Being Your Own Boss Shouldn’t Mean Working Alone | Dustyn Bailey

Being your own boss can give you freedom over your work, your schedule, and your life. It can also leave you without anyone to turn to at the end of the day. Dustyn Bailey built the Bebop Collective around that tension: independent creative people who want to stay independent, but still belong to something.

Raised in Bethel, Maine, Dustyn found that conventional workplaces didn’t always fit. Today, he brings together more than 50 freelancers, assembling teams around projects while preserving the autonomy that drew people to freelancing in the first place.

With Dr. Lisa Belisle, he talks about leading strong personalities without dictating, learning from failures, and why the most useful feedback doesn’t always come from the person with the biggest title. Their conversation also takes up AI and a question that reaches beyond the creative professions: what do we lose when we skip the hard work of learning?

Join Dr. Lisa Belisle for this conversation with Dustyn Bailey today on Radio Maine.