Dorie Clark

As Henry Wadsworth Longfellow noted, “we judge ourselves by what we feel capable of doing, while others judge us by what we have already done.” So when you’re a finance guy who moves into marketing, a venture capitalist who wants to become a career coach, or an executive trying to win a promotion to the next level, your path may make perfect sense to you, but that doesn’t mean it’s clear to everyone else

Finally, you’ll be able to ask better, more-informed questions once you start meeting with other professionals to talk about your goals. Stein tells her clients, “If one of the things they’re exploring is being a lawyer, I don’t want them going to a lawyer and asking a dumb question like ‘What’s it like to be a lawyer?’” Executive coach Michael Melcher agrees: “You want to show that you’ve done your homework—that you’ve taken it as far as possible before talking with the person,” and urges people to consider the “highest and best use” of the person they’re interviewing. In other words, if you can find out certain information online or through books, don’t waste a professional’s time with it.

If you really want to get to know what an industry’s like, you have to talk to seasoned veterans.
The CEO—the public face of the company—is bombarded with requests. That’s why Elizabeth started her initial research one notch lower, with the office of the chief operating officer, “because that secretary knows everybody,” she says. Her goal wasn’t actually to score an interview with the COO, which was probably unlikely. Instead, it was to get his imprimatur: “You can say, I know the COO is probably not the right person to talk to, but who is your best salesperson, or your rock-star marketing person? And then you can say the COO’s office recommended them, and they’re not going to blow you off.”

Volunteering to Build Experience
At the time of her career transition, Joanne was young and single, and she was willing to take a low-wage job in order to learn new skills. It’s a great path if you can afford it. But even if you can’t, volunteering on nights and weekends provides an opportunity for any professional to build skills and get a taste of new possibilities.
Rebecca Zucker, the San Francisco–based executive coach, says of volunteering, “It allows you to network with a new group of people in your target area, it helps you to keep your skill set fresh or build a new skill set, it’s something you can put on a résumé—and it shows your commitment to a particular path.” She recalls one client who wanted to explore clean tech, a popular industry in Silicon Valley that was hard to break into without previous experience. “He volunteered to do research for a private equity firm in a certain niche within clean tech,” she recounts. “Not only did he learn a ton and have something to put on his résumé, it was instrumental in helping him get a job in the field.”

Her first skill was relentless hustle. “In those days, you were selling the concept of having your hair styled,” she recalls. “It was more expensive than going to the barbershop, so you were not just selling the idea of ‘I’m the best hairstylist’; you were selling the idea that you should spend three times more on your haircut, but I managed to get them in.” She cajoled customers to provide referrals, and when business was slow, she’d call them up: “John, it’s six weeks since your last haircut, and you’re going to look shabby.” She’d hit executive watering holes after work, and flirt and pass out business cards; instead of taking a lunch hour, she’d fit in extra clients who only had time to come during their own lunch breaks.
In short order, she’d developed a clientele of powerful Bay Area professionals from major companies like Levi Strauss and Wells Fargo, and eventually launched her own salon. And she made good use of her time with them. “When I had people sitting in my chair, I’d say to people in the public relations business, ‘If you had a small hairstyling salon, how would you promote it?’ Or I’d ask what made you the best salesperson in your company, or what did you do in your company that prompted a big company to want to buy it? I’d say to other stylists, ‘Why would you talk drivel when you have the most interesting people in your chair?’ You take advantage of having interesting people in front of you who know more than you in certain areas.”

Heather’s experience illustrates the best reason to head back to graduate school, that is, when it’s essentially mandatory. That’s the case if you want to move into a job that requires specific technical training (like transportation engineering) or professional licensure, such as becoming a doctor or lawyer or acupuncturist. Another valid reason is when you want to expand your skills and networks, and feel ready to get the most out of the experience.

Heather’s experience illustrates the best reason to head back to graduate school, that is, when it’s essentially mandatory. That’s the case if you want to move into a job that requires specific technical training (like transportation engineering) or professional licensure, such as becoming a doctor or lawyer or acupuncturist. Another valid reason is when you want to expand your skills and networks, and feel ready to get the most out of the experience

All the while, inspired by the working moms around her, she pursued her art: “If they’re getting up at all hours to raise a child, I can find the time to advance my work.” She began rising before 5 a.m. to paint for three to four hours before work, and realized how much happier it made her. But she could also be hard on herself: “If I overslept until 5:15 and got to the studio at 5:30, I felt like I had failed. It was just crushing.”

getting my work to a place where I felt good about it, having a chance to get it out there, getting to be respected—that’s what success is to me.”
At times, as an executive very much outside the New York art scene, she questioned whether her painting would be taken seriously. But she reminded herself, “The starving artist in the garret is a convention, and artists break conventions all the time. Look at Wallace Stevens, who was an insurance salesman. You can find examples of people who’ve done bizarre things to feed themselves and keep the lights on.”
But in her graduate program, Alice found someone who did believe in her work. Years before, she’d met a prominent Boston art professor when she’d taken classes with him. They reconnected when he was a visiting artist in Provincetown, and he loved her work. Says Alice, “He told me, ‘If I can help, get in touch.’ And I said sure, but then he came back into the room and said, ‘I mean it.’ If he hadn’t come back into the room, I wouldn’t have done it.” But she got up the courage to create a wish list of Boston galleries she’d like to represent her. With her professor’s help, Alice’s first choice said yes

It’s true that top-tier programs can provide valuable networking and connections (and I wouldn’t advise anyone to turn down the opportunity to attend Harvard Business School or one of its elite peers).
But unless we’re talking about the pinnacle of top schools, my answer is generally no. As someone who has a great but perfectly useless (in the professional world) degree in theology, I have firsthand knowledge that a master’s degree doesn’t win you extra points or gain you any additional respect. It’s your demonstrated expertise—not your academic credentials—that counts in the business world.