What happens when you move abroad with absolutely zero plan? In this episode of Almost Local, I sit down with James Hammond (host of the Winginit Travel Podcast) to talk about his 10-year journey of long term travel, surviving on working holiday visas, and the unfiltered reality of expat life.From running out of money and finding work via payphones before smartphones existed, to getting "stuck" in Canada during COVID and navigating Vancouver's insane cost of living, James shares the highs and lows of living abroad. We dive deep into Canadian bureaucracy, what it's really like to work 9-to-5 abroad, and why, even after getting his Canadian citizenship, he's planning to move back to the UK. If you are considering moving abroad or just love raw, honest digital nomad podcasts, this episode is for you!We break down the core challenges and invaluable insights of living unconventional:How to navigate the complexities of visas, bureaucracy, and cost of living in countries like Canada, Australia, and the UKWhy sometimes winging it can lead to the best opportunities, and when to build for stabilityPractical advice for anyone dreaming of long-term travel, global work, or relocating without a fixed plan🎙️ Guest: James HammondJames Hammond is a globally-minded travel podcaster, content creator, and entrepreneur. His work focuses on living authentically abroad while monetizing the journey—a real-world blueprint for turning wanderlust into a thriving lifestyle.🔗 Guest LinksInstagram: https://www.instagram.com/wingingittravelpodcastYouTube: https://www.youtube.com/@roamingwithhammoFacebook: https://www.facebook.com/jameshammondtravel/LinkedIn: Send us a message!Level8: Upgrade your travel experience with luggage designed for people constantly on the move. Durable, sleek, and built to last—Level8 makes every trip smoother. Get 10% off with code LEVEL8Expat10. StartAbroad: Planning a move abroad doesn’t have to be overwhelming. StartAbroad helps you navigate visas, paperwork, and the entire relocation process—especially for Costa Rica, Panama, Spain, and Portugal. Get 5% off with code ALMOSTLOCAL.PodMatchLike a dating app by matching hosts and guests for podcast interviews with process automations.Slate and KeyThe Key To Your New Life. A experience to curate the life of your dreams in the Portugal.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the showCheck the episodes in video in Youtube 🎥:https://www.youtube.com/@almostlocalstoriesFollow us on social media 📲:https://www.instagram.com/almostlocalstories⁠https://www.tiktok.com/@almostlocalstories⁠https://www.facebook.com/almostlocalstories🌎✈️ Join our Almost Local Network now and connect with a global community of like-minded adventurers!