Episode 005: The Philosophy of Sailing from the Millennial Perspective

In Episode 005, we talk with Derek and Grace Rupe of Captineer! Derek and Grace are a fellow 30-somethings sailing couple living aboard full time in Connecticut. Grace is a teacher, and Derek is the owner of Captineer, a company doing electrical refits for sailboats specializing in electric propulsion. 

In our discussion, we stumble into the philosophy of sailing: What does it mean to be out there sailing when we're "supposed to be" working, contributing to our retirement plans, and living fully insured? What was it like - mentally, emotionally, physically - to break away from the life everyone thinks we should be living? How does sailing play a role in that? 

Take a listen to some wonderful moments: 

"Like a lot of things, there are lots of bigger lessons to be learned... Lately, I've seen how much the more I learn, the less I realize I actually know. My time on the ocean has given me a good lesson on humility." - Derek Rupe, Captineer

"I think people have a hard time reconciling living on a boat with reality." - Sheena Jeffers, Seas Life

"People will think, 'When are you going to do real life? When are you going to move off the boat, get a house and have a family?'" - Grace Rupe, Captineer

"It's really insidious when you see it. It creeps into people at an early age what all their motivations are and it's so hard to sit down and ask why. Why do I want all of this stuff? Why do I need this life? It's what we're supposed to do, but it's hard to break it down." - Derek Rupe, Captineer

"Even with that advantage [growing up with an adventurous childhood], there was still a fair amount of psychological angst that was required to move away from what we ought to be doing." - Derek Rupe, Captineer

"The ocean is this vast universe that little is known, and there is something so relaxing going under the water and holding my breath and not hearing society and your body is weightless." -Ryan Carroll, Seas Life