The First Step Is Never the Plane Ticket

Before you pack your bags, quit your job, or Google, “How much does it cost to ship a dog overseas?” there’s a quieter, sneakier first step to making a big life change: deciding to entertain the possibility that your life could look different.

That sounds simple. It’s not. Most of us are experts at shrugging off ideas that don’t fit the current version of ourselves. We tell ourselves things like, That would be amazing… for someone else. Or Sure, they moved to Portugal, but they probably had a secret crypto windfall/a job lined up. Spoiler: they didn’t.

So before the paperwork and the passports, before the Instagram updates and the inevitable “Why Portugal?” conversation, there’s a quiet moment where you say to yourself: What if I really did this? That’s the first step. Not booking a ticket. Not picking a city. Just allowing yourself to consider it.

And yet, that part might be the hardest.

When I see the Euro-mom fantasy, I get it. The allure is strong. Who wouldn’t want the promise of a simpler, slower-paced life where children play independently in flower-dotted fields while their parents sip coffee in a sunny plaza? But the version that gets sold on social media—often by influencers or startups trying to capitalize on this ideal—is not what living here really looks like for many of us.

Our brains love routines

The human brain is a professional routine-seeker. It loves predictability, even when the current routine kind of stinks. You’d think it would be easy to leap toward change when you’re bored, burnt out, or stuck. But your brain would rather stay in the land of familiar frustration than venture into unknown possibility. It’s just doing its job, and by that I mean, trying to keep you safe. Unfortunately, “safe” and “satisfied” don’t always live on the same street.

That’s why preparing for a big change starts internally, not externally. You don’t need a plan (yet). You need a mindset that’s flexible enough to imagine something different, and curious enough to ask why not me?

Clarity before action? Overrated

One of the most common roadblocks I hear is this: “I’ll make a decision once I’m clear on what I want.”

Here’s the thing. Clarity doesn’t usually arrive fully formed and ready to go. It tends to show up after you’ve started walking toward something new. The mental shift starts with giving yourself permission to explore, even if you’re not sure what you’re looking for yet.

When we moved to Portugal, we didn’t have a perfect plan. We had a rough sketch, some scribbled hopes, and a healthy dose of what I now lovingly call “productive delusion.” But before any of that, we had a string of small, slightly uncomfortable conversations that began with What if we actually did this? and Would that be totally nuts?

Only later did the logistics come in. But the mental door had to open first.

Start with this 30 minute exercise

Here’s one small, concrete way to begin. It’s not dramatic. You don’t have to make a decision. You just have to sit down with yourself (or your partner, if you’re dragging someone along for the ride) and do this:

The 3-Lives Exercise

Take 30 minutes. Write out three versions of your life. They can be completely fictional or loosely based on what you might want in the future.

Life 1: Stay the course. What does your life look like if nothing major changes?
Life 2: Pivot gently. What does your life look like with one significant shift (career, location, lifestyle)?
Life 3: Go wild. What does your most adventurous, slightly scary life look like?

You’re not committing to any of these. You’re just playing. The goal is to loosen your grip on “the way things have to be” and start noticing what excites you. If all three versions feel uninspiring, that’s data too.

Once you’ve written them, ask yourself: Which one am I most curious about? Which one makes me feel something other than dread?

That’s the seed. That’s where change begins.

Making a big life decision isn’t a single, bold moment, it’s a slow loosening of the stories that keep you stuck. It’s learning to sit with uncertainty and still move forward, even if you don’t know where exactly you’re going. If you can do that, you’re already way ahead of the game.

And who knows, maybe one of those imagined lives includes sipping coffee in a tiny Portuguese café, wondering how you ever talked yourself out of this before.

Until next time,

Benn (+ Melissa)