Flying Coach to First Class

The strategic use of a career coach can take your career to new levels.

Tami Blake’s corporate job was paying the bills, but she wasn’t happy. She felt herself being tugged in a new direction. “I really wanted to make the leap to entrepreneurship,” she says.

She knew that would be a challenge, so she decided to hire a career coach to help her navigate the waters. Blake found her way to coach Jenn Lin, chief dreamer at 10 Things U Dream of Doing! (, who quickly earned her trust. “Tami asked me, ‘What is it like to be an entrepreneur?’” Lin remembers. “And I said, ‘It’s great. I love it. And at times, it’s scary.’ Her whole body language changed, and in that moment, my intuion was that she was going to sign with me because I was being real and authentic.”

Having a coach in your corner who will tell it to you straight—and then work with you to set goals and blast through the barriers—can spur you to exciting new heights.

“Some of the most successful people have coaches,” says Connie Thanasoulis-Cerrachio, a partner at SixFigureStart ( “Derek Jeter has a hitting coach, a fielding coach, and a sports psychologist. That’s why he’s a top performer.”

The concept of career coaching is nothing new. At the height of the Great Depression, for example, a group called the Thursday Night Club formed to help new grads from Harvard Business School define their uniqueness and better sell themselves in a fierce job market. Today, scores of people are seeking the services of a career coach, whether they want to find a new job after a layoff, spring to the next level in their career, or (like Tami Blake) make a dramatic career change.

But unlike back in the Depression—or even in the 1980s—today’s career coaches are taking a more holistic approach to their work that recognizes our shifting priorities.

“We live in an age where people are being asked to work longer, harder, and faster than ever before, and the title and the money are no longer enough,” Lin says. “People are looking for something that’s soul satisfying. The question they’re asking themselves is, ‘What am I going to do with my life that’s going to give it meaning?’” Research conducted by Paul Fairlie of the School of Human Resource Management found that the desire for meaningful work has increased in the past 20 years among people in all age groups.

Digging Deep
To create a fulfilling work life, career coaches like Hayya Lee start by helping clients pinpoint their core values. “A lot of people will say, ‘Oh, I have values,’” says Lee, CEO of HayyaLiving LLC ( “But if you ask them, ‘What are your core values?’ some can’t tell you, or they wouldn’t be able to tell you why those are their core values, or how they’re living their core values in their personal and professional life. So we start there. I go through 150 values with them, and we assess. Once we get them down to five, they might say, ‘Okay, where I am right now is not working for me. This runs counter to what my values are.’ And it’s like plug and play. Once you know what your values are, it’s easier to make decisions about where to go next.”

That was certainly the case with Blake. Lin guided her through a core values assessment that shed light on why she was eager for a change. “We discovered that my core values were freedom and creativity, and my current position wasn’t going to meet those needs,” Blake says.

But she had a career idea that did get her motor revving: she wanted to open a waxing and skin-care salon. Being an entrepreneur would give her the freedom and creativity she craved, and the salon she envisioned would allow her to live her values. “I’m passionate about natural skin care, so I wanted to introduce sugaring, a natural form of hair removal that’s pervasive in the Middle East,” Blake says. “One of my other passions is working with and empowering women. In the beauty business, there’s a lot of turnover. Women jump from one salon to the next because they’re unable to build up their clientele. Sometimes they don’t have the business skills to make a decent living, and some have children.” Her salon would train employees well and help them thrive.

Clearing the Hurdles
Even when you’re excited about your goals, taking the first steps forward can be difficult. “Change is hard because we’re not programmed that way,” Lin says. “When I do a workshop, I ask everyone, ‘Given a choice between 
uncertainty and unhappiness, what would you choose? Raise your hand if you’d choose uncertainty.’ And pretty much everybody raises their hand. Then I’ll say, ‘Lower your hand if you’ve ever stayed at a job longer than you wanted to.’ A bunch of hands will go down. And then, ‘Lower your hand if you’ve ever stayed in a relationship longer than you wanted to.’ By this time, everybody’s hand is down. So we choose unhappiness all the time, because uncertainty is so scary.”

But once you’re ready to make a change, a coach can help you do it. “The type of person who will come to me—or who will hire any coach, for that matter—is somebody for whom the pain of being where they are has gotten too much, and fear of the unknown is no longer as painful as where they are right now,” says Lee.

As she embarked on her new endeavor, Blake admits that she had some concerns—especially when she learned that she was pregnant. She worried about failing. She worried about not having enough money or enough resources. “Jenn helped me manage those fears that can make you talk yourself out of doing something that you really want to do,” Blake says. “We had names for the two parts of my mind—one is the practical, pragmatic side, and the other is the flighty, fearful side. When I was freaking out, I’d say, ‘This is the flighty one. This is my inner saboteur. This is not who I am. This is just a piece of me who’s creeping in and taking over.’”

