Ep 156 Milestones and New Beginnings

from What Could Go Right? · host Erik Orton + Emily Orton

What if your biggest milestones are still ahead of you? In this episode of What Could Go Right?, we explore what happens after graduation, after the big life moments, and into midlife transitions—when life opens up in new and unexpected ways. Through real stories from our sailing trips, we talk about personal growth, trying something new, and finding purpose in your next chapter. From learning to sail to building confidence and reimagining what’s possible, these are the milestones that don’t come with a ceremony—but change everything. If you’ve been feeling curious, restless, or ready for more, this episode will help you see that you’re not behind—you might just be getting started. ⭐⭐⭐⭐⭐ Rate. Review. Subscribe.   Try Living on a Sailboat for a Week:   No experience required—and yes, you’ll take the helm. Not a party charter. Not a certification course. A small-group, hands-on sailing experience that’s been called the “unicorn of sailing trips.” See if it’s your kind of adventure: Sail with us. Erik + Emily Memoirs: Seven at Sea: Why a New York City Family Cast Off Convention For A Life-Changing Year On A Sailboat  Knock: The Spiritual Journey of a Door-to-Door Salesman Connect with Erik + Emily: Email Subscribe to Encouragement Youtube Like, Comment, Subscribe Instagram  Facebook

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This episode is 22 minutes long.

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This episode was published on June 11, 2026.

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