For some reason, when many people reach a certain level of material affluence in life, and find that the things they had to do to get there are starting to feel meaningless, many such people begin to develop a keen interest in . . . sailing.
And when they do, Anthony Sandberg is right there, ready to take them out onto the water. “That’s when they come to sail with me! They realize that maybe they were missing out on something. My world is about opening adventure up to people who have deferred that their entire lives in favor of checking all the right boxes and following the script.” Anthony runs one of the largest and most successful sailing schools in the world, the OSCS Sailing School on the Berkeley Marina. His story is directly relevant to this chapter.
Now sixty-two, Anthony dropped out of Dartmouth his senior year in 1971. Tensions were boiling in the United States around the Vietnam War, and during those final years Anthony was at college, the campus protests against the war were reaching a frenzied height.
Anthony spent most of his time organizing busloads of people to go down to Boston, New York, and Washington, D.C., to participate in the protests. When the invasion of Cambodia started in 1970, “schooling didn’t mean anything to me anymore. I wanted to be where what’s really happening in America. I took off that last term, and started organizing students full-time in D.C. So I never got a degree. I suppose I could go finish and get one now [chuckling], but I’m not sure it would do me any good.”
Anthony was the first person in his family to attend college. His father was a cook and his mother was a waitress. He grew up in lower-middle-class Hawaii, and then California, in what he describes as a troubled family life.
Wanting to escape, he left home and high school at sixteen, got a job on a ship, and sailed around the world. He returned to high school later that year, though he moved out of his home and was supported himself fully on his own at that point on.
Dartmouth was impressed with his self-determination and the writings he showed them about his self-funded sailing adventure. They offered him a full scholarship.
While he did well his first two years there, toward the end of his time at Dartmouth—in addition to the little matter of barely attending class due to his organizing—he began to feel a profound cultural alienation from his peers as they readied for life beyond graduation. “At the same time, my senior year, all my friends—who had long hair throughout college—starting cutting their hair and buying suits. It was like watching lemmings getting ready to jump. The biological clock kicked in, and they had to please their parents or please whatever they thought the process was. They didn’t seem to me to be in touch with what they wanted in life. In fact, there were no rewards for doing what you were passionate about. There were rewards for behaving.”
After leaving college, and after the protests died down, Anthony drew on the same enterprising spirit that got him into college in the first place, and he supported himself from a number of entrepreneurial ventures. He started a sporting goods business, then a leather goods business. He got crew jobs on multimillionaires’ yachts in the Mediterranean, Greece, Turkey, Croatia, and Spain. He then joined the Peace Corps in Nepal. “I was spending time with the richest people on earth, and the poorest people on earth.”
When he got back from the Peace Corps, he tried other endeavors. “I was curious about a million different things that I wanted to explore.” He got passionate about the budding solar energy industry. He apprenticed himself for six months to a top plumber—in those days solar energy involved water as a heating element—and started a solar installation and plumbing company, hiring licensed plumbers beneath him. At this time, he also began teaching sailing part-time at sailing schools.
It was at one of these schools that he got a piece of advice that changed his life forever. “I had a very well heeled and important client. He said, ‘Anthony, without a doubt, you’re one of the best sailing instructors I’ve ever had. But, there is no future for you in being a sailing instructor. You need to capture what you do, identify it, and codify it, so it can be taught to many, many people. First teach it to a team, and then beyond.’”
A lightning bolt hit Anthony through that one piece of advice (read Chapter 2 on finding the right advisers in life). He became possessed with the vision of starting his own sailing school. At that time, sailing was only for superrich elites. There weren’t accessible sailing schools then, like there are today (with Anthony’s school being a prime example of one today—he started the trend). He wanted to take his passion and love for sailing and make it accessible for as many people as possible.
“I was living in my plumbing van at the time. With a fever, staying up late every night in my van, I wrote out a business plan. Every aspect: how the boats should be cared for, how people should be trained, how visitors should be greeted, what the progression of studies will be.
“I started the school by borrowing boats on the Berkeley Marina. How do you borrow a boat? Well, have you ever seen an empty marina? [Laughing.] They’re filled with boats that are owned by people who don’t know how to sail them, and who will sell them to somebody else every three years. I walked the Berkeley Marina, saying to people, ‘Look, I’ll take care of your boat, and I’ll teach you how to sail, if you let me use it for my school during the week.’ I had my pick of the boats! Honestly, I think a kid could still do that today, it hasn’t changed a bit. [Laughing.] As I was doing that, I would get one client, then three, then five. I bootstrapped it entirely. No investment, no debt. A six-dollar business license.”
