WEBB Magazine Feature: When a Career Ladder Isn't a Ladder

Gig 13

the new world of work

When the Career Ladder Isn’t a Ladder

How Webb Alumni Are Finding Success in the Gig Economy

BY DEBBIE C ARINI

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Anyone who has ever felt bound by those strictures— confined in a cubicle, distracted by a micro-managing boss, or exhausted by office politics—has probably dreamed of going-it-alone.

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ot so very long ago, the question “what do you want to be when you grow up?” had a somewhat limited set of answers, for example: a lawyer, a banker, a teacher.

What most of these jobs had in common was a traditional 9-to-5, be-in-the-office-5-daysa-week, employees-report-to-management, arrangement. Individuals worked for the same company for 30 or 40 years and walked off the job with a fancy plaque and gold watch engraved with their name and a company logo.

And today, potentially transformative new digital platforms such as Airbnb, Uber, and Upwork are creating bigger, and more efficient, marketplaces to connect entrepreneurs with buyers of their services.

Welcome to the “gig economy” which is defined in several ways including, as “the sharing economy.” People who work in this arena also call themselves many things, from freelancers to 1099 workers. Inc. magazine says “there are also many different aspects of gig work, which lets people find a good fit for their skills but also makes it more difficult to define. Some work is more flexible, other work is rigid; some work involves growing a client base, other work is solitary; some positions require previous skills and a certain educational background, other positions can be learned on the job.”

Just this past spring, WorkMarket Inc., a freelancermanagement startup, raised $25 million in its latest round of fundraising (bringing that figure to a total of $56 million since the company’s founding in 2010).

Growth in the “gig economy” has exploded as companies do more work with fewer employees and look to freelancers to pick up the slack. According to researchers at Harvard and Princeton universities, some 16 percent of the U.S. workforce in 2015 comprised people in contingent work arrangements, up from 10 percent in 2005. Others say these numbers are even higher.

Traditionally, artists were the original “gig” workers. In fact, Merriam Webster dictionary includes this definition of “gig”—“a job usually for a specified time, especially: an entertainer’s engagement.”

On his Twitter page, Jack Gilliat ’13 describes himself as an actor, filmmaker and dreamer. His company is Eye of a Fly Productions, whose tagline is “where art meets reality,” and whose mission is to “create, fund and produce groundbreaking; controversial; topical; provocative; evocative theater and film, with a strong message, to set an alternative entertainment agenda.”

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onathan Ying ’07: Game Designer

Jonathan Ying ’07 is relatively new to the gig economy and describes it as “simultaneously more independent, and more harrowing a career path. It’s still the wild west – people take what they can get with various degrees of success.”

Ying is perhaps most well-known for designing the popular board game Star Wars™ Imperial Assault while working at Fantasy Flight Games, located in Minnesota. A combination of weariness with the weather and being handed projects he didn’t always want to work on, helped push him into independent work.

“There’s been a board game renaissance over the past 10 years,” explains Ying.

But he cautions that the freelance economy can be very cutthroat. He often feels he oscillates between two states: too much or too little work. He also misses the resources that were available to him at a larger company including art teams and sculptors.

“I have to make sure I keep an eye on my schedule,” he says. “It’s really important that I estimate my time properly.”

He recently launched an LLC for which he raised $50,000 through crowdfunding via Kickstarter to design a new game that is exclusively of his design, and in the process, commenced a career as a small business owner.

An important aspect of his work is cultivating and nurturing connections.

“I’ve doubled-down on going to conferences – I’m not sitting in a cave somewhere,” he says. He also maintains a strong social media presence and keeps his website up-to-date.

Exposure can be a double-edged sword however.

“Reviews are a huge thing in my field,” says Ying. “I’m always thinking, ‘where am I on Amazon?’ It’s hard not to check all the time to see how many stars I’m getting.”

Jack Gilliat ’13, actor, filmmaker, dreamer and founder of Eye of a Fly Productions.

He measures success, however, in the most basic manner – “I can keep myself fed!”

And, he credits his Webb experience with giving him the confidence to approach more famous or experienced professionals in his field for advice.

“At Webb, the small class sizes and the availability of teachers helped me to learn how to communicate with my peers and with the adults on campus. I could go to a teacher’s house, knock on the door, and be welcomed in to have a lemonade,” he says. “Today, I have the confidence to talk to even famous people in the industry and say to them, ‘you’ve been doing this longer – can I ask you some questions?’”

