Why Multi-Hyphenate Leaders Are Crucial Now
The future of business is cross-functional, innovative and experimental. Leaders must embrace these multi-hyphenate qualities, so we can inspire them in others.
The multi-hyphenate movement is coming for you and your company
Welcome to a new era: the age of the multi-hyphenate. You may not have heard of this word yet, but you will. A multihyphenate is someone who has so many professional roles and skills that they need a series of hyphens to link them all together.
For example,
Taylor Swift is a musician-songwriter-producer-fashion icon
LeBron James is an athlete-activist-thought leader
Paris Hilton is, by her description, a “CEO-entrepreneur-artist-DJ-model-actress-singer-humanitarian-activist-artist-investor-boss babe.”
And then, of course, beyond the many widely skilled celebrities, there is your cousin, neighbor, or maybe even you. According to Emma Gannon, who literally wrote the book on the multi-hyphenate movement, by 2021, around 64% of US millennials were running a side hustle to supplement their income from their full-time jobs. Vloggers, DJs, podcasters, designers, models, Uber drivers… suddenly, the gig economy had blossomed into a full fledged working identity.
The notion of work has shifted away from simply doing a job to building a career, and the hyphen has become shorthand to conflate personal identity with professional capability.
The rise of the “multi-hyphenate” has ironically eliminated the need for any specificity at all, instead implying a complex creative identity grounded in a jack-of-all trades ideal that conflates production potential with individual worth.
Everyone you know is a multi-hyphenate, The Outline, Nov 2019
Back in 2019, however, most people assumed that the multi-hyphenate career path was restricted to entrepreneur. Sure, multihyphenates might be, in the words of one multi-hyphenate, “wedding photographers who practice law to registered dieticians who influence millions of followers on Instagram.” But for many, the key factors of the multi-hyphenate seemed to be about achieving one’s individualized goals.
A multi-hyphenate might be driven by passion or be propelled by meaningful work; she might be navigating fundamental economic insecurity or be caught within the impossible trade-offs associated with individual choice and circumstance. But when push came to shove, it was thought, a multi-hyphenate needed to be someone who worked on their own.
In other words, the opposite of a multi-hyphenate was assumed to be a corporate employee, because by definition working in a big company has meant staying and thriving within one’s lane or corporate silo.
Then, the pandemic happened, and in a blink of an eye, the reality of how businesses work has changed. Suddenly, businesses themselves have been using words once associated with the multi-hyphenate movement, like agility and purpose, flexible work and networked leadership, versatility and creative innovation.
As organizations spill beyond silos, could it be that the reality of corporate structures and the multi-hyphenate movement are… overlapping?
In other words, does your organization need to start thinking like… Paris Hilton?
Join me on a journey into the multi-hyphenate realm, and let’s discover why embracing this dynamic approach is key to improving how you navigate the future of work—and maybe your personal fulfillment, also.
We are experiencing an evolution in the professional identity of leaders
I remember, back in 2022, when I attended one of my first conferences post the pandemic lockdowns. I was listening to the Chief HR Officer of the Royal Bank of Canada—quite literally the largest employer in my country, with around 90,000 employees in the time.
She was describing how, in the first weeks of lockdown, back in March of 2020, the bank’s executives had to make a series of unprecedented decisions—starting, of course, from just teaching all the senior execs how to use Zoom. The whole world was reeling, and there was no precedent at the bank for working from home. Suddenly—I’m paraphrasing here—the executives found themselves “winging it”. They were making decisions with impacts in the tens of even hundreds of millions of dollars in the blink of an eye—because there were literally no other alternatives at the time.
In other words, these senior bank employees who had spent a lifetime within corporate structures were suddenly forced to think like entrepreneurs.
Looking back on those early days of the pandemic, I remember how a common phrase that people used was “new normal”. The common assumption—spoken and unspoken—back then was that once the worst of the health crisis passed, then the whole world would return to the way it had operated back in the fall of 2019.
A few years later, that assumption seems almost laughable. Since then, there have been so many fundamental shifts in the world, from wars, to sociopolitical shifts, to one of the biggest—generative AI. In some sense, 2019 is as far away from today as the 19th century.
If the old leadership question was “what is the right solution”, the new question is “how many different things can we try and see what works?”
Corporate leaders are being challenged to start thinking and being multi-hyphenates.
We’re operating in a world where work is no longer defined by jobs, the workplace is no longer a specific place, many workers are no longer traditional employees, and human resources is no longer a siloed function. These boundaries, once assumed to be the natural order of things, are falling away and traditional models of work are becoming boundaryless.
