There’s a quiet thought many of us carry around.

Someday I’ll go to that place I've ALWAYS wanted to see.
Someday I’ll finally take that trip.
Someday, when things calm down.

Someday sounds hopeful—but it’s also sneaky. It feels productive without requiring action. It lets us dream without committing, plan without booking, and scroll travel photos without ever stepping into the life we imagine.

If you’ve ever had a mental list of places you want to go—Italy, Iceland, the national parks, a cozy mountain town for a long weekend—but none of them have actually made it onto your calendar, this post is for you.

Because the truth is this: people who travel more aren’t less busy, richer, or magically more organized. They’ve simply learned how to turn intention into momentum.

Let’s talk about how to stop treating travel like a vague future wish—and start treating it like a real, doable part of your life.

Why "Someday" Trips Stay Stuck

Before we talk about solutions, it helps to understand what’s really holding you back. For most people, it’s not laziness or lack of desire—it’s one (or more) of these:

1. You’re Waiting for the “Perfect” Time

You tell yourself you’ll travel when work slows down, when the kids are older, when you’re in better shape, when finances feel more secure.

Here’s the hard truth: life rarely hands us a perfect season. There will almost always be a reason to delay. Waiting for perfect often means waiting forever.

2. Travel Feels Overwhelming

Flights, hotels, time off, packing, money—it can feel like a lot. When something feels complicated, our brains naturally avoid it. That avoidance quietly turns into another year without travel.

3. You Don’t See How It Fits Into Your Real Life

Most travel inspiration online shows two extremes: ultra-luxury vacations or months-long trips. If your life looks like PTO limits, responsibilities, and a full calendar, you might assume travel just isn’t realistic right now.

But travel doesn’t require quitting your job or blowing your savings. It requires intention and strategy.

The Shift That Changes Everything: Treat Travel Like a Decision, Not a Dream

Here’s the biggest mindset shift that separates people who travel “someday” from people who actually go:

Dreamers say, “I hope to travel.” Travelers say, “I’m going—now let’s figure out how.”

Once travel becomes a decision, your brain starts looking for solutions instead of excuses. You stop asking if and start asking how.

This is where momentum begins.

Step One: Get Specific (Vague Dreams Don’t Get Booked)

“I want to travel more” is too abstract to act on.

Instead, try this:

• Pick one destination (not five)

• Pick one rough timeframe (even just a season)

• Pick one reason you want to go

Example:

“I want to visit Iceland for 7–9 days next September to see waterfalls and experience something completely different from my everyday routine.”

Specificity creates clarity. Clarity creates action.

Step Two: Anchor Travel to Your Existing Life

Most people think travel requires a total lifestyle overhaul. It doesn’t.

Look at:

• Long weekends

• Holidays you already get off

• PTO you haven’t used

• Work-from-anywhere flexibility (even for a few days)

Instead of asking, How do I escape my life to travel? ask:

How can travel fit into the life I already have?

A 3–4 day trip taken consistently can add up to a richer travel life than one “big trip” you keep postponing.

Step Three: Put Travel on the Calendar First

This one step is wildly underrated.

If travel lives only in your head, it will always lose to urgent tasks. But once it’s on the calendar, it becomes real.

You don’t need everything planned. Start with:

• A tentative date

• A placeholder on your calendar

• A conversation with your boss or family

Momentum doesn’t require perfection—it requires commitment.

Step Four: Separate Planning From Booking

Many people get stuck because they think they need the perfect plan before booking anything.

Try this instead:

1. Book one non-refundable anchor (flight, hotel, or tour)

2. Let the rest fall into place around it

Once money is spent and dates are locked in, your brain shifts from “maybe” to “this is happening.”

Step Five: Create a Simple Travel System

People who travel regularly don’t reinvent the wheel every time. They have systems.

That might look like:

• A go-to airline

• A favorite hotel brand

• A packing list saved on your phone

• A trusted itinerary template

Systems remove friction. Less friction means more follow-through.

Step Six: Stop Saving Travel for Milestones

Travel doesn’t have to be a reward for finishing something.

You don’t need:

• A promotion

• A birthday with a zero

• A major life event

Travel itself can be the thing that restores you, refocuses you, and reminds you who you are.

Life is happening now—not after everything is crossed off the list.

Step Seven: Redefine What “Worth It” Means

If you only measure travel by luxury, you’ll always feel like it’s out of reach.

Instead, ask:

• Will this expand me?

• Will this give me memories I’ll actually keep?

• Will future-me be glad I went?

Often, the most meaningful trips aren’t the most expensive—they’re the ones that broke your routine and reminded you what life can feel like.

Practical Tips to Turn Someday Into Booked Trips

Here’s how to move from reading this post to actually traveling:

1. Choose one trip today. Write it down.

2. Pick dates within the next 12 months. Far enough to plan, close enough to feel real.

3. Set a small monthly travel fund. Even $50–$100 builds momentum.

4. Book the flight first. Everything else is flexible.

5. Use ready-made itineraries or frameworks. Don’t start from scratch.

6. Tell someone you’re going. Accountability matters.

7. Stop over-researching. Good enough plans still lead to incredible trips.

Action beats inspiration every time.

Your Life Isn’t on Hold—Don’t Put Travel on Hold Either

One day, you’ll look back and realize the trips you took weren’t interruptions to your life.

They were the moments that made it feel bigger.

You don’t need more time. You don’t need permission. You don’t need to wait until everything is perfect.

You just need to decide that someday is no longer good enough.

Ready to Turn Someday Into Booked?

I share practical travel tips, realistic itineraries, and mindset shifts to help you travel more—without quitting your job or overwhelming your life.

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Let’s turn your travel dreams into actual boarding passes.