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When You Fail To Make Money Doing What You Love


In an attempt to make music for a living, I moved to Nashville in 2008. To be fair, my wife moved too. But not without striking a deal before agreeing to. Here was our compromise:

I get to see about the music thing, if she gets to see about a graduate degree from Vanderbilt University… Deal.

Five years later, here’s the shakedown:

My wife has her Master’s degree from Vanderbilt. (I got at least a quarter of her degree from all the porch time we spent talking).

I haven’t seen a dollar from the songs I wrote in Nashville. However, what I learned by trying has helped my wife and I launch a business this year that’s not only been meaningful, but profitable as well.

Here are a few things I learned on the journey:


1. It’s Supposed to Be Hard.

“…the best art happens when it requires something from the artist.”

I had some illusions of grandeur when thinking about what being a successful artist would actually look like. Inasmuch as I don’t like to admit, it probably came from the movies. I was pretty stuck on the idea that my destiny was hinging on whether or not I’d “make it.”

The hard work that had informed so much of my actual experience of being human, oddly, was always missing from my fantasies. I wanted the Big Easy, and didn’t want it to cost me anything. So, when writing songs became hard I felt like something was wrong, and that it might be a confirmation of something I was pretty damn scared of: that I wasn’t a good artist.

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I’ve learned that the best art happens when it requires something from the artist. It’s not easy when inspiration runs out. Everything in you wants to run too. But there’s an invitation in that moment, and when I’ve had the courage to stay with it, that’s when the good stuff happens.


2. Meaning Is Like Money

“Money isn’t a leader, it’s a follower…”

Meaning is really what we all make a living on. Viktor Frankyl was right; it’s what we’re all searching after. If meaning and money were to switch places, how much would we be earning a year? Would we be living below the poverty line? Would we be rich?

I’m convinced that what’s meaningful to us is what’s most valuable. It is the magic. The best of art overflows with it, and the worst barely has it. Meaning is the real leader, and always will be. Money has always been a follower, and seems destined to always be one.

As a personal experiment, I began trying to quantify the meaningful things in my life. I mean, I actually tried to place a dollar value on them. I imagined what a monthly budget would look like if meaning really were like money. All of it was my own creative way to challenge the money mindset whispering endlessly from the made-up-world of advertising that permeates American culture.

I didn’t expect it, but I began to feel differently about my daily experiences. I started to notice small and simple things I might not have considered as deeply before. And oddly my experiences began to feel more like things I would actually spend money on. They started making more sense as a currency too, even more than real money made sense. What does all this have to do with art? More than I thought actually.

I became more keenly aware of the value of art, the expensive stuff, the average stuff, and the cheap stuff. I began to see that the best art was rich with meaning, and came from individuals living meaningfully rich lives. I recognized that “Crime and Punishment” was one of the richest books I had ever read, and that Hemingway’s body of work reflected he’d been both rich and bankrupt multiple times in his lifetime. Reading Bill Gates’ blog and seeing his life, it became clear why so much money has followed him for a long time. I even noticed, no matter the fluctuating opinion, that Coldplay would never have real money problems in life (you can laugh at that one).

Paper money isn’t bad, but it’s only a tool. Exploring the value of meaning was like a shot of clarity for me, especially in this confusing world. Whether you are an artist or an entrepreneur, you have probably experienced at least once how much it sucks to chase money. Money isn’t a leader, it’s a follower, and following after it is about as smart as following a follower is. If standing in a big line is what we want from life, than followers will get us there quickly. If the DMV isn’t what you had in mind for ‘the good life’, then follow the value not the money. For us humans, what’s meaningful to us is often what’s most valuable.

3. Perfectionism is a Pretentious Jerk

“Perfectionism promises us safety if we’ll only sell ourselves short first.”

I am convinced that if we could see Perfectionism as an actual human being, we’d all call him out for being such a jerk. He’d be the worst friend of all time. In reality it’s harder to see it that way.

Perfectionism offers us something if we choose to relate with it. It’s sneaky, harmful for us, and can lead to a lot of disappointment. But in vulnerable moments it’s awful hard to resist.

Perfectionism gives us the ability to reject ourselves first to ease the possible blow of being rejected later. It convinces us to find all the (possible) imperfections ahead of time, so it’s less shocking to our self-esteem if others should point them out.

Another offer (at least it offered it to me) is an ideal. And I used the hell out of it. This one is nasty, and looks a lot like pretentiousness.

My work was never good enough no matter how good it actually was. So instead, I’d take pride in the high standard, like the perfection (i.e. the idealistic vision in my own head) was the art itself.

This gave me the opportunity to both inflate any compliment (i.e. if you think this is good, you should’ve seen the perfect idea it came from in my head!) AND deflect potential criticism (i.e. of course any mortal attempt would fall short of the pure perfection in my mind from which it came, blah blah blah).

Perfectionism promises us safety if we’ll only sell ourselves short first. But after the smoke and mirror show all we get in return is a ripped ticket stub and a ton of disappointment.


4. Sometimes You Just Have to Become a Better Person.

“You are not your art, but you are always in your art.”

The first six months of Nashville were tough. Frankly, I was depressed and filled with anxiety. I put an intense amount of pressure on myself to write a hit song. So much so that every writing session tangled me up in knots.

It got even worse. I began to have physical reactions from all the pressure. I’d feel an ache behind my eyeballs, and then behind my ears, and in the back of my neck.

I’d wake up, get anxious, pick up a guitar, dismiss what I had written because it wasn’t good enough, feel more anxious, and then get in a fight with my wife about it. I was one big depressing lump of shitty. My quality of life had decreased to nil. It’s not surprising I couldn’t write good songs.

I’ve noticed there isn’t a clean line of separation between how you live your life and what you make as art. What exists in your art always exists first in you. You are not your art, but you are always in your art.

Good art may come from technical skill but great art always goes beyond it. In some ways (or at least in the long and romantic version) when someone undergoes the art of another, they can only go as far as the artist has gone himself. That the artist’s own experience almost paves the path for the audience’s experience, in that it’s often the only handle to guide where they’re going.

The shorter and less romantic version is basically this: if you want to be a better artist, you have to live a better life because your life is part of the experience too.


5. Learn Self-Compassion

“Give yourself as many options as possible.”

Learn to be kind to yourself, and I don’t mean by talking sweeter to yourself. I mean by giving yourself as many options as possible. I started learning this for myself after reading the inspired, “Eat, Pray, Love” (yes, I just referenced that book).

When facing one of the hardest times in her life, Elizabeth Gilbert didn’t just change the voice in her head to say nicer things so she’d feel better about her situation. She was courageous enough to change her whole situation.

Why? Because she took her happiness seriously. She devoted a whole year to acting differently than she had before. She didn’t know it then, but her adventure to Italy, India, and Indonesia wasn’t over after that year, it was the beginning of a whole new life.

When options in life all look crappy, instead of accepting that pile of crap, questioning our line of sight instead, offers a better chance at happiness.Give yourself as many options as possible, especially when the present ones are depressing.

Elizabeth Gilbert’s courage was contagious and I too started challenging the options I simply assumed I had for my life. Thank you Elizabeth Gilbert. Sincerely.

This article is also found on Medium and is published here with the permission of the author
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in your inbox everyday at 10am CST.

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