I was talking the other night with a new friend, Erynn Montgomery of Landed, who makes a living as a “trip designer,” creating unique travel itineraries for high-profile clients wanting to explore South America.

Wanting to know more about her creative process, I asked how she begins planning with her clients.

“Most people have a good idea of what they want to see before we talk,” she explains. “They call me with their ‘bucket list’ already established.”

She listens to their to-do and to-see list, captures their wants and desires, all with little interest.

“Quite honestly, I don’t care about what they want to do,” she says frankly. “I can handle any to-do list with ease.”

She lets them finish explaining, then says:

“You’ve told me what you want. Now, what do you need?”

This, she explained, is when the conversation gets messy.

“Asking what someone needs from a trip usually brings a long silence on the other end of the line,” she says with a smile.

“That’s fine, I don’t mind awkward silence.”

She sits there and leaves the question simmering until finally, something bubbles to the surface.

“It’s not uncommon to have a client end up in tears after I ask this” she says. “Others will experience a moment of clarity or insight, and realize something they never considered before.”

This, she explained, is where real trip designing begins.

Not traveling for the eyes and ears, but for the soul.

You get what you need, whether you like it or not

“When we get out of the glass bottle of our ego and when we escape like the squirrels in the cage of our personality and get into the forest again, we shall shiver with cold and fright.

But things will happen to us so that we don’t know ourselves.

Cool, unlying life will rush in.” — D.H. Lawrence

I’m a last-minute planner by nature.

Most of my best ideas happen less than 24 hours before lift off. It’s not uncommon for me to have a “great idea” the night before any given day.

Such was the case last summer, when I decided one night our family should pile into our French minivan early the next morning and visit the Chateau d’If, the island prison made famous by Victor Hugo’s book The Count of Monte Cristo, or for some unfortunate younger audiences the action movie featuring Guy Pearce.

I pictured in my mind’s eye the gentle rocking of the boat as it set off out of Marseille’s port, the sight of the fortress island on the horizon a few moments later, my little boys clamoring up and down stone steps that had been walked by some of France’s most famous celebrity prisoners.

We’d drive down, see the island, have lunch, and be back in time for dinner.

Easy peasy.

What I didn’t foresee was jumping onto the freeway on France’s busiest travel day of the year, where the entire country seemed to be heading to the beach via our tiny stretch of freeway, thus nearly tripling our time on the road.

I didn’t plan on stand-still traffic for kilometer after kilometer, nor did I plan on getting a flat tire the minute traffic lightened up, or not being able to replace said flat tire.

I also hadn’t imagined drifting into a parking garage in Marseille late-afternoon or the last-second sprint past gobs of tank-top clad tourists to catch the very last ferry of the day.

I also didn’t plan on having to drive home, hundreds of kilometers, on a tiny spare tire at 37 miles per hour, praying the whole way that God would deliver us long enough to get back to our beds before sunrise.

In the end, the list of things I didn’t want from my trip far outweighed my wants.

This is precisely the reason it’s stuck in my brain.

In the end it didn’t matter where my kids ended up that day. What mattered were the lessons we would learn while on the adventure.

Patience, perseverance, optimism, faith — these ended up being the real needs of our wreck of a road trip.

Which is precisely why the trip will forever be more valuable and lasting then if the original plan had gone off flawlessly.

So, what do you need?

“A journey is like marriage. The certain way to be wrong is to think you control it.” — John Steinbeck

Given summer’s popularity for “bucket-list” trips, it’s likely you’ve got one or two vacations lined up.

Instead of pouring over the list of to-do’s and to-see’s today, why not take a few minutes to ask yourself the real question behind your travel plans.

What do you need?

Why are you really wanting this time away?

• Are you wanting to reconnect with loved ones?
• Are you wanting to reconnect with yourself?
• Are you wanting to test your limits?
• Are you wanting to explore new frontiers of your mind?
• Are you wanting to simply breathe again, released from the suffocating weight of your daily life?

Taking the time to figure out what you and your travel companions need might not be as easy as looking for the best place to stay or eat.

It might, like my friend’s clients, just leave you in tears

Guaranteed, you’ll be all the better for it.

Thanks for Reading!

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