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The Rock Band Wilco Changed My Life Once and They’re Trying To Do It Again

Read this reflective narrative about the Wilco band.

Mike is one of Wilco’s biggest fans, and was excited to dive into lead singer Jeff Tweedy’s new book about the creative process called How to Write One Song. He just wasn’t prepared to be so thoroughly persuaded to sit down and actually write one song.

I was bored on a bus ride from my college in Indiana to catch a flight in Chicago when I first heard the song that would change my life.

I remember how I shot up in my seat as the song played, that my focus snapped to after a couple hours of gazing out the window at farms next to the interstate. I remember how it felt inside, the emotional equivalent of the sound “whoa.” The song was “I Am Trying to Break Your Heart” by the band Wilco.

The song opens with some distorted, high-pitch electronic sounds, then scattershot drums, chimes, and a ringing bell thing. Then there are some plunked piano notes and a repeated strummed chord on an acoustic guitar. It’s a solid minute of these bizarre sounds swirling around each other, like the song is forming and emerging out of a primordial ooze.

Then lead singer Jeff Tweedy finally begins to sing, and the first verse was all it took to convince me I was listening to my new favorite song:

I am an American aquarium drinker
I assassin down the avenue
I’m hiding out in the big city blinking
What was I thinking when I let go of you?

Those unexpected combinations of words — not to mention that weird title! — made me listen with more attention than I almost ever give a song. There are five verses — the chorus arrives just once — a sixth verse, then the song collapses back into noise. The runtime is 6:58. I played it again and again.

If this makes the song sound inaccessible and unlistenable, it’s not: “I Am Trying to Break Your Heart” is just three chords with a steady beat and a straightforward melody. You could imagine someone singing a simple folk-style arrangement with just a guitar at a coffee shop. But the sounds down at the foundation of the song take it to a whole other level.

In the lyrics, we hear about a fractured relationship, about self-doubt (in that repeated line, “What was I thinking?”), about feeling isolated in a big city — and all of these themes hit harder thanks to the noise. There is no peace here. The music reflects the singer’s multiple levels of dis-ease.

It was this blend of elegant song structure, lyrics that were wild and poetic and direct and obtuse all at the same time, and the noisy soundscape underneath it all that grabbed me. It has not let go for 15 years.

Wilco has been my life’s primary soundtrack ever since that day: I’ve been to more than a dozen of their concerts, often with my closest friends. My wife let us use a Wilco song for the first dance at our wedding. I read Wilco books, watch Wilco movies, wear Wilco t-shirts, and play Wilco songs on the guitar. More than any of their other songs, or any other piece of art at all, “I Am Trying To Break Your Heart” shaped my aesthetic taste. I still seek out other work that takes standard forms and makes them original through weird or surreal detail like this song does, from the short stories of George Saunders to the FX show “Lodge 49.”

You can imagine how excited I was, then, to see that Tweedy, Wilco’s singer/songwriter and the creative genius behind the band, was putting out a book called How to Write One Song. I couldn’t wait to get a look behind the curtain at his process and learn more about my hero!

Even though the book was pitched as a sort of how-to guide, I dismissed that whole part of it in my subconscious as I went to order an autographed copy. I’m never going to write a song — my ego is way too fragile for that, and I know I’d never make anything as good as Tweedy — but it’d be cool to see how Jeff suggests one might want to approach it.

I devoured the book in a couple of sittings. It’s an insightful, fun read and I can’t recommend it highly enough. But Tweedy doesn’t let the reader approach the text as a disinterested bystander, the way I had planned to read it. I just wanted to learn about Tweedy without putting any skin in the game myself! If I’m going to take the message at the heart of the book seriously, however, I think I have to try to write a song now. Which is terrifying.

A list of “buts” readily stood up to divert me, but Tweedy anticipated them all.