Lee says helping clients get mastery over their emotions around change is one of the most important things she does. “A lot of clients come to me with business challenges, but often the challenge is actually their belief system, so we spend time working on that,” she says. “You cannot achieve your external goals until you deal with the internal—just plain and simple. Sometimes, because we’re so close to our own lives, it’s hard to see a way out. If you are taking the step to hire a coach, it means that you’re trying to accelerate your progress.”

Adapting to Thrive
As the working world rapidly changes—due to technology, a more competitive global economy, and even entire job categories becoming obsolete—career coaches are helping their clients keep up. A coach can help you adapt and reinvent yourself so you remain marketable as the changes come.

“We used to think that there were certain tasks that could only be done by human beings, like driving, because of the multitasking and the decisions that we had to make,” Lin says. “Well, guess what? Now Google has a car that drives itself. What that tells me is that the people who are going to be able to survive in this fast career-changing market are the people who can adapt, be flexible, and have optimism. They’re the ones who are going to come out on top.”

Now more than ever, stepping up to new challenges is key. “People sometimes take themselves out of the game before they even get to play,” Lin says. “Unfortunately, that’s actually more critical for women. We read a book when I was in business school called Women Don’t Ask [by Linda Babcock and Sara Laschever] about how we’re conditioned by the age of seven not to take up so much space. So we decide not even to apply for that position, and that’s devastating.”

“A lot of people got upset about that Claire Shipman article in The Atlantic about how men and women differ [“The Confidence Gap,” by Katty Kay and Claire Shipman],” Lee adds. “But having worked with women all this time—and thinking about myself when I first started—I know that it’s true. Yes, maybe men and women have different strengths and different ways of approaching things, but it doesn’t mean that, as a woman, you’re any less capable.”

Meanwhile, as women navigate their careers, research shows that they often don’t get the compensation they deserve because they don’t ask for it, and a coach can help with that, too. “Women do not negotiate the way men do,” Thanasoulis-Cerrachio says. “It is in the DNA of a man to negotiate a higher salary. My first questions are, ‘Do you think you’re well compensated? How do you know? What will the market bear?’”

Going Holistic
Although it’s tempting to segment our lives mentally—into our work life, home life, social life, and so on—experts say that’s a false construct. So gone are the days when a career coach focused on a singular goal in isolation, like helping a client get to the next rung on the corporate ladder. Today’s best career coaches recognize that their clients are well-rounded human beings with complex lives.

“Everything is integrated—your career, your family relationships, your friendships,” Thanasoulis-Cerrachio says. “So when I work with clients, I like to know where they are in their personal life, as well. Do they have support? For example, if someone has children but doesn’t have good day care, that’s going to detract from what they need to do at work. I like to find out about their life and what kinds of stresses there are. You have to troubleshoot to get rid of those stressors.”

Blake says having a good support network was key. “This was a venture that my sister and I were going to do together,” she says. “I had my family and my husband supporting me, and I had a team of experienced entrepreneurs to call for support.”

And she had Lin to help propel her toward her goal. In March of 2013, Blake and her sister opened True Waxology & Skincare in Walnut Creek, California—the same month that her baby arrived. “So they both launched at the same time,” she quips. “I wouldn’t advise most people to start a business and a baby at the same time. It’s crazy, but we did it. Having coaching with Jenn helped me psychologically prepare for the hard work but also cut myself some slack.”

Today, Blake says she couldn’t be happier. Her salon offers natural skin-care services, just as she envisioned, and she’s proud that her employees are making healthy hourly wages. “I feel like I’m honoring my core values, and that’s what brings me the joy—being creative,” Blake says. “I’m always challenging myself to create new products and services and learning new ways to market. And I also like being able to make a big impact, not only on our employees’ lives but on my sister’s life. She’s got three kids, and I’ve seen her life change as she’s had this wonderful opportunity to learn her leadership style and evolve as a manager. It’s hard work, but I feel so energized.” DW

Kimberly Olson is DW’s managing editor.

Getting the Most from Your Coach

Follow these tips to get the best benefits from your relationship with a career coach.

Have an Agenda
Be clear about what you want to achieve so your coach can create a road map, pinpoint any potential roadblocks, work with you to find solutions, and help you be accountable.

Interview Candidates

Meet with at least three career coaches to explore whether there’s a good fit. Many coaches offer a free trial session. Ask yourself, Do I feel comfortable with this person? Will her style and approach work for me?

Ask for References
Feel free to ask prospective coaches for references.

Be Prepared to Work

Make sure you understand how the process will work, how often you’ll meet—and for how long—and what your responsibilities will be.

Switch If Needed

If at any point you realize that you and your coach are a mismatch, find someone who is a better fit.

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