Fail and Be Scared

"How will I know if it's the right thing?" That has always been one of my biggest fears. Making the wrong decision, taking the road with the dead end, wasting my time by pursuing something that ultimately didn’t get me to the place I wanted.

It’s still a very real fear, but in making decisions and taking risks, I’ve discovered along the way that you almost always “kinda know” which way to go. Whether it’s your gut, or your heart, it’s as if there are imaginary sign posts guiding you along.

I just turned 33 and I’ve had a lot of long drives the past week on tour, so I’ve had a lot of time to reflect. There has been a theme popping up in my life — something I’ve heard from a few musician friends, podcasts, and in conversations on the road.

The gist of this theme is “do something that scares you”. I’ve heard varying ideas on the theme; do something scary every day, welcome the adventures that don’t seem comfortable, sometimes you have to take a leap and go down the path of most resistance when you are at a cross road. 

This continues to resonate with me more than ever right now as I’m in the throes of my new life as a full time musician, having quit a really wonderful job to do something that is both exciting and scary — to survive in a very fragile and contentious industry.

Doing music now has been a calculated risk. I spent 10 years working while also pursuing my love for music — putting time towards those 10,000 hours both in the studio and on the stage. Working was a great way to build a skill set in the ‘professional’ world, spend hours helping to build someone else's business and be passionate about something besides my music. I was able to build a lot of momentum locally, meet a lot of people, and invest a lot of the money I made there into my music. But there comes a time to put your eggs in one basket, otherwise you risk missing your window.

It’s scary to be a touring artist in your 30s, and it’s not easy. My fears center around my growing age — the misguided fears of relevance, evolving commitments, waning energy level from my younger years. It’s interesting to try and calculate unknowns, like the evolving music landscape, as the financial pie seemingly decreases for musicians.

But, my gut tells me that it’s sink or swim and I know how to swim.

The reason I’ve been thinking about this is, one of the sign posts from early on in my career e-mailed me the other day to grab dinner while I’m in DC on tour this week. We worked in our first job together.

Back then I resided at small strategic communications firm of 8 people or so. When I wasn't at work I was writing songs and playing coffee houses around Seattle. I had just moved to that big (little) city from Bellingham, Washington. 

Those formative years playing coffee shops were exciting — getting up in front of a lot of my friends and a few strangers to play songs that I’d created. The polish wore off when people stopped coming to shows. I found I was spending more time trying to fill the room through marketing efforts than actually playing. I wanted to give up and do something else, it felt forced at times, but one of my coworkers Carl came to my show and told me that I really had something. That was one of the sign posts for me. Someone besides my mom and dad, who didn’t owe me anything, was telling me that the songs really spoke to him. It was enough to drive me forward.

It seemed like every time I was about to give up, to consider my life without music at the forefront, something or someone would come along, shifting my perspective. 

Even now, I still have days where I think, “what am I doing, maybe this isn’t for me anymore” — maybe it feels like I’m not making any progress, or I’m comparing myself to other musicians, but I soon realize how fulfilling music is for me — a way to make a difference in people’s lives, to connect with others, to get things out of my head that I wouldn’t know how to communicate otherwise. I also have this gut feeling about the bigger picture and how it feels like this is what I'm supposed to be doing.

Yes, it's scary. There are so many unknowns. It’s not the practical career. It’s not the most stable job, BUT the adventures, the people I’ve met, and the impact my songs have had on people besides me makes it all worth it. If I hadn't quit my job, if I wasn't doing something that scared me, I would regret it for the rest of my life.

That's my diatribe from the road. I realize this next sentence and whole post may come off a little contrived, but please do yourself a favor and don't always live a practical life, live a fulfilling life. 

My one disclaimer: Make sure you do your homework and don’t quit your job without a lot of planning and thought around how to survive doing what you love. It won't always happen right away.

Feel free to write me or comment below, would love to hear what you are up to, and where your passion is taking you.