When Where Should We Go Isn’t Working
Okay… if you’ve been stuck on “where should we go?”… same
Like you open your phone, scroll a little… maybe check a few resorts…
save something you might like…
and then just… close out of it.
Because nothing is actually making you go
“yes, that one.”
And then a week goes by and you’re like…
cool, still haven’t planned anything 😅
This is where it quietly falls apart
Most people are still planning trips like this:
Pick a place
→ then figure out what to do
→ then hope it all comes together
Which… sometimes works.
But a lot of the time it ends up being one of those trips where you get back and you’re like
“it was good!”
And that’s it.
No story. No standout moment.
Nothing you’re still talking about later.
So here’s the shift (and I have opinions on this)
Instead of starting with where…
start with
what do you actually want to do??
Which sounds simple… but it changes everything.
Because now you’re building the trip around something real
instead of trying to force it later
What this actually looks like (real examples, not theory)
I’ve been planning more trips like this lately and it just hits different.
Like…
- Harry Potter in NYC (very specific, but if it’s your thing, you’re obsessed)
- Maine Lobster Festival (chaotic in the best way, super fun, very unique)
- Macy’s Thanksgiving Day Parade (this is not just “watching a parade”… it’s a whole experience)
These trips already have a moment built in.
You don’t have to go searching for it.
Why these trips feel better (and why people remember them)
It’s not just that you did something cool.
It’s that you experienced it with someone.
You’re reacting to it together, laughing about it later,
retelling the story 500 times when you get home
That’s the part that sticks.
Not the resort.
Not the flight.
The moment.
Also… the “this might be crazy but…” ideas?? I love those
These have been coming up a lot lately and I’m not mad about it 😂
Because sometimes it turns into:
- Christmas markets across Europe (done right, not rushed through 6 cities in 5 days)
- Bigger, once-in-a-lifetime trips
- Even private jet group setups (I KNOW… sounds wild… but in the right situation, it’s actually doable)
A lot of these things feel like “someday” ideas…
until you actually start mapping them out.
But let’s be real… sometimes you just want easy
Not every trip needs to be a whole strategy session.
Sometimes you’re just like
“I want it to be warm, easy, and good. That’s it.”
Totally fair.
That’s why I’m still booking a ton of Caribbean right now.
- Aruba
- Dominican Republic
- Virgin Islands
They’re consistent, easy to get to, and you don’t have to overthink them.
Which… honestly… is the whole point sometimes.
If you don’t change this, here’s what usually happens
You stay in the “I’ll look later” loop
Then later turns into nothing
Or you panic-book something just to have a trip on the calendar
And it ends up being… fine
Which we are no longer aiming for 😅
This is usually where I step in
Not with a giant list of random places
But by helping you figure out
what would actually feel exciting for you
And then we build around that.
Simple. Not overwhelming. Actually makes sense.
If this has been sitting in your head…
You don’t need to have a full plan.
Honestly, most people come to me with
“I don’t know… I just know I want to go somewhere”
and we figure it out from there.
No pressure, nothing formal
Just talking through what would actually feel worth it
Because once you start there…
everything else gets a LOT easier.