Working doubletime – having two or more careers: includes a list of five steps to successful parallel careers – Career Management

Working doubletime – having two or more careers: includes a list of five steps to successful parallel careers – Career Management – Cover Story

Caroline V. Clarke

CONSIDER SUPERMAN: A diligent newspaper reporter by day, he was also a superhero. On call around the clock for global world-saving duty, he had quite a balancing act.

And remember the Henleys, that comical West Indian family on TV’s In Living Color? For them, two jobs at any one time was appallingly too few.

Now meet William Thompson. He’s an entrepreneur. And a commercial airline pilot. And a lawyer (and husband and father). Simultaneously. Actively. Enthusiastically. On a day-to-day basis, Thompson makes Superman and the Henleys look almost lazy, especially since, unlike them, Thompson is real.

While everyone thought the Henleys were hysterical back in 1990, today their gung-ho approach to diversified employment makes serious sense. It also requires a serious commitment. Contract workers have multiple employers, but no loyalties. Moonlighters take a second job as a temporary fix to a financial problem. Hobbyists pursue their passions, but generally not for pay. “Parallel careerists,” as they are now called, have a long-term commitment to more than one career. It’s an ultra-demanding endeavor, and yet the superman–and superwoman–phenomenon is thriving, according to employment experts. There are four major reasons for the resurgence of what is really an old-time career strategy, especially for African Americans.

The first is, not surprisingly, downsizing. Never before has the wisdom behind not putting all of your eggs in one basket been so obvious. The second is about transitioning from one career to another with minimal risk. Your mother’s advice to never leave one job before you have another is taken to the next level when you simply work at both.

Reason No. 3 is preparation for retirement, which more and more people are beginning sooner than they expected. And, finally, many pursue a second career for therapeutic reasons: to fill free time, broaden skills or fulfill personal goals or dreams they would have otherwise deferred.

While there are no precise numbers, the trend is strong enough to have spawned some new terminology. Experts describe those who undertake parallel careers as developing “simul-talents” and dual professional profiles while–let us not forget–collecting multiple paychecks.

But typically, it’s not the money that drives parallel careerists. More often, it’s the determination to literally be all they can be. (Even a couple of BLACK ENTERPRISE editors manage other full-time careers–one as a teacher, another as a flight attendant.) Make no mistake, however: working two jobs isn’t easy. It demands high levels of energy, organization and enthusiasm; strong time- and stress-management skills; and the ability to negotiate potential conflicts between parallel careers (see “Five Steps to Successful Parallel Careers”). Last but not least, it requires some sacrifice of social, vacation, and family time, not to mention plain old free time.

CB Bowman, president and CEO of Career Strategies Inc. in New York, insists that despite the challenges, it’s worthwhile. “Parallel careering is more than a trend,” says Bowman, who keeps five jobs afloat herself “It’s a realization that this is what you have to do to secure true independence and control over your own destiny.” And for black folks, she adds, that must be a priority.


Thompson is the quintessential multi-careerist. This dynamic entrepreneur can be found in his Boston office Monday through Wednesday running the Summit Group Inc., a 15-year-old conglomerate that includes a computer systems integration company, an engineering services firm and six food franchises (four subways, a Dunkin’ Donuts and a TCBY).

On Wednesday evenings, Thompson trades his business suit for a Delta Air Lines pilot’s uniform and spends the next three days flying the skies between the U.S., Mexico and the Caribbean. He returns home to his family on Saturday afternoons, turning his attention to his home and community (he’s on the national board of directors of the American Cancer Society, among other things). On Monday morning, it’s back to Summit, where, in addition to serving as chairman and CEO, Thompson dons a legal hat serving as in-house counsel.

