How I failed.

I wrote my first song when I was 19 and living in Rogers Park, on the north side of Chicago. I had been playing guitar somewhat seriously for a few years at that point, but it wasn’t until, sitting in a tiny bedroom and thinking about a woman, it occurred to me I could write my own songs.

Those first songs were simple and unencumbered by expectation. Just a guitar and a voice in crude approximation of whatever I was listening to at the time; Palace Brothers, Built to Spill, Tribe Called Quest, Lou Barlow, Beck. The vast majority of them were composed within a few days, sometimes less. Within a year or two I had scraped together enough of them to record a cassette EP (Lightbulb, Fork, String) and a 7” record (Disco Nap), both of which brought me to the attention of a small indie label, Truckstop Records.

From there, things accelerated. In 2001, Truckstop Records released my full-length debut record Get There. 3 short years later, in 2004, I came out with my second full-length record Nothing Personal. Despite its limited release, it opened the door to a handful of coveted radio appearances, some positive national (and international) press and a few surprisingly well-attended live shows.

Buoyed by all of this — the momentum in the press, my growing confidence in the studio — I immediately set about writing my follow-up record.

For reasons I’m about to detail, that record never happened.

As I write this it is 2017. Which means I’ve been not making music longer than I ever actively made it. The final tally? Over an uneven decade or so I released one cassette EP, one 7” record, 2 full-length records and a smattering of one-off singles and B-sides. And that, as they say, was that.

For some time now I’ve wanted to explain what happened, even if mostly to myself. Why it all went wrong. Where I fucked up. I’ve wanted to document, in as much unflattering detail as I can, how I failed.

This has been hard to write and a long time coming. On one level the essay you’re reading was composed over the course of a week sitting at my kitchen table in the early morning hours. On another, more actual level it’s something I’ve been writing in the back of my head for the better part of 7 years, roughly around the time I realized it was over.

You’ll find the bulk of these comments are firmly in the realm of the practical and geared towards musicians, but there are some obvious parallels you can draw and apply to other pursuits.

In no particular order:

1. Time vs. rhythm

Art isn’t generally something you can cram for. While there are those people who can hit an internal switch and go despite not having picked up a guitar or a keyboard in months, most people aren’t like that. I’m certainly not like that.

For most people, the rhythm of when they do something is more important than the time they spend doing it. This is not to say time isn’t important. Doing anything well requires investing an extraordinary amount of time into learning how to do that thing. I’m simply suggesting that you can’t get to that level of extraordinary time investment without establishing a rhythm to it. Preferably at the same time each day. Even, and especially, when you don’t feel like it. It’s okay if you just sit there with your guitar or laptop and nothing comes. That’s part of it, too.

I should know. I have an unhealthy relationship with time. For something so jealously guarded, I’ve been a historically poor steward of it. Towards the end, when I sensed my grasp on music slipping, I would attempt to make up for lost time with these ‘lockdown’ weekends where I would hole up in my little studio on South Michigan Avenue and force myself to play guitar nonstop in the hopes that inspiration would strike.

It never did. Well, sometimes it did. But it was unsustainable and after a day or two of this I’d get exhausted and my attention would wander. The only sustained progress I ever made was against a backdrop of consistency — when I would arrive early to the studio every morning on the weekends or after work during the week, coffee in hand, and patiently sit there and play random stuff on the guitar until something caught my ear.

2. Your own, personal demilitarized zone

This took me an unconscionably long amount of time to figure out: you need to give yourself a buffer of at least an hour at the start of the day or the conclusion of it, and you need to devote this time to your art/music/writing. No checking email, no reading blogs or otherwise faffing about. Just an hour or two of unbroken, uninterrupted space in your day.

For me this is the morning. I’m never particularly thrilled to be up at 5:00 or 6:00, but it’s the only time I can guarantee I’ll be available to myself. Whenever I’ve tried to make time for music or writing after the day has begun in earnest, it almost never works. Something always comes up — a work email, an unexpected errand — and the next thing I know it’s midnight and I’m tired and the thought of sitting down with my guitar and starting up that particular set of mental machinery seems very, very far away. So the morning it is.

