Chasing Fear, Purpose and 30ft Mountains of Water

Today we talk to Drew Smith – a sailor, storyteller, and seeker who just completed a six-year voyage to the far side of the world on his 32-foot sailboat.

Drew set out to reach his antipode – the exact opposite point on Earth from where he was born. He’s got incredible stories, but the one that still haunts me is getting caught in a storm in 30 foot waves, 750 miles off the coast of Australia, in the middle of the night, all alone.

I grew up around boats and I could listen to Drew’s tales of nautical disaster for hours. There are so many takeaways from this conversation. But the most dramatic is this idea that not only can you spend your life consumed by these big goals that are never as satisfying as you think when you achieve them, but that you come back to a life, friends, a job that no longer fits. Everyone expects you to be the same person but you've changed. You don’t need to sail around the world for years to know what this feels like. If you’re working on yourself and sometimes feels weighted down by an old life that no longer serves you, you’ll love hearing how Drew is navigating his way back to a life that fits this new version of him. You’re never going to forget this conversation.

Batten down the hatches, and please enjoy, Drew Smith.

Key Takeaways

• Drew’s journey started with a question: what’s the farthest he could go from where he was born without leaving the planet? The answer became a six-year solo sailing mission to his geographical antipode.
• Growing up in a small town in eastern Canada, Drew developed a thirst for something bigger—and he's been chasing horizons ever since.
• Reaching your goal is never as satisfying as you think. The real reward is in the journey, the rhythm, and the self-discovery along the way.
• After years of wandering, Drew’s realizing that what he wants next isn’t distance—it’s community, purpose, and something that lasts.
• The scariest moment of his voyage? Being caught in a 10-meter swell 750 miles off the coast of Australia, completely alone, relying on gear he’d never tested in real-world conditions.
• Solo sailing is both isolating and deeply meditative. You become one with your boat, hyper-attuned to every sound, every shift in the wind, every creak of the hull.
• Coming home was harder than expected. The thrill of arrival fades fast, and the question quickly becomes: “Now what?”

Links & Resources

Drew on Instagram

Drew on TikTok

Jordan Series Drogue - A storm safety device used in extreme offshore conditions.

Ze Frank’s “Earth Sandwich” Concept - The fun idea that inspired Drew’s Earth Sandwich celebration at his antipode.

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