CHAPTER 6

CREATE YOUR PORTFOLIO CAREER

You don’t want to be the best at what you do, you want to be the only one.

—JERRY GARCIA

Ever since high school graduation nearly thirty years ago, every four-ish years, something shifts. Almost like clockwork, I shed a skin. I get restless and need to level up. I’m ready to grow new roots or change direction. Sometimes it’s a major shift: leaving the practice of law, for example, or ditching grad school to guide hiking trips. Other times it’s more subtle. Regardless, it becomes time to reorient my compass and write a new chapter in my book of life.

Early on, in my twenties, people gave me all kinds of flak for this. They said my résumé made no sense and forebode that my future would crash. I felt like something was wrong with me because I was interested in so many things and wouldn’t settle on one pursuit. How could I possibly pick just one area of focus, even though everyone else was laser-focused on climbing corporate ladders and staking out their domain of expertise?

Fast-forward to today: broadening one’s career focus no longer seems so strange, yet we still largely lack the language and infrastructure to develop this kind of career. Globally, labor policies and expectations remain rooted in units of work we call “jobs.” The implicit expectation—and often, the goal—is that you will work for someone else, for a long time, and not veer from that path (at least not willingly). True, there are many ways to work and build a career, but the vast majority still revolve in one way or another around this script.

Yet this old script is giving way, and these expectations are increasingly inconsistent with reality … more so every day.

For the past several years, I’ve given keynotes on the future of work. I’ve spoken about the rise of independent workers and free-lancers, the growth of remote work and digital nomads, the effects of automation, and the implications of all of this on education and public policy. The coronavirus pandemic made it clear that the future of work isn’t in the future: it is now. We blew through ten-year forecasts for remote work and “work from anywhere” in two quarters. Meanwhile, unprecedented unemployment left millions of workers wondering what’s next, schools and universities scrambling, and no clear path forward.

Professionals wonder: What does all this mean for my career?

Parents wonder: What does all this mean for my kids?

Leaders of organizations wonder: What does all this mean for our team, strategy, culture, and the organization’s future, period?

My hunch is that you may be asking all of these things too. The old script was already crumbling, but in many ways it was easy to mask. Then the pandemic lit it on fire, and all of a sudden we realized just how outdated it is. Now each of us—you, me, and talent across the board—must write a new script for our careers, livelihoods, and professional purpose. Yours may have been in draft mode already, and with a Flux Mindset, it can get the kind of attention it deserves.

THE SUPERPOWER: CREATE YOUR PORTFOLIO CAREER

For success and satisfaction in a world in flux, treat your career as a portfolio to curate rather than a path to pursue.

Serial entrepreneur Robin Chase sums it up well: “My father had one career his entire life. I will have six careers in my lifetime. And my kids will have six careers at any one time.”

Alex Cole spent ten years in entertainment, another ten years in marketing, and ten years in consulting before finally launching his latest venture in his early fifties: a yoga studio, co-owned with his wife and daughter. The studio recently had its tenth anniversary party, so he’s thinking about what’s next.

Diane Mulcahy thinks of her seasons as verbs. She’s a financial whiz, strategist, lecturer, and author who crafts each quarter differently. This also allows her to split her year between the United States and Europe, where she holds dual citizenship.

Binta Brown left a successful legal career advising Fortune 100 companies to launch her own firm representing musical artists, while she plays the saxophone and produces documentaries along the way.

Mari Nakama is a project manager and trainer at a scientific research company. She’s also a fitness instructor, designs her own clothes, and co-runs a pottery studio with her partner. Each role nurtures her in a different way.

As a professor of marine conservation, Enric Sala saw himself “writing the obituary of ocean life.” So he left academe and pivoted to full-time conservation, leading research teams and working with governments to create first-of-their-kind marine-protected areas.

Each of these people has a portfolio career.¹⁰⁶ Their careers have not been straight lines but a series of twists, turns, pivots, and jumps—sometimes because they needed to or were nudged to, and often because they wanted to. They have sensed that there was more to do, learn, build, and try in life, and they rose to those occasions.

The new professional script is not about pursuing a singular path. A Flux Mindset knows that the career of the future looks more like a portfolio: a diversified professional identity, with resilient roots and customized to you.

Practically speaking, a portfolio career typically leads to:

Creating a portfolio career does not mean lacking ambition or not having a “real job.” In reality, portfolio careers are quietly yet quickly becoming the most sought-after livelihoods of all.