The school grew and grew from there. It now occupies a spectacular six-acre campus facing the Golden Gate Bridge. In his thirty-plus years in business, Anthony’s school has taught over twenty-five thousand people to sail, and now employs over eighty staff members, managing a fleet of over fifty boats and yachts. He lives in a gorgeous apartment directly overlooking the bay, part of the school complex. In the course of his work, he has led flotillas of sailing students and adventurers throughout Antarctica, Patagonia, Turkey, Greece, the Galápagos, the Caribbean, Central and South America, Tahiti, Australia, and the South Pacific, and regularly finds time for his own wild sailing adventures as well.
Although he’s lived an incredibly rich life so far, and plans to keep the school going strong, Anthony is now in the process of figuring out what the second stage of his life is all about. He knows it has something to do with teaching entrepreneurialism to kids. To that end, he’s been mentoring underprivileged children in the Bay Area on how to start businesses. “I don’t want to teach them general classes. I want to find the ten kids who want to learn how to be an entrepreneur. I can teach them to start a business out of nothing. Give me two twigs, and we’ll start a business out of it.”
Anthony wants to teach kids entrepreneurialism for a very specific reason. He believes the future of our planet depends on young people learning these skills.
“We are in a critical state right now. We’ve got maybe ten years to save our oceans. And there are all kinds of problems of that magnitude. However, I believe the future of our world is not going to come from the nonprofits. I think it’s going to come from business—because business is incredibly powerful. I just don’t think that holding bake sales and begging for little handouts by nonprofits is going to act quickly or powerfully enough. Business knows how to get things done. But it has to have a conscience, it has to want to make the world a better place and not just make a profit at any cost. It clearly doesn’t today.”
Anthony Sandberg may not be famous. He may not be a Silicon Valley billionaire. But he is a wealthy man, in every sense of the word. And to achieve this wealth, he never once deferred any meaning, purpose, adventure, or excitement in his life. He has always gone toward meaning, purpose, adventure, and excitement. His life is profoundly meaningful to him and to the many people he teaches and leads.
“Our motto at the school is ‘Inspire Confidence,’” he says. “It’s not ‘Learn to Sail Better.’ It’s about being confident to take that little journey from the shore, and then a little further, and a little further, and all of the sudden, the whole world becomes your playground.”
So this is “Art of Earning a Living.” It is the art of creating a career path that both provides a high likelihood of financial security and allows you to follow your dreams and make a difference in the world.
To understand what it involves, let’s go back for a moment to the argument between Parents and Daughter at the beginning of the chapter.
The parents and their child are arguing about the relationship between money, financial security, and safety on the one hand and passion, purpose, meaning, and making a difference on the other.
The parents and the daughter—though they are on opposite sides of the argument—are all operating with the same basic presuppositions: Money and financial security are completely separate from living with a sense of purpose and creating a meaningful life. These spheres bear no relationship to each other. The parents are advocating basically a droll, boring life, in which the daughter pursues a career she cares nothing about (and even finds morally repugnant) in exchange for financial security. The daughter is advocating a life of passion, purpose, and meaning, with no thought or regard for how she’s going to pay the bills.
The Art of Earning a Living is the art of finding creative ways of bringing the spheres of money and meaning together and making them overlap significantly.
I call it an art because it’s not always apparent how to best achieve financial stability while at the same time making a difference in a way you care about. Remember, we’re not talking about “work-life balance” here—the “write plays in your spare time as a hobby while you’re a lawyer” philosophy espoused by the parents. We’re talking about creating a path where your work is your life’s purpose is your income is your meaning is the difference you’re making on the planet. Significantly more elusive—yet infinitely more rewarding—than the much-hyped “work-life balance.”
The Art of Earning a Living requires a great deal of self-inquiry into what, exactly, the difference you want to make is, and also a lot of creative, entrepreneurial problem solving to figure out how you could make decent money while making that difference.
You’re going to have to create a solution unique to you and your circumstances. No similar solution will have ever existed before, for a very simple reason: in the whole of human history, no one has yet made the difference you want to make. If they had, the impact you want to make wouldn’t be a “difference” anymore, it would be a sameness! Making a difference, not a “sameness,” means doing things no one has done before, at least, not for the people whose lives you want to impact.
And doing things that no one has done before—that is, leadership—involves uncertainty, risk, and danger. Which means, as Anthony suggests, losing sight of the shore. The greater the impact you want to make in your field, market, career, industry, or profession, or in the world, the farther you have to travel from shore.
I’m not going to pretend there aren’t dangers in trying to make a difference. But in this book, I am going to give you a set of tools and skills that will minimize the dangers and maximize the chance of making a difference. Starting right now.
Next: Four Steps to Aligning Your Money and Your Meaning: Putting the Art of Earning a Living to Work
