It’s been raining all day. The Chicago street corner outside the window is shimmering under the light of dozens of lamps and neon signs.  As night falls, the scene only seems to be getting brighter.  Countless coat-clad pedestrians have taken shelter under umbrellas, because what was a light drizzle for several hours, has just become a torrential downpour.  It seems like everyone’s in a hurry.  I’m sure I would hear horns if it weren’t for the music blasting in my headphones.  Cars, buses, and bikes are stacked up at the light in both directions.  A taxi is blocking half the intersection.

The scene doesn’t even look hectic to me right now.  It’s somehow comforting and beautiful.  It’s cozy in here and exciting out there.  I’m thrilled with the movement and the life… this urban display is everything I imagined when I dreamed of living in the city as a naïve kid growing up in Montana.

I don’t live here yet, but for quite a while, I’ve been able to see the potential in a place like this to really spend more of my life the way I want to.  I’ve been on the road on and off playing shows for almost three months now, and some of the shows have been exactly what I want my musical life to be about.  As I sit here in this corner coffee shop, oddly inspired by my location and circumstance, I’m back to wondering what I’ve missed out on by being cautious with my life and career.

There is a fine line between being responsible and being too safe.  The question: where is that line?

It’s almost impossible to know for sure, but I didn’t get into this so that everything could be pretty and easy and well put together.  I got into this so that I could move people and dare I say… make a difference.  I clearly can’t let go of responsibility.  Dignity and personal responsibility have only become more important to me as I’ve gotten older and further along in this pursuit, but there’s got to be a way.

I write music to make sense of experience.  I write when I’m feeling almost anything that’s intense enough to describe, because I know other people have been in exactly the same place, and knowing they’re not alone could make all the difference.  And making that difference is why I’ve chosen this over everything else as a career.

Quite a few people have been requesting expanded versions of the stories that I tell about songs at shows – as blog posts… so here we go… from the beginning.

Here's a YouTube video of the song this post is about:

Sometime in the winter of 2002.

I was 17 and the absurdity of High School and the unsure beginnings of a jaded “real life” were starting to merge in my consciousness. I had been sitting in my Mom’s home-office for hours staring into the blue light of a monitor, attached to the slowest computer I can ever remember using for anything other than terrible 2d games in the early nineties.

My mind was distracted and muddy, my legs felt like jello from a long run, I had a headache, and I should have paid attention to the intensity with which my body was begging me to get my ass in bed, but I couldn’t…because my ears were fully engaged by just about the only thing that had ever been able to keep me still for longer than a few seconds: great music.

As I sat there in what would soon feel more like pre-dawn than late night, I felt both inspired by the music I was listening to, and crushed by circumstance.

I was thinking about how very small my life felt… confined to the sterile and mind-numbing halls of my school, the institution that was supposed to someday lead me to the American dream… which – in my mind at the time – meant something very close to death.

The way I saw it, I was there in HS for a couple more years and I had to do well… then college… then grad school… then fight, race, claw my way into the “real world” in pursuit of an arbitrarily chosen “career.”  I’d make my parents and peers proud and finally have enough money to pay for a life I’d built around the means of paying for it.


At least I would be self sufficient right?  Hopefully it would compensate me enough to allow me to keep my dignity and semi-satiate my appetite for status. I would eventually make enough to take out a 30 year mortgage on a nice house in the burbs, have 2.5 kids, and throw a weekly Sunday barbecue.

“Hey,” I thought, trying to muster some optimism. “Maybe I’ll find enough depth and purpose in my family to make up for the fact that I spend most of every day doing something I hate and really didn’t put much thought into choosing.”

It’s funny to think back on it now, because I actually see a family and a house in a rad neighborhood in my future at some point. There’s nothing wrong with a lot of what I just mentioned.   But as a 17 year old with big dreams, I couldn’t have imagined anything worse…

“I’m getting ahead of myself” I thought, “I’ll be alright… I have my music.”

Or did I?