I now see that back in my twenties, I was interested in a portfolio career but had few options to express it. Thankfully, that’s no longer the case.

Today, this goes far beyond individual preferences. When the old script of jobs, employment, and career paths is fraying before your very eyes, and the future of work itself is in flux, a portfolio career offers resilience and a proactive strategy to thrive in your career, rather than being tossed around by the winds of change.

WHAT EXACTLY IS A PORTFOLIO?

When we think about a portfolio, most people usually think of finance, business, or art:

A portfolio career takes inspiration from these different usages. Portfolios can be sequential (one role or vocation at a time) or simultaneous (multiple roles and activities at once). Career portfolioists often create professional niches and lifestyles that are more complete, personalized, modern, adaptable, and personally rewarding than any single role could be.

The term portfolio comes from the Italian words portare (to carry) + foglio (sheet of paper). In other words: How do you carry your most important papers? What contains your book of life?

In my case, each of my professional hats is the equivalent of a sheet of paper, a sketch, or an investment. My portfolio includes speaker, futurist, adviser, lawyer, hiking guide, global development executive, investor, yoga practitioner—and soon, book author. Most of my pages now last longer than four years, though my leveling-up-every-so-often continues unabated.

Importantly, one’s portfolio isn’t limited to only professional roles: it includes capabilities that are customarily left off your résumé yet fundamentally make you, you. For example, my status as an orphan, globetrotter, insatiable handstander,¹⁰⁸ and mental-health advocate are included in my portfolio.

Similarly, portfolioists are clever and resourceful about skills development. When I was a hiking and biking guide, some people ribbed me for not taking my career seriously. What they didn’t see was that as a guide, not only was I usually working eighteen-hour days—first up and last to bed—but also every day I was learning how to project-manage, accommodate differences, balance budgets, build teams, ensure safety, create serendipity, forge lifetime friendships, and make sure everyone had fun. Guiding provided a practical mini-MBA on the trail that would have been hard to replicate in a traditional classroom.

Moreover, one’s portfolio isn’t strictly about “being your own boss.” Ultimately, creating a portfolio empowers you to do this, but your portfolio itself should include every role you’ve ever had—including jobs with a boss, jobs you hated, and jobs where you followed the old script. (My portfolio includes these things too. The jobs I hated still taught me a lot.) A portfolio is a container where all of your skills and capabilities, wherever and however you learned them, can be mixed together.

Several years after people gave me flak for my “unconventional” résumé, those very same individuals resurfaced on my radar. I still remember the day, and the conversation could not have been more different. They said, “We see what you’re up to now. On second thought, how can we do that too?”

FROM PATH TO PORTFOLIO

For most of the twentieth century, a model career path looked like a ladder, an escalator, or perhaps an arrow. The old script was firmly in place and the message was clear: progress up the ladder, rung by rung, each promotion lifting you another step towards your eventual goal at the top. The arrow would fly far and in a straight direction. The escalator would continue to move. If all went well, your future could be preordained, ideally near the bull’s-eye of targets established by family, society, and other external metrics.

For this ladder or escalator to work, large numbers of people needed to believe that they could climb it successfully. So we developed a linear view of career progression, which went more-or-less like this:

This linear way of thinking worked all right for a long time. There were enough jobs and plenty of work to be done. Most workers went to the same office or place at the same time every day. They followed the script: stay on the path and avoid detours. Most people strayed from their career path only unexpectedly; career changes were generally seen as unfortunate mishaps. Résumés with strange detours were liabilities. The corporate ladder remained firmly in place, with promises of a corner office, fancy title, and prestige at the top.

Along this linear path, individuals became defined by what they “do.” Your sense of self-worth got wrapped up in what rung of the ladder you occupy. Once you landed a job and started working your way up, you—and many others—didn’t pause to consider what might happen if the ladder teetered or broke, or if someday you no longer wanted to be on it.

Yet in recent years, this ladder is most definitely teetering, and the old script is in tatters. Consider these pre-pandemic stats:

Although many of these stats are from the United States, the trends they represent are global. Freelancer growth rates are somewhat lower in many countries, but the overall growth trajectory is similar.

These shifts are driven by the one-two-three punch of corporate action, individual awakening, and technological innovation. Both push- and pull-side dynamics are at work:

To all of this we can add the Pandemic Accelerant, which put these shifts into hyperdrive.¹¹⁶ Alongside unprecedented unemployment, companies are pushing to automate faster—not least because machines don’t get sick or protest—without a full appreciation of the human implications of doing so. As future of work strategist Heather McGowan says, “We’ll be getting there—wherever there is—with fewer people”: fewer blue-collar workers, fewer white-collar professionals, fewer recent graduates, fewer employees, period.