It also turns out that giving myself the same chunk of time day in and day out has the nice side effect of establishing that all-important rhythm. Which in turn helps quiet any background anxiety about not getting anything done with my day because, before that first work email or random task intrudes, I’ve already accomplished more in a morning than I used to get done in weeks. And because I’m not trying to shove it all into one marathon session it doesn’t feel like a burden. Less Bataan Death March, more 5K Fun Run.

3. Don’t chase the tools

There’s this tendency among musicians, especially electronic musicians, to think “if I just had x, I could do y.” The x could be a better guitar, a fancy new reverb plugin or a, umm, new bag, etc.

And sometimes this is true. There is sometimes a genuine need to buy or acquire something in order to do something else. Like for example, if you primarily play and compose most of your songs on a guitar, as I do, then you’ll probably need a guitar to do that.

But as some point diminishing returns kicks in. You start buying things that aren’t strictly necessary. In many cases, these things may promise or purport some interesting sound options or workflow efficiencies, neither of which is inherently a bad thing.

The problem is we’re trying to write a song, and all these options we’re adding present complexity which can very easily derail your ability to finish something because now instead of having to make decisions about 3 things, you find yourself having to make decisions about 30 things.

I learned this the hard way. As I got more into making music on a computer, I found myself paralyzed by the sheer amount of things I could do. Non-linear editing! Vintage amp modeling! Sidechain compression! Subtractive synthesis! I could easily waste an entire Saturday morning auditioning nothing but snare sounds and tweaking them over and over, going in ever-smaller circles until I’d get frustrated and give up and put the song down for a few days.

It was much, much easier for me to write (and finish!) songs when I only had a 4-track, an egg shaker and my nylon-stringed guitar. The lack of options, far from feeling like a constraint, presented its own curious sort of complexity that in many ways rivaled the world of endless possibility I would later find myself (lost) in.

4. Don’t compare yourself (too much)

This one killed me. I’d spend a whole weekend working on a guitar part, feeling pretty good about it, and then I’d listen to something by Elliott Smith or Nick Drake and be reminded of the impossible gulf between what they were doing and my own efforts. Those parts I was so excited about only minutes earlier now sounded childish, predictable.

Which isn’t to say they weren’t. Looking at myself as objectively as possible, I was never exceptionally talented at songwriting. My guitar playing was uneven and perennially teetering in and out of time. My voice was barely passable. (I remember quite vividly the helpful suggestion that I should hire someone to sing my own songs for me). I never figured out how to write bridges.

During the good times, I knew all of this and sometimes it bothered me but mostly I didn’t care. Nor did I dwell on how I compared to my peers or whatever I was listening to; I was too busy worrying about my own chord structures and inversions and lyrics and voice to pay much attention. The sheer, delightful agony that went into making a record, that came with being in the service of Something Bigger Than Myself, had a liberating effect and insulated me against idle comparisons.

5. A message from Dear Comrade

My songwriting process has followed a predictable pattern for years: I’ll have an initial idea or outline in my head and spend a few days working it out to where the song feels like it’s 90% done. Around this time I’ll decide that the reason I can’t close the 10% gap is because there is something fundamentally wrong with the 90% I’ve already written.

Cue anywhere from 1–10 years laboriously re-writing every single part in an effort to uncover and fix this fundamental flaw. Cue the tardy realization at the end of this exhaustive process that the original 90% was mostly there but just needed a small tweak. Maybe even something as simple as a different chord going into the chorus. Cue the realization that, because I am not a savant, this small tweak could only have been found at the end of that giant circle composed of endless hours and effort.

There’s a quote by, of all people, Stalin, that I really like. It’s “quantity has a quality all its own.” If you’re not sure where to start or what the best order to start something in is just start anywhere. You don’t need a plan. Just start anywhere and do it a lot and eventually the sheer volume of what you’re doing will reveal the true order of things. You need the haystack to find the needle.

I couldn’t tell you why this works, only that it does. Is it the most efficient process? Definitely not. But we’re not going for efficiency. We’re trying to get something, anything going and the best way to do that is to pretend it already is.

Even, and especially, if it isn’t. That’s part of it, too.

Special thanks to Awkward Sauce for the editing advice. The original draft was about 3x longer and even more self-indulgent, if that can be believed.