As 24-year-old, Harvey Goldberg stepped off the plane in Florida in 1974, his Uncle Izzy immediately took note of the look on his face. Directionless in life and caught in the throes of a tough breakup, he was distraught and depressed. But Izzy was unfazed as he put his arm around his nephew. “Welcome to the human race,” he said.

A fearless risk-taker with big dreams and the discipline to achieve them, Izzy had recently retired at a relatively young age to spend more time with his family and enjoy the success he had spent his lifetime building. A savvy investor, he had gotten in on the ground level of the first Washington Investment Real Estate Trust, riding it all the way up. “Most adults I knew were products of their culture, and very similar,” Harvey reminisces today. “But he was so different from my parents, who played it safe and didn’t reach beyond the life that was expected of them. If it wasn’t for him, I’m not sure I would have known it was possible to live your life colorfully, confidently, and courageously. Just him being him was such a gift to me.”

On their first morning together, Izzy set the stage—not only for the week they would spend together, but also for the rest of Harvey’s life. “You’re a very irresponsible kid right now,” he pointed out. “But if you’re responsible for the next 25 years, you can go back to being irresponsible for the rest of your life. So I want you to make one decision before the week is over. What kind of lifestyle do you want? Do you want to be a have or a have not?”

Harvey didn’t need any more time to know he wanted a life like Izzy’s—successful, happy, and unhindered by financial worries. With that, over the next week, the two had breakfast together every morning and took a walk on the beach each afternoon. They figured out how much money Harvey would need by age fifty to only work if he wanted to, targeting the exact number and then working backward from there. “For the first time, I thought vividly of how I wanted to live my life, and how hard I’d need to work to get there,” Harvey says. “It was almost like I’d been asleep all my life, but he woke me up. That was the first business plan of my life, and it never left my mind.”

Now a Chair and Speaker for Vistage International, a peer-to-peer executive coaching firm with over 22,000 members worldwide, Harvey does for his members what Izzy did for him all those years ago. “It was the most magical week of my entire life,” Harvey recounts. “As he put me on the plane at the end, he reminded me that life isn’t about finding yourself; it’s about creating yourself. That’s what Vistage is about, too: giving CEOs and executives the tools they need to create success as they create themselves and the lives they want to lead.”

Launched in 1951 by Bob Nourse in Milwaukee as The Executive Committee, Vistage originally sprung from a model used by Benjamin Franklin. As a printer in Philadelphia, he began convening a small group of people to help each other professionally by offering different points of view. The Executive Committee spread across the Midwest, then across the country, and then across the world, eventually changing its name to Vistage International.

Today, Vistage Chairs across the country lead groups of around a dozen key executives in discussing challenges, sharing best practices, and supporting through good times and bad. Each group represents a time commitment of around forty hours a month, and each chair can start as many groups as they want. “The fascinating thing about Vistage is, there’s no one way to be a great chair,” Harvey points out. “I travel the country and see that each Chair does it their own way. If you’re a high performer, the organization gives you a lot of latitude to build your own business and lead your groups.”

Most driven to work with executives who play to win instead of playing not to lose, Harvey is particularly drawn to the nonprofit space. He works with the Girl Scouts and the Humane Rescue Alliance (formerly the Washington Humane Society), both with over 150 employees, and also highly values his smaller and mid-sized group members. “We all learn from each other,” he affirms. “Over my past eighteen years as Chair, I’ve learned things that would have allowed me to grow my business five times bigger if I were still running it today. But that’s what the first thirty years of my life were about—working to make money. I was living on the take. But now, through my work with Vistage, I live strictly on the give, focusing on the impact I can have.”

Harvey saw a remarkable opportunity to magnify this impact when, in 1999, his Vistage group brought in an impressive speaker from California who gave a presentation on mastering triggers. The talk discussed the seemingly insignificant triggers encountered on a daily basis that knock top performance down to B- or C-grade effort, resulting in a dramatic loss of productivity that compounds over time. “The message was, when people learn to manage their triggers, they can completely shift the dynamic to maintain positivity and productivity in the workplace.”

