The rise of the portfolio career

When Ricklyn Woods quit her corporate job in April 2020, it wasn’t for money (she was making a six-figure salary) or the commute (under 10 minutes). It was a matter of personal fulfillment.

“I wanted to make an impact. I wanted to do work that I enjoyed, and I wanted to be able to make money on the side too. And then, one day, I looked up and I was in the midst of a portfolio career,” Woods says.

To be clear, a portfolio career is not the same thing as the oft-discussed gig economy. Gig economy refers to people who pick up work on an as-needed or as-wanted basis. (Think grocery-delivery or ride-sharing services, for example.) Employees can choose when to work based on their preferences and the availability of shifts. They might cobble together a full-time schedule among several companies, but they essentially work for one or more such organizations.

A portfolio career, on the other hand, is more about channeling your skills, expertise and plenty of personal branding into, as Woods puts it, “multiple streams of income, whether that be teaching, speaking, consulting or coaching.”

In Woods’ case, her portfolio career began in human resources. She eventually launched her own career-coaching practice, which led to a role at University of Phoenix, where she currently works full time as a career advisor.

But Woods, who describes herself as “multi-passionate,” pursues other interests as well. She hosts a podcast called So You Want to Work in HR, which she produces before and after normal working hours. She also maintains a private coaching practice on weekends, and she occasionally accepts select speaking engagements.

Woods’ portfolio career presents just one example. As Kitiara Pascoe notes in her article on Medium.com, portfolio careers can look a variety of ways. They might combine short-term projects, freelance work and full- or part-time employment. They might encompass roles across industries. They might consist of a series of freelance projects in one industry but with different roles.

“A portfolio career is a career that incorporates lots of different jobs, often simultaneously, or sometimes back-to-back,” Pascoe writes.

Perhaps more tellingly, portfolio careers speak to an intellectual openness. People who develop these careers tend to have, as Woods does, a range of interests and aptitude — and a fearlessness about exploring both professionally.

Way back in 2019, the accounting software company FreshBooks conducted an annual report that revealed 24 million Americans wanted to become self-employed.

It’s maybe not the biggest surprise that the year that changed everything (hello, 2020) helped speed up that transition or, in some cases, turned a pipe dream into a reality.

Some people lost their jobs because of the pandemic. Some simply reevaluated their priorities. And as the pandemic’s effects continue to reverberate, others are finding it preferable to strike out on their own rather than return to office work.

Woods explains: “People are starting to get their creative juices going, researching what they can do to still be able to make a living without being forced to do something they don’t agree with.”

Portfolio careers, however, are rarely manufactured overnight. Woods, for example, recognizes how hers is really the result of cultivating opportunities over the course of her entire career.

“I’ve always been really intentional about creating options for myself,” Woods says. “I never want to be without an option.”

To create those options, Woods has both diligently pursued education (she earned her master’s degree) and maintained a steadfast openness to opportunities.

“The work informs what you do next,” Woods explains. “When I first started my private practice as a career coach, I didn’t know I’d work at University of Phoenix. But had I not taken that step to cultivate that experience, then I probably wouldn’t have been qualified for this position. I didn’t know this was coming.

“So, I think one other difference between a traditional career and a portfolio career is, while your career path may be prescribed in a traditional setting, the portfolio career actually opens you up to more opportunities for what’s next.”

In other words, if you get experience in roles or industries you are passionate about, that opens the door to related opportunities.

Of course, sometimes the reverse is also true. Taking a role you don’t love but that is in the right industry or at the right company might give you the experience and network you need to position yourself to better negotiate your next move.

“It’s really about looking at your career from the perspective of a journey and not a destination,” Woods notes.

A portfolio career can seem almost mythical to some people. For those committed to a 9-to-5 routine, the freedom and flexibility inherent to a portfolio career can feel like the stuff of dreams. But a portfolio career doesn’t have to be the exclusive domain of writers, artists, consultants and tradespeople.

“One thing that’s blown up with the pandemic is online teaching and online learning,” Woods observes.

By way of example, she points to a contact who used the pandemic to study up on a software program. He became so proficient in it that he now works as an independent consultant training other people how to use it.

“So that’s the other thing I’ve seen, this kind of knowledge economy where people can take what they know and turn it into a business or stream of income,” Woods says.

Of course, this hinges on some pretty solid networking skills. But it doesn’t require that you be the proverbial last word in a subject.

“Some people think that to be an expert you have to know everything,” Woods says. “You just have to know a little bit more than someone else.”

The advantages of a portfolio career transcend flexibility and autonomy. They include, Woods says, the fulfillment that accompanies pursuing multiple and varied interests. Yes, a traditional job will guarantee a paycheck and usually a benefits package including health insurance. But a portfolio career lets you tap your interests to find a sense of purpose that can be hard to pinpoint when you’re hired to execute someone else’s vision.

“It’s very empowering to be able to say, ‘I can do this,’ and not have to wait for someone to give me permission,” Woods says.

As for the financial part, Pascoe, of Medium.com, turns on its head the traditional thinking that a traditional job offers financial security.

“When you have only one skill, focus or income stream, you leave yourself vulnerable,” she writes.

Still, it’s not all rainbows and unicorns for portfolio careerists. For starters, balancing a full- or part-time job with freelance gigs can be exhausting. It can also create a conflict of interest, so Woods recommends clearing any side hustles with your boss before you get started.

And while having a lot of experience means you can add value in a variety of ways, know that not all employers will see it that way. If your resumé or LinkedIn^® profile includes every job, role and side project you’ve ever done, a prospective employer might see you as noncommittal. Instead, be strategic about what you include on each platform or piece of collateral. You can promote your primary career and skill set on your resumé but use LinkedIn to spotlight your work on your passion project. Or you might even create profiles and resumés for each!

Explore all your options. We take a closer look at what’s ahead for the post-pandemic job market.

While some employers may balk at the prospect of hiring someone with a nonlinear career path, Woods predicts companies will increasingly have to get on board with a different way of thinking.

After all, portfolio careers aren’t going anywhere. “I absolutely think they will continue to be a trend, especially with technology continuing to get better and better,” Woods says. “There’s an app for everything. There’s a way to connect people who need services. … I don’t see that changing because of the convenience of it.”

All of which leaves the question: When you work for yourself, how do you measure success? Job promotions are off the table. No one is going to give you a performance review. And while you can use your bank balance as a barometer, money is rarely what drives portfolio careerists.

Instead, evaluating your sense of personal fulfillment becomes the new metric for success. Are you learning? Are you stimulated? Are you satisfied?

For Woods, it’s a matter of understanding her impact. She explains: “With my podcast, I don’t make any money from it. But [because of] the feedback that I get from the people who listen and the impact that it has on their careers, I probably feel most successful with my podcast.”

Which goes to show money isn’t everything. Sometimes the most important part of your career is how you feel about it.