05/03/2013 12:54 pm ET Updated Jul 03, 2013

5,178 Gigs: Do Quit Your Day Job

I was 22-years-old the first time I quit my day job. I had been promoted to a supervisory position at a Wall Street law firm, in charge of the messengers, the law library and tracking filing deadlines published in the New York Law Journal. I trekked to the Male Shop (Ralph Avenue and Avenue J) where I purchased three cheap suits from their "Borat" collection.

Suzanne and I were just married and our rent was $300 a month for an entire floor of a Park Slope brownstone.

Putting on those suits and commuting to Exchange Place made me feel like such a phony. I lasted about two weeks.

I was 35-years-old the second time I quit my day job. I was Operations Manager at a midtown market research facility, where they conduct focus groups with a one-way mirror. Suzanne and I owned two co-op apartments in Jamaica, Queens. Leila was three-years-old and Coralynn was one.

It was a lot scarier the second time.

I never pass judgment on a musician who doesn't pursue their art full-time. They deserve respect for finding the time and energy to practice, rehearse or perform after a long day doing something else.

But at some point in your life, you must make a wholehearted, open-ended effort if you hope to become a full-time musician. No self-imposed deadlines. Nothing held back. Whatever it takes. You have to see yourself as someone who could never not do music. You must have the unshakeable determination that music is your life's work. Your belief system must accommodate the idea that music is the reason you are living on this planet. Nothing else would feel legitimate; nothing else would be authentic.

Unequivocal statements are not my style. Nevertheless, I can't overstate this. Your music career will make many unreasonable demands on your life. Well-meaning friends and family members will not understand why you're choosing a profession with such a remote chance of success.

Let's say you have a day job that provides you regular income, structure and predictability in your daily routine and positive feedback for being responsible and conscientious. Why on earth would you put in any effort to get ahead in a field where money is erratic at best, you have to invent your routine every day and your best work is subject to constant rejection?

Or imagine that you've got a freelance gig that lets you pick and choose your assignments and deadlines. How motivated would you be to make cold calls, write pitch letters or search the Web for long-shot opportunities? Why waste time on something that is unlikely to pay off?

There are opportunities Suzanne and I would have never considered if we weren't desperate for music work of any kind. We did not have the luxury of rejecting offers because they weren't hip enough, required us to learn new material or didn't match the career path we had sketched out for ourselves. When you've got nothing, you don't say "no." Some of these gigs didn't turn out well, but quite a few pointed us to new audiences and new markets to explore.

The last recession was brutal on everyone. My heart goes out to families that had to make painful adjustments as their primary breadwinner lost a high-paying job with benefits. Our business suffered too, but it was nothing we hadn't been through before.

I often wonder what would have happened if I had chosen the safer path when I was 22 or 35. What if I had traded my dreams for a job with security, predictability and a reasonable certainty of advancement? And then I got sacked and I had to start over as a 50-something who's been out of the job market for decades?

Maybe quitting my day job was the practical, responsible thing to do after all.

If you've got five minutes to spare, watch Harry Chapin's story of a cleaner from Dayton Ohio who wanted to quit his day job.

Please feel free to comment on how this story could have played our differently. I welcome your feedback and suggestions on issues you'd like to discuss in my blog. Next time, we'll focus on fame as a career objective.