But hang on:

For all of these questions, a portfolio career is part of the answer. It is your—and yes, your kids’—superpower to thrive professionally today, tomorrow, and throughout the future of work.

REDEFINING YOUR PROFESSIONAL IDENTITY FOR A WORLD IN FLUX

For centuries, one’s professional identity—as a tradesman, farmer, nurse, soldier, monk, or scholar—shaped one’s entire life. Our script embodied our vocations, so much so that many surnames are occupations: Cooper, Miller, Sawyer, Smith.

In recent times we’ve seen an evolution from “I-shaped people” (with deep expertise in one topic) to “T-shaped people” (having both breadth and depth of exposure and expertise), “Pi(π)-shaped people” (who have depth in more than one area), and even “X-shaped people” (with breadth, depth, diversity, and the ability to stretch into new domains).¹¹⁷ A world in flux is a world for π- and X-shaped people. You may already sense this shift, or already be a “π thinker,” but didn’t realize there’s a name for it. Rest assured you are not alone. This is an incredibly empowering shift.

The future of work is fluid, not fixed. Your professional future is similarly fluid, not a predetermined path. You are no longer bound to an old script, given to you (or taken away from you) by someone else. It’s time for a new script—and your unique, bespoke professional portfolio.

BUILDING YOUR PORTFOLIO

When jobs, employment, professional development, and the future of work itself are in flux, a portfolio career offers a more likely path to thrive. But how does one actually write that new script? And what does an identity fit for this future look like, anyway?

Developing a portfolio career involves two phases: creation and curation. Let’s take each of these in turn.

Step 1: What’s Already in It?

First things first: whether or not you realize it, you already have a portfolio career. You just haven’t necessarily been strategic about it. This exercise helps you get started. It takes time, but it’s worth it.

Pull out a piece of paper (or a blank Google document) and into it put the following:

Take this list and put it aside. Sleep on it, and tomorrow take another pass at filling it out. Be expansive. Did you list every skill, including those you’ve never been paid for? Did you include every topic, including those beyond what the old script would call your “domain of expertise?”

Some people like to think about their portfolio like a bento box, with each skill in its place. Others think about it like a jungle gym or a lattice, rather than a ladder. I like to think about it as a flower. Every few years, I create a new petal by gaining a new skill or stretching into a new or adjacent space where I can use my skills (more on that below). Over time, my career flower becomes bigger, more colorful, more interesting, and more valuable. In all of these iterations, I’m rooted in what makes me, me—and I continue to evolve.

Step 2: Be(come) the Only

Once you’ve assembled what’s in your portfolio today, then the real fun begins. The following steps are part personal ikigai, part professional jiu-jitsu, and part responsible risk management. It’s also about making yourself automation-proof for the years ahead. You’re charting your unique career landscape and horizons.

Ikigai is a Japanese concept that means “reason for being.” It translates as life purpose or meaning, or what makes one’s life worthwhile.¹¹⁸ It’s why you jump out of bed in the morning. It is also your highest calling. Your ikigai is uniquely you.

Ikigai is often depicted as the intersection of four circles:

This is where your portfolio can shine. No two people have the same ikigai because no two people are the same!

A career portfolioist 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 that allows for ongoing adaptation. The point is not to reach “the top” of a ladder, the end of a path, or a specific salary. The point is ongoing fulfillment and joyful contribution to the world.

Go back to Jerry Garcia. Don’t be the best. Be the only. What is your only? The key to one’s “only” is that it’s not about one skill. It’s about your unique combination of skills, capabilities, interests, and dreams. This is your unique new script.

For example, you may be trained as a lawyer, love history and cooking, and take long bike rides on the weekend. There are savvier lawyers, more knowledgeable historians, more adventurous cooks, and speedier bicyclists than you. But is anyone a better legal adviser to travel companies leading cycling trips focused on food, wine, and history worldwide than you? Probably not.

Or you’re a finance wonk who loves physics, photography, and cares for your elderly parents. Or an engineer who loves orchids, helping youth learn how to code, and Bernese mountain dogs. (The more specific you can be, the better. Not that you’re guaranteed to find a perfect match, but it makes your “only” easier to define.)