A new Chair himself, Harvey was so taken with the presentation that he invited the speaker to come before his own group. He then made a pitch to partner, with Harvey taking the East Coast territory that was less than desirable for the speaker. “He charged me a regular coaching fee, and once I got the basics of the program, I started inserting my own stories,” Harvey says. Harvey went on to do hundreds of presentations and enroll in speaker school to polish his game, later developing another partnership to take on a leadership presentation. “Now, I can go into a company and spend a whole day with them, with a morning session on performance and an afternoon session on leadership,” he says. “It’s a great offering.”

Today, the speaking programs he organizes for his Vistage group are still among his favorite parts of the job. He brings in four to six speakers each year, carefully selected and shared with nonprofits that don’t often have access to such great developmental potential. “They don’t get a lot of training like this, so when they do have access to it, they truly make the most of it,” says Harvey. “It’s really allowed me to develop my niche, and I’d like to roll out our training and expertise to other Humane Societies across the country who could benefit so much.”

While devoutly oriented to his goals today, Harvey’s pendulum swung in the opposite direction for the first 24 years of his life. Born and raised in Baltimore, Maryland, he grew up the middle child with an older and younger sister in a middle class suburban home. His father was a pharmacist, while his mother stayed at home. He was a decent student and athlete, a good kid, but he lacked any semblance of drive or vision, and instead thinks of himself as lazy and entitled. “In my group of friends, we all figured we’d go into our fathers’ businesses,” Harvey recounts. “None of us tried too hard, and I just wasn’t motivated. I was blind to the future for a long time.”

Every single night, every member of the Goldberg family sat down for dinner at six o’clock, and Harvey’s mother made each individual person whatever they were in the mood for that night. There, his father would talk about how rough things were at work. “He was an incredibly hardworking guy, and a very good provider,” Harvey recounts. “Family always came first, and he pushed us to pursue our educations and reach for success. My mother, as well, was all about family. As the matriarch of our entire family, she was very warm with a big heart, and in many instances she was too doting on us.”

Growing up, Harvey would sometimes go to work with his father and help the employees catalogue and restock inventory. He made his first buck working a summer job at another pharmacy, but he got fired for his lack of enthusiasm. Despite his apathy, it was always expected that the Goldberg children would go to college, and that Harvey would become a professional. He enrolled at the University of Miami for its laid-back reputation, and then transferred back to Maryland after his freshman year because his mother missed him. “That was a big mistake,” he says.

After two more years of college, Harvey enrolled in pharmacy school for three years. He lived in College Park, Maryland, and commuted into the city for courses, though he had no interest in the material. “I didn’t really want to do it; it was just the easiest professional path for me to follow,” he remarks. “I was scared of everything—scared of challenge, scared of girls, scared of experiencing life.”

When Harvey graduated from pharmacy school at age 23, he started working in his father’s store. But when he should have been excited at the outset of his career, he was really only going through the motions. “I hated being a pharmacist from the day I walked into pharmacy school,” he says. “But our generation kind of just did things like that, moving forward without stopping to consider that there might be a better path.”

Once Uncle Izzy opened Harvey’s eyes to the power of creating success while creating yourself, he didn’t waste a minute getting to work on the plan they put together. He began reading prolifically, absorbing business books and knowledge as fast as he could to make up for lost time. He saved $10,000 a year for the next six years, building up enough to put a down payment on his first pharmacy—his father’s partner’s store—when he was thirty years old. His father and partner did not get along and did not talk to each other, and before long, Harvey and his father stopped talking to each other as well, until the family accountant stepped in. After his father saw he was holding the young man back, they joined their efforts, and Harvey became the managing partner over both stores.

From then on, he began buying stores every one to two years. His mother couldn’t understand why he wanted to buy more businesses and why he wasn’t happy with what he’d already created, but Uncle Izzy had prepared him to disregard that kind of doubt from others who were simply cut from different cloth. Then, once Harvey had amassed four locations, he bid on the outpatient pharmacy at Johns Hopkins Hospital. “Of the seven bidders, I believe I was the smallest,” he recounts. “But I won it. There would be 1,200 patients coming through our doors every single day, with 5,000 employees, and I’d have the only retail pharmacy on the entire campus. It was like I had just won the lottery. I was 42 years old at the time, and it was the moment I realized that there wasn’t anything I couldn’t do.”

From that moment in 1992, Harvey had the confidence to play in the big leagues and compete against the best, overcoming his fear and delivering excellence. A mentor observed that, one day, he’d have to stop being a pharmacist running a business and instead become a businessman running a pharmacy. “I had to make that switch in my head, so I did,” Harvey says. “I read books, went to workshops, mastered financials, and learned how to interview—anything to make me a better businessman.”

