Why Waiting Until Retirement To Travel Will Be Your Biggest Regret
Winging It Travel Podcast
Why Waiting Until Retirement To Travel Will Be Your Biggest Regret
Have you ever said to yourself, “I’ll travel when I retire”? In this solo episode of the Winging It Travel Podcast, I dive into why I believe waiting until retirement to travel could become one of your biggest regrets.
After travelling to more than 75 countries over the last 15 years, I’ve realised that there will always be another excuse not to go — another promotion, another bill, another responsibility, another reason to delay your dreams. In this episode, I explore why so many people postpone travel until “someday,” and why I think that mindset can be dangerous.
I talk about the realities of health, time, energy, work culture, fear, and the societal expectations that keep people trapped in routines they don’t actually enjoy. I also share personal stories and reflections from my own travels through places like Central America, Ukraine, Canada, and the USA, alongside lessons I’ve learned from years of backpacking and long-term travel.
This is a deep, honest, and motivational episode about creating freedom, prioritising experiences, and making travel part of your life now — not decades into the future.
In this episode, I discuss:
- Why retirement is never guaranteedHow the “someday” mentality leads to regretWhy travel becomes harder later in lifeThe importance of time freedom and flexibilityHow geopolitics can suddenly change travel opportunitiesWhy memories mean more than possessionsThe employee mindset vs lifestyle freedomWhy taking a sabbatical or career break can change your lifeHow travel improves confidence, perspective, and personal growthWhy meaningful experiences matter more than material things
If you’ve ever dreamed of taking a career break, backpacking the world, travelling long term, or escaping the traditional 9-5 lifestyle, I hope this episode gives you the motivation to stop waiting and start planning your next adventure.
Need help taking a break to travel? Check out my other podcast, Taking A Career Break with Katrina McGhee below.
YouTube - https://www.youtube.com/@TakingaCareerBreakwithKatrina
Apple Podcasts - https://podcasts.apple.com/ca/podcast/taking-a-career-break-with-katrina-mcghee/id1772602758
Spotify - https://open.spotify.com/show/1lRPigXIghYUw82Eqak0mF?si=30ab153333794e19
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
⏱️ Timestamps
00:00 – Why “I’ll Travel When I Retire” is dangerous
02:23 – Introduction to the podcast
04:03 – Reason #1: Retirement and life are never guaranteed
06:30 – Why health and energy matter for travel
07:55 – The employee mindset and time freedom
10:18 – Why geopolitics can change travel forever
12:30 – Ukraine, Central America & travelling while you can
13:47 – The danger of the “someday” mentality
15:55 – Quick podcast break & ways to support the show
16:39 – Reason #5: Memories are worth more than possessions
18:55 – Why travel memories stay with you forever
20:28 – Are jobs really worth sacrificing your life for?
23:20 – How travel improves confidence and worldview
24:45 – The value of career breaks and sabbaticals
26:05 – Doing things outside your comfort zone
26:58 – Alex Garland quote from The Beach
27:45 – Why millennials should travel now, not later
28:40 – Final thoughts and listener takeaway
29:27 – Outro
--------------------------------------------------------------
Produced by Winging It Productions - https://www.wingingitproductions.com
Voyascape: Travel Podcast Network - https://voyascape.com/
Winging It Travel Podcast - Website
--------------------------------------------------------------
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:
TikTok
--------------------------------------------------------------
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 - Here
Use Revolut Travel Card - Here
Book Hostels With Hostelworld - Here
Booking.com - Here
Book Experiences With Viator - Here
Discovery Car Hire - Here
Book Buses With Busbud - Here
Book Trains With Trainline - Here
Travel Insurance with SafetyWing - Here
Book Flights With Expedia Canada - Here
--------------------------------------------------------------
Thanks for supporting me and the podcast!
Cheers James.
Mentioned in this episode:
Check out the Smart Travel Podcast
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:
Smart Travel Podcast
Check out all of our other travel podcasts from around the world
This podcast is part of Voyascape, a podcast network that brings together the world's best travel podcasts. You can find all of our podcasts from around the world at Voyascape.com. If you are interested in advertising or sponsored content on any of our shows you can find out more at the link below.
Voyascape Podcast Network