How to Start Planning Your First (Or Next) Career Break Today (Using 5 Simple Steps) with Cali O´Connor

How to Start Planning Your First (Or Next) Career Break Today (Using 5 Simple Steps) with Cali O´Connor

Have you thought about hitting pause on your career to travel the world but are unsure how to make it a reality? It's not as unattainable as you may think! Cali O'Connor shares her experience of taking multiple career breaks and offers 5 practical steps to start planning your own career break today. Cali is a former chemical engineer who traded her career in the oilfield for a life-changing adventure of quitting her job to travel around the world. Now, Cali helps working professionals find clarity in their lives by taking a career break that gives them the freedom to travel, explore, and realign with their life goals. Whether you dream of quitting your job or taking a temporary pause, this episode will give you the confidence and strategies to take that leap. You'll hear about her biggest mistakes during her first career break (and how to avoid them), insights on overcoming common fears such as financial insecurity and leaving a stable job, travel advice to save time and money, and lessons on concurring travel burnout. If you could take a career break tomorrow, where would you go, and why? I'd love to hear your thoughts, and I hope you'll share them by sending me an audio message. Premium Passport: Get ad-free episodes, exclusive content, and access to all episodes for only $3/month. Subscribe now! Tune In To Learn: What led to leaving her career and how she was able to get out of the "achiever" mindset The most important but obvious step in taking a career break The purpose of having goals for your time off Insight on when to start your career break and deciding how long to go for How to budget and financially plan for long-term travel Advice on talking to your boss about your decision Her experience working for a hostel and why they're not just for young travelers 3 places she'd visit again in a heartbeat And so much more Resources: Join Zero To Travel Premium Passport Sign up for our FREE newsletter Visit Cali's website Listen to her podcast Follow her on Instagram Want More? Learning Through Travel: Gap Year, Career Breaks, and Beyond w/Jennifer Miller from BootsnAll.com Sherry Ott from Meet, Plan, Go! on Taking a Career Break to Travel Lessons from Quitting a Job and Selling Everything to Motorcycle Around the World with Mike Barr Thanks To Our Sponsors Babbel - Learn a new language with Babbel! Visit babbel.com/zerototravel to get up to 60% off your subscription. Women Who Travel Podcast - Pack your bags and go on a journey with the Women Who Travel podcast. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Top 7 Uganda Hidden Gems with Lynett Nakamanya

Top 7 Uganda Hidden Gems with Lynett Nakamanya

What if one of Africa's most diverse and rewarding destinations has been hiding in plain sight — and most travelers only ever see a fraction of what it has to offer?  Lynett Nakamanya is a tourism pr...

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Reconnecting to Nature with Adventure, Purpose, Fun, and Travelers’ Curiosity with Alastair Humphreys

Reconnecting to Nature with Adventure, Purpose, Fun, and Travelers’ Curiosity with Alastair Humphreys

What if the travel mindset you bring to far-off places is exactly what's needed right where you live?  Alastair Humphreys is a British adventurer, bestselling author, and speaker named National Geogr...

7 Heinä 1h 21min

Adventure Filmmaking for YouTube, the Art of Storytelling, and Life on the Road with Molly McDonald

Adventure Filmmaking for YouTube, the Art of Storytelling, and Life on the Road with Molly McDonald

Molly McDonald is a London-based YouTube producer and founder of Blue Door Productions, a YouTube-first content agency that brings broadcast-level production to digital storytelling. She studied journ...

30 Kesä 1h 11min

Y We Travel Podcast: To Meet The Neighbours (Bonus Episode!)

Y We Travel Podcast: To Meet The Neighbours (Bonus Episode!)

This week, I'm sharing a bonus episode from a brand new podcast called Y We Travel, co-hosted by my friend Eric Weiner, who has joined me on the show a few times over the years. Eric is a New York Tim...

25 Kesä 40min

7 Travel Tech Trends Worth Knowing in 2026 + 3 Emerging Hot Spots to Spend Quality Time with Matt Gray

7 Travel Tech Trends Worth Knowing in 2026 + 3 Emerging Hot Spots to Spend Quality Time with Matt Gray

Matt Gray is the founder and CEO of Pangea, a free social travel app built to help people coordinate travel plans, share recommendations, and connect with their network around the world. After a decad...

23 Kesä 1h 18min

How to Live an Unconventional Life of Adventure and Purpose by Becoming “Dirtbag Rich” with Blake Boles

How to Live an Unconventional Life of Adventure and Purpose by Becoming “Dirtbag Rich” with Blake Boles

What would it mean to stop measuring your life by the conventional yardstick and start building one that actually fits?  Blake Boles is a writer, experiential educator, and the founder of Unschool Ad...

16 Kesä 1h 27min

Uruguay: Top 7 Hidden Gems (That Most People Miss) + Testing the Remote Work Lifestyle with Lucia Krygier

Uruguay: Top 7 Hidden Gems (That Most People Miss) + Testing the Remote Work Lifestyle with Lucia Krygier

Ever considered traveling to or working from Uruguay?  Lucia Krygier is a Uruguayan entrepreneur and innovation consultant based in Montevideo. In early 2025, she spent two months working remotely fr...

9 Kesä 1h 6min

How to Transition to a “Normal Life” After Travel with Tom Turcich (10th Person to Walk Around the World)

How to Transition to a “Normal Life” After Travel with Tom Turcich (10th Person to Walk Around the World)

What do you do when the adventure ends?  Tom Turcich is a motivational speaker, author, and the tenth person in history to walk around the world. Over seven years, he and his dog, Savannah, covered 2...

2 Kesä 1h 16min

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