The Messy Middle: The Plan Was One Thing. Reality Had Other Ideas.
Midlife is messy. If you're juggling shifting plans and competing priorities, you're not alone — and it doesn't mean you're off track or falling behind.
✈️ Welcome to Midlife Nomads, your weekly hit of real talk, smart ideas, and helpful tools for building a location-independent life through remote work, travel, and business.
There’s this life script many of us were handed, even if no one said it out loud.
Graduate. Pick a career. Buy a house. Start a family. Work hard. Retire early, mortgage-free, margarita-in-hand by 55 or so. Maybe 65 if you were a blue-collar worker.
For a long time, I thought I was just running late to that party. Like I missed a step, or took a wrong turn somewhere.
But I’ve come to realize I wasn’t behind. I was just on an entirely different path. One with scenic detours, unexpected plot twists, and a few characters I never saw coming.
And right now, I’m right square in the Messy Middle of it.
Not the shiny beginning where everything feels full of promise… but not the neat, resolved ending where the credits roll and everyone claps, either.
I’m in the middle; the part with the plot holes and the pacing issues. The part where you’re juggling a dozen responsibilities, second-guessing your decisions, and wondering if the map you’re using was drawn for someone else entirely.
The middle is where plans fall through and new ones haven’t quite formed yet. Where you’re managing family dynamics, financial curveballs, and shifting work landscapes, all while trying to carve out space for an ounce of happiness and maybe even a little bit of understanding the meaning of it all in between.
It’s not the part that gets Instagrammed. But it’s where the real stuff happens.
Listen, this Messy Middle is a real thing. My friend and writer colleague Ann Douglas wrote a whole book about it, and so many of us are trying to navigate it.
Maybe you’re in the sandwich generation, juggling elder care and teenage angst. Maybe your career took a weird turn. Maybe your marriage ended, or never started. Maybe the dream changed. Or maybe life just veered somewhere unexpected while you were busy making spreadsheets.
I’m sure there are people who think I’m completely full of it when they ask about my plans, I share them confidently… and then everything changes a few weeks later. Believe me, I don’t love feeling flaky or unreliable. But sometimes life just doesn’t play by the rules of our Google Calendars.
Things shift. Plans unravel. Priorities compete.
So we roll with the punches. We adjust. We do our best to show up, even when we’re not entirely sure what we’re showing up for yet.
That’s the paradox I keep running into… dreaming of adventure and spontaneity, while also craving a little certainty. I want freedom and choice, but sometimes secretly wish someone would just tell me where the hell I’m supposed to be, and when.
If you’re feeling pulled in a thousand directions and your plans are up in the air, just know: this isn’t failure. This is the middle. It’s messy, but it’s where you figure out what actually matters and what’s just noise. It’s where you let go of weighty expectations and start making decisions based on reality, not the version of your life that only worked on paper.
If you're navigating shifting plans or thinking about your next move (be that logistically or emotionally), here are a few reads worth your time this week. From global policy shifts to personal growth on the road, this week’s roundup is part inspiration, part reality check.
Portugal’s Expat Boom is Changing the Game for Nomads
Foreigners now make up 15% of Portugal’s population, with Americans leading the surge in Digital Nomad Visas. As visa programs evolve and immigration systems strain under demand, Portugal is fast becoming a global hub for remote workers, retirees, and entrepreneurs.
From rising contributions to social security to shifting real estate dynamics, the ripple effects are big — and worth watching if you’re planning your next move.
👉 Read Portugal's Foreign Population Hits 15%: An Industry Perspective from the Investment Migration
Why You Should Travel Somewhere Uncomfortable (At Least Once) - The Free Nomad
From roundabout confusion in Cyprus to icy lake plunges in Finland, Lukas makes a bold case for seeking out discomfort as a tool for growth. This isn’t about suffering for the sake of it; it’s about how feeling awkward, out of place, or uncertain can spark resilience, perspective, and real inner peace. A thoughtful, entertaining invitation to choose challenge over comfort and see what you’re really made of.
👉 Read Lukas’ full story on The Free Nomad
What Changed About U.S. Alien Registration in April—And Why It Matters
Heads up if you’ve been traveling in the U.S. On April 11, DHS launched a new online registration system, putting long-standing alien registration laws into active enforcement mode. While these rules aren’t new, the stepped-up checks and potential penalties—including fines or jail time—are. If you’re in the U.S. on a visa, TPS, DACA, or other legal status, now’s the time to double-check your compliance.
👉 Read the full update from USCIS
Bonus Read: A Turks & Caicos Guide for Wanderers
If you’re craving a little armchair escape, take a bonus deep dive into a different side of Turks & Caicos. Think: wild beaches, mangrove paddles, roadside conch, and ferry rides to places most tourists never see. Not exactly budget, not exactly luxe… doing T&C off-resort might be just right for the curious wanderer.
👉 Read Turks & Caicos: Get Off the Resort and Explore the Untamed Islands on Midlife Nomads
That’s it for this week. If your plans are up in the air or your calendar keeps changing on you, don’t worry… you're not doing it wrong. You’re just in the messy middle of figuring it out, like the rest of us.
Miranda
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