Crafting a Music Career Part 1: My Strange Path Through the Music World

For the last few months, I’ve been thinking about writing something about music careers. Maybe I’m feeling the itch because I see more people focusing on the hot topic of musical entrepreneurship.

I’m not sure.

I’ve written about the topic of careers in music quite a bit in the past. In fact, my first book Road Warrior Without an Expense Account covered this topic in great depth. But that was written way back in 2008. A lot has changed since then!

I’m calling this new series Crafting a Music Career. In it, I’ll dig into career-building for musicians through an autobiographical lens. I’ll look at the stages in my career and what I did well, what I could have done better, and how I accomplished what I accomplished. My hope is that this can be useful information for younger musicians as they approach the daunting task of carving out a place for themselves in the music world.

This series is divided into five parts:

• Part 1 – Preface: My Strange Path Through the Music World
• Part 2 – Building My Freelance Career
• Part 3 – How Sinking My Freelance Career Helped Me
• Part 4 – Working in Education – What My Career Looked Like Right Before Bailing
• Part 5 – Starting From Scratch – How I’m Building My Portfolio Career

Today, I’m doing an overview of the bigger phases of my career. It’s an homage of sorts to James Altucher, a favorite writer of mine with a distinctive writing style. Channeling James Altucher for this post just seemed right to me. The subsequent parts will be “meatier” for sure, but I hope you have fun with today’s post skimming through my music career!

By the way, I’ve recently talked through this whole journey on a few podcasts, so check out my appearances on The Entrepreneurial Musician, A Musical Life, and The Musician’s Guide to Hustling if you’d like to learn more!

Preface: My Strange Path Through the Music World

My career in music has unfolded in ways that I’d never have predicated.

I’ve had times when I’ve been on top of the world, followed by stretches of deep frustration and discouragement.

I’ve failed more often than I’ve succeeded.

Time after time, I’ve forged a new path, built a career, and become “successful” (whatever that means). Then I’ve intentionally set fire to everything and gone down a different path.

I think that a lot of musicians “find their level” in the world and basically chug along on that level for decades. Maybe that’s an orchestra job. Perhaps it’s a university teaching position. It might even be a freelance career built around the same set of gigs.

Regardless of what it is, I see so many musicians operating in job paths that resemble what our parents did.

Work in a job for 30 years.

Put in the time.

Get the pension.

Get the watch.

But these paths are eroding all around us, and not just in music. People don’t stay in jobs for 30 years. The average American doesn’t even keep the same job for five years!

I’ve spent the last 20 years trying to find my level. I started out freelancing. I added in university teaching and private teaching. I took on a fairly standard freelance life and chugged away at this for seven years.

But it always felt like wearing tight shoes.

I was always looking left and right to see if there was a way out. What else could I do?

I felt trapped. I couldn’t see the forest for the trees.

So I got out.

At least, I tried to get out.

I went back to school. For music education, of all things.

I never really wanted to do this. It was never my calling. But there was light at the end of the tunnel.

A traditional job.

Pension.

Benefits.

Maybe even a watch if I stayed long enough!

But a funny thing happened during that period of transition. Isn’t that when the most interesting things happen in life? John Lennon once sang “life is what happens to you when you’re busy making other plans.” I think about that quote a lot.

I started a blog. I started to vent my frustrations. I organized those frustrations into pieces that resonated with people. I started to build a platform. I just didn’t know that was what I was doing.

But it was too negative! There was no light at the end of that tunnel. Only more darkness.

So I started a podcast. It was positive!

I talked about people’s experiences in music. We geeked out. It felt good to do this. It resonated with people. The platform continued to grow.

People saw value in what I was doing. They wanted to exchange value for value. They wanted to advertise with me. They wanted to hire me to work on their project. Or give them advice. Or come talk to their group.

I thought that I had self-immolated my career by writing critically about it.

But people liked it!