That’s in an “ideal” week. The fact is, Thompson can’t always control his flight schedule, and conflicts do arise. Luckily, with more than 70 employees, he’s able to do much of his managing for Summit on the phone and on the run if necessary. It’s a pace Thompson concedes is not for everyone, but he is unsympathetic to those who claim generally that having more than one job is too much, too hard or too hectic. “We all have the same 24 hours, and if you take a look at what you’re doing, you’ll probably find you’re wasting a lot of it,” he says. “If financial success is a priority for you, if it’s way up there on the list, you’ll make the time.”

Now 46, Thompson was always a multilevel achiever. In high school, the Orangeburg, South Carolina, native was an Eagle Scout, honors student and star athlete. The first African American from his state to receive an appointment to the U.S. Air Force Academy in Colorado, Thompson completed jet pilot training, got his college degree and entered law school during his 11 years in the service. In 1980, he left the Air Force to fly for Delta, relocating to Boston where he received his law degree.

Summit began as a tax-planning firm. Thompson, who started with a bar exam buddy who was a hospital administrator, speculated that between pilots and doctors they’d easily establish a strong client list. He was right. He was also lucky.

It wasn’t long before one of his clients asked him to invest in a shopping center with a group of doctors. He did, they turned it over in 18 months, and all made a sizable profit. That, says Thompson, “gave me the cash to do other things,” which, over the years, have included numerous real estate investments and several diversified businesses–some created, some acquired. His current companies grossed a combined $3.7 million last year.

There are two primary questions that people like Thompson always get: Why do you do it? And how do you do it?

Thompson’s responses to both are surprisingly simple. He flies because he loves to. “I would pay [Delta] to let me fly,” he says. “It just so happens that that’s the thing I do for pleasure, and it pays me quite well.” Business, on the ocher hand, is all about making money, and Thompson makes no bones about it. “I had the goal of owning a Mercedes 450SL with a phone,” Thompson recalls with a smile. “This was back when not everybody had a car phone.” Once he achieved that, his next goal was to have $1 million cash in the bank. Thompson, who earns close to $200,000 as a pilot alone, says he now has that, too, thanks to his entrepreneurial success.

“I’m a firm believer that there’s not much I can’t accomplish if I want to,” he says. “That doesn’t mean I can be Michael Jordan because I don’t have that gift. But most people succeed not on talent or gifts, but on perseverance. It took two years for me to open my first Subway. Most people give up after the first roadblock. I keep pressing, no matter what.”

As for the difficulty of balancing competing demands, Thompson, who got married in his late 30s, says he purposely postponed family life to focus entirely on his professional and financial goals. “The tough part is not juggling two careers, but juggling two careers and a family,” he says. “When it was just me and my wife, if I had to fly on thanksgiving, she’d just come with me.”

Now that Thompson has two daughters, Taylor, 8, and Sydney, 3, his priorities have shifted again. “I used to be in the office by 8 a.m. Mondays. Now I take the kids to school first,” he says. “I’m at a point where I have the luxury of not having to do anything anymore, especially anything I don’t really get satisfaction from.” But even as Thompson contemplates liquidating some of his businesses, he is certain that he will continue to have a career in addition to flying–possibly as a motivational speaker. “I don’t fly every day,” he explains, “so there’s still a lot of time to fill. I have to do more. It’s just who I am.”


While it may simply be part of Thompson’s fiber to burn the candle at both ends, others fall into parallel careers more by accident than by design. About three years ago, Charlotte Clarke, then a process engineer for Pitney Bowes in Stamford, Connecticut, began taking acting classes at night. “I thought it would help me in my corporate life,” says Clarke, 34. “I tend to be somewhat introverted. I thought this would bring me out, help with my presentation skills and communicating with strangers.” Beyond that, Clarke, who is single and began modeling as a hobby when she was 13, simply saw it as “a spare time thing.”

