In this deeply personal solo episode, I take you through my full travel journey—from growing up in Norwich with no real concept of travel, to building a life around it in Vancouver and around the world.
This isn’t just a story about where I’ve been—it’s about how my mindset around travel has completely evolved over time.
From partying through Southeast Asia in my early 20s, to seeking culture, connection, and purpose in my 30s… this episode breaks down the different phases of travel, what changed, and why I now see travel as a long-term lifestyle rather than a short-term escape.
I also share honest reflections on burnout, money, building a travel-focused career, and what the future of travel looks like for me.
If you’ve ever wondered how travel fits into your life long-term—or how your relationship with it might change over time—this one’s for you.
To finish, I want to share with you, the audience, an episode where you get to know me more. I have been doing this for five years, and I believe sharing more personal details will help build a tighter Winging It community.
I hope you enjoy the episode and that it inspires you to travel for the first time or to dream about making it a lifestyle. Drop me a comment on your thoughts, too.
Support the Podcast
If you enjoyed this episode:
⏱️ Timestamps
00:00 Why I’m sharing this story
02:00 Growing up in Norwich & early curiosity about the world
05:30 School trips & no real travel mindset yet
08:00 Moving to London & first exposure to diversity
09:30 Australia 2010 – the trip that changed everything
11:30 The moment I decided to travel long-term
12:50 Ukraine road trip & first taste of raw travel
14:30 Planning the 2013 backpacking trip
15:20 Leaving the UK & heading into the unknown
17:00 First culture shock in Bangkok
18:30 Southeast Asia – party travel & backpacker life
20:00 Australia – working life & maturing
22:30 Smartphones & how travel started to change
23:30 South America solo travel & shift to culture
25:00 Realising travel had evolved for me
26:00 India 2016 – second major culture shock
27:30 Meeting Emma & planning long-term travel
28:30 Health scare & motivation to live fully
29:30 15 months of travel as a couple
31:00 New Zealand, Cook Islands & finding “paradise”
32:00 Turning 30 mindset shift & continuing travel
32:30 Moving to Canada & new chapter
33:00 COVID & travel uncertainty
34:30 Starting the podcast during lockdown
35:00 Planning the 1-year world trip
36:00 Travel becomes a lifestyle, not a phase
37:00 The reality of trying to make money while travelling
38:00 Returning to work & rebuilding
39:30 How I see travel now
40:00 The future: combining work & travel
41:00 Why having a base matters
41:50 Upcoming trips & current lifestyle
42:00 Travel in my late 30s vs early 20s
43:00 Advice for travellers (young & older)
44:00 Final reflections on travel & life
45:00 Personal facts & closing thoughts
46:30 Where to find me & support the podcast
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Produced by Winging It Productions - https://www.wingingitproductions.com
Voyascape: Travel Podcast Network - https://voyascape.com/
Winging It Travel Podcast - Website
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Winging It Travel Podcast Credits
Host/Producer/Creator/Composer/Editor - James Hammond
Contact me - jameshammondtravel@gmail.com or james@wingingitproductions.com
Social Media - follow me on:
Instagram
TikTok
Facebook
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Thanks for supporting me and the podcast!
Cheers James.
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This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:
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