In this episode of The Career Flipper, host Jenny Dempsey sits down with sisters Wendy and Elizabeth Pochop of Baltimore, Maryland, co-founders of Untethered Voyages, a side hustle turned passion project that creates cruise-based retreats for leaders, communities, and organizations.

We connected through Support Driven, a global community for customer support professionals, and what started as a conversation about side hustles turned into an inspiring look at building something new from burnout, curiosity, and passion for travel.

What You’ll Hear in This Episode:

• How Wendy’s burnout in customer success led to a sabbatical, curiosity, and eventually a pivot toward travel and hospitality.
• The family cruise that sparked the idea for Untethered Voyages and how it evolved from “workations at sea” into curated community-building retreats.
• The unique way Wendy and Elizabeth balance their strengths, vision and execution, while building a business together as sisters, roommates, and travel buddies.
• Why structure, accountability, and small sacrifices are key to making side hustles work alongside full-time jobs.
• Practical advice for anyone feeling stuck in their career: start small, find joy outside of work, and solve a problem you’ve already faced for others.
• Their big vision: living and working full-time from cruise ships while helping groups create unforgettable experiences.
   

Connect with Untethered Voyages

• Join their Alaska adventure next summer www.untetheredvoyages.com/alaska.
  • BONUS: They will waive the planning fee for Career Flipper Podcast listeners, if you go on the trip, use code "Career Flipper"!
• Connect on Instagram: https://www.instagram.com/untetheredvoyagesvacations/
• Connect on LinkedIn: https://www.linkedin.com/company/untethered-voyages
• Book your own group retreat at sea: untetheredvoyages.com

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🎵 Music Credits

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

And hey, remember my favorite question: What’s the best that could happen? 💫