A Career Choice is a Life Choice LogoThis week we are sitting down with Dylan Gallagher, Senior Tour Director and Wilderness Guide at White Wolf Private Tours and Orange Sky Adventures. Both companies provide memorable tour experiences and are based in the San Francisco area. Read about Dylan’s journey to his current roles.

DB: Hi Dylan! Thanks for joining me today. Can you start by telling us what your current roles are? 

DG: I am the Senior Tour Director and Wilderness Guide at White Wolf Private Tours and Orange Sky Adventures. 

DB: That sounds fascinating! What brought you to your current position?

DG: I majored in Civil Engineering from the University of South Carolina. Then, I graduated and took a seat at my first desk. After I thought long and hard about my job (about two weeks), I said no thanks to my employer and moved to California to become a tour guide. Ten years later and numerous, adventure-filled road trips across North America, here I am. 

DB: That was quite the shift! What do you value most about your current role?

DG: The freedom. In the busy season I work like everyone else, with few resting hours. And in winter, the slow season, I am completely free. I can work on projects, visit family or participate in any hobby I choose. 

DB: What would you say has been the biggest learning to date from your career path?

DG: My biggest learning to date is how to rely on yourself when a problem arises. Many times we have a team to help, however many times we do not. That means you need the smarts, and maybe even psychology, to get you and your group to safety when it’s required. It’s a lot easier said than done.

DB: What is your favorite question to ask candidates during an interview? 

DG: If you can have lunch with three guests, dead or alive, who would they be and why?


Deanna Backos is a partner at the midnight oil group, a Detroit marketing agency offering full-service communications for clients. We live and breathe our clients’ brands, always developing new ideas, strategies and creative solutions to build awareness, engage with their target markets, and develop true brand advocates.