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Winging It Travel Podcast

Winging It Travel Podcast

By: Voyascape Media
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The Winging It Travel Podcast is your weekly ticket to the world—dropping every Monday and hosted by me, James Hammond, proudly part of the Voyascape Network. This is more than just a travel podcast—it's a cinematic audio experience that takes you deep into the heart of each journey. Through rich immersive soundscapes, on-the-ground reactions, and authentic storytelling, I bring you right alongside me—whether I’m hiking up volcanoes in Guatemala, navigating the chaos of a city market in India, or camping under the stars in British Columbia. With over fifteen years of travel behind me, I've met incredible people, seen breathtaking places, and collected unforgettable stories—and now I get to share them with you. Expect a mix of: 🎧 Immersive-Audio episodes that let you hear the world as I experience it 🎙️ Raw, reflective solo episodes filled with insights, tips, and honest travel tales 🌍 Guest conversations with some of the most diverse and well-travelled people I've encountered on the road Every episode blends anecdotes, practical advice, cultural insight, and moments of pure adventure. This podcast is for travellers, dreamers, backpackers, and anyone who’s ever thought, what if I just went for it? So, if you're looking for stories to tell, tips to share, and experiences to inspire, you're in the right place. There’s so much travel content coming your way, it just might spark that trip you’ve been dreaming about for years. Welcome to a world of travel! Thank you for listening in. Please get in touch with us below. Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠ Finally, please rate the podcast five stars on your podcast app and give a positive written review. This helps the podcast grow, for free. Website - https://www.wingingittravelpodcast.com Buy Winging It a coffee - buymeacoffee.com/wingingit Voyascape - https://voyascape.com Linktree - https://linktr.ee/jameshammondtravel Email - jameshammondtravel@gmail.com Roaming with Hammo YouTube channel - https://www.youtube.com/@roamingwithhammo Happy Winging It!385914 Social Sciences Travel Writing & Commentary
Episodes
  • Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)

    Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)
    Jun 22 2026
    Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)This week on Winging It, I'm sharing a special crossover episode from my other podcast, Taking A Career Break with Katrina McGhee. I really feel our two audiences do crossover, so I am sharing one of our most popular episodes with you. Please check out the rest of the catalogue for everything relating to a career break.Episode 67 - Why You Should Stop Waiting for the “Right Time” to Take a Career Break ShownotesIf you've ever dreamed of taking a career break, travelling the world, changing direction, or simply pressing pause on the life you've built, you've probably told yourself the same thing many of us do:"I'll do it when the timing is right."The truth is, there may never be a perfect time.In this episode, Katrina and I dive into one of the biggest reasons people never take a career break: waiting for the mythical "right time." We explore why life will always present obstacles, why fear often disguises itself as practicality, and how delaying your dreams can lead to years of wondering "what if?"Is there ever a right time to take a career break—or are you just waiting forever?From economic uncertainty and job market fears to internal pressure and workplace guilt, they unpack why it always feels like the wrong time—and why that thinking is keeping you stuck.Katrina introduces the concept of PHOBO (Fear of Becoming Obsolete) and explains how this fear shows up both before and during a career break—often preventing people from fully committing to the change they need.You’ll learn why the “perfect moment” doesn’t exist, how your brain is wired to keep you in survival mode, and what it actually takes to create a good enough time to step away and reset your life.If you’ve been telling yourself “maybe next year” or “once things settle down,” this episode will challenge that narrative—and help you take your first real step toward a career break.Taking A Career Break with Katrina McGheeApple Podcasts - https://podcasts.apple.com/ca/podcast/taking-a-career-break-with-katrina-mcghee/id1772602758Spotify - https://open.spotify.com/show/1lRPigXIghYUw82Eqak0mF?si=b956d5b826df4cf1YouTube - https://www.youtube.com/@TakingaCareerBreakwithKatrinaReady to stop "running on empty" and start running toward a life you actually love?