reba mcentire

Photo: Courtesy of Oprah's Master Class

Follow the Less Glamorous Road
Country superstar Reba McEntire started out in the business thinking that once you got on the radio you were rich, but the journey was not as luxurious as it has originally seemed.

"You're in pick-up trucks and U-Haul trailers, and I was converting a horse trailer into a trailer I could take my instruments and the equipment in, changing clothes in the horse trailer before we went on to perform; so it was a long road to get to that first number one record." And the day she found out her song "Can't Even Get the Blues" topped the charts, she was waiting for her broken down tour bus to be fixed at a bus barn in DeSoto, Texas. Once she got off the phone with her manager who told her the news, she called her mom and then got back on the road to her next small gig. "It was a long hard road to that number one record, but very well worth it—worth waiting for."
robin robers

Photo: Courtesy of Oprah's Master Class

Be Flexible with Your Goals
Good Morning America anchor Robin Roberts made her dream of being at Wimbledon come true—she just took a different path to get there.

"I wanted to be a professional athlete. But there's something called ability that you must have. I knew that for me to be a professional athlete was to be a sports journalist. Tennis was my real love. I used to dream about one day being at Wimbledon. I could taste the strawberries and cream I could see myself curtseying there at center court. And I didn't make it there, obviously, as a tennis player, but let me tell you even though I had a mic in my hand instead of a tennis racket for ESPN when I went to cover it for the first time; to me it was like 'check! Wimbledon.' You have to be creative in reaching your goals and I think that's what really helped me so much in my life both professionally and personally. Just not being too rigid. Having goals and setting goals, but being flexible with them and knowing that it might not quite look like I think it's going to look and that's okay."
truvee wine

Photo: Michelle Magdalena

Break Down Barriers
Half sisters Andréa, who grew up in New Zealand, and Robin McBride, in New York City, met for the first time in 1999, after their father's passing, and bonded over a common passion.

"We both grew up in wine regions," says Robin. Says Andréa: "We geeked out over wine so often, we knew it was more than an interest." In 2010, they founded Eco.Love; Truvée debuted in January. Sisterly squabbles aren't an issue, but they've faced other challenges: Only about 10 percent of California winemakers are women; fewer are people of color. "We've been mistaken for assistants," Andréa says. "We don't take it personally. Our wine does the talking."
cicely tyson

Photo: Courtesy of Oprah's Master Class

Wait 26 Years for It
When legendary actress Cicely Tyson saw Geraldine Page's moving performance in the 1985 film The Trip to Bountiful, she told her agent that she would happily retire if he could get her a role like that. From time to time, she would remind him, "Where's my Trip to Bountiful?"

"Years later this woman came in and she said to me, 'I'm planning to produce one of my father's plays. With an all-black cast.' And she said, 'My father was such an admirer of you and your work that I know that there isn't anyone else that he would want to do this role.' So I said, 'Who's your father?' She said, 'Horton Foote.' And the play is The Trip to Bountiful."
genevie kocourek

Photo: Coral Von Zumwait

Go Back to School in Your 50s
In high school, Genevie Kocourek dreamed of becoming a doctor, until a guidance counselor insisted that it wasn't "appropriate" for a woman. Then in 2000, she enrolled in a wilderness first-responder course and had an epiphany.

"It was 38 degrees and raining," she recalls of the course, "and I was having the time of my life!" When she learned that her employer was offering early retirement, she mulled "retiring" to a brand-new career. She first took premed courses such as chemistry on her lunch break while working as an information technology director or at night. But by 2004, she'd retired from her IT job, taken out a loan and enrolled as a first-year student at the University of Wisconsin's medical school. She nearly quit during her third-year rotations, when she worked two days at a stretch, with no time for exercise and little contact with friends and family. She stuck it out and in 2011, after finishing her residency, she founded her own holistic medicine practice, which combines traditional medicine with alternative therapies like massage and acupuncture. Says Kocourek: "The process of getting here was exactly what it needed to be—humbling, exhausting and wondrous."
donna brazile

Photo: The Washington Post/Getty Images

Let One Path Lead You to Another
Political strategist Donna Brazile landed her dream job, which ended up leading her in a new direction.

"In 2000, I achieved my dream of managing a presidential campaign—Al Gore's. Though I really believed he could make a difference, the job was stressful and thankless. A few months after we lost, I found a new calling as a commentator and critic. Now I can give my opinion without taking a poll."
Jeni Britton Bauer

Photo: Kelsey McClellan

Don't Be Afraid to Fail
Ice cream connoisseur Jeni Britton Bauer, of Jeni's Splendid Ice Cream was an art student in Ohio, working at a pastry shop by day and studying perfumery by night, until one fateful afternoon, while eating chocolate ice cream, she mixed in cayenne pepper oil.

