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Travel Possibilities
Cali O'Connor
83 episodes
2 weeks ago
There is more to life than living for the weekend and trying to strategically finagle your vacation time to coincide with holidays so you can travel for longer. There are ways to bring more travel into your life. It may feel scary or uncomfortable, but it is POSSIBLE. The first step to making your travel dreams come true, however that looks for you, is to believe it is possible. Listen for actionable tips and strategies about career breaks, remote work, and more, plus inspiring interviews from those who have been there. This is not your run-of-the-mill travel podcast. It's a career break podcast, a remote work podcast, a travel job podcast, a digital nomad podcast, you get the idea...It encompasses everything that can make travel possible and more accessible to YOU!
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Places & Travel
Society & Culture
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All content for Travel Possibilities is the property of Cali O'Connor and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
There is more to life than living for the weekend and trying to strategically finagle your vacation time to coincide with holidays so you can travel for longer. There are ways to bring more travel into your life. It may feel scary or uncomfortable, but it is POSSIBLE. The first step to making your travel dreams come true, however that looks for you, is to believe it is possible. Listen for actionable tips and strategies about career breaks, remote work, and more, plus inspiring interviews from those who have been there. This is not your run-of-the-mill travel podcast. It's a career break podcast, a remote work podcast, a travel job podcast, a digital nomad podcast, you get the idea...It encompasses everything that can make travel possible and more accessible to YOU!
Show more...
Places & Travel
Society & Culture
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Travel Story: It's Never Too Late to Quit Your Job and Travel the World with Cindy Sheahan
Travel Possibilities
45 minutes 51 seconds
2 years ago
Travel Story: It's Never Too Late to Quit Your Job and Travel the World with Cindy Sheahan

Get ready to be inspired by my guest Cindy Sheahan!

In 2017, Cindy realized she wasn't getting any younger, the time was right and, "if not now, when?" so she quit her perfectly good job, packed a backpack and headed out the door alone to explore.

Five plus years later, she's been to 38 countries - mostly solo - such as Turkey, Madagascar, Sri Lanka, Georgia, France, Italy and North Macedonia. She's visited over 400 cities and towns, countless hostels and homestays, hikes and treks all over the world including the Portuguese Camino.

Along the way she's flown in a hot air balloon over Cappadocia Turkey, was a caretaker at a haunted villa in Tuscany, paraglided over burial sites in Madagascar, worked in a vineyard in New Zealand...and met a French paraglider on Tinder while in Nepal trekking, with whom she's traveled to 6 continents. Cindy moved to Portugal in October of 2022 and is living in Porto...for now.

She's written for a women's travel group called She Hit Refresh, been featured in The Points Guy and the New York Times, and has been a panelist on a Digital Nomad online summit, and just recently, as a "Move to Portugal" expert in an online seminar by International Living. She has 4 amazing grown kids and one grandson, with another grandbaby on the way - they all live in Colorado and support, admire and join her when able to - and they are her biggest cheerleaders in this crazy adventure.

Want to learn more about Cindy?

Cindy's Instagram

Cindy's Website

Cindy's Facebook

If you enjoyed today's episode and had a takeaway moment to share, be sure to take a screenshot and tag me (@thetravelshifters) and Cindy (@PostsFromAFlashpacker) on Instagram and let us know what it was! We love connecting with you. 

Also, I invite you to leave a review on Apple Podcasts or a rating on Spotify.

See you in the next episode!

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Travel Possibilities
There is more to life than living for the weekend and trying to strategically finagle your vacation time to coincide with holidays so you can travel for longer. There are ways to bring more travel into your life. It may feel scary or uncomfortable, but it is POSSIBLE. The first step to making your travel dreams come true, however that looks for you, is to believe it is possible. Listen for actionable tips and strategies about career breaks, remote work, and more, plus inspiring interviews from those who have been there. This is not your run-of-the-mill travel podcast. It's a career break podcast, a remote work podcast, a travel job podcast, a digital nomad podcast, you get the idea...It encompasses everything that can make travel possible and more accessible to YOU!