📞Schedule a call with Katrina - ⁠⁠⁠⁠⁠⁠⁠https://kmcgheecoaching.as.me/freeconsult⁠⁠⁠⁠⁠⁠⁠🫶🏼Join the BreakSpace community - ⁠⁠⁠⁠⁠⁠⁠www.gobreakspace.com⁠⁠⁠⁠⁠⁠⁠🎁Order Katrina's book (w/ special bonus!) - ⁠⁠⁠⁠⁠⁠⁠https://www.kmcgheecoaching.com/book⁠⁠⁠⁠⁠⁠⁠Support Winging It Travel PodcastIf you enjoyed this episode:⭐ Leave a 5-star rating or review on your podcast app☕ Support the show at buymeacoffee.com/wingingit🌍 Explore more episodes at wingingittravelpodcast.com✈️ Check out more great travel podcasts at https://voyascape.com📺 Now also on YouTube - https://www.youtube.com/@wingingittravelpodcast⏱️ Timestamps00:00 Introduction – Why this career break episode matters for travellers02:08 Winging It Travel Podcast intro03:47 Welcome to Taking A Career Break with Katrina McGhee04:39 Why do we keep waiting for the "right time"?06:34 The fear of becoming obsolete and falling behind08:13 Is there ever a good economic time to take a break?10:59 Why hard times don't mean you can't make a career break happen13:00 James shares his own fears about timing and entrepreneurship15:27 The "worst time fallacy" explained17:13 Why guilt keeps people stuck in jobs18:52 Break Space: Support for your own career break journey19:28 The target keeps moving – there will always be another excuse22:58 When has life ever truly felt certain?24:39 Planning versus endlessly postponing your dreams26:23 Why the perfect moment doesn't exist27:15 How fear of falling behind keeps you in survival mode29:32 Building the bridge before taking the leap31:05 Stop waiting and start making your career break happen32:17 Final thoughts and outro--------------------------------------------------------------Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠Voyascape: Travel Podcast Network - https://voyascape.com/Winging It Travel Podcast - Website--------------------------------------------------------------Winging It Travel Podcast CreditsHost/Producer/Creator/Composer/Editor - James HammondContact me - jameshammondtravel@gmail.com or james@wingingitproductions.comSocial Media - follow me on:InstagramTikTok Facebook--------------------------------------------------------------Affiliate Links If you click one of the below to book something, I get a tiny commission, which helps the podcast.Book Flights with Skyscanner - HereUse Revolut Travel Card - HereBook Hostels With Hostelworld - HereBooking.com - HereBook Experiences With Viator - HereDiscovery Car ...
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    34 mins
  • Why Travel Changes Everything - A Deep Dive with James Hammond on the Island Vacation Travel Podcast

    Why Travel Changes Everything - A Deep Dive with James Hammond on the Island Vacation Travel Podcast
    Jun 15 2026
    Why Travel Changes Everything - A Deep Dive with James Hammond on the Island Vacation Travel PodcastHello guys!Another guest appearance on another travel podcast today, and this time it is the Island Vacation Travel Podcast with Al Philogene, as we take a deep dive into the impact of travel on our daily lives, as a lifestyle choice and the impact on me personally too.You can watch this episode on YouTube here (please subscribe to Winging It) - https://youtu.be/XWfXoSQ5r7cI loved speaking with Al on his podcast, so please check it out below, too. Enjoy!Spotify - https://open.spotify.com/show/6IKCiUg5sZstUia5vOpK62?si=d9c56d650b754e28Apple Podcasts - https://podcasts.apple.com/ca/podcast/island-vacation-travel-podcast/id1579773196Website - https://islandvacationpodcast.com/#Island Vacation's