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How To Have Two Successful Careers At The Same Time

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In the past year I've met multiple women managing more than one career. There's the software developer who moonlights as a wedding photographer. The university professor who cooks at pop-up restaurants. And the banker who has a bourgeoning freelance writing career. These multi-jobs go well beyond weekend retail jobs as supplemental income of years past. Many find juggling two, three or even four jobs, fulfilling and necessary for their overall career and life development.

There's a term for this way of working – having a portfolio career. Instead of one, full-time salaried position, portfolio careers entail combining a full-time position with one or more part-time/freelance gigs or working multiple part-time positions that, in total, would amount to a full-time job. The appeal? Flexibility, independence, and an ability to pursue passion projects. Unfortunately, the data is still fuzzy on how many people actually participate in portfolio careers. But some estimates predict that within the next 10 years, half of all employed Americans – or 65 million people – will be "independent workers."

Millennials will be leading the pack, and from all the work I conducted for my book on gender inequity in the workplace, The Diversity Advantage, I have no doubt that women will be early adopters of this style of working. Indeed, a whopping 97% of millennial women surveyed by PwC said work/life balance was of critical importance to them. More millennials are seeing their career trajectories shaping up more like a jungle gym than a straight career ladder, where multiple self-directed activities could lead to a self-created version of career success.

But for highly-educated, ambitious women, building a portfolio career could be an anxiety-ridden choice too. Deciding to leave a high-paying full-time job that offers benefits and stock options can be confounding enough. Add in the uncertainty of freelance gigs and trading in set working hours for undetermined ones, and the decision isn't an easy one.

Samantha Clarke, founder of UK-based culture consultancy Samantha& assures me that portfolio careers can be both viable and successful – if planned correctly. Clarke offers classes and workshops on how to make the most of portfolio careers, while advising companies on how to harness the power of workers who want to juggle multiple gigs.

"It's important to have a portfolio plan that maps out your cash, lifestyle and skills," she says. Each "pie" or plan will be different for every individual; some value financial security and a certain lifestyle. Others want to build on certain skillsets or latent dreams. It's important to determine how much money you need to make to make your life worthwhile for you, she says. Not everyone can tolerate a career without a steady paycheck. But some prefer flexibility over that.

"I don't advise quitting a full-time job without mapping all of this out," she says. For the ones who still want to work in a corporate job, Clarke cites multiple clients who were able to negotiate a shorter work week in their full-time jobs to dedicate one day off to build their other careers. "A lawyer I know had a passion for jewelry-making. So she approached her boss, told him that she loved working for the law firm and didn't want to quit, but also wanted to explore her calling in jewelry," says Clarke. Not only was the lawyer able to work a four-day week, her jewelry business caters largely to professional women, especially lawyers, so she was able to develop new contacts and expertise without drifting too far away from her day job.

"Is there a way the different pieces of your portfolio career could overlap? Are there skills you could develop in one area that could be handy in another? These help make a stronger case for negotiating terms with your boss," she says.

She also recommends mapping out your week in advance. Many times people crash and burn when they take on too much without planning how to work. Do you have to work around a solid schedule, like the lawyer she cited? How much time would you need to dedicate to business development? What's the best time you can carve out to avoid distractions? Clarke says portfolio careers often don't work out "when people get burnt out by not planning their schedule properly....It's easy to find lots of shiny new things and take off in different directions." Once you have allocated your time, stick to the plan. 

Next, be clear about setting goals and a larger vision for what you want your career to look like. "If there's one piece of advice I think is most important in building successful portfolio careers, it's learning how to say 'no' effectively," she emphasizes. While the impact of taking on too much is harmful as it is, particularly for working women, for women in these careers, it could be the difference between success and failure.

"This isn't just a bunch of freelance jobs. You're building a whole life out of them," she adds. Be judicious with your time!

Clarke also recommends reading Ramit Sethi's work while making the transition, "because it helps people think about the psychological barriers to being successful," she says.

So are portfolio careers just a trendy term for entrepreneurs who work a day job while building a startup, I wonder? Clarke balks at this analogy. "I think the word 'entrepreneurship' comes with a lot of baggage; people get deterred by the term if they’re not a startup entrepreneur with massive seed funding or hugely successful in Silicon Valley," she says. "But you can have a successful portfolio career with, for example, an Etsy store and a great full-time job at a company. There's nothing wrong with either." While portfolio careers have given rise to well-known entrepreneurs in the past, that doesn't have to be the goal, cautions Clarke.