I had really stopped believing that music, outside of being an inspiration and a joy, could be of any value to my life. I had given up on a dream that I had been too young to understand in the first place, and I was still playing the role, as if pretending I wanted it bad enough would make me feel a little bit better about the fact that I would never have it.

So as I listened to song after song with dawn rapidly approaching, ideas started to form in my head. I don’t exactly remember when it happened or what led up to it, but I do remember that it came to me in an instant and without any warning:


Suddenly I understood the root of the heaviness of my whole life, and I knew exactly how to fix it. I would NEVER be happy with anything but music, and knowing that with certainty made all the difference.

Music had to be what my life was about or it would remain terrifying and dull, and the cognitive dissonance that ruled my life would follow me far beyond the reaches of high school.

“There are no complicated answers.  Music is it. Music is what I’m here for… I absolutely have got to do this – starting NOW.”

I had lost precious time doubting myself and procrastination seemed obsolete in the face of this new clarity. I picked up my guitar and wrote Sing Along.  To this day, it reminds me of how much I need this… these songs, this profession, the magic that is music… it’s what keeps me alive… and

certain that there’s a place in the world for my heart and what it has to offer.

And I can tell you right now – when you get right down to the reason I wrote this song, and the conclusion it leads to – not a damn thing has changed since that night.

Here's the video again –

I’ve said this before, but I’ll reiterate: the conundrum of making music both my passion and my living, is that – at times – the stuff that pays the bills is not the stuff I’m passionate about.  Granted, that’s life for almost everyone.  But I think the difference here is that in giving up everything to become a professional musician, I’ve put myself in the position where the time-consuming life obsession part has to happen independently of the rest… and yet the only way I’m going to get to a point where this is sustainable, is by spending my best energy on that and not on the stuff that has been – until recently – consuming my existence.

I’m really starting to wonder… if I let go of my pre-conception about what’s going to make me money versus what’s going to make me happy and allow me to share my passion with the world, would I find out that I’m dead wrong?  Maybe I’ve really just been lying to myself and slowing myself down by being afraid to take some chances and dedicate everything to the pursuit of the passion.  Maybe now that I know exactly who I am as an artist, the way to really touch lives and share music that matters, is finally open.

I hope so, because I’ve got to take this chance.  I mentioned my coffee shop Chicago scene, because, after eleven years in this business… after spending 8 months sleeping, eating, dreaming, and living recording to make a record I’m finally proud of… after about a thousand “NOW is the time!” moments… I still spent another year in Arizona, playing shows to pay off debts, save money, buy equipment I need etc… in hopes that on the other side of it all, I could relocate to Chicago and start doing the “real thing.”  And now that I’m here in Chicago on a totally music dedicated trip, I realize that it was never about the move.  That was just a metaphor – the excuse to start over and live a new life.  And even though I’m just visiting, being here feels like a new life already.

Moving to Chicago was the catalyst I thought I needed to take this leap of faith into total pursuit of the passion.  The thing that has stopped me from moving here, is that I’ve been so afraid to let go of my established connections and restart the process of booking restaurants and resorts so that I can make a living “while I go after what I’m really about.” Ironically, I’m getting now, that if I dedicate half of the time and energy to sharing my music and my passion that I dedicated to booking myself into restaurants and resorts in the first place… I would probably already be in the position that has been – as yet – barely more than fantasy.

I wrote this blog about fear and taking chances a while back  And in it, I promised to re-double the effort and really dedicate myself to this.  In a sense, I did just that.  What has come out of it has been the best six months of my life!

But it’s time for more.  I know I have it in me.  I know that if I let go of the way I think the world works, the sky is not the limit, but the beginning.  Things have happened over the course of this summer on the road… that have forced me to redefine possibility.  It’s not about fear anymore.  And I can’t hide from the truth.  Practically by accident, I’ve stumbled upon a lot of what I’ve wanted for years.

The point of no return was ten years ago.  But today, I set some things in motion, that are really going to make it impossible to turn back from the pursuit of the real thing.

Leap taken – I’m falling

I need more than maybe and I’ve never wanted anything this much.