Doing hard stuff takes courage, but more importantly it takes keeping the right perspective about the things we perceive as negative. I am a former playboy playmate, a caption, a YouTube and single mom, living on a tiny sailboat with a mission to sail around the world.
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Doing hard stuff takes courage, but more importantly it takes keeping the right perspective about the things we perceive as negative. I am a former playboy playmate, a caption, a YouTube and single mom, living on a tiny sailboat with a mission to sail around the world.
Behind the Collab: Sailing Doodles, Dating Myths & YouTube Reality
Go Sea the World
27 minutes
1 week ago
Behind the Collab: Sailing Doodles, Dating Myths & YouTube Reality
In this episode of Go Sea the World, Aubrey O’Hare and Jordan share what it was really like sailing in Greece with Sailing Doodles—from collaborating as creators to navigating chemistry, expectations, and the reality of life on YouTube.
We talk candidly about creator burnout, work ethic, thumbnails and algorithms, and what happens when an online connection meets real life. From age gaps and dating myths to sailing YouTube growth and collaboration dynamics, this is an honest, behind-the-scenes conversation about building a life—and a career—at sea.
Filmed during our time sailing the Greek islands, this episode pulls back the curtain on what it’s actually like to collaborate with another major sailing channel while staying true to yourself and your story.
Topics covered:
Sailing Doodles collaboration in Greece
Life as a sailing YouTube creator
Chemistry vs commonality in relationships
Online dating vs real-world connection
YouTube thumbnails, algorithms & burnout
Sailing, travel, and life at sea
Subscribe to Go Sea the World for honest conversations about sailing, travel, relationships, motherhood, and choosing an unconventional life on your own terms.
Go Sea the World
Doing hard stuff takes courage, but more importantly it takes keeping the right perspective about the things we perceive as negative. I am a former playboy playmate, a caption, a YouTube and single mom, living on a tiny sailboat with a mission to sail around the world.