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r. Aaliyah Yaqub ’01: Medical Advisor

Dr. Aaliyah Yaqub ’01 says she was on an academic career path, graduating from Rice University and the David Geffen School of Medicine at UCLA, when, during her internal medicine residency at Stanford University, she saw the future of health care taking shape in Silicon Valley, and decided she wanted to be a part of it.

Now she’s a medical advisor with San Francisco-based health care provider Forward, Inc. “It’s what the doctor’s office experience will be like 50 years from now, except we’re doing it now,” she explains. “It’s about leveraging human relationships and also technology.”

That theme has informed Yaqub’s career. It may be the theme of the millennial generation’s workplace experience, too. “We’re developing new technology that is making it easier for us to do the tasks that used to take a lot of time,” Yaqub says. She’s speaking about health care, where technology is replacing paper charts and notes with digital records, and the biannual checkup is giving way to on-demand health care monitoring.

The integration of technology doesn’t lead only to better data, though: it also frees physicians to spend more time listening to their patients.

This paradigm is new to health care, but it’s already become a hallmark of high tech industries, from Silicon Valley’s internet giants to New York’s financial powerhouses. The Silicon Valley companies with which she’s familiar are constantly looking for ways to make life better for their employees, Yaqub says.

Bringing more technology into the workplace and offering more benefits to employees allows them to focus on those things that add value to the company: thinking creatively and collaborating, freed from mechanical tasks that can be performed by a software program.

Webb, says Yaqub, is a fantastic school for preparing people to enter rigorous careers that require flexible thinking and engagement. “I often look back on all of my schooling and I think that Webb was the most challenging of all of my career,” combining academics and extracurricular activities with a vibrant learning community. “Webb does a really great job filling your time with productive activities.”

“I couldn’t handle working in an office,” says Gilliat. “In the arts, social media and the internet have made the audience accessible – you can form and define your own territory, your own destiny.”

Gilliat, who was always fascinated with the entertainment industry, realized early on that being an actor doesn’t always pay the bills. So, he decided to create his own work by forming a company that could service virtually every aspect of the industry.

He identified the industry’s least favorite part of entertainment production—the logistics of making a project work—for example, scouting locations, determining demographics, identifying distributors, as well as finding actors, musicians and other support personnel.

The beauty of the “gig economy” says Gilliat, is that “you can form and define your own territory.”

According to a report for the McKinsey Global Institute entitled, “Independent Work: Choice, Necessity, and the Gig Economy,” 20 to 30 percent of the working-age population in the United States and the EU-15 (European Union-15), or up to 162 million individuals, engage in independent work.

Zachary Kidd ’95 is an entrepreneur, and through his company, SwingSpace, he facilitates access to temporary office space for others in the gig economy. With his partner, Richard McBride, Kidd has created a more efficient way for tenants to find and lease small office spaces; McBride has dubbed it the “Airbnb of office leasing.”

The platform allows landlords to easily lease unused space in their offices to small companies in search of some space—for anywhere from a week to longer.

“Technology-enabled marketplaces are the future,” says Kidd.

“From Ebay in the beginning to the App Store to Bumble (a dating app), it’s all buyers and sellers interacting with the aid of technology. Ultimately, it’s easier to go on Ebay than it is to go to a bunch of garage sales.”

Kidd, who previously founded and still owns Dupont Studios, which provides custom computer programming services, says a core skill of survival in the gig economy is “being able to attract good people who bring something unique to the table— something different than what others have.”

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With a Master of Public Policy from Harvard University and an undergraduate degree from Morehouse College, Kidd seemed destined for a path in the corporate world and worked for a time in a private equity firm.

“The thing you miss most when you’re on your own is working with a great team,” says Kidd. “It takes time to build up another organization. It’s difficult to have the resources of an entire company and then not—to only have the possibility of success. As things develop though, if you’re lucky, it’s extremely gratifying to build something.”

Be that as it may, most gig workers will tell you that there are ups-and-downs to their work.

Adam Saltzer ’11 is an artist, a woodworker and the owner of Lucky Fish Designs, which he launched in January.

