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Are you yearning to make a big change to your career? Maybe you’re ready to take a big leap in responsibilities. Maybe you’d like to stay relevant in a shifting workplace. Or maybe you just want to get on a different track altogether. Whatever your dream, wouldn’t you be happy to inhabit your own little Cinderella story—one in which a team of experts swoops in with wise counsel to put you in reach of your career goal? Wouldn’t it be great to have a lineup of advisers offering practical strategies on how to get an edge and unlock your full potential?

That’s the fantasy that Money has made a reality for the three professionals in this story. They’re at different stages of their career, each with a different goal and each facing different challenges in reaching it. Coming to their rescue with advice tailored especially for them are four specialized pros: a human resources consultant, a job coach, a certified financial planner, and an image consultant.

What our three subjects have in common with one another—and perhaps you—is a desire to make a major change, a willingness to listen to good advice, and a readiness to act on what they’ve heard. Read their stories to learn about the challenges they face and the solutions that Money’s experts have devised. And prepare to take full advantage of their wisdom in order to land work that’s a great fit for you. In other words, get ready for the next dream career makeover: yours.

The Money Makeover Team

“Be the CEO of your own career.”

Jaime Klein launched Inspire Human Resources, an HR consulting firm, in 2007. She formerly worked for American Express and has a master’s degree in organizational psychology.

“Transitions aren’t failures, but times of opportunity.”

Linda Rossetti is a career coach in the Boston area who specializes in life transitions. She’s the author of Women & Transition and managing ­director of an ­angel-investor capital network.

“Changing jobs? Don’t jump off a cliff unless there’s water below.”

Donald Duncan is a certified public accountant and a certified financial planner with 35 years of experience. Based in Chicago, he heads D3 Financial Counselors, which he founded in 1997.

“Dress for the role you want to be in, not the one you have.”

Sylvie di Giusto is an image consultant and corporate trainer based in New York City. She’s the author of The Image of Leadership and a former corporate human ­resources executive.

Getting on the Right Track

Brittny Grady, 26, Account Manager, Nashville

The Job Hunt

Brittny Grady got hooked on marketing in college, in part through internships doing social media and community outreach for a local arts group. But after graduation Grady couldn’t find a job in her chosen field. Needing to repay student loans and meet living expenses, she landed a sales assistant job at a computer company. Promoted to account manager—she sells goods and services to firms that resell them to small businesses—she now earns about $45,000 a year, ­including commissions.

Grady hopes to pivot from sales to marketing, but she hasn’t seen many entry-level openings at her employer. Earlier this year she started applying for marketing jobs elsewhere. She has gotten encouragement and advice from a mentor who works in the field, but despite Grady’s sales experience and promotion, her five applications thus far have led nowhere. “I still can’t seem to land the job that’s right for me and get my shot,” she says.

The Financial Plan

Lighten up on plastic.

Given Grady’s $13,000 in federal student loans and $1,700 credit card balance, Donald Duncan says a top priority for her is to lower her debt—a move that will make it easier to handle the salary cut she’ll probably have to take to get her first marketing job.

Grady is paying the minimum on her credit card debt, but ­Duncan wants her to pay off the full balance at once by tapping her $2,300 emergency fund. “The interest you would save would be phenomenal,” he says. Afterward, she can focus on rebuilding that emergency fund to cover three months of living expenses. “Cutting down debt is my No. 1 priority,” she says.
“I’m going to pay it off in full, using my savings.”

Come up with a system.

Grady, who says she feels under­educated about personal finance, hasn’t really focused on where her money goes. Compensated via a combination of salary and commissions, she tends to spend her base pay on day-to-day expenses, except for automated savings of $25 per check. She uses her commission money on treats for herself like hair appointments.

Duncan says she can make headway toward financial stability by dividing her commission check into thirds, among student loans, fun stuff for herself, and savings—in both her emergency fund and a 401(k). “This is a great idea,” says Grady. “I’ve never taken the time to break it down before.”

The Image

Show maturity.

It’s important for Grady to present herself as a responsible, experienced professional, says Sylvie di Giusto. For women, makeup is an important finishing detail in their overall look, she says. “It shows you’ve put in effort.” But, she adds, “keep it simple and natural. You don’t want to stand out because of your makeup.”


Wearing a jacket to an interview will reinforce Grady’s professional appearance, says di Giusto. If the office is more casual than anticipated, she can take it off. But if she doesn’t bring one and the office is dressier, she can’t add a layer. “A jacket,” she says, “can be your lifesaver.” Says Grady, “I agree it gives a more polished look. I feel more put-together in it.”