They hired me for better things than I’d been doing. Trying to hack my old career into pieces kicked me a few rungs higher up on the musical ladder.

Weird.

Meanwhile, I was banging away at this music education degree.

Why was I doing this? I almost quit.

But by dad talked me out of it. Why throw away all that time and money when I was 75% of the way done with the program? Why not just finish?

So I finished. And I got a job.

It was a good job! I’d never really had a “job” job before. This was new.

I had a salary! Money magically appeared in my account. What did I do to earn the money? I didn’t know! I was so used to trading specific time for specific money. This concept of money for your overall service was foreign.

I had benefits! I could finally go to the doctor.

But I was busy. All my time disappeared. I didn’t know what I was doing with the new job. I had to learn. But learning was fun!

I set fire to the blog and podcast.

Well, not really. They just kind of faded into the ether.

People kept telling me how valuable it was.

But I ignored them.

I quit logging in online. I deleted all the emails people sent me.

Now I had a boss. And he had a boss!

I got evaluated.

Everything I know, do, and love was reduced to a series of ratings. That was strange.

My colleagues had been at this job for 10, 20, and even 30 years. It was like my parent’s generation.

I had to take tests on bullying. My day was divided up into tidy increments of time separated by school bells.

But I liked teaching! And I liked feeling like I was a part of something. Part of an organization. Part of a team. Shared goals… at least on paper. I’d never felt that freelancing.

So I embraced my role as a team member. I worked hard at my new job. I studied scores, conducting, and tips on managing hordes of teenagers.

It was fun.

Challenging, but fun. I was learning new skills. I was growing as a person but also as a musician. This was surprising!

Another job opened up. I took that job. More money. More demands on my time, and the job was, well… someday I’ll write more about that job.

Then I got another job. This was a really good job that everyone in my niche wanted. Or a lot of people wanted, anyway. It was the kind of job you stayed in long-term if you were in this career.

I was making more money with each new job. Now I was making “a lot of money.” At least, by my standards. I got more and more side gigs. People hired me to guest conduct. I was teaching university. Lots of clinic gigs. All this in addition to playing gigs.

I was a baller. Sort of, anyway… in some vaguely lame way.

But I had no time!

I was commuting from 35 miles away. My wife had a job in the city. I was working in the suburbs. Her job was “more serious” than mine. So I took the commuting hit.

I spent 3 hours a day at least driving. Often much more. This is what I hated so much about freelancing. Oh no! My old patterns repeating themselves.

Why can’t I break free?

My wife got hooked up with the best medical residency program in the country for her specialty. But it was in San Francisco. Oh no! All the castles I’d built! I can’t leave them.

So I stayed in my job. My wife moved thousands of miles away. Now I was lonely. Oh no! What did I do? What was really important in life?

I kept tending my castles, but my princess had left. So what was the point of staying? Was it ego? There are big egos in music and big egos in education. Sometime I’ll write more about that. But not now!

OK—I decided to move to California.

Wait a minute… that sounds pretty sweet! Goodbye, horrible never-ending winters. Hello, palm trees!

I started looking for teaching jobs in San Francisco. Education is really weird out there. Where are all the high-paying orchestra jobs? Oh no! What to do?

But then I had a moment of clarity.

I looked back at the past 20 years of my life.

What felt right?

Was it the teaching job? I loved it, but was it my passion or did I just bring my passion with me from job to job?

More on that later.

Did I want to go back to freelancing?

Yikes.

What about doing something new?

But what?

I saw the next 20 years of my life stretching out in front of me. I was standing at a crossroads, looking two decades backward and forward simultaneously.

I looked at that period of transition again. Why did those experiences resonate with me? What did I like about that time in my life?

What if I didn’t look for another teaching job?

What if I invested in myself?

What if I went all in on building that platform that I had unintentionally began to create ten years ago?

What if I treated that like my full-time job?

Where would that lead me?

I decided to give it a go.

Next: How I Built My Freelance Career…