You’re Not “Bad at Planning Trips”… You’re Just Doing It Backwards

Okay so I need to say this because it comes up ALL the time. 

People will tell me,
“I’m just so bad at planning trips.” 

And I’m like…no you’re not 😂
You’re just trying to do it in a way that makes it harder than it needs to be. 

This Is the Part Where It Gets Frustrating 

You start looking… 

Open a few tabs.
Check a couple dates.
Maybe text someone like, “Should we go somewhere??” 

And then suddenly it’s overwhelming for no reason. 

Too many options.
Nothing stands out.
Everything starts to blend together. 

And then you just…stop. 

Or you book something random just to be done with it. 

 

Here’s What’s Actually Happening 

You’re trying to make a decision without having anything to anchor it to. 

So everything feels like:
Maybe this.
Or maybe that.
Or I don’t know. 

Which is exhausting. 

And honestly…this is where most trips fall apart before they even start. 

 

What I’ve Been Doing Differently (And It’s Working) 

Instead of starting with where… 

I’ve been asking my clients,
“What do you want this trip to feel like?” 

Not even what you want to do yet. 

Just…what’s the vibe? 

Relaxed.
Fun.
Busy.
Something you’ve never done before.
Something easy that doesn’t require brain power. 

Once we figure that out…everything else gets way easier. 

Real Example Because This Literally Just Happened 

I had someone come to me like,
“I don’t care where we go, I just need a break.” 

Which sounds simple…but it’s not super helpful at first 😂 

So we talked it through a little more, and it turned into: 

“I don’t want to plan anything.
I don’t want to think.
I just want it to be easy and good.” 

Okay…perfect. 

That’s a completely different trip than someone who wants,
“I want something exciting and different.” 

Same person could have ended up in two totally different places depending on how we framed it. 

 

This Is Why Some Trips Feel Amazing and Others Feel… Fine 

If you skip this step… 

You might still end up somewhere nice, 

But it doesn’t quite hit the way you wanted it to. 

Because it wasn’t built around anything real. 

It was just…available. 

Also… Quick Note on Timing Because This Matters 

This is the part where people wait too long, and then everything good is gone and we’re all annoyed 😅 

Summer is basically here.
Holiday trips are already starting to fill up. 

And the trips that actually require planning…those don’t happen last minute. 

So if something has been floating around in your head like,
“We should probably do something…” 

This is your sign to at least start the conversation. 

 

What I Actually Do (In a Very Non-Overwhelming Way) 

I’m not here to throw 50 options at you. 

I’m here to help you figure out what would actually feel worth it…and then build something around that. 

That’s it. 

 

If This Sounds Like You… 

If you’ve been thinking about a trip but keep getting stuck in the same loop… 

we can just talk it through. 

No pressure.
No complicated process. 

Just figuring out what would actually make you excited to go. 

Because once you have that piece… 

Everything else falls into place way faster than you think.