She invested in a professional portfolio, but wasn’t doing much with it until she learned in early 1996 that her job was being eliminated. Although the possibility existed to land a new position within Pitney Bowes, Clarke was worried, and for good reason. As an engineer at Digital Equipment Corporation in Springfield, Massachusetts, in the fate ’80s, she had witnessed round after shattering round of layoffs. Although she was spared, her move to Pitney Bowes in 1992 had clearly been a matter of survival. In 1996, calling on those same instincts, she began passing around her resume within Pitney Bowes while also circulating her modeling portfolio, and landed several jobs. “It really helped me deal with the stress and uncertainty of my job,” she says. It also made her much more visible than she had anticipated.

By the time Clarke landed her current position as a commodity management engineer, her face was plastered across local city buses and on a billboard around the corner from Pitney Bowes offices advertising a managed health care company.

Clarke, who had wisely kept her other career to herself, was concerned. “I wasn’t sure how people would perceive it,” she says. “I didn’t want them to take me less seriously or feel that I wouldn’t take my job here as seriously because of it.”

Bowman says Clarke had good reason to be apprehensive. “It’s really better if your employer and peers don’t know [about your other career] because peers are likely to get jealous and your employer may question your commitment to them,” she says. “The reality, which employers don’t yet get, is that your productivity is enhanced because you’re happier, and you’re forced to be more organized.”

The responses Clarke got were mixed. “Some people asked why I didn’t just do [modeling] full time. Others said they thought it was great, but I still wonder if they really meant it,” says Clarke. Whatever their comments or questions, she did what experts advise: never volunteer more information than necessary. “I’m an engineer,” she says. “My job at Pitney Bowes is in no way impacted by my modeling. There is some financial benefit to it, but that’s not why I do it. Most people in corporate America play golf or tennis. I do this for the same reason–because I like it.”


LaCheryl Cillie has encountered outright difficulty from colleagues who, she says, were jealous of her parallel successes. Cillie, who is a licensed pharmacist for Eckerd Drugs in Birmingham, Alabama, is also one of the few African American auctioneers and certified appraisers in the country.

About a year ago, as her weekend estate sales business began heating up, a pharmacy partner started making remarks and became very uncooperative with trying to accommodate Cillie’s busy schedule. “I think he thought I was making a lot of money on the side,” she says.

Cillie, who earns $60,000-plus a year as a pharmacist, admits that her estate sales business is lucrative. Estate owners can net from $10,000 to $30,000 from the sale of basic furnishings, jewelry, linen and clothing, and more if there are valuable antiques involved. Her take is 20%-30% of the gross, but Cillie spends at least as much time and energy educating African Americans about the value of their ordinary possessions as she does auctioning them off. She recently co-authored a book on the subject titled, From Darkness to Light: A Modern Guide to Recapturing Historical Riches (Creative Inspirations Ltd., $16.95; 800-390-4742, ext. 92).

Cillie’s own appreciation for quality second-hand goods was acquired gradually. Noting that her high school sweetheart (now husband) grew up with antiques, she says, “I had no appreciation for them. In fact, I wondered why his parents had them.” But, as a fledgling pharmacist, the only bedroom set Cillie liked and could afford was found at an estate sale. From then on, she became a fixture at virtually any estate sale she could get to.

Her desire to pursue it as a career was furthered by two things: a growing disenchantment with pharmacist work (which she says is marked by grueling 12-hour days and disrespect from customers, doctors and nurses) and a realization that black people are missing the boat when it comes to cashing in on their own valuables. “I heard some white people in line at a sale talking about some purchases they made at a black estate sale and how little they got them for and how `these people’ didn’t even know what they had,” she says.

Cillie, now 35, launched her business soon afterward. In 1995, she graduated from the World Wide College of Auctioneering in Mason City, Iowa. Today, she has four to five assistants who work with her regularly on weekends. Although she recently cut back her pharmacy hours, she continues to juggle two careers with continuing education classes on antiques and appraisal. She doesn’t foresee ever relinquishing her pharmacist career, seeing it as “the anchor” that enables her to pursue her passion.


Gregg Ketter doesn’t just like his career as a weatherman for KTTV News in Los Angeles. He loves it, and can wax philosophic about the weather, the network and the thrill he gets on air without any encouragement whatsoever.

