Chandra Greer in her Chicago store, Greer

From Marketing Executive to Stationery Store Owner—Chandra Greer, 49

Know when to fold 'em: I was an executive at an ad firm, and I felt as if the space between who I was and who I had to be for my career was huge. In 1997 I quit with no idea what to do next. I spent several weeks in despair, convinced I'd ruined my life. Then I went shopping. I was drawn to paper stores, places that sold all the things you needed to make greeting cards or little books.

Put your stamp on things: I started making my own cards because they're such a positive product. You send them to make people feel better. When I took my designs to retailers, I was rejected. I knew I needed my own place. In 1998 I opened Greer in a tiny space in a wealthy suburb north of Chicago, with money my husband and I had saved up.

Play your cards right: The store did well enough, but my taste wasn't completely resonating with my suburban customers. My sales weren't as good as they could be, and the people who were buying had come up from the city. Obviously, I needed to move downtown—but Chicago has a lot of great stationery stores, and rents aren't cheap. Still, in 2005, I did it. My sales went right up. We started getting press, which generated even more business. Today we sell stationery and paper goods as well as soaps, pillows, vintage scarf button pins, even a little book called George Washington's Rules of Civility & Decent Behaviour. I should never have been in business anywhere else.
From corporate fashion executive to clothing company founder

From Corporate Fashion Executive to Clothing Company Founder—Jordan Veatch-Goffi, 30 (right), with her business partner, Lisa Pidge

Jordan Veatch-Goffi climbed the ranks at Gap for five years before she leveraged her corporate experience into Doce Vida Fitness. Her advice to office workers: You can make the jump in six (sort of) easy steps.

1. Treat your job as an MBA program.
To get the full picture of how to run a retail business, I applied to the Gap's retail management training program. Essentially, the company paid me to learn design, marketing (which is how to get publicity for your products), planning (meaning, have enough money on hand to pay the bills), and production (how to buy zippers from one factory and buttons from another and ship them to a third where they make the garment).

2. Find a problem.
I'm a very athletic, big-boned person, and I like my body. I want to look great when I work out, but nothing I bought in the United States ever fit right.

3. Let your idea be the solution.
I'm half Brazilian, and I visit the country at least twice a year. The women there are very curvy and very body confident. They show off what they've got. Brazilian fabric and design reflect that. I wanted to create athletic gear here that makes you look better, feel better, and work out better.

4. Stretch yourself.
Our fabric, which is made in Brazil, has 12 percent stretch—that's more than most American athletic fabrics. It really hugs your body. The compression not only makes you look smooth but also expands and contracts as your body changes. Expecting moms wear our V-top pants before, during, and after pregnancy.

5. Celebrate your success.
The Dallas Cowboys cheerleaders hired us to create their fitness wear—we celebrated by doing high kicks!

6. Make alterations.
We modified the Cowboys cheerleaders design before putting it in our catalog—their inseams are really short. No one but cheerleaders could ever wear those.

Rosanne Haggerty with Common Ground residents

From Nonprofit Staffer to Nonprofit Founder—Rosanne Haggerty, 47

In 1982 Rosanne Haggerty took a volunteer job with Covenant House New York, a shelter for at-risk youth. Eight years later, she would create Common Ground, an innovative solution to housing the homeless in Manhattan.

Did she know this would be her life's work when she started volunteering? No, I kept thinking I'd do it for one more year, then go back to a conventional career path. I bought an updated LSAT study guide every summer.

Why didn't she go to law school? When the 735-room, filthy, decrepit Times Square Hotel (a.k.a. Homeless Hell) went bankrupt in the late 1980s, I wanted someone to turn it into quality supportive housing—with employment services, a clinic, and caseworkers right in the building. Not a shelter but permanent, dignified housing. Because I'd been development coordinator for Catholic Charities of Brooklyn, I knew what questions financiers, tenants, and the city would need answered, and I wrote up a plan. Everyone I talked to was too overcommitted to take it on. They all agreed, though, that someone really ought to do it. Finally, I thought, "Oh, someone is me." In 1993 the first new tenants moved in. It became the largest example of permanent, supportive housing for individuals in the country. We've opened four others in New York [including the Prince George, above] and are helping to create similar projects in Los Angeles, New Orleans, and Australia.

