Why Planning Travel Feels Harder Than It Should (and How to Fix It)

If you’ve ever sat down with the best intentions to plan a vacation and somehow ended up two hours later with twenty tabs open, no flight booked, and a vague sense of overwhelm, you’re not alone.

We tell ourselves travel is supposed to be exciting, that it’s our reward for working hard and showing up for everyone else. But for so many women, especially in our 30s, 40s, and 50s, planning travel doesn’t feel freeing. It feels like another item on the to-do list. Another thing that needs our attention.

And I get it. I’ve been there too.

The Mental Load That Comes With Travel

When I ask women why they haven’t booked that dream trip yet, the answers sound familiar:

“I don’t have time to plan it.”
“I don’t even know where to start.”
“I’m already the planner for everyone else.”

It’s not that you don’t want to travel. You do. You crave adventure, connection, a change of pace, and a reason to exhale. But the process of getting there can feel like too much. Searching flights, comparing reviews, checking safety, coordinating dates, making sure everyone else is happy. The joy drains out before you even pack a bag.

The truth is, women carry an invisible mental load. We’re the organizers, the caregivers, the ones who hold it all together. Even when it’s supposed to be our time off, we find ourselves still managing.

So it’s not that travel is hard. It’s that we’ve been conditioned to carry too much of it ourselves.

Why It Feels Like Too Much

Planning travel is a perfect storm of decisions. Where to go. When to go. Who’s coming. How much to spend. What if the weather doesn’t cooperate?

And in a world that keeps whispering “make the most of it,” the pressure to plan the perfect trip can weigh heavy. We start to second-guess ourselves, feel guilty about spending money, or worry about making the wrong choice.

But what if it didn’t have to be that way? What if travel could feel easy again? Simple, joyful, something that happens for you, not because of you.

The Fix: Plan Less, Say Yes

Here’s what I’ve learned while building Say Yes Travel Co. The problem isn’t that travel is hard. It’s that you’ve been trying to do it all alone.

When you take the mental load out of planning, the magic comes rushing back. You stop worrying about logistics and start feeling anticipation again. You look forward to meeting new people instead of managing everyone’s expectations. You actually have space to be present.

That’s what I want for you. Not another vacation that feels like work. Not another week where you’re still the one keeping the schedule. I want you to experience a true reset.

At Say Yes Travel Co., every detail is thoughtfully planned so you can finally relax. The beautiful stays, the local adventures, the long lunches, the quiet mornings, even the shared snacks are designed to help you breathe deeper. You just show up with your suitcase and a willingness to say yes. I’ll take care of the rest.

Let It Be Easy

You deserve a trip that gives more than it takes.

Travel isn’t supposed to feel like another job. It’s supposed to remind you who you are when you’re not managing everyone else’s world. It’s supposed to fill you up, not drain you.

So if you’ve been waiting for “someday,” consider this your sign that someday can start now. You don’t need to have it all figured out. You just need to say yes.

Let me handle the details. You handle the joy.

✨ Join the waitlist for upcoming Say Yes trips and see how good it feels to plan less, stress less, and finally say yes.