Using design thinking to move across the country 2/2

Skipper Chong Warson
6 min readJul 7, 2020

This is the second of two articles where I talk about a couple of the specific challenges we encountered while planning to move from New York City to San Francisco

Starting in July of last year, my family and I began the process to relocate from the east coast to the west coast for new digs and work. We decided to drive, sure, but how do we start? Where do we go from here? Metaphorically and literally.

Which way is the best to go? Start with empathy

Same mode as before, I needed to know what my wife wanted out of a drive and she wanted to know what I wanted. Not the freeway, we said at the same time. Or as little as possible, we agreed.

What all did we want to see, my wife asked. I volunteered Mount Rushmore, Four presidential heads on the side of a mountain in the middle of South Dakota? The real question is, Why wouldn’t we go? She agreed and suggested Niagara Falls, We’ve lived in New York City how long and we’ve never gone.

I asked, Have you ever been to Yellowstone? It’s the first national park. She said, I’ve seen some amazing photos. I asked, Wait, wasn’t that Yellowstone in those old Yogi Bear cartoons? Moonstone, Jellystone, I don’t know. My wife shook her head as if to say, What are you talking about?

Yellowstone National Park photo by Stephen Walker (left) and Yogi Bear in Jellystone Park with a pick-a-nick basket, no doubt stolen (right)

I repeated, Jellystone. Yellowstone. Pic-a-nic baskets. And she gave me a second look that said very clearly, I have no idea what you’re talking about. And I threw up my hands.

There’s nothing quite like a joke strikeout when you’re a child of cartoon reruns and it’s with your own wife. Cue sad trombone. And with that, we blew right past the second stage — read: define — and dug right into trip planning.

Ideation, the planning layer

After our initial round of divergent thinking, we dove right in. After we’d spent our daylight hours packing boxes, donation runs, and selling a few things in the neighborhood, we stayed up late and dug through Lonely Planet, Roadtrippers, Roadside America, and the Internet at-large among others. After a few days, the shininess of taking a road trip was beginning to wear thin as we were increasingly wearied in our digital research and not making much headway to boot.

So, we decided to plan in some other way. We procured a map of the United States and threw it up on one of the newly spackled walls in our apartment. And with a handful of pins, we quickly marked a number of points of interest — including Niagara Falls, Mount Rushmore, and Yellowstone.

Detail of map pins, west coast and San Francisco (left) with east coast and New York City (right)

It was nice to not be scouring through ubiquitous online articles with FOMO (read: fear of missing out) titles like:

  • Top 10 Places to Stop on the Way to Niagara Falls from New York City
  • Five Iowa Scenic Drives You Haven’t Taken Yet
  • Best Road Side Stops in Montana

You know the drill. The endless scroll was endless.

And then an idea came up — what if we stopped at towns where our family had previously lived? What if we visit a few family graveyards no one has been for years, if ever?

All right. Niagara Falls, Mount Rushmore, Yellowstone, and three different family graveyards. That felt like the beginnings of a good starting plan. Score one for the analog process over digital.

So, that was the first challenge — how we were going to drive across the country. Next, how would we make sure that we were driving in the right direction? A lot of the areas that we’d be driving, we’d never been in before. Which brings us to our second challenge.


We couldn’t really take our pushpin map on the road with us, we knew that. Sure, there’s a ton of digital maps but we also knew we’d have a that there would parts of our trip where there would be no signal — in parts of Yellowstone National Park, for instance, there’s only 20–30% coverage for both Verizon and AT&T. As far as I can tell, Waze and Apple Maps don’t even have an offline mode and even with offline Google Maps, we wanted to have some kind of fallback.

Imagine being out in the middle of the Montana and South Dakota badlands with no signal and completely lost.

The character Moira Rose from Canadian television sitcom Schitt’s Creek looking for signal
Moira Rose from Canadian television sitcom Schitt’s Creek looking for signal

No. No, thank you.

So, we’d need a physical map. And wouldn’t you know it? We had mistakenly packed our 2018 road atlas in one of the many boxes now stacking up in our apartment that was more and more crowded by the day.

And so we purchased a new Rand McNally 2020 road atlas which was indispensable on our road trip, even with the car’s Global Positioning System (GPS) and using our phones with CarPlay.

Having a physical map was a lifesaver on this road trip across the country

There would be so many times where our signal would drop out or the algorithm would try to over-optimize our route — think about how many times you’ve punched into some starting point and some ending point into a map program where you end up asking yourself, This is how you (read: Google, Apple, Waze) want me to go? Really?

If I had my wish, I would’ve wanted something like Happy Maps but with my family’s happiness and the notion of adventure in mind as we were traversing the country and within our time constraints. Why Daniele Quercia couldn’t have devised our trip, I don’t know. (Pst, watch his TedTalk on Happy Maps, it’s great.)

The trip itself

To jump ahead to the end, we made it to San Francisco in just under two weeks, all told. We did see Niagara Falls from the Canada side, saw Mount Rushmore — our daughter is now the keeper of a faun stuffie from the gift shop named Fauline — and saw bison, bears, elk, mule, and white-tailed deer along with a ton of birds, fish, amphibians, and reptiles in Jellystone, I mean Yellowstone. We visited three family graveyards — the one in Radersburg, Montana was the quietest place I’ve ever been outdoors.

A panoramic shot of the Radersburg Cemetary in Toston, Montana

Literally, you could hear a pin drop.

We also drove through Custer State Park and Badlands National Park; had a glass of ice water in Wahl, South Dakota; sat on roadside dinosaurs; witnessed the deaths of way too many Pandora moths in Bend, Oregon; and stopped in Eugene, Oregon to catch up with some friends from New York City there for the summer. Whew!

We survived the trip, our dog was over the moon excited to see us in San Francisco, and we’ve been settled in a house with some amount of furniture for almost a year now. We can talk about how our lives have changed as a result of the COVID-19 pandemic.

All in all, I consider our road trip across the country a success, and design thinking helped along the way — along with my wife’s willingness and patience throughout.

Thanks for reading. And let me know what you think.

If you missed the first part of this article, you can jump into the general how we made the decision to road trip versus flying or taking a train. It was originally published on the thoughtbot blog.



Skipper Chong Warson

Leadership coach, design director at SoftServe, and host of How This Works. Formerly at thoughtbot SF, Fjord NYC, and Shep (acquired) among others.