After graduating from the University of Puget Sound, Saltzer had several “gig” jobs—in catering, as a bartender, even as a pop culture analyst for Source3, a company that recognizes, organizes and analyzes branded intellectual property in user-generated content.

“The flexibility of all those different jobs helped me to have extra money while I was growing Lucky Fish,” explains Saltzer.

At Lucky Fish Designs, Saltzer handcrafts wood furniture, cutting boards, even handbags. He is still working 9 to 5, and even beyond.

“I can never miss a gig,” he explained. “I’ll meet a client at the coffee shop at 8 p.m. to discuss a job.”

He also describes himself as “being on everything” to advertise his business—LinkedIn, Facebook, Yelp, Instagram, Craigslist and more.

“I’m very fortunate to be able to choose a creative path,” he says of the support he’s received from his family. “But in this line of work you do miss out on some things—even a 401K. I’ve worked at a desk, at a company—you made the sale, did the data, kicked it to someone else. Now I work with a 400-lb., 3-dimensional object—you never get to experience that in an office!”

Adam Saltzer ’11, artist, woodworker and owner of Lucky Fish Designs.

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Kenny Tsai ’05, manager of current programming at Universal Television.

Kenny Tsai ’05 actually does work in an office—he is the manager of current programming at Universal Television— but says that the entertainment industry is mostly comprised of gig economy workers.

In the “gig economy,” Tsai says the most important attribute to have is flexibility.

“People work on a show, then they’re on to the next one,” he said.

“You never know what can happen—your job description can change on a daily basis,” he says. “In Hollywood, you need to have a thick skin, to be able to adjust, to deal with temperaments and be open.”

“That’s how I came up,” he explains citing his work as a showrunner’s assistant on the HBO series, Boardwalk Empire.”

It’s also crucial to maintain your reputation. “I’m always honest, diplomatic and respectful of people.”

“I didn’t have family members or a lot of connections in the entertainment industry. I tried to intern a lot and draw on those experiences,” says Tsai. “There is no ‘set’ career ladder in Hollywood—my boss was going to be a doctor, she went to the Johns Hopkins School of Medicine.”

In fact, the future of work looks a lot like Hollywood and its coterie of independent—or gig—workers, from directors and actors to gaffers, caterers, and accountants.

In an article entitled “The Future of Work Will Look A Lot Like Hollywood,” author Stephane Kasriel, the CEO of Upwork, a

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global freelancing platform where businesses and independent professionals connect and collaborate remotely, writes: For top-shelf talent, striking out on your own may be the best way to maximize your earning potential, letting you sell your services on an open market that’s willing to pay you what you’re worth. And like movie stars, some of these super-talented technologists have even hired agents.

In and outside tech, it seems likely that working teams will soon be a lot more like movie crews. This shift may be unsettling to some, but it can benefit companies as well as the people who work for them. Businesses will gain efficiency and flexibility.

Professionals will gain a better lifestyle, more control over their work, and in many cases better income.

There are some downsides to the gig economy—in addition to the lack of a team, gig workers usually don’t get employerpaid benefits, such as premiums on health insurance and contributions to retirement plans. There is also no sick leave— or paid time off; no work means no pay. Finding a steady stream of work and scheduling jobs can also be complicated.

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Linda Silva, Webb’s director of instrumental music, has worked “gigs” nearly all her adult life, and in fact, in addition to her responsibilities at Webb, she still teaches clarinet independently, and plays in orchestras around Southern California.

“We called ourselves ‘freeway flyers,’” said Silva of the musicians she worked with after moving to the Los Angeles area. She has played professionally with the Riverside Symphony; San Bernardino Symphony; Redlands Symphony and has taught at Pomona College; University of California, Riverside; California Polytechnic State University, Pomona; and California State University, San Bernardino.

Silva attended the Oberlin College Conservatory of Music where she earned a Bachelor’s of Music degree; she received her master’s degree in orchestral studies from Rice University. She has been playing the clarinet and piano since she was a child. But she knows the perils of “gig” work.

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ichael McDermott ’83: Executive Producer/Founder, Gung-Ho Films Michael McDermott ’83 may include in his resume gigs like The Amazing Race, The Daily Show with Jon Stewart, the film Her, and working with Fortune 500 companies such as Apple and Nike, through his company Gung-Ho Films.

But he says the best way to start in any business … is from the bottom.

