Rainy Days, Heavy Baggage & Fighting Off Digital Nomad Funk in Estonia
This week in Midlife Nomads: Location independence isn't always a rose garden. We're talking about the slippery slope of inactivity and isolation, and enjoying recommended reads from the nomad sphere.
✈️ 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.
It’s been rainy here in Tallinn, and I’m waffling back and forth between feeling like I’m getting into a routine and being in a bit of a funk.
Some days feel super productive, and I’ve made some headway on several fronts. Yay!
I have the layout proof copy of my book on Flowerpot Island in hand and am reviewing it this week. My Borderless Income Blueprint course, a primer on earning money from global clients without losing your shirt in processing and conversion fees, is almost ready to launch. I’ve tackled a few big stories lately for Owen Sound Current (my local news Substack).
So why do I still feel like such a slug?
I think part of it is the weather. It’s been 30 degrees and sunny at home in Canada (a treat we enjoy for a few short months each year). But I haven’t been there in over a month. Here in Estonia, I’m getting all the biological cues of late autumn… rainy mornings, windy afternoons, evening temperatures that make you bundle up and brace for it when you need to venture outside.
Between Scotland and Estonia, I missed out on a true summer this year and am already sliding into my hermit season.
At home in years past, I had the boys to get me motivated. Mom, can I get a ride? Mom, we need groceries. Mom, you haven’t left the house in six days… let’s go.
Out here, it’s just me and my (deeply entrenched) habits and tendencies… and I realize they need some work.
I have some pretty compelling health reasons to get moving. But still, left to my own devices, there’s a real risk I’ll become so sedentary I’ll morph into a piece of furniture.
I remember sitting at my desk in Canada a few autumns back and suddenly realizing a spider had spun down from the ceiling and was RIGHT in front of my nose. Would she have spun a web around me if I’d let her? I think probably.
So I’ve been trying to get myself motivated and move more. Being in the city without a car helps, and I’ve logged an average of 5,000 steps a day over the past 30 days. That may seem small to you 10,000-step superstar walkers, but it’s huge for me. I need to keep it up.



The beautiful park across the road is helping. A full loop is 2,000 steps, so if I can convince myself to get out there between the rain showers just twice, I’m good.
There’s still plenty to see in this city, too. I’ve been here several times before, and discover new things to love about it each time. Staying here for a month, I don’t feel the need to race around and hit every recommended landmark and restaurant in a weekend. There’s time to wander, appreciate the contrast of the old Soviet infrastructure with the modern architecture, check out side streets and small shops.
The closest tram stop is three blocks, but there’s a great market a few stops away and if I walk there, I can grab a treat to enjoy on the tram or bus. Little incentives help.
Having access to a coworking space is a bonus, too. I love the energy of a creative space… even without knowing anyone, there’s a buzz about it that fills me up. And so committing to getting out of the apartment I’m housesitting for work at least three days a week has been a positive.

Working from anywhere doesn’t have to mean working from home, or working alone all the time. Some may enjoy it, but it’s a slippery slope for me that leads to an unhealthy degree of isolation and inactivity, so I’m learning to take a preventative approach.
Here in Tallinn, that means making the effort to get out to a coworking, taking walks — short ones throughout the workday, and longer ones to explore in free time — and giving myself incentives to be more active.
Recommended reading:
Do you feel ready to battle the worst parts of you, tackling ingrained habits again and again in new environments, coming up with new routines to combat your insecurities and bad habits in foreign places with very little familiar to fall back on?
You, too, could be a digital nomad!
(Way to sell the lifestyle, Miranda.)
Hey, I didn’t promise you a rose garden. Location independence can be super rewarding, but we don’t really get to “leave it all behind.” Regardless of what’s in your suitcase, we all have some extra baggage that rides along whether we like it or not.
Mine is feeling a bit heavy this week, but sharing this has helped. Thanks for reading, and I hope you enjoy the rest of this week’s newsletter. Here’s what I’ve been reading and writing this past week.
ICYMI:
Recommended Reads
I really enjoyed this piece from Brian Clark. He makes the case that it’s not money but continuous learning that most strongly predicts a longer, healthier life, which hit me right in the feels of why I do this work.
As midlife nomads, we’re not just chasing stamps in a passport. We want the healthspan — the years of energy, mobility, and clarity that make all those adventures possible.
Beckett Johnson’s story of how he went from supporting his partner’s channeling practice to accidentally becoming an “intergalactic correspondent” reminds me that sometimes the scariest part of new experiences isn’t the unknown itself, but whether we’re willing to be seen stepping outside the box. I think that’s a lesson every midlife nomad can relate to.
Moldova is Launching a Nomad Visa
(The email version of this post had the wrong flag for Moldova… sorry!)
Moldova's impending digital nomad visa program will offer residency permits requiring just $1500-$2000 USD in monthly income. It will allow remote workers to live there for 2 years, and is expected to launch at the end of September.
👉🏼 Read Moldova Digital Nomad Visa: Launching September 2025 from Nomads Embassy
Because we need something fun and uplifting this week, and Gregory Garretson’s essay on the funny, awkward, and only-in-retrospect-hilarious moments that come with expat life delivers. If you’ve ever stumbled through a new culture or language while trying to “fit in,” this one will make you laugh and nod in recognition.
That’s it for this week… stay tuned for more remote business-building tips and lessons in the days ahead.
✌🏻 Miranda