Wear a fitting shoe.

Especially for job interviews, di Giusto tells Grady to find a comfortable midsize heel that makes her feel happy: “When you wear a great heel, your body language changes. You walk straighter. Your shoulders go back. You appear more confident.” Grady reports that she likes the heels she wore in the photo shoot: “They had a bit of personality.”

Bigger Stage

Gerald Sorokin, 52, Nonprofit Administrator, Iowa City

Over the 17 years Jerry Sorokin has been executive director of the Shulman Hillel Foundation at the University of Iowa, the Jewish group has tripled the number of students and community members it regularly serves. Both the organization’s finances and the physical plant have gone from “precarious and leaky” to “secure and updated,” he says. This year, however, the foundation’s income fell when longtime tenant UI ended its lease. After the ­Hillel board said it would cut his post’s total compensation, including health benefits, by $45,000—his salary is now $83,000—Sorokin decided it was time to move on. He’d like to work as an executive director at a larger ­nonprofit organization, not necessarily a religious one. But he fears that the Hillel’s small size—he supervises only three ­employees—has been a strike against him in past job interviews. “I could just see it in the eyes of the people asking me questions,” he says.

The Job Hunt

Don’t underplay your oversight.

Just because Sorokin supervises only three employees doesn’t mean he lacks the skills to manage a larger staff, says Rossetti. On his résumé and in interviews, she says, he can play up his manage­ment experience in other ways. For example, Sor­okin currently oversees a 20-member student board. He also provides leadership development, informal religious education, and personal, academic, and career counseling to students. Klein says it could be a plus for him to explain that he has learned to lead teams over which he has no formal authority. Sorokin agrees: “That’s definitely a direction I’m going in,” he says.

Toot a louder horn.

Sorokin’s résumé doesn’t do his accomplishments justice because it’s phrased weakly, Rossetti says. He needs more action verbs, and should highlight major achievements as specifically as possible, showing off measurable results. For instance, he mentions “Ability to secure key leadership endowment.” She says to restate that as “Secured $1 million leadership endowment.”

Sharpen your delivery.

Unsurprisingly for a man who has spent his life in academia (he has a Ph.D. in political science from the University of Michigan), ­Sorokin confesses that he tends to speak in paragraphs—a habit that has alienated search committees comprising action-oriented businesspeople. “They often find me tedious,” he says, based on feedback he’s received. Rossetti suggests he outline bullet-point answers to questions he might be asked; after providing a brief initial response, he can ask permission to continue with, “Now I’d like to go into depth. Is that okay?” Sorokin says he fully intends to break out of “50-minute lecture mode.”

The Image

Break out the clippers.

To help present himself as a leader, says di Giusto, Sorokin needs a more polished, businesslike image. Sorokin, who has worn a beard for most of his adult life, is worried di Giusto is going to tell him to shave it. She says he just needs it trimmed, along with his hair, “so it all looks kept together.” Sorokin dutifully heads to the barber.

Fix the smile.

Also detracting from Sorokin’s image, says di Giusto, is a chipped front tooth. Repairing it will cost $1,000, he tells her. She is unequivocal. “Fix it,” she says. “If you don’t take care of yourself, people will think you don’t have the ability to take care of others.” He takes her advice seriously. Asked if he plans to follow up, he replies, “Nine-thirty ­tomorrow morning.”

Dress for the boardroom.

Though attire in the nonprofit sector tends toward business casual, ­di ­Giusto says that because Sorokin is applying for posts in which he will be responsible for finances, he should dress more like a banker for the initial interview. That means wearing a dark suit in a color such as navy, a light-colored shirt and tie, and good-quality leather shoes—or perhaps a sport jacket if he makes it past the initial interview and is feeling comfortable. “People want to see someone they can trust,” says di Giusto. Sorokin says he’s game.

Not Ready to Retire

Byron Caplan, 61, Videographer, Jacksonville

With more than 30 years of experience shooting, editing, and producing video, Byron Caplan is a television news pro. He’s covered everything from potholes to the presidency, in places ranging from Maine to New Orleans. He’s also taught jour­nal­ism and digital media, and has spent the past two years as a pro­fessor of digital media at Florida State College in Jacksonville.
But with his $55,000 teaching job ending in June, Caplan, who lives with his girlfriend, is now at a crossroads. He has applied for local media jobs for which he feels “eminently qualified,” but he has gotten no response: “I start to wonder if it’s the age thing.”