“In college, [at UCLA], my first job in the entertainment business was as a production assistant,” says McDermott.

“I was at the very bottom of the food chain. But I was hungry, and worked extremely hard. While at UCLA I also started a video equipment rental business. We worked on music videos for legends like David Lee Roth, John Fogerty, Barbara Streisand, Billy Crystal and a lot more.”

At UCLA, McDermott also took his first class in Mandarin Chinese. Soon after graduating, he moved to China and continued studying at the Beijing Film Academy and a graduate school in Taiwan. Later he became a United States diplomat in Beijing. In total, McDermott has been in China for 27 years.

In 2001, McDermott set-up Gung-Ho Films, a film and TV production services company. Today, they have offices in Beijing, Shanghai and Hong Kong.

As a Webb boarder, McDermott says he became eager to learn another language as he had many classmates who spoke multiple languages. “I was upset that I could only speak one,” he says. “So I signed up for French.”

“As it turned out, one of my favorite teachers at Webb was Jacques Pauwels who taught the French classes. And every summer, Mr. Pauwels took Webb students to France. Unfortunately my parents had other plans for me during the summer. But it ignited a love of language, and was a big catalyst for me going to China,” says McDermott.

“Webb gave me the confidence to follow my instincts, even though when I first arrived in China I knew no one, nor did I speak the language. Webb taught me that anything is possible when you work hard, think boldly, and, above everything else, act with integrity,” he explains citing his experiences as tennis team captain, honor committeeman, and editor of the Blue and Gold. “I never thought I would do any of these things.”

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ailey Stockdale ’11: Unmanned Aerial Vehicle Consultant

Use your time wisely, Bailey Stockdale ’11 tells students. “Try to fill your summers with experiences that matter”— experiences that put your knowledge to practical use. Stockdale, who graduated from Colorado College in 2015 with a major in economics, has built a career combining the theoretical and the practical, and his knowledge of economics and business with his interest in computer programming.

A consultant based in Mato Grosso, Brazil, Stockdale uses unmanned aerial vehicles and airplanes to collect crop data, and computer analysis to interpret it, giving Brazil’s large-scale farmers information and advice on how to best manage their crops and their lands. He is also the founder and director of the Unmanned Agriculture Institute, an association for professionals in agricultural robotics.

His advice to those considering their career paths: identify the skills you need, and develop technical skills, no matter where your interests lie. “Technical skills of any kind at any level are critical.”

When you enter the workforce, he continues, focus in on the industry in which you want to work and begin to build a network, positioning yourself as a connector. The biggest difference between new graduates and seasoned professionals, he reminds, is experience, and connecting with both new and experienced professionals is a foundation for career success.

Living and learning with students from across the United States and around the world on a daily basis, Webb students develop a global outlook and strong multicultural skills. Webb is also, Stockdale adds, an environment that encourages students to develop time management skills. “That’s huge,” he says. “Just that basic discipline of small habits and routines” to accomplish tasks.

Stockdale advises recent graduates to have confidence, “but also know when you’re right and when you’re wrong.” And no matter where you are in your career, he says, you should be willing to develop and ask questions.

“I

called a lot of people— looking for work—and didn’t say ‘no’ to anything. I tell my students about my experiences because I don’t think they know about it or have a sense of what it is to be a professional musician,” she explains.

Silva has also brought professional groups to campus to talk to students about having music in one’s life, no matter what career path one chooses.

“We had a string quartet play for the students, and one of the musicians is a full-time physics professor,” she says. “I want students to know – no matter what path you choose, you can have music in your life.”

Silva stresses that Webb’s honor code is a good standard for gig workers.

“I’ve worked hard to maintain a professional reputation for 37 years,” she emphasizes. “It’s important to live-up to that, to work hard, be prepared, continue your education.”

She also said that gig work has life lessons—“You develop the tools to do something, plus discipline and problemsolving skills.”

Not having a traditional chain of command through which to report and be assessed is also an unusual aspect of gig work.

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A core skill of survival in the gig economy is “being able to attract good people who bring something unique to the table – something different than what others have.�

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oiceover artist, Stephanie Riggio ’85 jokingly says, “everything is easier than all the homework we used to get at Webb!”

“It’s a constant self-reassessment that goes on,” said Silva.