The point is: your ikigai is unique, and it can play out in myriad ways, each of which is exciting for its own reasons. A portfolio career isn’t about doing one thing for many years, hitting a wall, and then wondering what to do next. A portfolio career contains multitudes: of possibilities, combinations, and opportunities.

Step 3: Cross-Pollinate

With a portfolio career, you rarely stay in your own lane. You’re a cross-pollinator. You take a useful skill or expertise and parlay it into opportunities elsewhere, often in a completely unexpected arena. You translate across problems, roles, teams, and industries. You use your compass’s orientation to discover new insights. In the process, you create new value, help others level up, and inspire them to write their own new scripts too.

The old script says: get a job and do what others tell you to.

The new script says: create a portfolio of roles and do things no one else dreamed of.

The old script says: if you go to law school, then be a lawyer.

The new script says: a law degree is one of the most malleable, powerful degrees that exists. It invites creativity. Do more with it.

In my case, many of my colleagues today don’t realize that I am trained as a lawyer. Some of them are incredulous when they find out: “But you’re nothing like a typical lawyer!” I managed to filter out the bigger-picture potential of a legal background early on, so although I haven’t practiced law in decades, I still draw on this skill set almost every day. It has been one of my most effective sources of cross-pollination.

Go back to Robin Chase. You are likely to have six or more careers, perhaps even at the same time. Cross-pollinate within your portfolio too.

Every time you cross-pollinate, you’re collecting and synthesizing new knowledge along the way. You’re simultaneously honing your compass and strengthening your roots. When done well, it’s an upward spiral, and you improve everything you touch along the way. You bring new insights to siloed sectors that badly need them. You help others see not just the forest and the trees but what is beyond the forest. You remind them that the path forward is not to be found in the trees but between them: the space that’s right there in front of us, yet which we all too often miss.

To cross-pollinate effectively, it’s essential to understand the old script and to redirect resistance to portfolioist thinking in a productive way. More often than not, the source of resistance is fear, lack of awareness, or both. People working from the old script and mindset often get confused by portfolio careers. They assume that each move means starting from scratch. The attitude is one of “Why on earth would you do that?!”

Meanwhile, anyone who has opened a Flux Mindset and is writing their new script sees portfolio careers as an evolution: each move is an improvement, addition, expansion, and adventure that aligns with your evolving self. The attitude is an enthusiastic “Let’s get started!”

Step 4: Redefine Your Identity

When you have wrapped your arms around your portfolio, you’re ready to take this step.

Embracing a portfolio career means transcending any one identity, story, or narrative about yourself.

With a Flux Mindset and a portfolio career, you are no longer defined by “what” you do. You are not defined by a title, a specific salary, or a corner office. You are not defined by one profession. While you have many skills, you are not defined by them.

Rather, you harness all of your capabilities and continuously reimagine how they can be combined and offered in new ways, creating new value and opening new doors.

Your portfolio reflects your roots. It is your new script, your foundation for the future, and an ever-evolving identity that fits you.

Step 5: Curate, Forever

Once your portfolio is sufficiently established, you can shift to curation mode. This is your ongoing, evergreen career: it is the script that, so long as you are breathing and thinking, you will continue to write. Depending on whether the investor, executive, manager, or artist portfolio perspective resonates most with you, curation can take a few different forms:

The essential point of portfolio curation is that it mirrors your growth, so long as you proactively take care of it. In a world in flux—and the future of work—a curated portfolio career provides an unparalleled combination of flexibility, stability, longevity, and meaning.

PORTFOLIO CAREERS AND THE FUTURE OF EDUCATION: WELCOME TO LIFELONG LEARNING

Universities continue to make the promise to “help graduates get a job.” Yet as we saw, 43 percent of recent college graduates hold jobs that don’t require a college degree, and nearly two-thirds remain underemployed after five years. What kind of promise is that?

Career services centers continue to focus largely on attracting employers to campus. Yet as we saw, more than half of Millennials are independent workers (rather than salaried employees), and more young adults are likely to be their own boss than ever before. Why are career services advisers still so focused on the old script?

By and large, educational institutions today appear to have not received the future of work memo, or if they did, they did not read it thoroughly.

True, many colleges and business schools offer courses on entrepreneurship. But they miss the mark when it comes to the reality of many students’ professional journeys. They fail to offer dedicated services to help students be their own boss, and they have yet to harness the (super)power of portfolio careers.

If you’re a young adult or a parent, this is a bright red flag for the future of education—and all the more reason to take this chapter seriously.