As a Plan B, Caplan is considering starting a business to create videos documenting older people’s life stories. “I am very youthful and healthy,” says Caplan, whose 84-year-old mother still plays the harp professionally. “I’d like to remain vital and make an income.”

The Job Hunt

Network better online.

For Caplan to start getting responses to online applications, says Klein, he should be looking for people in his LinkedIn network who can put in a good word for him. “If I get a recommendation from someone in my network,” says Klein, “I always give that person a phone interview.” Along with adding contacts on LinkedIn, Klein says, Caplan should post work samples and more information about awards he has earned, since many recruiters use the site to scout for talent.

Prepare for Plan B.

Caplan needs to spend some time on the logistics of working in a gig econ­omy, says Rossetti, especially since so much media employment is on a freelance basis. In launching his own venture, he’ll have to learn how to tackle details like financing, marketing, and pricing. He can get started by using the Small Business Administration’s “Create a Business Plan” online tool (sba.gov/tools). Caplan can also get free help from a local volunteer at SCORE (score.org), a nonprofit organization that provides guidance to small businesses. Caplan, in fact, has already met with a SCORE mentor, and says he got good feedback on his idea.

Set yourself apart.

Caplan is already networking in person at meet-ups (meetup.com)—gatherings of people with a particular interest—where he tells people about his work experience. Says Rossetti: “They are fantastic.” But rather than dwell on his job chronology, he needs to introduce himself in terms of what makes his work special, she says. Later on, through a connection he had already made at a meet-up, Caplan secured a gig directing a fashion video that will be submitted to a film festival. “That was great,” he says. “I got to direct and did well—and people saw me doing it.”

The Financial Plan

Speed up the job search.

With his $155,000 home fully paid off and $322,000 in retirement savings, Caplan isn’t panicking. But though his expenses are low—right now he spends about $1,500 a month—he’ll need a new gig to live as well as he’d like, says Duncan. With $2,000 in liquid savings and his paychecks on the way out, Caplan has until roughly the end of October to get a job or dip into other funds. Health insurance could cost him up to $1,000 a month until he qualifies for Medicare at age 65. Basic living expenses could take a bite out of Caplan’s budget for travel and entertainment. ­Caplan, who is busy job-hunting and developing his business idea, says he isn’t worried he’ll run out of funds this fall. “I feel like I’ll get a job ­before then,” he says.
Caplan thinks he’ll need $15,000 to $20,000 to launch the video busi­ness, but Duncan suspects it will cost more; when he himself went solo, he had three years of living expenses in the bank.

Plan for the long haul.
Caplan will qualify for about $2,200 a month in Social Security if he waits until age 66, but only $1,600 if he starts taking it at age 62. If Caplan can’t get a job, ­Duncan suggests living off his retirement account first, since that would let his Social Security benefits grow—and he’d lower his IRS bill by being in a low tax bracket while drawing down his retirement savings. Caplan agrees with Duncan, calling taking Social Security ­early a “Plan F.”

The Image

Demonstrate some flair.

Caplan needs to show that he’s creative and lively, says di Giusto—but in a way that suits his age. He should start by replacing his professorial tweed blazers and T-shirts with a sport jacket in a “power” color like black or navy blue and a contrasting-color dress shirt left open at the neck. “You are going into multimedia,” she says. “What people want to see is creativity.” An accessory, such as a pocket square, adds some personality, she says. “I could handle that for a job interview,” agrees Caplan.

Skip the Hollywood hair.

On the subject of creativity, Caplan half-jokingly asks whether he should color his hair all white, like Rutger Hauer’s character in Blade Runner. Di Giusto objects: “What are you going to do with your eyebrows? Your eyelashes? Whiten them?” she asks. “It’s a little bit of maintenance. Are you willing to do that?” No, he says. A better way to make a statement, she says, would be a dramatic new pair of eyeglasses. He disagrees. “These are timeless and fit the shape of my face well,” he says.

Dress your age.

Caplan asks about wearing skinny hipster pants, but di Giusto rejects that idea. “Although you should go with trends, you have to look age-appropriate,” she says. “I don’t want you to dress like a 30-year-old.” Caplan deems that wise advice, but later says he may still buy a pair of tapered pants to see how they look.

Put the right foot forward.
Instead of his Chuck Taylor sneakers, Caplan should wear some new leather shoes, though nothing too fancy, to match the look. “If your shoes are dirty or worn,” di Giusto says, “everyone will focus on the shoes.” ­Caplan says he can see himself wearing a pair of brown bucks.