• Act Three
  • Posts
  • From Chicago to Madrid: Redefining Retirement

From Chicago to Madrid: Redefining Retirement

A Journey Through Spain’s Capital Reveals the Art of Aging Adventurously

Dear Friends,

A few weeks ago, I jetted off to Spain 🇪🇸, eager to visit two sets of friends who had embraced the country as their retirement destination just a year ago. I was curious to see how their lives had evolved and what parts of their old routines they’d carried with them across the Atlantic.

My journey from Chicago to Madrid, despite the luxury of a lie-flat bed, left me wide awake. Arriving at the Madrid Edition hotel around 9 am, I was grateful for their hospitality in providing an early check-in (best ever use of an exorbitant amount of American Express points - the staff at this hotel made me feel so taken care of - highly recommended!). A refreshing shower and a strong café con leche ☕️ later, I was ready to meet my friends Mark Johnson and James Harger.

We spent a delightful autumn 🍂 day wandering through the heart of Madrid. The city unfolded before us, a mix of grand boulevards, hidden alleys and majestic squares, each turn revealing a new facet of Spanish life. We indulged in local delicacies - crispy churros dipped in rich chocolate, savory croquetas that melted in our mouths, and wines 🍷 that spoke of sun-drenched vineyards. It was wonderful to see Mark and James in their element, proudly showing off their adopted home.

As we explored, our conversation naturally turned to their new retired lives. They were keen to hear about my work as a retirement coach, and we discussed the possibility of a future session to unearth more ideas for their retirement years ✨. From what I observed, they seemed to be thriving in their new environment, adapting well to both the Spanish culture and language and the freedom of retirement.

Intrigued by their experiences, I asked Mark and James to share some anecdotes about their journey. Here, in their own words, are glimpses into their expatriate adventure:

Why Madrid?

“We always wanted to retire to Europe and started visiting cities there about 20 years ago. Our favorite wound up being Spain and in particular, Madrid. We visited Madrid multiple times including one 2 week long trip and one 3 week visit. We took time to wander around outside of the tourist districts and took a hard look at the neighborhoods we could consider moving to. After weeks of visiting and research, we felt confident that Madrid was a place we could settle down in. Now that we’ve been here for almost a year full time, we are really glad we took that time to research the city. We feel right at home and have no doubts about our decision.”

Should I Hire An Immigration Attorney?

“On one of our visits to Madrid we took time to research local immigration professionals. After looking at referrals we settled on a well known immigration firm that offered a packaged service charge to facilitate the property purchase and residency applications. The service was well worth it as they personally attended all of our residency meetings to ensure that everything was completed correctly. I speak some Spanish but having a local attorney fluent in Spanish and English who knows the system was a life saver. They also helped us evaluate the properties we decided to bid on and managed the entire property closing process. The package even included setting up the phone, internet, gas and electricity. These things seem simple until you’re on the phone trying to remember the word for cable! :-)”

What About Taxes?

“I had considered retiring in May and moving permanently to Spain. I realized that I hadn’t thought about the Spanish tax liabilities, and I reached out to a local Madrid expat tax adviser. They advised me that my tax liability for Spain would start as soon as I hit day 181 of residency in Spain. I already had about 50 days in Spain due to traveling and the tax adviser explained to me that I would be liable for Spanish taxes for the current year if I moved permanently in May. While I had always planned on the higher Spanish taxes, I had thought it wouldn’t start until the year after I moved. This changed my plans and I decided to wait on retirement until December of that year and then move to Spain to start the next year fresh. it saved a good chunk of change and stress!”

Do I Need an Apostille?

“Learn what apostille means! We found out at the last minute that we needed our marriage license apostilled in order to complete the residency application. It was an easy 2 day process for us in Chicago but if you don’t live in a major city you may have to wait a few weeks for that apostille to be finalized. During the process do not be afraid to call/email your representative if things are taking too much time in the federal apostille office or you need help expediting. Our senator had a direct form for just this on their website.”

As always, I like to give you additional curated resources to explore this topic further.

💡 Remember - retirement is an opportunity to intentionally design the rest of your life!!

Stay tuned for weekly content about travel, health, relationships, identity, spirituality, doing good and starting a new venture as it relates to retirement/the next chapter in your life ✨

Please subscribe and forward this newsletter to others who are thinking about retirement planning or are already retired. Thanks for your support 🙏.

Warm regards,

Cara Gray
Retirement Coach (CPRC), CEPA™️

P.S. If you want to start planning your retirement, set up a time on my calendar for a chat: Schedule a Chat with Cara

P.S.S. If you are curious about my coaching, there are two options to work with me: deep-dive, transformative 1:1 coaching or a 90-minute intensive, quickstart coaching session. Details about both options can be found here.