And then she adds: “At Webb, I learned to be confident

Kidd also chimed in with advice for those entering the gig workforce: “When you work for yourself, or in a small team, it’s important to seek out people who work in the same industry to serve as mentors.”

in myself.”

Saltzer stressed the need to establish a community of likeminded entrepreneurs, in his case, other artisans.

“I’m missing out on some things – like a 401K,” he says. “But the artistic community in Austin is great. I’ve connected with other woodworkers, even metalworkers – everyone is trying to lift each other up, everyone wants you to succeed.”

And having a Webb experience has been advantageous.

“I wasn’t the straight A student at Webb, but you could be anybody you wanted to be there. Whatever you chose to chase in life, you had a community at Webb ready to support you. That acceptance from teachers and friends gave me the confidence to go my own way later in life,” says Saltzer.

Tsai mentioned the sense of responsibility he internalized at school through the block schedule and carving time out of his day to study.

Kidd invoked the honor code: “I think about that a lot,” he said.

“There are times when I’m looking at a financial model—you might think to yourself that the numbers aren’t as good as what people assume, you could go with the popular opinion without raising an objection—but that’s not the honest thing to do.”

Self-employed Americans and the workers they hired accounted for 44 million jobs in 2014, or 30 percent of the national workforce, according to a Pew Research Center analysis of data the U.S. Census Bureau recently made publicly available for the first time. The self-employed, 14.6 million in all, represented 10 percent of the nation’s 146 million workers, and they in turn provided jobs for 29.4 million other workers.

According to several experts—the biggest driver of the gig economy is time—an elusive commodity. New York Times bestselling author and serial entrepreneur Gary Vaynerchuk explains: “Time is the one commodity we can’t get enough of and will pay to preserve at any cost. No matter where you are or what your economic situation is, you will never have more time. It’s why we as humans will do anything to purchase it. It’s also why

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tephanie Riggio ’85: Voiceover Artist

Stephanie Riggio ’85, an accomplished voiceover artist whose client list includes Fortune 500 companies, nonprofits, major retailers and even World of Warcraft, the world’s most subscribed massively multiplayer online roleplaying game, says she actually had no plans to go into the voiceover industry.

After she graduated from Northwestern University with a B.S. in theater, she wasn’t sure she wanted to be an actress after all. While filling time as a substitute teacher for the Los Angeles Unified School District, working as a waitress, and temp office work (9-to-5 jobs which she described as “torture”), she took the suggestion of a friend and signed up for a workshop in voiceover – work soon followed.

She’s enjoyed a successful career, but says, in her line of work: “you have to be okay with not knowing what’s coming next.”

the gig economy is here to stay, as it goes so far towards satisfying our need to free up a few hours.”

A Webb education prepares students for the rigors of a shifting global community and imbues their day-to-day experiences with the spirit of “unbounded thinking.”

“That slogan—unbounded thinking—it’s thinking not about who you are or where you came from,” says Gilliat. “It’s more about the sense of how hard you work and how creatively you can solve a problem. And I’ve brought that into my work—don’t give up, no problem is too big to solve. Webb gifted that to me. It’s helped me so many times not to give up and to realize, ‘I’m worthy of my success.’”

Today, she enjoys the variety and even unknown aspects of her various voiceover work.

“I like it. Every job is different; it’s exciting,” she says.

She attributes some of her success to having a great agent, but says an artist needs to keep hustling and trying to learn. In addition to her voiceover work, Riggio also works in film in ADR/looping (dialog that cannot be salvaged from production tracks must be re-recorded in a process called looping or ADR) and is also hired as a singer for animation projects.

“I still take workshops and pound the pavement,” she says. “I still hustle.

There’s always somebody else who wants the gig.”

Riggio designed her own website and logo to market herself. She’s also flexible in her ability to get work done. “If I have a Wi-Fi signal and can make a fort of sound efficiency, I can do a job,” she explained. “I’ve worked from Costa Rica, Tennessee, Hawaii.”

She also said that she auditions for everything – promo gigs, radio, television, animation and video games. Riggio is an accomplished singer with a 4-octave range and also dabbles in songwriting and watercolor painting.

A career in voiceover work is competitive and can be complex. The actor must be able to get a point across, relate a feeling, and act into a microphone.

“I trust the people in the field who tell me I’m doing a great job,” she says.