I'm an adventurer and food lover who values time freedom. I retired at 36 and now I teach overworked high-achievers how to design a life they love. Subscribe to my newsletter for a kind and supportive approach to personal finance, small business growth, and early retirement.
I was afraid to share this
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In case you're wondering where I've been the last six months, the short answer is: living out of a suitcase in 9 states, from Montana to North Carolina, and 3 countries. It's been the most disorienting, exciting, terrifying six months of my life. And if you're wondering why you haven't heard much from me during all this excitement, it's because the fear took over. I didn't post curated photos of the adventure or send my usual email updates along the way because this whole time I've been scared. I was scared of failing.Yes, again. Because I've spent my whole life achieving. First-gen college grad from Colorado School of Mines, checking all the boxes of life we "should" want, even shirking that pressure and retiring early. So when it came to applying for a Portuguese visa, a process that was **gasp** out of my control, things got real scary, real fast. Nothing is guaranteed, especially in this unconventional way we're approaching life. So the thought of being denied a visa scared the shit out of me. Not because it would mean we'd have to pivot and design life differently, but because I'd have to share with everyone, including you, that it didn't work out the way I'd planned. And that felt like a failure I just couldn't face. It was easier to stay quiet. You see, this dream has been something I've been working towards for almost 10 years. The idea first showed up when I learned about financial independence and started looking for a "home base" country to stretch my dollars while exploring the world. At first, it was a flicker. An itch. A subtle tug I just couldn't ignore. But the more conversations I had, the clearer it became that the lifestyle I longed for was at the core of this idea to expatriate. And it's that lifestyle design that's carried me over the last decade, embedded deep down in every major life decision I've made since then. Hell, Jamie and I talked about this dream on our second date, back in 2020. So when I finally got the email saying "Your Portuguese visas have been approved," I literally jumped for joy and punched the air. People around me at the gym were definitely confused, but I didn't care. I drove back to our little Airbnb in Greensboro, shared the great news with Jamie, and I'm not afraid to admit that I cried nearly as many tears of joy as on our wedding day. I felt like a thousand-pound rock had been lifted off my shoulders. And now that we've finally found space to unpack and settle into our new home, I'm reminded daily of why I put myself through something so difficult. I finally feel like my urge to slow down and be intentional is the norm.
It just feels... right. So now, with more time and space to think, to actually process what this all means, I'm back and ready to share again. This massive life change has challenged some of my deepest beliefs while gently nudging me toward more curiosity and wonder. I'll be back in your inbox on a more consistent schedule, sharing lessons from this journey alongside new insights and ideas I'm still working through. I want to share what's been hard, for me and for our family, as this new chapter unfolds. And Jamie and I have something new in the works, a short two-session program aimed at helping those of you who want to feel genuinely good about your finances without it consuming all your time. More on that very soon. But most of all, I'm hoping to hear from you. Moving around the US and the world has reminded me just how much community matters to me. So when I say I read every email, I mean every single one. I want to hear what's resonating, what's hard, what's working. I'm here to listen. Just don't be surprised if you get my reply at 2am your time. 😜 — Joe P.S. In case you were worried, Mili survived the journey just fine. She's currently napping in a patch of Lisbon sunlight and has absolutely no notes. Joe Maddux |
Level Up Financial Coaching
I'm an adventurer and food lover who values time freedom. I retired at 36 and now I teach overworked high-achievers how to design a life they love. Subscribe to my newsletter for a kind and supportive approach to personal finance, small business growth, and early retirement.
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