That effort led Harvey to join The Inner Circle, a peer group in Baltimore. He enjoyed the experience, but after a year, he admitted that no one in the group was challenging him the way he was challenging others. So the group leader decided to introduce him to Vistage, a more intense version of the organization. “Not only did I want to switch to Vistage, but I also wanted to switch cities,” Harvey says. “I decided I wanted to get out of my comfort zone in Baltimore and instead join a group in the Washington, D.C. area.

With that, in 1996, he joined Vistage. Sitting next to Bob Roberts, the owner of a $125 million business called Roberts Oxygen, Harvey looked around his group and felt like a small fish in a big pond. “I made a point of sitting next to Bob every time because I admired him so much,” Harvey says. “One day, he told me I was operating under two false beliefs—I thought everyone in the room was smarter than me, and I thought everyone in the room made more money than me. I came to realize that fear is the biggest self-interference that any human being has. I knew I was smart, and I was making good money, but my Vistage Group took me to a level I didn’t even know was there. They turned me into a CEO.”

Thanks in part to the Vistage impact; Harvey’s Johns Hopkins facility was so well run, efficient, and profitable, that the university ultimately expressed interest in resuming ownership of the business. In 1998, Harvey sold the pharmacy back to Hopkins, which freed up his time somewhat to think about his next steps. “With so many locations, I couldn’t be everywhere all at once, so I knew I’d have to work really hard to develop the great people on my team,” he says. “Then, as I spent more and more time coaching, I found I was good at it. I was able to develop great managers that allowed us to dominate the neighborhoods of each of our locations. I was very intentional about creating a culture of laughing while learning, looking at mistakes as opportunities to get better. It worked very well, and after a while, I became very driven by the process of coaching itself.”

A tough but fair leader and coach, Harvey learned to hold his employees to a high standard and didn’t tolerate unacceptable behavior. “They usually lived up to it,” he says. “I didn’t have much turnover because I never asked anyone to do something I wouldn’t do, and because I adapted my leadership style to fit each employee. If someone needed a hammer, I’d do that. If they needed sensitivity, I’d do that. I also made a point to always do what I said I was going to do, which cultivated a trust with my employees. There were no signs on my wall saying what my virtues or values were; I lived them, always focusing on being consistent and predictable.”

Now, Harvey has built the life he and Uncle Izzy mapped out together all those years ago. Pursuing his calling, he decided to become a Vistage Chair in 2000, and began selling off his businesses one by one over the next decade. His choices are not guided by need, but by want. He works with the people he wants to work with, as many or as few hours as he wants, making space for travel or volunteering at animal shelters. “This is what he was talking about,” Harvey says. “A master in the art of living draws no sharp distinction between his work and his play.”

Now that he’s achieved financial security, Harvey eagerly looks forward to meeting the love of his life and getting married sometime in the future. He adores animals, especially dogs, and notes his work with the Washington Humane Society as a particularly transformative and meaningful experience. Equally as rewarding was the moment several decades ago, before his father’s passing, when he was running five pharmacy locations at once. “My father came up to me and said, ‘How can I help you?’” Harvey recounts. “He said, ‘I don’t want to stand in your way; I just want to help you.’ That was the moment I knew he finally dropped all his negativity and doubts and truly believed in me. It was his way of saying he wanted to be along for the ride with me. It meant a lot.”

In advising young people entering the working world today, Harvey underscores the importance of getting a mentor. “Feedback is the breakfast of champions,” he says. “Ask for it, absorb it, and don’t take things personally. Also, when you fail, make sure you fail forward and not backward. Remember that the path to mastery is through knowledge learned mostly from setbacks, so always be in a state of continuous improvement.”

For Harvey, creating success while creating himself is nothing if he isn’t focusing his energy and skill on helping others do the same—people who might be walking through life with their eyes closed, as he once was. “This incredible potential and ability is inside everyone,” he insists. “It’s just dormant sometimes. Maybe no one ever talked to them about it or opened their mind to the possibilities. It’s all about asking the right questions and getting the person thinking. It’s what Uncle Izzy did for me, what I have tried to do for my nieces and nephew, and what my Vistage members do for each other. Just start asking questions, and more often than not, by the time you’re done, you’ve created the solution you needed all along.”