Shownotes below.James Hammond shares his unforgettable travel experiences in Bhutan, Japan, and Bolivia, highlighting the importance of practical budgeting and lifestyle centered around exploration. He emphasizes the significance of people, culture, and food in each destination, and provides valuable insights on planning a six-month backpack trip to South America, including budgeting, route planning, and avoiding common travel mistakes.The conversation covers topics related to visa rules and immigration, the difference between hidden gems and tourist-heavy spots, the choice between travel and a traditional career path, financial trade-offs and the balance between freedom and stability, and the impact of COVID-19 on travel. The conversation covers the impact of COVID on travel, the rise in travel costs, the experience of over-tourism, and the financial considerations of long-term travel. It also delves into the importance of cultural familiarity when starting to travel and the need to adapt to changing travel costs and conditions.Takeaways• Unforgettable travel experiences in Bhutan, Japan, and Bolivia• Practical budgeting and lifestyle centered around exploration Visa rules and immigration are important considerations for travelers, and it's essential to research and understand the rules of each country.• Choosing hidden gems over tourist-heavy spots can lead to a more unique and less crowded travel experience.• The decision to prioritize travel over a traditional career path involves a trade-off between stability and freedom, and the pursuit of experiences over material possessions.• The impact of COVID-19 on travel has led to increased costs and a surge in travel to popular destinations, highlighting the importance of exploring hidden gems and off-peak travel periods. COVID has impacted travel costs and led to a rise in expenses.• Cultural familiarity is important when starting to travel, and it's advisable to start small and gradually explore different cultures.• Adapting to changing travel costs and conditions is crucial for long-term travel.Support Winging It Travel PodcastIf you enjoyed this episode:⭐ Leave a 5-star rating or review on your podcast app☕ Support the show at buymeacoffee.com/wingingit🌍 Explore more episodes at wingingittravelpodcast.com✈️ Check out more great travel podcasts at https://voyascape.com📺 Now also on YouTube - https://www.youtube.com/@wingingittravelpodcast⏱️ Timestamps00:00 - Introduction & Welcome02:02 - Meet James Hammond: Building a Travel Lifestyle02:56 - Top 3 Countries: Bhutan, Japan & Bolivia05:32 - Memorable Travel Experiences from Around the World08:14 - Why People Matter More Than Food or Culture09:12 - Why Everyone Should Travel at Least Once10:39 - Planning a 6-Month Backpacking Trip13:41 - Essential Gear Every Long-Term Traveller Needs15:14 - Travel Budgets: How Much Money Do You Really Need?17:33 - Route Planning Across South America19:21 - Biggest Travel Mistakes to Avoid22:31 - Hidden Gems vs Tourist Hotspots25:46 - Why I Chose Travel Over a Traditional Career30:07 - Freedom vs Financial Stability37:42 - Upcoming Trips: Finland, Estonia & French Polynesia38:51 - Travel After COVID: What's Changed?43:21 - My Least Favourite Destination (And Why)46:55 - Countries Still on My Travel Bucket List49:19 - How Much Money Do You Need to Travel the World?54:07 - Advice for First-Time Travellers58:00 - Where to Find Winging It Travel Podcast & Roaming with Hammo59:43 - Final Thoughts & Outro--------------------------------------------------------------Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠Voyascape: Travel Podcast Network - https://voyascape.com/Winging It Travel Podcast - Website--------------------------------------------------------------Winging It Travel Podcast CreditsHost/Producer/Creator/Composer/Editor - James HammondContact me - jameshammondtravel@gmail.com or james@wingingitproductions.comSocial Media - follow me on:InstagramTikTok Facebook--------------------------------------------------------------Affiliate Links If you click one of the below to book something, I get a tiny commission, which ...
