The Road Less Traveled

Moving big ideas forward. Literally.
To show driving a road trip
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Neither snow nor rain nor heat nor gloom of night stays these James & Matthew co-founders from visiting their friends in other parts of the country.

We have and have had clients all over the country. While Jim and I attempt to limit our travel to focus on running our agency to the best of our ability and live the lifestyle we’ve set for ourselves, we love seeing our clients! The pandemic changed the rules slightly, but as things start to float back toward some semblance of normality, our travel requirements will eventually get back to their pre-pandemic levels.

Over the last ten years, we’ve racked up plenty of flying hours and miles, but about three years ago, a client engagement changed our perspective on flying.

Just Close Enough, Yet Still So Far

Our agency office is located in the quaint little New England town of Shirley, MA (about 45 minutes from Boston, on a no traffic day), but we’re now 100% remote. Partners and team members are scattered between central MA and the Midwest. In 2017, we started working with a financial brand in Albany, New York. For those of you unfamiliar with the distance between Albany, New York, and Central Massachusetts, it’s about a three-hour drive. They have an airport in Albany; it’s only a stone’s throw from this client actually.

The thing was, though, by the time we would gather up the team and drive into Boston, sure to be at least an hour early for our flight, we’d already used up the same amount of time (if not more) as it would take just to drive there. So we started to pack everyone up in my car and just go.

After years of flying, driving just felt right. So much so that we extended that road trip mentality to other parts of the country. When we had work to do in Virginia, it was a drive. DC? A drive. Even Michigan. We’d rather drive. Here’s why.

It Yields Important Discourse

When Jim and I first started this version of our agency in 2012 (editor’s note: James & Matthew operated under another name from 2007–2012), we spent a lot of time driving around New England to meet with prospective clients. We learned how to spend extended amounts of time together in a car, and I’d say we’ve had some of our best, most profound, most meaningful conversations in that car. There’s just something about a car ride for Jim and me that lets us dive into the more significant questions life is asking of us.

Due to constant battles with motion sickness, I do nearly all the driving, and Jim has adapted to this by becoming an excellent passenger. He never just kicks back and sleeps while I drive. He always has plenty to talk about, looks for lunch/dinner destinations along the way, and packs some pretty excellent snacks. We lean into this time together as an opportunity to work on strategies and planning.

It’s hard to do this on a plane, as it’s loud as hell when you’re up in the air, especially on the smaller regional flights. We both put on our noise-canceling headphones on a flight, close our eyes, and wait it out, which doesn’t feel like the most productive use of our time. 

We Aren’t Gassed

This is one point about driving that we really value. Air travel is stressful. Yes, if your objective is to get where you need to go within a set amount of time, then air travel might be your best option. 

The thing is, getting where we need to go and back home again quickly is probably a sign that we’re doing too much, and won’t be fully present once there.

We had this former colleague; we’ll call him Bill, who would travel like this. In at 9, out at 2. At first, I thought this guy had this travel thing down to a science. But as I would observe Bill in client meetings, I noticed that the air travel, the stress of getting back to the airport in time, etc., made Bill a zombie in these meetings. He wasn’t fully present, which is an essential part of any strategy session. Instead, he was worried about getting to his next destination.

Clients can feel that sort of energy. When you’re just meeting with them to check off a box, it’s not a good look. Yes, you’re physically present, but our client relationships demand more.

It Puts Our Hands Firmly on The Wheel

Not only is driving less stressful than flying but sometimes more comes of the visit than we expect. We show up and meet, and since we’re still there, maybe we get invited to dinner by the board of directors. Of course, we’ll attend (well, except for Bill, who needs to be back at the airport for 2). It gives us time to ask ourselves, did we accomplish everything we set out to? Do you need us to stay another day? No problem! Are we done early? Really done? Okay, we can head back. Like Gandalf, we arrive when we want to and leave when we want to.

Driving also allows for some more accessible packing options. There’s that all too familiar dreaded moment when you’re on a red-eye flight from wherever and you need to wait for your bags at the carousel, and you just want to be in bed. I mean, we’ve all been there. Then there’s the lost luggage debacle. These annoyances have made us pretty good at packing a carry-on and skipping claiming bags altogether. But, when we drive we can pack a little more comfortably knowing that bags will easily fit in the car’s trunk and not get squeezed into a tiny overhead bin.

The Intersection of Journey and Understanding

This one is significant to me in a near-spiritual sense. To me, when you’ve flown somewhere, rented a car, etc., you are merely a visitor — a stranger in a strange land. But what I learned in my trips back and forth to Albany is that when I can trace a line from my house to a destination, I feel more connected to that area. As our creative leader, it’s on me to understand the areas we work within from a higher level than just demographics, and it’s the journey that informs a lot of my thinking. I know the major highways; I passed the different exits and landmarks on my way in. I’m not insulated to the geography; I understand how to get around, like a local. I’m in my own car, a slice of home, and I’m exploring and charting new territory.

This Might Not Be for Everyone, and That’s Ok

Don’t get me wrong; there are times that flights make a lot of sense. If we had to visit clients on the West Coast, for example, that drive would eat up far too much of our time. At that point, it sure makes sense to choose the 6–8 hour flight over the two weeks of driving. Though, there are times when we’d consider it. Driving instead of flying isn’t for everyone, but after years of doing it, I can say it’s definitely worth it for us.

See you on the road!

Bonus Content:

This is one of our favorite playlists for longer road trips. We alternate between this, Jazz radio, Folk/Bluegrass, and Metal for those times when we need to wake up.


Matt Maguy is co-founder at James & Matthew, an advertising agency located in Massachusetts.