Before You Book Your Flight to Madrid, Listen to This Episode (The Ultimate Madrid Guide) episode artwork

EPISODE · May 6, 2026 · 27 MIN

Before You Book Your Flight to Madrid, Listen to This Episode (The Ultimate Madrid Guide)

from Reclaiming Bossy · host Maahika Singh

What if Emily in Paris was actually set in Madrid and was culturally accurate?In the first episode of the Reclaiming Bossy Madrid season, I sit down with Maddy, the creator behind Maddy in Madrid, to talk about what building a real life abroad actually looks like beyond the romanticised TikToks and Netflix versions.We talk about the reality of moving to Madrid, learning Spanish as an adult, making friends when you know nobody, navigating culture shock, understanding the unspoken social rules in Spain, and creating a life that feels exciting and authentic.This episode is part Madrid city guide, part deep dive into identity, reinvention, and what happens when you stop waiting for “someday” and actually move abroad.We also get into the cafés worth working from, the rooftop bars and picnic spots locals actually go to, how to find community in Madrid, and why embracing the culture instead of recreating your old life abroad changes everything.If you’ve been dreaming about moving abroad, taking a solo trip, becoming a digital nomad, or building a slower and more intentional life overseas, this episode will either make you book the flight or finally give you the honest guide to doing it properly.TIMESTAMPS00:00 - Introduction and moving to Madrid00:50 - Maddy’s background and learning Spanish01:54 - Embracing a new culture vs. Emily in Paris03:12 - Why English speakers struggle with learning languages05:16 - Advice on making friends in a new country07:12 - Biggest culture shocks in Spain08:27 - Best coffee shops for working, dates, and relaxing11:26 - Finding Madrid’s authentic hidden gems12:41 - Cultural norms and respecting the Spanish way of life15:21 - Representing Spain online and navigating expat stereotypes17:15 - Dealing with reverse culture shock and homesickness19:07 - Advice for taking the leap and moving abroad20:03 - What people get wrong about Spain and Americans21:16 - Best bars, rooftops, and picnic spots in Madrid23:58 - Communities to join to make friends26:15 - What’s next for Maddy26:51 - Reclaiming the word “bossy”Connect with  MaddyWebsite: https://maddyinmadrid.com/Instagram: https://www.instagram.com/maddyinmadrid_/Tiktok: https://www.tiktok.com/@maddyinmadridBUILD YOUR BOLDEST + BOSSIEST LIFE/ CAREERBossy Behind the Scenes: Essays, reflections, resources and all the behind-the-scenes of building a bold, bossy life.⁠https://substack.com/@bossybehindthescenes⁠WORK WITH MECreator/Founder Office Hours: Bring me your ideas, questions or whatever you’re stuck on, and we’ll turn it into a plan.⁠https://calendly.com/maahika/mentoring?back=1⁠Founders + brands: Work with me on storytelling, personal branding, content and strategy through Empower Sounds Media.Book a Strategy Session : ⁠https://calendly.com/maahika/branding-strategy-session?back=1&month=2026-07⁠Book a discovery call : ⁠https://calendly.com/maahika/discovery-call?back=1⁠Join the next personal branding sprint : ⁠https://docs.google.com/forms/d/e/1FAIpQLSeNPFNgdt02CyvYsb6n9i8kmvEJRxQDmTwOVusTxII_tMoJ7Q/viewform?usp=header⁠Follow The Podcast/ Connect With MePodcast Instagram: @reclaimingbossyPodcast TikTok: @reclaimingbossyMy Instagram: @maahika.sMy TikTok: @maahika.sCollaborations + enquiries: [email protected]

Episode metadata supplied by the publisher feed · Published May 6, 2026

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Before You Book Your Flight to Madrid, Listen to This Episode (The Ultimate Madrid Guide)

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