The career of the future looks more like a portfolio than a path

The career of the future looks more like a portfolio than a path.

My friend Diane says that she “works in seasons.”  Her work, and the location in which she completes it, often changes as summer turns to fall or as fall turns to winter. Over the years, she’s worked in a combination of new and familiar places and employed skills as diverse as financial management, teaching, research, and writing, and each of these work seasons has had a different balance of introspection, independence, and income.

When Diane first told me how she thinks of her working style, something clicked for me. In the prior month, I had been working hard in the U.S. and Europe and was about to depart for Latin America. There was no such thing as a typical week. On any given day I could find myself advising a startup in Estonia about immigration policy, speaking with a policy maker in South Africa about tourism, or workshopping new insurance platforms in the U.S. I might be in one place in a month, or seven places. My husband—who has a similarly fluid profession—might join me, or I might tag along on one of his adventures.

Diane and I weren’t alone in this oddball work style. Another friend Shelby, who is a yoga instructor, Airbnb host, and successful startup entrepreneur, launched a venture that uniquely blends these skills. A college student who wants to carve an independent career and yearns to be a “global nomad” reached out. And just last week, I spoke with two semi-retired individuals who—even later in life—have discovered that it has never been easier to be your own boss.

This kind of diversity, variety, change, and rushing-about had begun to feel quite normal to me. But in that moment, I had a very different thought: wow, this is not what normal work used to be like.

Welcome to the world of “portfolioists.”

Portfolio what?

Usually, when we think about a portfolio, we think of finance, business, or art. Investors use a portfolio approach to risk diversification; traditional financial advisors recommend a portfolio that includes equities, bonds and cash. Venture capitalists build portfolios of investments, placing bets on companies, and hoping that one in 20 wins big. Businesses often use portfolio theory (pioneered by BCG’s portfolio growth matrix in the 1970s) to analyze their business units, revenues and risks. And of course, a fine artist throws open her portfolio to show the works of which she’s really proud.

In my vocabulary, a portfolioist takes inspiration from these other disciplines to create an adaptable, diversified, and personal career. She does the hard work of figuring out what the world truly needs, maps that to a range of skills she possesses (and enjoys), and folds that into a business model. This “portfolio” of skills, experience, roles or responsibilities might be wildly diverse, which both distributes risk and allows for experimentation. Unrelated experiences may combine to create very specific and valuable expertise. The portfolioist’s career is a bento box, with each skill in its place.

Is this just a nice way of saying freelance?

Being a portfolioist goes beyond freelancing, though some portfolioists may also be self-employed. It’s not about merely logging into platforms that bring you occasional work: it’s about creating your own platform and honing valuable skills. In short, it’s about curating a portfolio of work that reflects you and maximizes your potential in the world.

Portfolioism builds upon well-known paths. We’ve always had multi-talented people, polymaths, Renaissance men and women and, more recently, multi-potentialites. But what is new about the way portfolioism can be manifest today is the degree to which individuals have agency over the portfolios that they build.

In my case, I leveraged my rather traditional law degree in distinctly non-traditional ways and used my time working in emerging markets to share insights that are difficult to find at home. Today I advise companies and policymakers, speak and write, travel and cross-pollinate. My advice is valued because it is out of the ordinary, relevant and relatively rare to find inside organizations. It results from a blend of unique experiences and the very fact of being independent, external, or, as some would say, an outsider.

Like me, Diane, Shelby and scores of others have experimented, tested, failed, recombined, tested again, and ultimately—over time—achieved better integration of their lives and livelihoods. We’ve crafted and refined unique combinations of skills, combinations that no robot can emulate. We have also created multiple sources of income, which help us mitigate risk. We’re arguably better prepared for the future, because while not everything in our respective portfolios will thrive, we’re working with a greater variety of people, models and technologies than the average employee, which boosts our resilience and positions us well for the uncertainties ahead.

So where should I start?

The most important baseline criterion for becoming a portfolioist is open-mindedness. With that, take a page from traditional portfolio theory and focus on diversification. Most successful portfolioists have a blend of short-, medium- and long-term engagements, with different pay levels and working arrangements. For example, my work with governments pays less than the private sector, but it teaches me key skills that are helpful far beyond the public sector. Some of my work with startups allows me to be paid in equity rather than cash, which further diversifies my income—and if the startups do well, could also be worth more.

Some ways to consider diversification include:

  • Timeline, horizon and maturity: short-term projects vs. long-term relationships
  • Place: do you enjoy doing things locally and in person, or would you prefer to work remotely or become a digital nomad?
  • Level of risk: your portfolio should contain things that really stretch you and feel “risky” as well as things that place you squarely in your comfort zone. Entrepreneurial portfolioists often are paid in many ways, including fees, retainers, equity, services in kind (such as free office space or professional services), and of course pro bono or for the upside of learning.
  • Community connections: as a portfolioist, colleagues take on new meaning. You have the ability to be part of far more communities of practice than the average employee, and to work with people whom you really like. Take advantage of this! Your portfolio will probably include co-created masterpieces; you might even develop a shared name.
  • Number of commitments: I generally find that more than four or five engagements in my portfolio at any one time reduces both the quality of my work and how much I enjoy it. Of course, this depends on how much of my time each requires. There is no exact science to this; just take care not to stretch yourself too thin.

If you’re just starting out, focus on effectively creating a skills portfolio. The more skills you build, the more valuable (and employable) you become. This is the time to prototype madly and to apprentice yourself to people who are good at the things you want to excel at in 15 years. If you’re not sure what prototyping is, a wonderful place to start is Designing Your Life. And if you’ve done that and it still feels scary, pick up a copy of What Color Is Your Parachute?, which is relevant today as it was when the first edition published in 1970.

If you’re looking for a mid-career change, focus on curating a results portfolio. Your roles to date may span different industries, skill sets and practical arrangements. But if you’re building something unique, then titles or job descriptions matter less than what you actually did. Now it’s time to show the world that your track record of achievement, coupled with your vantage point and flexibility of being a portfolioist, are an unbeatable match for colleagues and collaborators. Cull those skills you know you excel at and enjoy; layer them and mix them up in new ways.

Portfolioists in the later stages of their careers are able to craft a master portfolio. Personally, think of a master portfolio as a kind of legacy, perhaps closest to an artist’s portfolio whose works can be appreciated by generations to come. From a business perspective, as companies increasingly worry about losing expertise when older workers retire, this becomes an essential model. Not only do we keep expertise in flow, but we allow for suitable structures for two-way mentorship and healthier aging.

I have a strong suspicion that moving forward, portfolioists of all ages will play a meaningful role in reshaping and resizing how companies (and organizations of all stripes) work. Organizations will come to realize that portfolioists are valuable not as a cost-cutting measure (and to be clear, we’re not talking here about merely a side effect of the gig economy) but rather because they amplify diversity of thinking and maximize the potential for new insights. They leapfrog employee group-think and have a richer palette of insights from which to draw, because everything in their portfolio cross-pollinates everything else. In other words, because the results are genuinely better.