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Millennials Rely on ‘Side Hustles’ to Climb the Corporate Ladder

Bloomberg logoBloomberg 8/1/2019 Arianne Cohen

(Bloomberg Businessweek) -- Welcome to Bloomberg Work Wise, a series of reports aimed at helping young professionals navigate their way to financial and career success. To learn how your salary stacks up and how much your dream job might pay, try our career calculator.

You know today’s job scene: long hours, low raises, zero job security. You could grind out 60-hour weeks for years only to find yourself suddenly laid off. It’s tough enough to stay sane in such an unforgiving environment, but what if you’re one of those ambitious types who actually wants to climb the company ladder?

As recently as 20 years ago, the path was simple. Bosses guided employees along the career track, and they toiled dutifully until promotions were offered. Invariably, those who worked the most hours won. Some even went on to spend their entire career at one company—chief executives who got their start in the mailroom weren’t unheard of.

These days, the average American’s career includes 15 job changes, according to a 2016 LinkedIn report. Getting to the C-suite is no longer a linear pursuit: It’s more like a meandering climb up a tree, with each branch adding a skill-set you’ll need to reach the top.

“Modern careers have many more ebbs and flows,” said Elisabeth Kelan, professor of leadership and organization at the University of Essex in the U.K. and author of Rising Stars: Developing Millennial Women as Leaders. “It’s no longer about finding a career for the rest of your life, but what could you do for the next few years—and what would you learn.”

Sound like a wild reconceptualization of what a career is supposed to be? It is.

First, you should mastermind a series of three- to five-year job experiences that will leave you extensively skilled, employable and able to land in multiple sectors, Kelan explained. The goal at each stage is to find roles that earn you proficiency in “exactly the expertise you need to know in your field,” she said. “You cannot stagnate.”

One way to accomplish this is to negotiate a rotation to a different department or office, either in the U.S. or abroad. Another is to switch jobs often. A third strategy, however, involves adopting “side hustles” that aren’t necessarily related to your full-time gig. Anything from developing software to giving gardening advice to running your own nonprofit, such extracurricular activities will help strengthen other muscles—and could make you more desirable to other employers.

Just as important as developing a side hustle is making sure you have time to pursue it. Having enough time for yourself—both to work on other projects and just to recharge—is integral to someday reaching the corner office. Many employers understand that flexibility for you is also good for them, in terms of loyalty and productivity. In some cases, though, you’ll have to be careful about negotiating that leeway.

Brigette Muller, 31, a social media specialist at Etsy, works from 10 a.m. to 6 p.m. After hours, she runs a separate social media channel focused on living intuitively and reducing waste (she has 24,500 followers). She also uses her personal Instagram account for closet sales, selling vintage pieces she owns or finds.

Muller previously managed social media for the clothing brand Free People, which required round-the-clock monitoring of multiple online accounts. That made it pretty hard for her to work on outside projects. But at Etsy, a set schedule has allowed her to build an audience and even do brand collaborations. 

Such side hustles have become a critical way for young professionals to differentiate themselves in the traditional workplace, said Nathalie Molina Niño, author of the career guide Leapfrog: The New Revolution for Women Entrepreneurs. “One of the most common terms you see in job descriptions is ‘entrepreneurial,’ ” she said. “The idea that you might be learning customer service or marketing on the side is not something you need to hide. It makes you a stronger employee.”

Another way to stand out is to develop specific skills you’ll need for your next goal. Niño, an investor-turned-author, earned a master’s degree in playwriting because she wanted to learn storytelling, for example.  

“Focus on what skill you need and, second, where to find it,” she said.

Rasheed Sulaiman, 35, is the vice president for product and creative at LockerDome, an advertising platform where he’s worked for seven years. He’s considered taking other jobs over the years but chose to remain at his startup. “Not a lot of people join a startup planning to stay on and retire,” he joked. Much like Muller, though, his job allows him time for a broad range of side projects.

Sulaiman has either founded or is a partner behind a web app, a sneaker convention show, a hair company and a clothing brand. He plans to start his own company someday, he said. “The projects allow me to spread my knowledge and test the waters and see if what I’m learning here is gonna be valuable to that next stage.”

“Take cues from people with the career you want.”

The side hustle can also be a cure for that disease common to many overachieving employees: putting a job before your career. 

Sally Helgesen, leadership coach and co-author of How Women Rise, said she knew a legal assistant who became so indispensable to her law firm that it hurt her ability to move up. “Everyone in the firm came to her for great briefs, and didn’t see her as able to do anything else,” Helgesen recalled. “You don’t want to become indispensable. And you also don’t want to get caught feeling extremely loyal to a boss or a team and then feel guilty about leaving.” 

Making sure your boss gives you the time and opportunity to expand your horizons isn’t just good for your well-being—it’s great for your career.

It’s best to start thinking about side hustles from the outset. If you’re interviewing for a job and it’s not clear what the schedule is, or whether there are flexible policies for time off, do the research. Don’t, however, make it the first question when you sit down with your prospective boss, advised Lindsey Pollak, a generational workplace expert and author of The Remix: How to Lead and Succeed in the Multigenerational Workplace.

“Know your audience,” Pollak said. “Take cues from people with the career you want. What’s their work-life practice? Maybe they come in early but always take an hour to go to the gym.” Over six months, you’ll have a good sense of what other people do and can express your own changing priorities, she said.

That six-month window also gives you time to prove your competence and dedication to the company’s mission, which makes it more likely your request won’t raise eyebrows. Options for workplace flexibility can range from nontraditional schedules—compressing your workweek so you hit 40 hours in four days—to working from home.

Lisa Renée Adams, 35, manages Medicare and compliance at Sedgwick, a risk and benefits administrator in Chicago. She started working from home after only a few years on the job. She still travels to meet clients, but face time is minimal and can usually be handled by conference call. “I slowly transitioned out of the office,” she said, “My schedule is so flexible now.”

Smart employers—companies you want to stay with—will understand the long-term benefits that flow from flexibility. “I have an incredible amount of trust from my leadership,” Adams said. That’s kept her committed to the company and able to grow at Sedgwick over the long term, she said.

Adams said she recently earned a promotion after merging two teams into one, saving the company resources. “I let my people know, as soon as I attain one goal, that I am thinking about the next one,” she said. “We always have those conversations about what’s next for me. When I go to the table, I’m talking about that: How am I going to grow professionally?”

Beyond making time for other pursuits, Kelan emphasized that enlightened employers will be receptive to requests for extended time off—from letting you bundle weeks of vacation time to a longer-term absence. In fact, your boss may understand exactly why you’re asking. Over the course of a career that could last as long as 60 years, extended time off is becoming more commonplace at the top.

Blake Irving, CEO of GoDaddy, took a year off to travel the world with his young family, and Popeyes CEO Cheryl Bachelder took two separate three-year breaks to raise her children and care for her parents.

“It’s important to plan breaks—sabbatical or travel, or times when you focus more on your family, or gain new experiences you might use when you return,” Kelan said. “Many employers are very open to that idea.”

(Updates with details of Muller’s Instagram account in the 10th paragraph. An earlier version corrected a reference to her former Etsy shop.)

To contact the author of this story: Arianne Cohen in New York at

To contact the editor responsible for this story: David Rovella at, Dimitra Kessenides

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