to be a quiet one. I prefer my music to have a lot of space in it. And after forty-some years on planet earth I still can’t decide what I like more, books or music.

If you think this note is a plug, I guess it kind of is. Next Sunday I’m trying out my ideal in the town where I live (Nashville). Most of you probably couldn’t attend if you wanted to, but some of you can and you to whom I write. Randa and I are inviting you to our studio in East Nashville to listen to some very gifted people share their talent. On a Sunday afternoon and for a cause greater than ourselves.

East of Eden is the name we gave it, and each one of these guests do what they do at the highest level (yes I’m on the bill as well but I leave it to you whether I can rightfully count myself among such creative juggernauts). It’s a benefit for a program dear to Randa and I — providing assistance to low-income single mothers with high-risk pregnancies), so, a worthy cause. The tickets are $25 and all proceeds go to said benefit. Here is the link for more info. You can use promo code APPLE to save 15%.

Mair, who headlines, inspired the idea for East of Eden. She was a guest on the podcast in December and we were talking about the way the music business works, and how toxic it is for the musicians: the late nights, the endless travel, the road food. It’s not good! She imagined a gig that happened not at a bar (though admittedly we will have beer and wine available) but at some place dedicated to the enjoyment of music for performer and audience alike, one that happened in a pleasant atmosphere, during a gentle hour of the day. Mair is perfect artist for this gentle hour.

Adam Ross will read from his latest book, Playworld, presently enjoying enormous success in the lit world, with rave reviews from everyone from the New York Times Book Review to the Washington Post to Emily Ratajkowski. I loved Adam’s book and — as I caught him on the podcast a few days before Playworld’s release and the resulting media frenzy — I’ll be curious to hear his thoughts about the experience of being in the spotlight after so many years working alone.

Anthony da Costa will share some songs of his own making. At 34 he’s been in the industry for almost 20 years. He is a wunderkind of virtuosity and a musician’s musician. He’s played and/or written songs with Sara Jarosz, Madison Cunningham, David Wax Museum, Katie Pruitt and in addition to producing my latest song Meet Me at the End of the World, he teamed up with me to play the live version of the same, which you will like if you like the Milk Carton Kids.

Randa and I caught Anthony at a house concert last month and she’ll back me up when I say his performance was spellbinding.

I’m currently reading Sheba Karim’s The Marvelous Mirza Girls, a coming-of-age tale about a young Indian American woman who travels with her mother to New Delhi for the first time, to assuage her grief at the loss of a beloved aunt. It’s a page-turner and, for this Idaho kid picked from the potato patch, a fascinating glimpse into a culture that couldn’t be different than the one I grew up in. Ms Karim’s book Miriam Sharma Hits the Road was an NPR Best Book of the Year, and her feature-length script, Blighted, was a finalist for the 2022 Austin Film Festival. She is currently a writer-in-residence at Vanderbilt University.

This is going to be cool. I hope you’ll be able to make it. Tickets and info.

Okay I just checked and baby and mama are still sleeping.

So I was talking with Randa on the couch last night, reflecting on the past two months, basically thinking through some of the things I described above.

She listened to me pick my way through my feelings while we shared a piece of carrot cake.

I was midway through one of my trademark run-on sentences. Suddenly she poked me with a sticky fork.

“Yes, but what was the most fun?”

“Fun?” I asked.

“The funnest thing, of all the things you did.”

Sometimes you just need a poke. I didn’t even have to think about the answer.

The most fun I had was recording this song, which I did over the last two weeks, here and there between other things. Basically there’s an artist I like — Bon Iver — who released an album last month. There are a lot of good songs on it, but there was one I heard where I just felt like crying while I was listening to it, a song about choosing to move forward, choosing to do something different, to accept your life as it is and not wallow in whatever you see in it that’s supposedly ‘missing.’

I have a kind of categorical aversion to learning a cover song that doesn’t have personal meaning to me, but since this one did, and because it had a melodic thing that was interesting to play on piano, and because it’s in my favorite key which is Eb, I decided to see if I could do it justice.

I played piano, bass, acoustic guitar, made a drum kit out of my old merch box, played percussion and lest you think I’m some kind of pretentious asshole, put a bit of fiddle on there, which I barely know how to play. Randa got in there and added some harmonies to the bridge.

My friend Jared Hammond helped me film the thing and I edited it together. Maybe you’ll enjoy it.