Married to the CEO
Twenty years of cannonballing into life together
Wassup! Dakota here with Traipsing About, my AI-free newsletter where I get credit for all typos and rndom asides. In it, I explore living an intentional life while reclaiming creativity as an adult, spiced up with my travel experiences, pictures and daily drawings.
Today is my 44th birthday and we’re up in the Canadian Rockies! I’m very stoked to spend the entire summer exploring Alberta and British Columbia while camping with Chelsea’s bro and his lady.
On the drive up, we passed the headwaters of the Columbia River, which had a sign about a farmer along with an excellent quote:
It has been said that to be happy, you only need three things—something to do, someone to love, and something to look forward to.
Which plays right into today’s theme…
In case you missed it: Last time I wrote about the surreal, movie-script visit I took to my great-grandfather’s village in Italy with my mom.
Tracing my roots in Sant'Agata di Puglia
If I wrote a screenplay about me and my mom returning to her grandfather Annibale’s Italian village, it would feature random encounters with relatives, a hill town, classic Italian music (cue accordions!), old guys in piazzas, and pizza in the same piazzas.
Note: My trip to Italy delayed finishing this post I’d intended for April, so I’m publishing it now!
Two decades of cannonballing
Twenty years ago, Chelsea boarded a plane from Portland to Prague to meet me for a month-long first date in Europe.
We still laugh about why she did that, flew across an ocean to meet me after a series of conversations on MSN Messenger and Skype.
To be fair, she did some research. While we’d never met, I’d lived with her brother in college. Her dad had been my high school chemistry teacher.
His guidance: “Dakota gets what he wants.”
Her mom: “He likes to cannonball into swimming pools.”
At least one of those things is true.
At the time, I was penny pinching during a year traveling overseas. I had a vivacious young woman coming to meet me, so I went big with accommodations: couchsurfing for free!
As a testament to our shared views on finances, Chelsea didn’t bat an eye at shared lodging in a studio apartment. Even though she had a cool job with an expense account, it somehow made sense that my cheap ass wouldn’t book a hotel room.
I look back and shake my head at this idiocy, but that was young, thrifty Dakota. Now I’d drop at LEAST $25 on a shared hostel!
This was an exploratory first date. Sure, it was a month long, but if it didn’t work out, we’d still have a good time exploring eastern Europe. Chelsea even showed up with shirts labeled FUN and other entertaining items, including fake buck teeth.


Exploring Europe together
Our trip together had no agenda beyond getting to know one another. We took the train the wrong direction out of Cesky Krumlov, wandered cities and hiked mountains, rode buses and ferries around Croatia, ate a surprise dessert that some mysterious person bought for us in Rovinj, drove across Germany in a rented BMW with my friend Eric and a bushel of pastries…



Oh, and she and I fell in love.
This trip together set the tempo for our relationship. For our second date, she flew to Beijing to meet me (after I did the Trans-Siberian Railroad with my brother) and we traveled through China and SE Asia for a few months.
My impatience (especially when hungry) raised its ugly head when looking for restaurants with vegetarian options for her. She didn’t want to sleep in the dirtiest, cheapest hovels either, which was annoying.
Clearly, I was still learning to find middle ground with a partner.



After moving in with her in Portland, we were both in our 20s and working hard on careers. Our relationship was still fresh, evolving. Most conflicts centered around me wanting to change her. I can be *cough* a little intense about outdoor activity and wanted her to hike or bike like a maniac or rock climb with me.
Looking back, my relaxing that attitude over the years has transformed our partnership into a mostly peaceful one.
We balance each other well. In fact, if I’d coupled up with someone more like me—focused on physical activity, hard driving, a bit too much—I would have missed out on many experiences and activities. So many experiences and activities I treasure have sprung from her gentle nudges.
CEO vision
Oh what the hell, how about a list! Things Chelsea has initiated for us:
Saw a van in Colorado and kicked off our Sprinter life escapades.
Bike toured with girlfriends first and had the idea for our cross-US bike tour.
Wanted to downshift and stop in Bend after three years of van travels.
Bought me a piano out of the blue, kicking off my (second) love affair.
Did the initial research to confirm I could become an Italian citizen.
Got the wild ass idea to buy our Airstream trailer.
So many others, big and small, beyond that. I think of her as the CEO (ideas, vision) and me as the COO (make it happen).
Point me at something and I can create the structure, create the thing, from a DIY camper van to an Italian passport to WTF-traveling-with-a-trailer requires AND how to back it up without smashing things.



“It’s only after making all those compromises and forfeitures, and amassing a shared fortune in memories, regrets, in-jokes and secrets, fights and reconciliations, that that person becomes the only possible one for you, unique and irreplaceable.”
Tim Kreider, I Wrote This Book Because I Love You
The next decade
Ten years ago, I wrote a post about our relationship, concluding with:
“What is a relationship but a compilation of the moments shared with someone you care about? I dream of the expanding landscape of our lives, how many more adventures we’ll have, and how much we’ll learn and explore together. We’re just getting started.”
In 2016, I had no idea that October would be the end of our van trip. That we’d land in Bend and experience all we did there, the awesome people, the ups and downs of life.
Throwing caution to the wind to meet in a foreign country continues to be a counter-intuitive kind of bedrock we’ve anchored to, an expression of how we want to live. Even as we modify how and why we travel, we both fondly remember that trip. (Even if we disagree on who pursued whom: she definitely was the pursuer. #MyblogMyrules)
Now we’re in another phase, footloose again, no plans past September. I have zero idea what our lives will look like in another five years, let alone ten. Maybe I’ll get really into playing the recorder! (<--relationship deal-breaker for Chelsea.)
Whatever comes our way, so long as we can continue to grow together, support one another’s passions, and encourage adventure, it doesn’t matter. We’ll figure it out.
Here’s to another decade of cannonballing!
Onward!
Dakota






