In the summer after my second year of law school, I worked at a large law firm.
Like most “Big Law” summer associate programs, the program entailed a rotation through the firm’s various departments. The expectation was that by the end of the summer I would have enough experience and information to choose which department I wanted to join.
At the age of 24, I was expected to make a career-defining choice that would set the trajectory for the rest of my career — or at least the rest of my legal career.
This ritual still occurs at many major law firms, and it’s a prime example of the culture of specialization.
Our culture reveres people who pursue a single-minded path as focused, dedicated, and committed. Specialists are viewed as masters of their craft. They become sought-after experts.
Generalists, on the other hand, often have a reputation as being “jacks of all trades, master of none.”
They are derogated as dabblers, flighty, and uncommitted. The implication is that don’t have the willingness to commit to one path or capacity for the depth that specialization entails.
The Generalist Path
Contrary to this common myth, the generalist does have a path. It just doesn’t look like the single-minded, narrow pursuit that is most-often lauded in our culture.
Let’s go back to my career-defining choice.
At the time I was a summer associate, my law firm had a department called Trade Practices and Regulatory Law. It was a rare find in a top law firm: a mix of transactional work and litigation, focused on an array of subject areas.
We were the bridge between various departments in the firm. You might say we were generalists.
In my 7 years at the firm, I worked on matters across a wide range of subject areas: anti-trust, false advertising, intellectual property, sweepstakes law, sports law, first amendment matters, and more. Some of my matters involved counseling, others involved litigation, and others involved transactional work.
Each client I served, and each case on which I worked, allowed me to learn about and develop expertise in a new area of law and the underlying substance.
The approach was client-first. What was the issue for the client and what approach would best resolve it?
I took that approach to my career as a real estate agent, in which I work equally with buyers, sellers, and investors across all neighborhoods of New York City.
I quickly realized that the biggest issues my clients faced was not the logistics of the home buying or selling process, but the emotional components: clarifying values, determining what they wanted, making decisions, and navigating the waves of the various life events that precipitated their moves.
This led me to coaching, where, again, I’ve resisted the urge to niche. While on the surface I may appear to be a “business and productivity” coach, it’s more complex and nuanced. I could easily classify as a parenting coach, lifestyle coach, or relationship coach.
Beneath the surface, the fundamentals are the same: meeting my clients where they are, understanding their motivational drivers, and seeing their patterns.
I’ve coached CEOs and full-time moms, solopreneurs and team leaders, and can tell you this: under the surface of their titles, the issues they face are the same.
As a yoga teacher, I teach every style of class, from hot power to restorative.
A Non-Linear Path
Along the way, I’ve made space in my life to learn about things that interest me and pursue those interests. Even as a big law associate, I made time for a photography class, in which I learned the now-ancient process of developing my own film. I took a professional baking class.
I found a love for flying trapeze, circus arts, and weightlifting.
I’ve studied esoteric traditions like Tarot, astrology, energy healing, and Kabbalah and “practical” topics like coding, human anatomy, and biomechanics.
I’ve served on benefit committees and planned major fundraisers; I’ve gained large-scale event experience through volunteering at Tony Robbins events. I’ve helped people take big leaps and walk across fire.
The Detours are Fueling Stations
From the outside, it might seem like some of my pursuits have been diversions. After all, how do any of these things “get me further down the path?”
To be sure, over the past two decades I’ve had moments where I might have described my “career path” as being “littered with detours.”
But more recently, I’ve realized that they haven’t been detours at all. Instead, I’ve come to see them as fueling stations.
Each course of study or side project has been a way to fill my enthusiasm tank, as well gain new knowledge and experiences.
The relevance of these ventures may not have been obvious at the time — some still may not be obvious — but each is a piece in a larger puzzle.
Far from detracting from any single-focused expertise, they have expanded my mastery life and people. Each fueling station has introduced me to a new “language,” that I can use to connect with others, to build rapport and trust that leads to generative collaborations.
Skills for the Future of Work
In an era where the landscape of “work” is shifting beneath our feet, I have acquired the most crucial skills of all: versatility, agility, an appreciation for context, and the ability to see patterns across a range of areas.
I speak the “languages” of many disciplines with enough fluency to fit in across a range of communities. I can meet people where they are and translate from one realm to another. I’m equally comfortable in a weight room as in a board room, in a group of moms as in a group of CEOs, in the company of Gen Z and boomers.
From the outside, my path may look scattered, unfocused, and lacking direction. But, my refusal to pick one lane has given me wide-ranging experience and expertise that allows me to bridge gaps. serve as a translator across more niche experts who are deep in their silos.
Because of the breadth of my knowledge base, I see the patterns that others miss. I’m able to drill down to a cause of a problem faster than most “experts.”
Specialists vs Generalists: Tunnels vs Bridges
The specialist’s path is like a tunnel: deep, focused, with no daylight coming in. Specialists often don’t see what exists beyond the realm of their domain.
The generalist’s path is more like a bridge, spanning disciplines, perspectives, and people.
In the landscape of life, the specialist builds depth, while the generalist builds dimension.
To be clear, we need both.
In a world that is increasingly complex, siloed, and rapidly evolving, we need translators, connectors, and integrators —people who can move between worlds, spot the invisible patterns, and synthesize what others can’t yet see.
Generalists may not have singular title or a neat elevator pitch. Our path may look messy and nonlinear.
That’s simply the nature of the generalist’s path.
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