From “Someday” to “How”: 5 Shifts That Helped Us Start Living Our Dream Life

ddsoesan
Jan 3
3 min read

If you've been dreaming of living differently, whether on a boat, off-grid, or just more slowly, these five mindset shifts helped us begin.

I remember exactly how it felt when this life sounded impossible.Before the boat.Before we became "that family" you see on your screen.

I used to watch people already out there, families living on boats, vanlifers, digital nomads, and feel a strange mix of awe and ache. There was inspiration, yes, but also something heavier. A feeling that they had something I didn’t. A secret manual. Some magical confidence. Money. Courage. A map I hadn’t seen.

And I would think: Wow. I want that. But also: Is it really possible? For me?

Turns out, it was. And still is.

Not easy. Not without fear. But absolutely possible.

And in the spirit of the new year, when many of us are whispering new intentions to ourselves, I want to talk about that shift. The one from “someday” to “how.”, from craving a different life to actually living our dream life.

Here are the 5 mindset shifts that moved us from dreaming to sailing full-time as a family:

1. Write Down Your Honest Why

Not the poetic one. Not the version you give at dinner parties. The real reason. The raw one.

“I want to breathe again”,“I don’t want to spend the next 10 years in traffic”,“I want my kids to know me, not just my tired reflection”,“I’m scared of wasting my life waiting for retirement”.

Write it down. That honest truth becomes your anchor when the doubt rolls in.

2. Name Three Specific Dreams

Vague dreams tend to float away. Specific ones start turning into plans.

For us, it was:

A boat instead of a house
Bonfires on wild beaches in remote islands
A lifestyle where we could live off-grid and see the world slowly

Think about yours. A place you want to wake up in. A journey you want to take. A rhythm of life that keeps calling you, even if you’re not sure how it works yet.

Let yourself want it clearly.

3. Say It Out Loud

This one is small… and huge.

The moment we said, “We want to live on a boat,” something shifted. We didn’t whisper it like a maybe. We made it a pact. A handshake.

Once we told our family and friends, it stopped being a fantasy and started becoming a project.

Say your dream. Speak it into a room, even if you’re alone. It starts to feel real.

4. Fill Your Feed with Possibility

Your brain believes what it sees often.

I started following families who made it their lifestyle. I watched boat tours and slow travel reels. Not to compare, but to normalize what I once thought was impossible.

I needed to fill my mind with proof that there’s more than one way to live a beautiful life.

Today, my feed is full of travel families, sailing families, creativity, courage, and unconventional freedom. And strangely, the "normal" life, started looking like the strange one.

5. Stop Saying “No” and Start Asking “How?”

This is the question that got us on the water. We didn't have it all figured out. Far from it.

But we started asking different questions - instead of “That’s not realistic,” we began with “How could it be?”

And when the doubt hit (which it still does), we’d come back to it: How could we do it differently? How could we afford it? How could we make it work with kids?

For us, the “how” became a sailboat. We bought it instead of a house. We weren’t “ready.” Not by anyone’s checklist. But we had reached a point where staying the same felt riskier than changing.

Even if your answer is just a shrug right now, asking “how” turns a closed door into a window.

And once that window opens, even just a crack, everything changes.