Exploring the Globe with Margaret Sullivan: Inside ‘Following the Sun: Tales (and Fails) From a Year Around the World With Our Kids’

Ever wonder what would happen if you packed up everything and left your career to travel? Meet a New York couple from the tech realm that did just that.

In 2019, Margaret Bensfield Sullivan, a former marketing executive at WPP’s Group SJR, and her husband Ted Sullivan, founder and former CEO of digital scorekeeping platform GameChanger, extracted themselves from their careers, took their kids out of school, and gave up their home to travel around the world for a year.

They tell the story of their adventure in the new book Following the Sun: Tales (and Fails) From a Year Around the World With Our Kids (December 2023). Author Margaret Bensfield Sullivan shares the story behind their whirlwind year in this exclusive interview with Silicon Valley News, and offers a glimpse into what can happen when entrepreneurship, family, and wanderlust intersect.

What inspired you and your family to embark on this year-long journey after experiencing success in the tech industry?

It really was an “ah-ha” moment that inspired our travels. We hadn’t considered doing anything like it at all, before that. Probably because life was pretty good. We lived in New York, had two healthy little kids – even a dog named Molly to complete the picture. Back then, our busy careers consumed most of our lives. The agency I’d help grow from a startup had been acquired by WPP, ramping up the pressure, while Ted’s startup GameChanger had recently been acquired by Dick’s Sporting Goods, where he had become an executive. We were doing what we were supposed to be doing, not looking for any deviations to our busy, but comfortable, routine.

But then in fall 2017, I flew to Arusha, Tanzania, to oversee media relations for a conference hosted by my longtime client, TED. While there, I had an unexpected realization. My book goes into the details, but the short story is that I could suddenly see how my New York life had grown transactional to the point of being forgettable: commute, work, bedtime, playground, socializing, rinse, repeat. I could see how little I knew about the wider world, and worse, how I might wake up in 15 years with kids in college, wondering where the time went.

On the 20-hour journey home, I reflected on this. I had never heard the terms “family gap year” or “worldschooling” or “RTW travel” — the acronym for Round The World — but that’s the wild idea that started to take shape in my mind. By the time I landed, I had a pitch for my husband: “A full year of global travel, with the kids, without jobs, on the move, seeing and learning as much as we can about the rest of the world. Not someday, but now.”

Eventually he came around, conceding that a family gap year would allow us to make the most of this fleeting chapter when the kids were still young and we were all healthy. A way to future-proof against regret. He was in.

How did your backgrounds in entrepreneurship influence the way you approached traveling with your family?

There’s no question our career experience came in handy. First of all, our travel year involved mind-boggling logistics: We visited 29 countries across six continents, flying on 79 flights and staying in around a hundred different places. All with little kids! Managing an itinerary like that required every last project management and leadership skill we’d ever learned from our careers.

And, of course, when things inevitably didn’t go according to plan, we could tap into that handy startup mentality. More than once we had to manage our snafus with a “duct tape and bubble gum” approach, comfortable with rolling up our sleeves and pivoting in the face of failure.

Specifically, there were three useful tactics drawn from our work lives that helped make the experience a success:

First, Ted and I assigned roles to keep things efficient and humming. This “jobs” system meant we each had distinct responsibilities, some with tongue-in-cheek titles like Chief Navigator, Head of Content and Minister of Finance. Everything got assigned, right down to packing: Ted was in charge of our son’s suitcase and I for our daughter’s, which meant packing, unpacking, and being responsible for any lost items or clothing in need of replacement. Logistics rarely fell through the cracks, and we never succumbed to the age-old “how-come-I-end-up-doing-all-the-work?” bickering.

We also knew when to outsource to professionals. Travel research and booking sounded really fun at first — wasn’t that all part of the experience? — but we quickly recognized that we didn’t have the knowledge or skills to find lodging and guides in all the obscure places we went. We ended up partnering with numerous travel agents that year, using their far superior abilities to get the job done well.

Last, we took very organized “notes.” My career in communications meant we logged narratives, lists, photos and videos for just about everything that happened that year. All this documentation was carefully catalogued, too, making for an easy and endless supply of information and resources. More important, it makes up a ready well of memories to draw from and reflect upon whenever we want.

