Why I Decided To Quit My Job And Become A Digital Gypsy

James Taylor in office
James Taylor in office
Dialing for Dollars

So I just quit my job!


Two years ago I moved from the cold shores of Scotland to sunny California to join pioneering San Francisco Bay online education startup ArtistWorks. Since then the company has seen explosive growth, launching 18 online music schools and putting out amazing content that’s been experienced by millions worldwide.  But there was a problem……

As a kid all I ever wanted to do was be an entrepreneur and play drums. My heroes were Richard Branson, Tony Robbins & Steve Gadd (although not necessarily in that order). When the opportunity arose to move to San Francisco, arguably the mecca for young entrepreneurs today, I grabbed it with both hands. OK, I would be leaving my friends and family and working on building someone else’s business but it would be an adventure. And it was…

Idol Worship

I’m grateful for the opportunity I was given to work with some of my musical idols including Nathan East, Billy Cobham, Luis Conte, Thomas Lang and John Pattituci (pictures below). It also sharpened my business skills as I spent time working with teams from ArtistWorks, Google and YouTube on the strategies and secrets of online marketing, raising money and building a successful online learning business. But here comes the rub….

I missed the freedom, excitement, fun and creativity of being an entrepreneur. I missed calling the shots, trying new things, taking calculated risks, learning from mistakes and traveling the world in the process. I wanted to be my own boss again. I wanted to get back to designing a life, not a living.

Although I’ll still be based on the west coast I’m becoming a digital gypsy; spending summers at our other home in Italy and winters in Asia. I’m currently working on my own super secret stealth startup at the moment in addition to consulting for a technology company, an investment bank and a well-known publisher. I also intend on picking up the drumsticks again and getting back to actually playing some music!

So I highly recommend asking yourself the following questions once in a while:


What am I excited about?

What would I be doing if I didn’t get paid for it?

What did I want to be when I was 11 years old?

What would I do if I had $100million in the bank?


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