The Moments You Start to Question Everything

There are moments, in our current case entire weeks, when you start to question your choices.

Not in a dramatic, everything-is-falling-apart way. But doubt creeps in through the cracks: the weather, the distance, the small cultural moments that remind you how far you are from what once felt routine.

We’re in one of those stretches now.

It’s been raining for what feels like a month straight. We’re on our fourth coastal weather event in a row. Storms stack on top of storms, and everything feels damp. Physically moist and emotionally a wet blanket. Buildings here are designed for sun and outdoor life, not long stretches of rain. When the weather turns, the options shrink.

At the same time, posts keep going viral on LinkedIn about why people are leaving Portugal. Why it didn’t work. Why the systems are too slow, the bureaucracy too heavy, the gap between expectation and reality too wide. Even if you’re not seeking them out, they find you. And even if they don’t change your mind, they have a way of lodging themselves in the background of your thoughts.

And then there are the smaller moments. The ones you didn't think mattered as much as they do.

Like spending the afternoon before the Super Bowl in a probably moldy basement bar, complaining about immigration appointments. Not because you want to be there, but because all the restaurants nearby are built around outdoor seating, and the weather has made that impossible. Or realizing that while friends back home are coordinating arrival times and who’s bringing the seven-layer dip, you’re surrounded by people who don’t know there’s a “big game” happening at all. Benfica played Alverca, that’s hardly a big match. 

You miss the rituals. The shared reference points. The ease of not having to explain why a particular Sunday matters.

None of these things are dealbreakers on their own. But together, they create the conditions where doubt sneaks in.

You start asking questions you thought you’d already answered.
Did we misjudge this?
Is this harder than it needs to be?
Are we giving up too much to make this work?

This is the part of moving abroad that doesn’t get enough airtime.

Difficult visas and logistics are well documented, but not always the emotional undercurrent. The way dislocation shows up is not as regret, but as nostalgia. God, nostalgia. Saudade. The quiet ache for the familiar, especially when the environment around you feels unsettled.

Add on top of that the Olympics and the unfamiliar surge of national pride, the stories that make you feel connected to millions of people you’ll never meet. Watching athletes represent the country you grew up in can stir something deep and unexpected. Even when things back home feel like it’s all going to shit.

So obviously, experiencing that from abroad is complicated.

The pride doesn’t disappear. But it doesn’t translate cleanly. You’re cheering in a place where the emotional weight is different, where the stakes aren’t shared in the same way. Conversations don’t automatically align. You realize how much of national identity is reinforced by being surrounded by people who are feeling the same thing at the same time.

As an American abroad, that dissonance can feel especially sharp. Pride and critique coexist in complicated ways. You carry both, and usually neither lands comfortably in your new context.

Add natural disasters, constant rain, bureaucratic frustration, and distance from familiar traditions, and it’s natural for your brain to start connecting dots it shouldn’t. To wonder if the timing is wrong. If the decision was naive. If the comfort you gave up was actually more important than you realized.

But here’s what keeps grounding us: None of this has changed why we’re here.

Hard seasons don’t negate thoughtful decisions. Missing events doesn’t erase long-term values. 

Moving abroad doesn’t remove discomfort. It redistributes it.

You trade one set of frictions for another. You let go of certain kinds of ease in exchange for different priorities: time with family, exposure to new perspectives, a slower rhythm, a chance to rethink what “success” actually looks like. That trade can still feel right even when it feels heavy.

Especially when it feels heavy.

This is the work of a mid-pivot: learning to hold complexity without immediately trying to resolve it. Allowing frustration and gratitude to coexist. Letting yourself miss what you loved without turning that longing into a verdict on your choices.

The rain will stop. The storms will pass. The sun will come back.

And when it does, it won’t just dry things out physically. It will soften the edges of these weeks, reminding you that no single season defines a life, and no single moment of doubt cancels a longer arc of intention.

If you’re in a stretch like this, abroad or not, you’re not failing. You’re integrating. You’re living inside the decision instead of romanticizing it from afar. That’s what commitment actually looks like.

If you’re considering a move, it’s worth asking yourself:

Am I expecting certainty — or am I prepared for seasons like this?

What discomfort am I willing to live with, and which kind feels more honest to who I am becoming?

Until next time,

Benn (+ Melissa)

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