One of the first things that made me realize I was no longer in Tallinn was the switch from the reserved, distant interactions I had gotten used to, to suddenly getting a constant stream of direct feedback. From my choice of bike lanes to where I chose to stand on the tram, people around me always had a strong opinion to share. I knew I was in a different place now—and it is time to write about how I got here.
In my last post, I was saying goodbye to Tallinn. Fast forward 2.5 years, and here I am writing from the Netherlands, where I’ve been living and working in the Amsterdam area since then. There’s a lot I want to talk about, but first, I feel the need to bridge the gap. It’s been quite a ride.
The Bold Decision
Rewind to February 2022, when I made one of those hard life decisions: I quit my job. At the time, I had been working in fast-paced food delivery tech companies for nearly seven years, almost without a break. Throw in a couple of years of pandemic restrictions and the challenges of being new parents living abroad, and you’ve got a recipe for burnout. It was time to hit the reset button.
But there was a catch. My Brazilian passport meant that once my Estonian residence permit expired, I’d only have another three months to stay in the EU as a tourist. With the clock ticking, I sketched out a plan—a three-month sabbatical to disconnect, regroup, and refocus on what I really wanted in life.
The plan looked like this:
- Month 1: Total Disconnect.
This was my “do-nothing” month. No work. No thinking about work. Just full-on relaxation. My wife made me promise I wouldn’t even consider job hunting. For the first time, I didn’t have another gig lined up. I’ll be honest, I was scared, but I knew it was necessary. After years of relentless hustle, I needed to reboot. - Month 2: Deep Reflection.
Once my mind had rested, I would dive into some serious self-reflection. I wanted to review my preferences, my interests, and where we, as a family, would be happiest. Up until then, I had mostly followed the path laid out in front of me—through recruiters, job promotions, or friends. Not this time. Now we would consciously steer our future in the direction we wanted. Define a vision. Chase it. - Month 3: Job Search.
With a clear vision, I planned to begin a laser-focused job search. Looking back, I realize that being a little naïve—maybe not knowing better—helped me take on something difficult. I expected it to be tough, but somehow I didn’t think this plan could fail. In my mind, Month 3 would be a formality—a straightforward process that would lead to landing the perfect job. That couldn’t have been further from the truth.
With that, I gained a new sense of control. And after thinking it over, I realized: I wasn’t quitting, I was beginning.
A European Adventure: Traveling While Job Hunting
To add a little adventure to the mix, we planned to do all of this on the move, ticking off some items on our travel wish list. Because why not? We’d use our tourist visas to explore Europe: our son’s first trip to Disneyland in Paris, revisiting Valencia (where I’d lived years ago), and, the best part, finally making a twice-postponed dream come true—playing in the World Series of Poker in Las Vegas.
The plan seemed solid, but soon enough, anxiety crept in.
Before I even finished my notice period at work, I started feeling restless. So, naturally, I did what I always do when anxiety hits—I made more lists and read books. One book that stood out was What Color Is Your Parachute?, which gave me clarity on approaching my career shift. I focused on changing either industry or role (but not both), which made the daunting task of transitioning careers feel more manageable.
Enter Amsterdam: A Dream and a Job Alert
As I researched cities, Amsterdam kept floating to the top of our list. It checked all the boxes: a great place to raise kids, lively (more so than Tallinn), and a strong tech hub. More importantly, it had Booking.com—a company that felt like the perfect fit for my skills and values. But landing a job there felt far-fetched. I had no connections, had never visited Amsterdam, and I was certain there were long lines of candidates for any position.
I wasn’t ready to act yet. I figured I’d sit on the idea, keep exploring, and stick to the plan—it was still Month 1, after all.
But then, the universe played matchmaker. I got a job alert via LinkedIn (which I didn’t even know was turned on). Booking.com had a position that fit my skills and experience perfectly. I uploaded my CV, and the website confirmed it: “strong match.”
I had mixed feelings since I had promised to rest in the first month, but I knew we can’t always control when opportunities present themselves. Would I regret passing this up in three months? I applied, but didn’t immediately tell my wife. I was sure it would lead nowhere.
The (Quick) Move
Before anything could happen, life took an unexpected and horrifying turn. The war broke out in Ukraine, and tensions rose in Europe, in Estonia and at our home. In the expat groups on Facebook and WhatsApp, people were actually making contingency plans in case the airspace was closed. Those were things I never even thought about. Every piece of news was devastating, but we kept the TV on almost constantly as it wasn’t clear where all this was going.
The relatively safe distance from the conflict didn’t keep us from getting scared too. With tanks parading the streets on the Estonian Independence Day and fighter jets flying overhead, we decided to fast-forward our move. Instead of leaving in a month, we sped up the plan. We had our trip to Disneyland coming up in a week, and from there, we wouldn’t be coming back.
It was in the middle of all this, as my family packed for Paris (and who knows where after that), when I got an email. It was a recruiter from Booking.com. She was asking what’s the best time for an interview.
Going Full Circle
I think I took each interview in the process from a different country. The final round, though, was in Valencia—a place that felt like more than just a coincidence. About nine years ago, after some gruelling years in advertising, I made a similar decision to shift gears, leaving Brazil to study in Spain. That decision brought me to Valencia.
I returned from there speaking Spanish, with a Master’s degree in hand and ready to start my own business and a new career in tech startups. Now, here I was again—returning to the very city that marked such an important shift in my life, this time at another turning point.
I remember vividly the moment I got the offer. We were walking through the shark tank at the city’s aquarium, sharks circling overhead in the dark room. My phone vibrated. It was an email from the recruiter. My son was fast asleep in my wife’s lap, so I whispered, “I think we’re going to live in Amsterdam.”
“We’re going WHAT?” she whispered back, eyes wide.
“I think they’re going to make me an offer. I need to go call the recruiter!” And so I did.
The Unexpected Wins
As if getting the job wasn’t enough, it got even better. The visa process for Amsterdam would take 10-12 weeks, which meant I had almost three months of downtime with a signed job contract in hand. During that time, I traveled back to Brazil to visit family, and yes, I made it to Las Vegas for the World Series of Poker. But that’s another story.
It wasn’t the sabbatical I had originally planned. It was better.
Settling into Amsterdam: A New Chapter
By the time we finally arrived in Amsterdam, it was summer. The canals were glowing in the sunlight. What a perfect city, we thought (completely unaware of the rainy, windy weather that dominates the other 90% of the year). After months on the move, we were just happy to unpack and call a place home.
Relocating isn’t easy. It’s exhausting, especially with a toddler in tow. But having the support of an experienced employer made all the difference. We had guidance with paperwork, house hunting, and even webinars on how to settle in.
A new chapter was beginning. And while I felt like an old hand at this “new country, new life” thing, the excitement and challenge of starting fresh never gets old.
My Takeaways
Looking back, my first takeaway is how liberating it felt to embrace endless possibilities. At the beginning, it was scary. No job, no permanent home, no line of sight beyond a couple months. But in the end it was entirely my choice and I got used to it. Eventually, it felt freeing, and then it felt amazing! I proved to myself that I didn’t need all the structure if I didn’t want it—not for a while, at least. I had the freedom to explore and define what would come next.
My second takeaway is that while plans don’t always work out perfectly, they’re still important. Life is random and unpredictable, but planning helps define what matters most. It’s not about the exact sequence of steps or timeline. It’s about understanding the key pieces and your target. So when you see it, you recognize it. And then you act on it.
So yes, life has its unexpected turns, but we can always choose how to respond. By taking control of my direction, I discovered that even the most uncertain paths can lead exactly where we want to be.
Claudio Maksoud Filho 