We Quit Route 66 Early

Tom and I recently quit the trip of a lifetime a full week early.

Seriously.

We had planned a three-week adventure driving historic Route 66 in our 1959 Chevy El Camino from Chicago to Santa Monica.

And on night 11, we decided to go home.

Why?

Because we rememberedwhat our actual objective was.

Our objective wasn’t:

· to drive every single mile of Route 66

· to perfectly follow the historic alignment

· to see every attraction

· or even to make it all the way to California in one trip

Our real objective was much simpler:

To have a great time together on Route 66.

That was it.

And once we got really clear about that, it became surprisingly easy to recognize when we were drifting away from it.

One of the first examples happened before we even started.

The official Route 66 beginning is in downtown Chicago, but Tom really didn’t want to drive a beautiful old car into heavy city traffic and potential crime areas.

I wanted to start at the “real” beginning.

But when I stopped and asked myself what mattered more — checking a box or having a great experience together — the answer became obvious.

So we started about 20 miles south of the official starting point.

No regrets.

Along the way, we also realized we couldn’t possibly see everything.
Apps malfunctioned.
Roads were closed.
Construction forced detours.
Museums weren’t open when we arrived.

And over and over we had to ask:
“Are we still having fun together?”

If the answer was yes, we were succeeding.

Then we reached Tulsa and learned about a massive classic car parade attempting to break the Guinness World Record for the largest classic car cruise.

At the time, we thought:
“Well… that sounds amazing, but we’re going to be in New Mexico or Arizona by Saturday.”

So we kept going.

But a few days later, after we had already traveled hundreds of miles farther west, we looked at each other and realized:
“We actually want to do this.”

So we turned around and drove six hours back to Tulsa.

And honestly?
It was one of the best parts of the entire trip.

Over 100,000 people lined the streets cheering as thousands of classic cars drove one of the most iconic stretches of Route 66.

It was emotional and unforgettable.

And interestingly,that detour also led to one of the most unexpected gifts of the trip.

On the drive back to Tulsa, I wanted to stop at a restaurant on the historic Route 66 alignment instead of eating right off the interstate.

Tom was a little grumbly about the extra miles because at that moment, his focus had shifted from “having a great trip together” to “getting to Tulsa in time.”

But during that little detour, he spotted a museum dedicated to one of his longtime car show mentors.

We stopped.
They met.
And now they’re texting and planning another visit this fall.

We never could have planned that moment.

And we almost missed it because we were temporarily more focused on getting somewherethan experiencing where we already were.

The trip also reminded us how incredibly kind people can be.

When our brakes failed less than a mile from Dead Man’s Curve, complete strangers brought us into their shop and spent four hours helping us repair brake lines so we could safely continue the trip.

Total angels.

Eventually, though, reality caught up with us.

Two long interstate driving days in extreme heat took a lot out of Tom physically and emotionally.

The El Camino had already suffered multiple breakdowns.

And we still had the Mojave Desert (which was going through a heat wave) ahead of us… without air conditioning.

So in Albuquerque, we made the decision to head home.

Did we feel a little disappointed?
Of course.

Did we briefly feel like quitters?
Absolutely.

But once again, we came back to the real objective:
Have a great time together.
Not prove something.
Not check a box.

And honestly, we succeeded.

This trip reminded me how important it is to identify your real objective before life starts throwing distractions, opportunities, ego, expectations, and “shoulds” at you.

Because if you aren’t clear about what really matters, it’s very easy to accidentally chase the wrong thing.

So whether it’s a relationship, a business goal, a project, or an adventure…

What is your real objective?

And are your decisions actually helping you achieve it?

Let me know — I love hearing from you.

With love,
Ariel