Jack of All Trades: Underrated or Overwhelmed?

Being a "jack of all trades" isn't a flaw—it's a superpower. Here’s how to leverage interdisciplinary experience for team leadership and impact.

NOTE: We’re trying audio! Below you’ll find two versions. Version 1 is me reading the newsletter “as is”, no variations. Version 2 “the riff version” is me mostly reading the newsletter but I also try a more conversational tone—i.e., I try to stay true to the newsletter while pretending as if I’m having a conversation with someone. Both are awkward—I’m experimenting! I welcome your feedback. Thanks!

Audio Version 1

Audio Version 2

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Today’s newsletter was inspired after an illuminating conversation with Bob Gilbreath. We covered a lot of ground and I look forward to many more exchanges in the future. He’s a brilliant storyteller and acute listener—a rare and powerful combination; I highly recommend his Substack “The Workaround”. He was also the catalyst behind me adding audio to my Substack; please note that my “rig” is unsophisticated and this is my first time recording myself—so please be gentle but be specific with the feedback! Anyway, enjoy today’s newsletter and be on the lookout for audio recordings of the previous newsletters as I’m told audio is a “thing”.

Sigh…I sound like such a luddite.

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The Phrase That Won’t Quit

“Jack of all trades, master of none” is often used as a backhanded compliment—a way to say, “You’re good at a lot of things, but great at nothing.” And yet, I can’t help but wonder: is this phrase a misfire?

If you’ve had a career like mine—spanning industries, roles, and functions—you’ve probably heard this phrase before. I’ve been a product manager in the military, a finance leader in both corporate finance and manufacturing / supply chain finance, a marketer in consumer goods, and a strategist at various levels. And the results? Fairly consistent, if not exemplary (I have proof!), across the board.

So, is being a jack of all trades a good thing? A bad thing? Or something more nuanced? Let’s dig into this for new and aspiring leaders trying to navigate their own career path and development plan.

The History of "Jack of All Trades"

Here’s something most people don’t know: the full phrase is often misquoted. It originally went:

"A jack of all trades is a master of none, but oftentimes better than master of one."

The last part flips the meaning entirely. It suggests that versatility and adaptability are valuable—sometimes even more so than deep specialization. And in today’s rapidly changing world, this sentiment may ring truer than ever.

The Case for Being a Jack of All Trades

1. Adaptability in Complex Environments

   • In an increasingly interdisciplinary world, leaders who can think across functions and industries are better equipped to solve complex problems. According to research by the Harvard Business Review, generalists often outperform specialists in unpredictable environments because they can draw from a wider range of experiences and perspectives (Epstein, 2019).

2. Creative Problem-Solving

   • Interdisciplinary leaders excel at connecting the dots between disparate fields, sparking innovation. Think of Leonardo da Vinci, whose expertise in anatomy, art, and engineering led to groundbreaking inventions. Studies on innovation ecosystems suggest that the most creative solutions come from individuals who combine knowledge from multiple domains (Uzzi et al., 2013).

3. Leadership Perspective

   • As a team leader, understanding a variety of functions allows you to empathize with and support your team more effectively. You can bridge gaps between departments and foster collaboration because you’ve walked in their shoes—or at least understand their challenges and can speak in a “language” that resonates with them.

The Counterpoint: The Risk of Dilution

Of course, there are challenges to being a jack of all trades:

1. Depth vs. Breadth

   • Critics argue that versatility comes at the cost of expertise. A study by McKinsey & Company found that in highly technical fields, specialists are often preferred because their deep knowledge allows them to address specific, high-stakes challenges with precision.

2. Perception of Focus

   • Being versatile can sometimes make others question your focus or commitment. If you’re constantly pivoting, people may perceive you as indecisive or scattered.

3. Burnout Risk

   • Balancing multiple disciplines or responsibilities can lead to overwhelm, especially if you’re constantly expected to switch contexts and deliver measurable results across diverse areas.

So, What’s the Verdict?

For team leaders, the real value lies in how you use your versatility. Here are some actionable takeaways for turning “jack of all trades” into a strength:

1. Anchor Yourself in a Core Skill

   • While breadth is valuable, anchoring yourself in a core expertise provides a foundation to build from. For example, if your core is finance, let that inform your approach to marketing or strategy roles. Think of it as your home base.

2. Leverage Your Range

   • Use your interdisciplinary experience to ask better questions, see blind spots, and bring fresh perspectives to the table. Being a “translator” between functions can be a superpower in leadership.

3. Communicate Your Value

   • Frame your versatility as an asset. When discussing your experience, highlight how it allows you to bridge gaps, innovate, and adapt to uncertainty. People often need help seeing how breadth translates into impact—make it clear for them.

4. Keep Learning

   • Generalists who continue to develop new skills stay relevant longer. Don’t let versatility become complacency. Keep adding tools to your toolkit while staying sharp in your core areas.

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Final Thought

The truth is, being a jack of all trades is neither inherently good nor bad—it’s what you make of it. For leaders, especially new or aspiring ones, the ability to draw from multiple disciplines and connect the dots can be an invaluable asset.

So, the next time someone calls you a “jack of all trades,” embrace it. Just remember: the real power lies in knowing when to go wide and when to go deep.

Simple, not easy.

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References:

1. Epstein, D. (2019). Range: Why Generalists Triumph in a Specialized World.

2. Uzzi, B., Mukherjee, S., Stringer, M., & Jones, B. (2013). Atypical combinations and scientific impact. Science, 342(6157), 468-472.

3. McKinsey & Company (2020). The Future of Work: Specialization vs. Generalization in the Workforce.