As rare as his enthusiasm is for that job, it’s rarer still to find that he is equally bowled over by his second career as a motivational speaker and corporate trainer. One question about it, and he’s off to the races again, quoting Bill Gates and Aristotle Onassis about the magic that occurs when timing and vision meet opportunity.

But Ketter’s career outlook wasn’t always so clear and sunny. In fact, the Philadelphia native tried his hand at everything from modeling to marketing and construction to sales before he experienced an epiphany that directed him toward broadcasting. Ketter still gives a detailed account of that day in 1989 when, at home watching TV, he saw Christopher Nance, a black weatherman on KNBC. He decided then that that was the career for him. With no broadcast experience, he began doggedly studying meteorology under Dr. George Fishbeck, a now retired L.A. broadcast weather fixture, and with scientists at the National Weather Service. Meanwhile, he kept his day job as a salesperson and corporate trainer for the retail appliance chain Circuit City.

It took two years, but in 1991, having been rejected by virtually every other station, he landed a job on KCOP, Channel 13. Within a year, however, he was working construction again, a victim of mass layoffs at the station. After several months of interviewing, KTTV provided Ketter with an opportunity that changed the course of his life–he was hired as the weekend weatherman for KTTV Fox 11 News. To land a network job in the second-largest market in the country was a huge break, and Ketter was characteristically euphoric. But he was also determined to never get blindsided again.

So, he began giving motivational speeches on a volunteer basis. Before long, it was for the price of admission. Today, Ketter’s paying clientele includes IBM, McDonald’s Corp., Citibank and Spelman College National Alumnae Association. “I love giving people good news,” Ketter enthuses. “There’s just so much bad out there.” Under the banner of the Ketter Group, his second career is thriving.

Balancing the two is not so difficult, says Ketter. Having juggled multiple jobs during college and most of the years since, “working a couple of jobs is like normal for me,” he says, adding, “I’ve inherited my father’s work ethic.”

Ketter, who is often called to fill in for others at KTTV during the week, has faced a few conflicts between the two, but notes that the station has been very supportive. “They understand that the more known I am as a speaker, the more likely people are to watch me on TV,” he says, adding that, in a pinch, “Fox always comes first.”

Single and in his mid-30s, Ketter concedes that the biggest downside to parallel careering is that he doesn’t get much chance “to have fun” outside of work. But he’s having plenty of it on the jobs. Sounding like the combination weather-fan and cheerleader that he is, Ketter raves: “I’m building a ship and I’m sailing on a ship. There’s bright sun all around me and I’m loving both.”


1. Do what you love. It’s tough enough to maintain one job you dislike. Attempting two is dooming yourself to failure and unhappiness. If you don’t really enjoy at least one of your careers, no amount of financial benefit will make up for your misery.

2. Make it flexible. The idea here is not to work from 9-5 and 5-9. At least one of your careers should have flexible hours. It’s nearly impossible to be accountable to two full-time employers with two rigid schedules and accompanying demands, which is why it’s so common to have at least one entreprenurial pursuit.

3. Keep it all separate. And keep it to yourself. You have virtually nothing to gain from your employer, colleagues or clients knowing about your other career(s). The less they know, the better. And never use one as an excuse (for lateness, absence, unpreparedness) with another. If you have to do that, it’s time to reevaluate your load.

4. Downplay, downplay, downplay. If your employer, colleagues or clients do lean about your other career(s), don’t feel obligated to explain or elaborate unless specifically asked. Bragging could inspire jealousy; complaining is even worse. Just be prepared with simple responses to questions that might arise.

5. Leave time for yourself. Even when you’re working at something you love, it’s still work. If you’re creative and industrious enough to make time for parallel careers, you’re up to carving out time for rest and rejuvenation. Without it, you’ll burn out on everything.

COPYRIGHT 1998 Earl G. Graves Publishing Co., Inc.

COPYRIGHT 2000 Gale Group