blue and green peacock feather

// Note: This was first published in August 2019 on LinkedIn

A few months ago, my mother recommended that I pick up David Epstein’s Range: Why Generalists Triumph in a Specialized WorldIt took me awhile to get around to it, but boy, am I glad I did. This book has fundamentally changed not only how I view myself, but also how I can best frame my diverse range of experiences.

If you look at my LinkedIn profile, you’ll notice a trend. In the 20 or so years I’ve been a working adult (God, that makes me sound old), I’ve had 12 jobs, across 5 different industries. I started out in tech support, was a researcher (including patent prior art research, general legal research and competitive intelligence at various times in my life), a journalist, a lawyer, an information security consultant, and twice, a business owner. And now, I’m straddling the fence again, working on honing my skills in two radically disparate career paths — threat intelligence and being a professional beer snob (aka, a beer sommelier). While the latter might remain more of an avocation, rather than a vocation, on paper, I look like a mess. But here’s the thing: In this economy, my range is a good thing, not a liability.

Every Job Interview I’ve Ever Had is Story Time

Since I’ve taken on so many different roles, that necessitates job interviews, and I always get asked some version of the same question: Why have you jumped around so much?

Although sometimes the answer is a question of company fit (e.g., I’ve learned that I truly do better at small- to midsize firms, rather than larger institutions), the truth is that my interests are wide, and have changed and adapted over the years. It’s not that I get bored, per se, but rather, that my passions get redirected as I find new experiences, explore novel problems (both within an organization, and external to it), and identify opportunities where I can make a real difference. I’m also a bit of a new junkie — I thrive on parachuting into a situation where I’m aware of a given problem–but by no means a specialist–and offering an outside perspective that bridges the knowledge I’ve acquired across many different industries.

In Range, Epstein talks about kind versus wicked learning environments, a concept coined by Robin M. Hogarth, Tom├ís Lejarraga, and Emre Soyer in their 2015 paper “The Two Settings of Kind and Wicked Learning Environments.” In kind learning environments, skills can be learned through experience, and future decisions can be guided by patterns and past results. Epstein uses chess as a frequent example here. The rules of chess are finite, and the sum total of effective strategies is learnable. Playing enough chess can help you reach mastery by learning the patterns of successful chess games (this is frequently referred to as the 10,000 hours rule).

By contrast, wicked learning environments, there’s a mismatch between outcomes and information. For example, Hogarth et al cite the case of an early 20th century physician who was amazingly prescient in accurately diagnosing typhoid fever. Since he believed that examining the tongue of his patients was key, he always palpated patients’ tongues before making his forecast. His diagnosis was almost always correct, precisely because he was the carrier. In this case, the feedback confirmed his diagnosis, but the underlying cause was missed.

It also bears out in another case, that I found extremely on-point: the difference between classically-trained versus improvisational musicians. I’ve been a student of the piano since the age of 8. I always enjoyed piano, even piano theory, but I hated the standard practice of memorizing Bach and Mozart. In fact, I hated it so much, I almost gave up on the instrument, until two things happened. First, my mother found me an amazing teacher who taught me the Circle of Fifths and jazz. Second, I began playing a variety of piano-adjacent instruments (marimba, vibraphone, glockenspiel, bells). Learning how to adapt the theory of what I’d previously learned both through improvisation, and to those new instruments, not only broadened my range, but it also renewed my love of music. I still play to this day, though now I’ve picked up the ukulele.

Analogies are Everywhere

The second point that Epstein hit on that really resonated with me, is the idea that the best generalists are analogists–finding answers to problems in one domain by looking for common elements in other domains.

One of the best things I got out of law school was the ability to think like a lawyer–and specifically, the ability to analogize. In law school, you realize that the law is often a wicked learning environment–thorny legal questions rarely have well-defined answers (e.g., how does one apply the concept of privacy to the internet, is AI-generated IP protectable, and who owns it?). Even though I don’t practice law, I find that I resort to analogy constantly in my life–applying concepts I learned as a journalist to my researching process, or my legal views on risk to my work as a cybersecurity analyst. And I routinely use analogy to translate hard concepts across fields between technical and non-technical audiences–a skill I had to patiently learn when helping people get on the internet using a 56k modem back in 1997.

Analogies also allow me to identify not only gaps, but solutions to problems that are often much more challenging for my specialist colleagues to see. Robert M. Lee, of Dragos Security, teaches a great course on Threat Intelligence for SANS. In his course, he spends a decent segment of time talking about how diversity of thought and experience is critical in the development of a good analyst team. Diversity of thought and background not only provides fresh insight, but it also helps to overcome many of the cognitive biases that plague specialist-driven groups. After all, if everyone on your team is an expert on Russia, they’re more likely to default to the conclusion that a given attack is Russia-based, even if it’s contrary to evidence.

Always Be Open

Epstein also argues in favor of late-bloomers–those who find their calling, often after exploring many different possibilities over those who specialize in one thing. My favorite example of this late-bloomer phenomena was his story of Frances Hesselbein, who at the age of 60, became CEO of the Girl Scouts of America, despite only limited (paid) leadership experience. She went on to revitalize the Scouts, diversifying and modernizing what had been a stagnating organization.

I’ve gotten a lot out of Epstein’s book, and the anecdotes he shares. It’s encouraging to see that my love of openness, new experiences, and a willingness to dive into ambiguity and turbulent challenges have given me a novel view of the world, one less encumbered by many of the pitfalls of specialization. As Epstein notes, we need both specialists and generalists to drive innovation, especially as the world shifts ever more into wicked learning systems.

While I expect that my LinkedIn profile will continue to lead to story time in interviews, I hope that the story I tell will continue to convince hiring managers that my range is a strength for their organization, not a weakness to overcome.