Nine years ago, I started traveling around Montana and the Northwest to play shows in bookstores and coffee shops with my first album.

I had no idea what I was doing.

I had booked a lot of this haphazard “tour” on a random determined Tuesday in the spring of 05, during the motivational afterglow of my twentieth birthday.

I lived at home. Most of the money I earned at the time came from being an overpaid janitor – two nights a week – at a Montessori School run by my Mom.  The only way to cover the expenses of these gas-guzzling trips, was to sell albums to strangers who hadn’t heard of me, weren’t expecting me, and didn’t necessarily even like the kind of music I played.

I remember the first trip to Billings like it was yesterday. It was a perfect Saturday in August.  I had been playing the violin on Main Street for tips since early morning. It was the weekend of Sweet Pea; and the thousands of Montanans that had come to Bozeman for the festival were incredibly generous. It was a goldmine for a kid who cleaned for a living. It was cool to be earning money with music.

But when my Dad pulled over to pick me up for the Billings show, my heart raced. It felt like the last day of high school as we drove out of town. I was chasing the real dream. I remember thinking: “This is it! I’m on my way to the big time!” I saw a whole future in my mind – of winning over small crowds, the small crowds growing until I had to move to bigger venues, the bigger venues filling up over and over until someone noticed and made me a big star… because that’s totally how it works…

I was – by and large – unburdened by reality. I was cocky.

But then…

After a two hour drive, we arrived at Hastings (a bookstore with DVD rental) in Billings to set up. Not only did the employees have no idea that I was supposed to be playing that day, they didn’t know that there was live music there… ever… at all.

I explained that I had called and arranged it several months before, that we had driven all the way from Bozeman, and that it would mean the world to me if they could let me set up somewhere… and play for an hour for the shoppers.

The manager on duty was kind enough to not point out that there were essentially no shoppers, as he led me to a “reading corner” surrounded by bookshelves that – to my delight – was directly in the middle of the main route to the movie rental area. I had learned from past shows that random sales to movie rental traffic could mean the difference between a break-even trip and a total bust.

So I unloaded the car to set up and laughed at the thought of the image I was presenting. My guitar was a horrible tin-sounding piece of junk. My PA – purchased for ninety bucks at a pawn shop by my Dad – had a blown speaker. My clothes were too big and out of fashion. I had started to realize that my original songs were weak; and I had very little performing experience.

But I was on fire.

So I set up my stuff… and there was still more than an hour left before the time of the show.  Considering the initial reception I had received, I figured I had to make the evening pretty memorable if I ever wanted to play there again. I was painfully shy, and totally uninterested in putting myself out there if I didn’t have a guitar in my hand, but I had an idea.

I had been to Kinkos a few weeks prior, and had printed some poorly-designed black-and-white handouts with my website and MySpace page, and a picture from my album graphics on them. I decided to walk around the store, strike up conversations with strangers, tell them about the show, and give them handouts if they would take them.

The place was nearly empty.  The first person I saw was a seventeen year old goth-looking girl with black hair, a perma-frown, and enough dark make up to lead me to the judgmental assumption that she might hit me if I talked to her.

I approached her anyway.

Me (tentatively): “Hi,”

Girl (HUGE smile): “Hi!”

Me: “Do you like acoustic music?”

Girl: “sometimes! It depends.”

Me (visibly nervous): “Cool. Well I’m playing here in an hour. Are you busy at seven?”

Girl: “No. That sounds cool! My friends are here too. We’ll come watch you for at least a song or two.”

Me: “Cool! I’ll start early so you don’t have to wait!” I was relieved and grateful, and she could tell.

Girl: “We’ll come over when you start!”

I handed her a handbill awkwardly.  She smiled and took it.

After that small (huge in my mind) success, I walked around the store and continued approaching strangers to tell them about my show. Fully two thirds of them said it sounded cool; and that they would come to watch a few songs. Anyone who didn’t, had other commitments. No one was rude.

I started 40 minutes early. Two thirds of the chairs we had set up for the event were full. More people sat down as the night went on. Two hours later, most of the crowd was still there. Everyone listened and clapped after every song. At the end of the night, I had sold fifteen CDs. It was my first truly profitable solo show ever.

That was the beginning of something pretty special. As the year went on, I started widening my circle. I started playing in more towns I’d never been to, and every time, I approached strangers with handbills before the show.  Billings crowds doubled. I made some killer friends in Helena, Butte, and Missoula.

Then came Spokane… I planned in advance for that show. A friend of mine at Whitworth College sent an email to a big student database. I performed for three local high school choirs and told the students about the performance that night. Another friend with her own following agreed to open. I did everything I could… and twenty minutes before the Borders show was scheduled to begin, the coffee shop was standing room only – more than seventy people had showed up.

I had momentum.

Sure… my Dad was the only reason the trips were possible.  We were sleeping on couches and I was still convincing strangers to give me a shot, but it was working… and it was paying for itself.  From the time my album released to the end of 2005, I had sold nearly a thousand copies.

So here’s where the story gets weird. Even as my momentum built, I started to get the feeling that I was doing something wrong.  In my mind, the shows were not legitimate because they didn’t fit the mold. If I was really touring, it would somehow feel… different.  Right?

I looked around for answers. I doubted every step. I stopped being as active on my MySpace page, and I stopped booking shows out of town. I decided to research and really figure out what I was doing… and then… nothing…

For years I tried to “figure it out.”

I’m writing about this for one reason: it’s a cautionary tale.

What I was doing was a “real” tour. I was building a real following. My CDs were selling to people who were excited for the next one, and yet… because I hadn’t put it together in a way that was sanctioned by some non-existent authority, I cast it aside and didn’t pick it up again.

I make my living from this now. I love what I do and it’s getting better every day. I have encountered some insanely incredible opportunities, and have played in some unbelievable environments.

And to this day… every time something truly great has happened in my career, I didn’t know what the hell I was doing.

It’s the nature of the game.

The truth is: studying does very little after the broad strokes. Whatever you can think of to do, just dive in to the unknown open sky and learn to fly while you’re falling. Trust me: with any investment of effort… you will fly.

No one knows what you think they do. And no one knew what to do when they started – not Einstein, not Steve Jobs, not The Beatles. Life is beautifully chaotic and the only way to make any sense of the mess is to take action.

I know it’s easy for me to feel like I’m the only person on earth who doesn’t know what to do. It’s easy to believe that the well-dressed, charming stranger in front of me in the coffee line has it all together, while I’m trying to remember if I made my bed this morning.  But that’s just not how it works. The truth is: we’re all the real deal – long before we’re willing to recognize it.