Ever think about becoming a lawyer? No, I bought my last LSAT guide in 1985.
Norrinda Brown at the Brown Betty Dessert Boutique with her grandmother, Betty, and mother, Linda

Attorney and Bakery Co-Owner—Norrinda Brown, 29

In 2004 Norrinda Brown and her mother were both feeling a little empty: Norrinda had just started practicing law and missed the creativity of school; her mother and father had split up after more than 30 years of marriage. Baking became their sweet weekend escape—then their business plan.

The basic ingredients: Many of our products are based on my grandmom's recipes. We wanted to see if our cakes would sell, so for months we held tasting parties for friends and family. We asked guests to write comments anonymously on cards. Mostly, people said nice things, but they also said "too moist," "too sweet," and "needs to be more pineapple-y"—which sort of got my mom's back up.

Sift gently: My mom worked on the recipes until people thought the cakes had just the right amount of moistness, sweetness, and flavor. Now she's meticulous about her instructions—down to the number of minutes you mix things and how much you sift them.

Set in a cool place: We took out a home equity loan to buy equipment and rent a space [for the Brown Betty Dessert Boutique]. We picked the Northern Liberties area because we could afford it, and it's the Philadelphia neighborhood that's supposed to grow the most in the next 10 years.

Watch the dough rise: My mom and I are both very risk averse, so she has kept on teaching and I still practice law. She works in the bakery after school and we both work on weekends. We're tired a lot. Four employees hold things together when we're not around. It's working. Last year we were voted "Best of Philadelphia" by a city magazine and a newspaper.

The icing on the cake: Opening the business gave everyone in my family a new way to talk to one another during a difficult time. Even my dad helped out with construction and finance.
From executive recruiter to renovation and design manager

From Executive Recruiter to Renovation and Design Manager—Robin Wilson, 37

Real estate is in my blood, four generations back. I got into it with my grandfather, who owned several Texas "shotgun" houses—studios where oil workers lived. He let me choose their exterior paint when I was 7 years old. I made one block the "rainbow" houses: one blue, one violet, one red, and so on. It made caring for property seem like art. On Sundays we collected rent. That made real estate seem like an ATM—you can get money out of it.

After college, I went into management consulting and then executive search. But I felt as if I only got to start projects—finding people jobs—never finish them. I might not learn until years later if it was a great match. When my firm went public in 1999, I instantly sold my shares and used the money to go to graduate school to study real estate finance.

I wanted to go into commercial property management, but no one would hire me. Most people suggested I become a broker, which is the real estate job "for girls." I wanted to be like my grandfather, so when a professor suggested I try residential property management, I talked my friends into hiring me to do their kitchen, bath, and baby nursery renovations. I said, "I'll be like the wedding planner of your project. You won't have to worry about one thing." And they didn't. Now I do whole apartments, homes, law firms, even former President Clinton's office. My budgets run as high as $7 million.

Women, especially Southern women, are taught to be demure. When I first opened, I didn't want to be a show-off and name my company after myself. Instead I called it WSG (Wilson Services Group) Consulting. Huge mistake. No one could remember it. Plus, my expertise and talent are what clients are buying. We rebranded this year as Robin Wilson Home. Business is booming.

Karen Berber in Key Biscayne, Florida, with fellow kiteboarders

From Stay-at-Home Mom to Adventure-Travel Company Owner—Karen Berber, 41

In October 2000, Karen Berber—pregnant with her third child and busy with a small but demanding business importing children's clothing that blocks UV rays—meant to run a quick errand. Instead, driving along Miami's Rickenbacker Causeway, she found a new career. Her transformation hinged on four questions that surfaced at just the right time.

What's that? I saw two guys on the ocean, riding boards attached to beautiful kites. I love anything you can do in the water or on it, so I pulled over and waited for them to come in.

How can I do that? They explained they were kiteboarding—a cross between windsurfing and kite flying—and one of them was starting a school to teach it.

Where can I do that? Being out on the water with the wind as your engine is so many things at one time—beauty, freedom, control, power, fear, and awareness. But it's often not windy enough to kiteboard in Miami. I was totally willing to travel, but no one could tell me where to go.

How can I get paid to do that? In 2004 I started Ozone Travel to create custom trips. European destinations had been scoped out, so I researched windy locations and hotels in the Caribbean and South America. Then I sent a press release to three influential magazines: Kiteboarding, SBC Kiteboard, and Kite World. They listed my business in their news sections. We've created about 300 vacations to more than a dozen different destinations. The best part? I have to check out the places we recommend.