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 guaranteed
• How the “someday” mentality leads to regret
• Why travel becomes harder later in life
• The importance of time freedom and flexibility
• How geopolitics can suddenly change travel opportunities
• Why memories mean more than possessions
• The employee mindset vs lifestyle freedom
• Why taking a sabbatical or career break can change your life
• How travel improves confidence, perspective, and personal growth
• Why 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 Podcast

If 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 - [email protected] or [email protected]

Social Media - follow me on:

Instagram

TikTok

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 - 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 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