"It was so good, it was like the sky opened up," she says. "I knew right then that creating flavors was all I wanted to do." Bauer made good on her new obsession, quitting school and opening an ice cream parlor. "My family thought I was crazy," she says; considering how little she knew about pasteurization and cash flow, maybe they were right. The shop closed after four years. But two years later, after completing Penn State's famed week-long ice cream course and devising a smarter business plan, she opened Jeni's in Columbus. Today Bauer, presides over a mini empire of shops from Chicago to Nashville.
whoopi goldberg

Photo: Courtesy of Oprah's Master Class

Create Your Own Path
When Whoopi Goldberg struggled to find her place as a woman of color in show business, she decided to take matters into her own hands and create her one-woman show, The Spook Show.

"I had to write a show so they could see what I was capable of doing. So I came to New York and I did it. And for the first few days nobody came. And then an amazing review got written and the next thing I knew Bette Midler was in the audience and then there was 15 people in the audience, and then 30, and then full capacity and then we were able to expand. Then Mike Nichols came and he said, 'I love the show and I'd love to produce it for you.' I thought he was kidding, but my phone rang a month-and-a-half later. And then six months later we were at the Lyceum."
renel broks-moon

Photo: Nik Childers

Be the First
Growing up in a Northern California family of baseball nuts, Renel Brooks-Moon spent many a weekend cheering at Oakland A's or San Francisco Giants games. Then her fandom led her to live out her baseball fantasy.

In 2000, when she was working as a morning radio show host and local sports correspondent, the Giants tapped Brooks-Moon—and her booming, throaty voice—to be the ballpark's public address announcer. She's the only woman in Major League Baseball holding the coveted position (and the third ever in the sport's history to do it fulltime).
cecily strong

Photo: Mary Ellen Matthews/ NBC

Take the Plunge
While honing her comedy chops, Cecily Strong of Saturday Night Live, worked in the box office at iO, a famed Chicago improv theater, and waited for her big break.

When SNL creator Lorne Michaels held auditions there, Strong tried out. "My family came and sat in the front row," she says. "Afterward they looked like they'd seen a murder. I was positive I'd done terribly." But soon Michaels called her back and, following screen tests in New York, offered her a spot. "I was so happy, I left the studio and wandered around Manhattan by myself—sobbing."
jenny rossen

Photo: Courtesy of Jennifer Rossen

Practice When No One's Watching
Professional sand sculptor Jenny Rossen treasured sand castles since she was a child, but didn't know she could turn that passion into a career.

"I've loved sand castles since I was a kid, so even as a grown-up I'd build them on my hometown beach in Australia. At some point people started tossing money on my towel, which I found offensive. I wasn't begging! But local malls, and then car shows and festivals in other countries started commissioning me. Twenty-seven years later, it's my main gig."
maxine kumin

Photo: Melanie Stetson Freeman/Getty Images

Sign Up for the Class
The late Maxine Kumin was caring for a family of small children in the Massachusetts suburbs and writing little more than "jingly light verse" in the 1950s, when she saw a brochure for an adult education creative writing course on poetry, and signed up.

It was through that course that she met classmate Anne Sexton; they started carpooling together and began holding raucous poetry workshops at each other's houses with fellow poets (Maxine's kids would see her setting out snacks for a workshop and say, "Oh no, not the poets again!" and ask to sleep in the room over the garage). Kumin honed her craft by working on poems in her head while chauffeuring her children to their various activities, and the connections she made through that workshop helped to jumpstart her career. In 1981, Kumin became Poet Laureate of the United States.
Candy Chang

Photo: Courtesy of Candy Chang

Explore the World
Candy Chang, the artist behind the blackboard project "Before I Die I Want To…" found inspiration halfway across the world.

In 2007, Chang—then pursuing her master's in urban planning at Columbia University—was offered a fellowship in a township in Johannesburg, South Africa, to help develop more efficient ways for the community to share information. New systems were sorely needed: Before Chang arrived, a young girl had wandered from home and been lost for three days. Though she was ultimately returned safe and sound to her family, the township's lack of neighborhood-wide communication—like a local radio station—had hindered the search. Chang's team devised a simple but brilliant solution: They installed blackboards in high-traffic areas, allowing residents to spread news, publicize events and post jobs.

The experience convinced Chang that better use of our public spaces could revolutionize how we interact in our communities—and give us a greater say in what happens to them. Through a series of large-scale projects that combine installation art with social activism, Chang has encouraged people to engage with public spaces to let their voices be heard.
Robin Lindsey

Photo: Nina Hall

Keep an Eye on What's Around You
Wildlife photographer Robin Lindsey cofounded the volunteer nonprofit, Seal Sitters, after one life-changing day.

"I was having lunch with friends on Seattle's Alki Beach in 2007 when I saw a mob of maybe 200 people crowding around this baby seal. The next morning, I returned to the beach to see if the pup would be back, and lo and behold, there he was. I named him Spud, and every morning for a week, he popped his head out of the water at 6:08 like clockwork. I didn't know a thing about marine mammals, but after that, I had to help protect them."