Gary took his first life break in 1989 while living in Boston, leaving behind a promising career as a waiter to travel around Europe for six months. He returned, only to work long enough to save money to take another leave of absence, driving cross-country to see America before finally settling in San Francisco after a three-month sabbatical. After working as a writer at several marketing agencies for the next six years, Gary once again escaped to live as a freelance writer in order to indulge his need for frequent travel. For the past several years, Gary has worked as a life coach, helping a variety of clients make their dreams of a life break come true.

Gary was graduated from the Coaches Training Institute in San Rafael, California, earning his Certified Professional Coactive Coach designation in 2004. He is the co-creator of the Kickstart workshop series in San Francisco, as well as the author of the bargain travel blog the Travel Coach.