Deloitte, 2024 Global Human Capital Trends Report
Being a multi-hyphenate is about more than multi-tasking
I remember the first time that I heard the word “multi-hyphenate”. It was in late 2021. With the desire to break out of lockdown doldrums, on a whim, I bought a ticket to a unique conference being held in Lisbon, Portugal, that was hosted by a unique European consultancy-slash-think tank called the House of Beautiful Business.
By this point in my career, I had attended and spoken at many conferences. I was used to the conventional flow—windowless conference rooms buried in the belly of some charmless hotel, attendees who look past you as they pass out their business cards, bad buffet food and drowning beneath the firehose of content. But right away, I saw that everything about this conference was different.
Rather than a conference center, the event was held in what had once been a warehouse in a seedy part of Lisbon. Vibrant digital art brightened the dour walls. At the center of the warehouse, the stage was circular and surrounded by folding chairs in a way that suggested that we, the audience, were fundamentally connected to the action. The speakers spoke about business—but they also spoke about art and culture, politics and the future, and the implication of social change.
Best of all, I realized that my fellow attendees were just as explorative and unfinished as I was.
Though it wasn’t billed this way, it turned out that the conference was an international gathering of multi-hyphenates.
Naturally, the pandemic was on everyone’s lips. In that warm and protective atmosphere, I found myself confiding to strangers about the challenges in my business. For years, I had been delivering storytelling trainings to businesses. It was work that I loved—but it was also a job fraught with tension.
My clients expected that I would “train” their people to be better storytellers. This expectation was codified in something that were called “learning objectives”—expectations that I was supposed to fulfill, as if there was some way to do this “right”. Now, suddenly, my revenue had plummeted as in-person gatherings everywhere had been cancelled.
I was asking myself how I might do things differently.
One memorable conversation shifted my perspective. It concerned the difference between balancing multiple task and embodying multiple identities. This was language I could understand.
In my one-man shop, I wore, as the cliche goes, many different hats. I was responsible for:
Designing and developing my products
Marketing and sales
Business systems design, strategy and leadership
Finance, HR, and all the other elements that go with entrepreneurship
This juggling act is surely familiar to many entrepreneurs.
In designing this system, I constantly felt the pressure to get it “right”. I studied business model canvases and hired virtual assistants. My dream was to create something that could be replicable—my own personal flywheel.
Which was ironic, because the skillset I was teaching was all about creativity and self-expression!
The truth was this juggling act was overwhelming me—and, as a result, it was affecting the product I was offering to my clients. In this conversation with a stranger, I realized that the challenge I was facing was identical to what my clients were facing within their organizations! They, too, were operating in environments where they were being forced to choose between diverse skills and roles. Their creative skillset was often misunderstood and rarely appreciated. The issue at play was not just how to communicate more effectively, but how to break down organizational silos so they could be more experimental and creative—rather than being beholden to “the way we’ve always done things”.
In retrospect, this a-ha moment changed my whole life.
Being a multi-hyphenate is about embracing our natural curiosity
Immediately before this unique conference, my wife and I spent a couple weeks walking on the Camino de Santiago—the famed European walking trail that tens of thousands of pilgrims have been traveling for more than a thousand years.
(If you haven’t heard about this journey, it’s fantastic.)
We chose a route that traveled north from Porto, Portugual towards the famed cathedral in the Spanish town, Santiago de Compostela. From there, we planned to turn west and walk out to the Atlantic coast, ending our journey in a tiny town called Finisterre—translated into English as “the end of the world”.
I find it hard not to be romantic on these quixotic journeys, especially knowing that I was about to attend an event presented by the House of Beautiful Business. So early into our walk, I began asking myself what it was I wished to leave behind once I reached the End of the World.
I scooped up a rock and slipped it into my pocket. I felt its weight there for the next couple hundred miles, reminding me to keep asking myself this big, open-ended question.
What would I leave behind when I reached the End of the World?
As I have said above, the pandemic had put my business into a toilet. I felt the victim of my circumstance, and I was trying to innovate my way into a new paradigm. Would I, too, just try to wait out the lockdown? Would, one day, everything get back to “new normal”?
When we finally got to Finisterre, I threw my rock into the sea and made a commitment to myself that I would be somehow different. Looking back, I now realize that the question I was attempting to answer was not what but how.
I believe that being a multi-hyphenate is about making a shift from product to process. It’s about choosing to embrace the balancing act, it’s about innovating how you do things, it’s about letting things go, and embracing the chaos and uncertainty.