Can you share a standout moment from your travels that profoundly impacted your perspective on life and business?

Yes, and it’s probably not what you’re picturing. It wasn’t some eye-popping elephant charge moment in Zimbabwe, though that did happen to us, nor some ghastly wakeup-call stomach bug in Beijing, which did, too.

Rather, it occurred at five o’clock on a March weeknight. We were staying in a rental house in Cape Town, South Africa, our longest stay of the year. Each evening, the four of us would settled in for a pre-dinner routine: cocktails poured, kids bathed and coloring quietly, grill ignited, salad chopping underway, our favorite new South African musician on the soundsystem.

To the casual observer, this scene looked a lot like our life back in New York. We’d often hung out together and cooked in the evenings at home. But there was a profound difference: In the Cape Town version of our evening routine, every extraneous claim on our time had been stripped away. The outsider looking in wouldn’t see how I didn’t have a pit in my stomach about a meeting the next morning; how Ted wasn’t thinking about his investors; how we weren’t bracing ourselves for the week ahead.

We were just enjoying the comfortable motions of a family routine, the four of us alone with nowhere to be and nothing to do. I had never known that before. Neither had Ted. It was the most profound feeling of peace we’d ever experienced in our adult lives. Does a family need to go halfway around the world to enjoy that simple feeling? No. Did our family need to go halfway around the world to discover it existed at all? Yes.

Today we hang on to that peace in all aspects of our lives, both personal and professional. Everything is just simpler. We have fewer belongings now, yes, but more importantly we’ve let go of the distractions that once consumed us, like real estate or distinguishing ourselves as “asskickers” at work. It’s not only been a relief, but also gratifying, the emotional equivalent of laying your arm on a cluttered table and pushing everything off in one large sweep. Nothing broken, nothing to clean up, just a way to proceed undistracted by mess.

Balancing family dynamics while traveling can be challenging. How did you navigate this aspect during your journey?

Challenging indeed! The short answer to your question is this: Like anything, we got used to the unbroken togetherness with time and practice. It became our new normal—our preferred state, even.

Here’s the longer answer: The unbroken togetherness did not come naturally to us. Getting to know our kids in a deeper way — and getting good at being full-time parents — took serious time and a steep learning curve. Notable lessons won the hard way included This Trip Was Our Idea Not Theirs, We Need To Meet Them Where They Are, and, eventually, my favorite, Our Kids Have Just As Much To Teach Us As We Have To Teach Them.

The “before” and “after” is dramatic. Before we left on our adventure, our family dynamic was something like The Married Couple, The Kids, and The World—none of it particularly enmeshed. My husband and I were the all-knowing grownups, and our children needed us to teach them the ways of the world.

Travel upended all that completely. Out in the world, the four of us were equally clueless, equally foreign, equally human. My husband and I were forced to admit we didn’t have all the answers. Our brave and funny kids proved they had just as much to teach us as we had to teach them. Today our foursome operates with that understanding. Our bond is fierce.

As a Silicon Valley insider, what lessons from your travels do you believe are particularly relevant to the tech and startup community?

No question, our experience showed us that my husband and I get our best ideas when we step away from the day-to-day. It reminds me of the Albert Einstein quote, “No worthy problem is ever solved within the plane of its original conception.”

This played out for us in two important ways. The first was that fateful business trip to Tanzania that sparked the entire idea for our adventure. It took going far, far away from my routine, both literally and figuratively, to see how my life needed a change. All that time alone on lengthy flights, all that exposure to new people and worldviews — it worked.

The second was that our year away gave us extreme clarity. We abandoned the idea of life plans and instead saw how we needed a list of priorities we could refer back to when making decisions

about our future—more guidepost, less blueprint. What had the travels revealed about us? What could we now see mattered? What had we once considered important and now viewed as irrelevant? What could we discard? What did we need to fight for?

The more we traveled, the more we could imagine what those might be, and started putting pen to paper. The title was Big List of Sullivan Life Priorities. The six items on our list took weeks to distill—not to mention almost a year of travel to conceive of in the first place—but we now have our essential criteria; the things we feel we need to create the life we wanted to live. It took leaving to see how badly we needed it.

Download Following the Sun: Tales (and Fails) From a Year Around the World With Our Kids today!