But I’m not a songwriter

It’s worth noting that Tweedy titled the book “How to Write One Song,” instead of something like “This is How I, Grammy Award-Winner Jeff Tweedy, Write Songs.” The invitation to the reader is baked in from the start. “I hope you, dear reader, will take this book in the spirit it was written — as a humble request to write your one song today and tomorrow and each day after that,” Tweedy writes on the dedication page. “We have a choice — to be on the side of creation, or surrender to the powers that destroy.”

That’s a stark decision! I want to be on the side of creation, but I’ve never been sure how to begin — at least not when it comes to writing music or poetry. I’m not a songwriter or a poet.

Tweedy invites us to set aside that paralyzing idea of “being a songwriter” or writing a whole bunch of songs (plural) and to focus on crafting just one song. “Because one song is all it takes to make a connection. And in my opinion, connection is the loftiest of all aspirations,” Tweedy writes. “At the core of any creative act is an impulse to make manifest our powerful desire to connect — with others, with ourselves, with the sacred, with God? We all want to feel less alone, and I believe that a song being sung is one of the clearest views we ever have to witness how humans reach out for warmth with our art.”

But what if it’s bad?

I certainly feel that sort of connection with others, and even with Tweedy himself, when I’m singing along with a Wilco song at a show. But trying my hand at creating it myself? What if it’s bad? It’ll certainly be bad.

“You have to sound bad to sound good, even if you’ve written five hundred songs. Being willing to sound bad is one of the most important pieces of advice I can give you,” Tweedy writes, as if he knows exactly who’s reading his book! “To me, showing up with a reliably open heart and a will to share whatever spirit you can muster is what resonates and transcends technical perfection.”

In other words, as a quote misattributed to G.K. Chesterton goes, anything worth doing is worth doing badly. I believe this intellectually, but I always find it easy to make excuses for not trying something hard or new. Once again, Tweedy has me boxed in.

But I don’t have talent

I’m always tempted to believe in the capital-G Genius, the person who has supernatural gifts and is on a different plane of existence from everyone else. I even like having conversations about whether certain people are Geniuses. Mozart and Picasso, certainly. Lucille Ball? Jay-Z? Billy Bob Thornton? Tom Brady? Jeff Tweedy, for sure.

But Tweedy says it’s not like that — yes, you might have certain natural gifts, but it’s all about putting the time and effort in and finding joy in the work of creating. He uses the image of a kid sprawled out on the floor, drawing, several different times in the book. Young kids are unaffected by self-judgement, and they don’t hesitate to create just for the love of it. That’s what Tweedy encourages in us: To give ourselves permission to be kids again in this one area of life.

But I’m not creative

What fully won me over and has me seriously contemplating trying to write my first song is the next part of the book, when Tweedy demystifies the songwriting process. He acknowledges that the process of human creativity can be mystical or even God-like — but most of the time, “inspiration has to be invited.”

It’s mostly through habit — “setting aside time to spend in the creative state” — that we can make something worthwhile. He even sketches out a sample daily schedule, with blocks set aside for exercises like freewriting, learning other people’s songs, and things like taking a walk and napping to clear your head. Tweedy also includes step-by-step instructions for activities like freewriting to help us get into a poetic frame of mind. (One example: make a list of 10 verbs related to the work of a physician; make a list of ten nouns from what you see in the room you’re in; then look for interesting-sounding, unexpected pairings between the two lists.)

Okay … so why not?

If I actually do this — if I actually put in the time and write a song and sing it for someone — Tweedy suggests I’ll be filled with gratitude at the end. Why gratitude? Creating is “a power that we reserve for ‘God’ — to manifest things out of thin air. How incredible is that?” he writes.

Yes, it’s incredible, and the times I’ve been involved in creative stuff — from recording a few cover songs with high school marching band friends all the way up to the birth of my children — I’ve been so grateful for the experience. Nothing else makes me feel so alive, so in sync with the divine creator.

This February, as I find myself in a “Covid has been going on for two years and I’m existentially tired” rut, writing my first song could be just the thing I need.

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