This is what I realized at the End of the World.
A new narrative around corporate multi-hyphenates
Not long after I returned, I read an article by McKinsey called New Leadership for a New Era of Thriving Organizations. I was shocked to see so much of what I had been thinking about in Portugal reflected back at me from such an august, mainstream consultancy.
In the article, the McKinsey writers argued that “we are moving from an era of individual leaders to an era of networked leadership teams that steer the organization.
This new approach calls on leaders to make fundamental evolutionary shifts, well beyond the standard expectation that they continually develop additional skills. They must, in fact, reimagine themselves, undertaking inner work to shift their mindsets and consciousness to see the world anew; to rethink their interactions, roles, and ways of working as part of leadership teams; and to reimagine their organizations and the industries in which they operate.
This sounded similar to what I had done myself on the Camino de Santiago.
Since then, I have noticed how this trend has exploded. Today, the demand for change is everywhere.
In a recent report put out by another mainstream consultancy, Deloitte, the language is even clearer:
Reimagining boundaryless work…is no longer hypothetical—or optional.
Organizationally, many people are focused on the product of transformational change. They are focused on how organizations are going to look once transformation gets a hold of them. But I believe many are overlooking the corresponding reality—that leaders as we know them need to change as well.
The old leadership model of a single person overseeing a team, a division or a company presupposes clarity and specialization. But as the old silos coming, I believe we will see the rise of the multi-hyphenate corporate executive.
How might this multi-hyphenate executive appear?
Characteristics of the Multihyphenate Executive
Experimental
The multi-hyphenate executive is not tied to a specific plan or end point. They are fluent in innovation frameworks, like Design Thinking and Backcasting. Their job isn’t just to manage but to create
Facilitative
The multi-hyphenate executive works as a facilitator. They are responsible for encouraging change, creativity, and collaboration in others—often working from the center, rather than leading from the top.
Comfortable Amidst Chaos
The multi-hyphenate executive knows that chaos can be a creatively generating state. They understand that chaos is required for change to be sustainable. When the unexpected happens, they embrace the positive tension between choice and circumstances—they embody the philosophy of turning lemons into lemonade.
Willing to Explore Outside their Lane
Rather than being limited by the old idea of being a “jack of all trades, master of none”, the multi-hyphenate executive embraces the beginner mindset. They try new things often—outside work as well.
Breaking the Barrier Between Personal and Professional
The multi-hyphenate executive knows that creativity is a flow. They are consistently exploring unexpected hobbies, especially those that are outside the box—podcasting, vlogging, dancing, improv, yoga, adventure racing… They linkt their creative expression through all aspects of their life
Willing to Lead the Change
The multi-hyphenate executive will face all kinds of pressure to conform. They will be reminded about all the reasons why creativity doesn’t work in a corporate environment—again and again and again. The multi-hyphenate executive is purposefully and playfully disruptive. They have the confidence to inspire others to see the world differently. They see their difference as valuable.
My new narrative around being a multi-hyphenate
Every time I try to make changes in my business, I can hear the same voices popping up inside my head: are you allowed to do that? Stay in your lane!
I have been continually amazed to uncover how deep this rabbit hole goes within me.
Slowly, though, I have transformed my perspective—and my business:
Totally redesigned my flagship product—storytelling workshops—to bring in more creativity and diruption. Not only do I find more fulfillment in my work, I'm getting way better reviews from my clients as well.
Received the most genuine and meaningful feedback for my keynote speeches—much better than anything I received prior. And I was good speaker back then also.
Developed way more closeness with my consulting clients. I really feel appreciated now, in a way I never did back then.
Substantially redesigned my entire business model—and embraced my weird.
Plus I've found much better relationships with my partner, family and friends. Seeing myself as a multi-hyphenate has made it much easier to accept myself—and find satisfaction in what I do.
My Advice to You: Future Multi-Hyphenate!
No one can tell you how to be a multi-hyphenate. What we can do is share stories of our own individual success breaking outside of the box. What I'm finding, as a consultant, is that clients keep calling my perspective "refreshing." It's honest, it's real, and they are responding to that in kind.
Today, even more than back in 2021, the world seems to be fraying at its edges. Some people are doubling-down on things that used to work in the past; others are more bravely stretching towards something that's never existed.
For me, that's what being a multi-hyphenate represents.
What's your experience with being a multi-hyphenate? Send me a message—I'd love to hear about it.