Chapter 3

Frontiers

“Anyone can achieve their fullest potential[;] who we are might be predetermined, but the path we follow is always of our own choosing. We should never allow our fears or the expectations of others to set the frontiers of our destiny.”

—Martin Heidegger

We often think of frontiers as wild places at the edge of the known world, full of risk and danger, and so while they might make a great movie setting, we tend to avoid frontiers in our own lives. We forget that they are also the places where we learn, discover, and grow—and we find them everywhere, not just in faraway lands. A frontier is really any boundary between where we feel comfortable and where we don’t. And there are an infinite number of frontiers available to each of us, because every aspect of our lives includes a comfort zone that we have taken as a given and that constricts the possibilities available to us.

Born into humble origins, Denis O’Brien had already achieved a great deal by his family’s standards when he was hired by the local bank after attending university. Always restless, however, O’Brien cold-called Tony Ryan, founder of Guinness Peat Aviation and Ryanair, landing a job as his personal assistant. Later, as mobile phones started to mature, he left Ryan to create his own mobile company, ESat Telecom, which he later sold to British Telecom. Still looking for the next frontier, O’Brien founded Digicel to lead the development of mobile networks in over thirty Caribbean and Pacific islands.

When we asked O’Brien about navigating the uncertainty of so many frontiers, he answered by recounting his experience creating a mobile network in Haiti, one of the poorest nations in the world, crippled by underinvestment and corruption. “No one wanted to invest, absolutely nobody,” O’Brien told us. But he flew to Haiti anyway. “It took me two hours driving around Port-au-Prince to see that we could do it. Everywhere, people were transacting—selling food, car parts, and other stuff. I could see people had a few dollars to invest in something that could transform their lives.”1

Despite his optimism, O’Brien could only convince one other investor, who in the end dropped out, leaving Digicel to fund the full $160 million up-front costs to establish the network. Digicel Haiti has since weathered earthquakes, fuel riots, hyperinflation, and other uncertainties to become the first mobile operator in a place where everyone thought it was impossible. “So in answer to your question,” O’Brien told us, leaning in close with a smile and a wink, “all anyone could see were the risks, but I saw possibility.” Pushing into the frontier has made O’Brien one of the wealthiest entrepreneurs in the world, allowing him to build over two hundred schools in Haiti and to rebuild its famous Iron Market after it was flattened by the 2010 earthquake.

However, for most of us the frontier will be found not in other countries but much closer to home. Clare and David Hieatt are a creative couple who cofounded the clothing brand Howies while working jobs at advertising agencies. But when Howies started to take off, they left their high-paying jobs in London to focus full-time on their eco brand, ultimately selling to Timberland in the hope that they would have greater impact with more support. Imagine their devastation when Timberland chose to go a different direction, moving the company to the United States. The Hieatts left the company, and while the financial exit made them comfortable, they missed the entrepreneurial frontier.

One weekend, hanging out with friends, they wondered aloud, “How can we keep learning, like we did when we had Howies?” Remembering that one of the hardest things about being an entrepreneur is feeling alone, they started to think about developing an “encouragement network” to help others trying to do new things. In some ways, it didn’t make sense for the Hieatts to lead an encouragement network. They had moved to Cardigan, Wales, a tiny town of four thousand people on the remote western edge of the UK. What could they do from such a small place? But they had bought a farm, with old chicken sheds and large fields. What if they could attract top-notch speakers, provide great coffee, let attendees camp in the fields, and broadcast the resulting encouragement to the world?

The idea grew to become the Do Lectures, the SXSW of the continental innovation world. Featuring lectures from people like Sir Tim Berners-Lee, Marion Deuchars, Tim Ferriss, and Maggie Doyne, it created a global impact—there are now Do Lectures in the United States, Australia, and Costa Rica. The experience not only expanded their frontier as a couple but led to the creation of a new business, Hiut Denim. Looking back on the journey, David Hieatt now champions frontiers: Although they can be scary or intimidating, “you can only do your best work when you are at the frontier,” he argues. “You have to be at the frontier if you want to do something new.”

Frontiers can also be personal internal boundaries with equally transformative rewards. Benjamin Gilmour is an author, filmmaker, and paramedic who has worked, written, and filmed all over the world. His film Jirga is about an Australian soldier fighting the Taliban who, during a village raid, kills the innocent father of a family of three. Racked by guilt, he returns to the village three years later to make amends and is put on trial by the village elders. The film’s climax is as touching as it is surprising: the oldest son holds a knife to the throat of his father’s murderer and forgives rather than seeks revenge. The village elders, Afghani tribespeople who many Westerners have been taught to fear, then express the film’s valuable lesson: “forgiveness is mightier and more honourable than taking revenge.”

When we asked Gilmour why he wanted to flip the script on so many of our Western stereotypes, he said, “I wanted to push the boundaries of empathy, of what people can feel for someone who is so different from them, even someone they have stereotyped as bad.”2

Not all frontiers have to be emotionally charged, entrepreneurial, or daringly adventurous. Signing up for a new workout session, trying a new haircut, and even going to a restaurant that you assumed you wouldn’t like are all frontier-expanding pursuits. When we spent time with author Brad Modlin during his visit to Paris, we had a hard time meeting up with him on several occasions. What we didn’t know is that this nationally recognized author and poet was either lost or just running a couple minutes late. Why? He didn’t have a map … because he doesn’t carry a smartphone … on purpose. He welcomes getting lost because he knows it means he will discover new places and see new things. It’s something he learned walking the Camino de Santiago, the ancient pilgrim trail that cuts through the heart of France and Spain. Amid the sudden rainstorms, blisters, and faulty gear, he found his most interesting experiences happened when he got lost or had setbacks. “I learned to love it,” Modlin told us, “and now I let myself get lost just to see what I find. It’s so fascinating!”3