Portfolio careers are for all ages, and the sooner we can open a Flux Mindset to create them, the better for all: students, graduates, families, the workplace, and society as a whole.

If you’re twenty years old today, there’s little reason why you should not have already hung your professional shingle online. This represents the first piece of your portfolio. (If you’re thirty years old, this is even more true. Ditto for fifty years old. And if you have a child who’s twenty years old, consider this your joint call to action.)

Here’s the crux: it has never been easier, cheaper, or made more common sense to start your own business. You’re not signing away your professional life; you’re simply learning the basic how-to’s of technology, branding, and business acumen. Whether it’s for childcare services, custom T-shirts, Gen Z expertise, or whatever you love to share with other people, the experience of hanging your own shingle will teach you more than almost any formal course. Learn by actually doing it! Moreover, the experience will open other doors. It becomes part of your portfolio, and you can always upgrade, reinvent, or combine it with other folios down the road.

Portfolio careers transform not only how you think about your career but how you think about learning and growth, period. To echo Heather McGowan, “The future of work is learning, and the future of learning is work” and “Learning is the new pension. It’s how you create your future value every day.”¹²⁰ Portfolio careers are aligned with both. In a world and workplace in flux, you will never stop learning. Ever.

Insofar as “What do you do?” is the classic question of the old script, “What are you learning?” becomes a quintessential question of your new script.

Gone are the days when people will study for a profession and do that profession for life. Even if you stay in the same industry, given the pace of change, chances are good that it will transform within a generation. Anyone who believes that they are somehow immune from these changes will face the rudest wake-up of all.

With a portfolio career, you’re awake to a future of work in flux. You see how your unique blend of skills—your portfolio—mitigates your risks of professional obsolescence and empowers you to widen your range. You can be both a generalist and a specialist, and you know which one is appropriate in a given situation. You see how a portfolio career is a natural catalyst of lifelong learning and vice versa. As you identify new additions for your portfolio, you also true up your ikigai.

So what are you waiting for?

WORKING TOGETHER: TWENTY-FIRST CENTURY GUILDS

Crafting a portfolio career isn’t only about what you do or how you do it. With whom you do so matters as well.

Career portfolioists have colleagues, partners, and professional peers just as people with a linear career path do. But thanks to new technologies, there are more options to meet new people and collaborate than ever before. Twenty-first century guilds are one of the most useful such options.

The guild concept is not new. Guilds date back many centuries and have long served to bring people focused on the same craft or trade together, to keep quality high, and to pass on the trade’s skills and practices to others. Blacksmiths, carpenters, cobblers, and accountants were among the many professions with guilds. While guilds took a back seat (and at times were actively undermined) as industrialization, corporations, and single-employer work rose in prominence, they never disappeared—and they are now making a comeback.

Modern guilds serve many purposes, from (in today’s terms) vocational training to business development, networking, and mutual aid.¹²¹ Guilds help their members learn and develop expertise in the profession. They help members network, collaborate, and source other types of expertise beyond the guild. Guilds also serve as an informal gauge of reputation and trust: a sort of collective orientation. For example, Enspiral is a guild of 150+ individuals from around the world who spawned multiple ventures together, wrote an open-source handbook about their collaborative practices, and use participatory co-budgeting to further support Enspiral membership.¹²²

As portfolio careers and more diverse work arrangements take root in the twenty-first century, guilds are a vehicle to accelerate learning, professional community, and responsibility. They are fit for flux.

YOU ARE SO MUCH MORE THAN YOUR CURRENT JOB DESCRIPTION

Back in 2012, the phrase Generation Flux was used to describe the kind of person who excels in a fluid, chaotic workplace.¹²³ Today, thriving as a GenFluxer means having a career portfolio too.

At its core, a portfolio career reflects how you see yourself and what you do in the world. It is your script. The shift from a linear, conventional career path to a unique and ever-evolving career portfolio strengthens your roots and boosts your resilience. With a portfolio, your professional development is no longer an exercise in anxiety and change management, remedied by a course here or glorified by a promotion there, yet constantly at risk of being lost or hijacked by forces beyond you. In contrast, your portfolio career reflects your Flux Mindset at work.

Portfolio careers still face challenges, primarily from people and public policies stuck in the old script. But these are shifting little by little (and occasionally, a lot), and the fact is: portfolio careers align with the future. Already today, every job is temporary, whether we admit it or not. The future—including the future of work—will favor those who can think beyond jobs, create portfolios, and know how to flux.

CREATE YOUR PORTFOLIO CAREER: REFLECTIONS