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    1 hr and 2 mins
  • Wellington Travel Guide: Why I Spent a Year Living in New Zealand's Capital

    Wellington Travel Guide: Why I Spent a Year Living in New Zealand's Capital
    Jun 8 2026
    Wellington Travel Guide: Why I Spent a Year Living in New Zealand's CapitalWellington is one of my favourite cities in the world, and in this episode I'm sharing exactly why.I first visited New Zealand's capital in 2013 on the Kiwi Experience and instantly connected with the city. In 2017, when Emma and I arrived in New Zealand on a working holiday visa, we spent weeks road-tripping around both islands before deciding where to settle. I already had my sights set on Wellington, and thankfully Emma fell in love with it too. We ended up spending nearly a year living there, giving us the chance to experience the city far beyond the typical tourist highlights.In this Wellington travel guide, I share the places, experiences and local tips that made the city so special to us. From riding the iconic Wellington Cable Car and exploring Te Papa Museum to walking the waterfront, climbing Mount Victoria and discovering all parts of the city, I cover the attractions that I think every visitor should experience.Of course, no episode about Wellington would be complete without talking about coffee and brunch. This is the city where my love of coffee began, and over the course of 11 months I worked my way through more cafés than I can count. I share my favourite spots for brunch, great coffee, waterfront views and local atmosphere, including some long-time Wellington institutions that I still think about today.I also dive into the practical side of visiting and living in Wellington, including where to stay, the best neighbourhoods to base yourself, transport options, day trips, travelling between the North and South Islands, and what it was like finding work while on a New Zealand working holiday visa. If you're considering moving to Wellington or spending time there as a backpacker, digital nomad or working holiday traveller, there's plenty here for you.Along the way, I share some personal stories from our time living in the city, including working in government ministries, surviving a late-night earthquake, becoming known as the office "serial monster", buying a $1,000 road-trip car and somehow making a profit when it was written off.Whether you're planning your first visit to Wellington, preparing for a New Zealand working holiday, or simply looking for inspiration for your next trip, this episode will give you an honest look at one of the most creative, quirky and liveable cities I've ever experienced.In this episode:• Why Wellington became our home for nearly a year• The best things to do in Wellington• My favourite cafés, brunch spots and coffee roasters• Where to stay and the best neighbourhoods to explore• Working holiday and job-hunting advice• Transport tips and South Island connections• Road-trip recommendations and day trips• Stories from everyday life in New Zealand's capitalSupport Winging It Travel PodcastIf you enjoyed this episode:⭐ Leave a 5-star rating or review on your podcast app☕ Support the show at buymeacoffee.com/wingingit🌍 Explore more episodes at wingingittravelpodcast.com✈️ Check out more great travel podcasts at https://voyascape.com📺 Now also on YouTube - https://www.youtube.com/@wingingittravelpodcast⏱️ Timestamps00:00 Why Wellington became my favourite city02:30 Wellington explained: location, culture and first impressions03:20 The "Serial Monster" work story05:50 Working holiday jobs and finding work in Wellington08:10 Best things to do in Wellington10:50 Waterfront walks, Mount Victoria and local neighbourhoods12:05 Day trips, sporting events and road trips13:30 Where to stay in Wellington15:55 Support the podcast16:40 Earthquake experiences in Wellington17:50 Best cafés, brunch spots and coffee in Wellington22:15 Food markets and eating on a budget23:15 Wellington travel and transport tips25:40 Kiwi Experience and travelling New Zealand26:40 Buying a car and road-tripping New Zealand28:05 Why Wellington is still one of my favourite cities--------------------------------------------------------------Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠Voyascape: Travel Podcast Network - https://voyascape.com/Winging It Travel Podcast - Website--------------------------------------------------------------Winging It Travel Podcast CreditsHost/Producer/Creator/Composer/Editor - James HammondContact me - jameshammondtravel@gmail.com or james@wingingitproductions.comSocial Media - follow me on:InstagramTikTok Facebook--------------------------------------------------------------Affiliate Links If you click one of the below to book something, I get a tiny commission, which helps the podcast.Book Flights with Skyscanner - HereUse Revolut Travel Card - HereBook Hostels With Hostelworld - HereBooking.com - HereBook Experiences With Viator - HereDiscovery Car Hire - HereBook Buses With Busbud - HereBook Trains With Trainline - HereTravel Insurance with SafetyWing - HereBook Flights With Expedia Canada - Here---------------------------...
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    31 mins
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