Why Do Your Best Problem Solvers Keep Leaving

Chris Brown

29 Sep 2025 — 9 min read

Understanding the Polymath Paradox in Modern Business

A comprehensive guide to identifying, retaining, and leveraging multi-domain expertise in insurance and technology organisations

The Misunderstood Quote That Defines a Misunderstood Workforce

"Jack of all trades, master of none."

If you've heard this phrase thrown around your office, usually with a dismissive sneer, you're witnessing a 400-year-old character assassination still claiming victims today.

Here's what most people don't know: the phrase was originally a compliment. When it first appeared in 1612, being a "Jack of all trades" meant you were versatile, capable, and valuable. The "master of none" sneer was added in the 18th century by specialists seeking to protect their turf [1]. The complete version that's emerged in modern times? "A jack of all trades is a master of none, but oftentimes better than a master of one", a recent addition that attempts to reclaim the original positive meaning.

Contrary to popular belief, this isn't from Shakespeare. But here's the delicious irony: Robert Greene used the Latin equivalent "Johannes factotum" in 1592 to attack someone he saw as an "upstart crow" dabbling in too many areas. His target? William Shakespeare himself, who went on to revolutionise theatre, poetry, and the English language by refusing to stay in his lane [1].

This historical weaponisation of the phrase perfectly captures how modern organisations treat their polymaths: with suspicion, resentment, and systematic undermining. Yet these same organisations desperately need exactly what polymaths offer.

Executive Summary

Your most valuable employees might be the ones who don't fit neatly into boxes. These polymathic individuals, those with genuine expertise across multiple domains, can literally perform the work of 2-3 specialists, potentially save organisations millions while driving innovation through cross-domain insights.[2] [3]

Yet nearly 9 out of 10 high achievers report their achievements are undermined in the workplace.[4] For polymaths, this discrimination is amplified. They're viewed as threats by specialists, dismissed as "interfering know-it-alls," and systematically pushed out of organisations that desperately need their skills.

This isn't about defending generalists or justifying career meandering. It's about recognising that the technology sector is haemorrhaging its most versatile problem-solvers and providing a roadmap for both organisations and polymaths to change this dynamic.

Understanding the Modern Polymath

From Renaissance to Revenue

The term polymath dates from 1624, though the concept extends back to Renaissance Italy, where Leon Battista Alberti declared that "a man can do all things if he will".[5] Leonardo da Vinci remains the archetypal example, excelling as a painter, engineer, scientist, and inventor through what biographers called "unquenchable curiosity" and "feverishly inventive imagination" [5].

Ironically, even Shakespeare, now considered the greatest writer in the English language, was mocked as a "Johannes factotum" (Latin for Jack of all trades) by his contemporary Robert Greene, who sneered at this "upstart crow" for daring to write, act, and produce.[1] Greene's attempt to keep Shakespeare in his lane failed spectacularly. The lesson? Those who excel across domains have consistently challenged those who define themselves by a singular expertise.

But today's business polymath isn't painting the Mona Lisa between engineering sessions. They're the CTOs who started in sales, understand compliance, and can model financial scenarios. They're the actuaries who code, design user experiences, and negotiate vendor contracts. They're the executive who can step into any departmental crisis and fix it, not just coordinate the fix.

What Sets Them Apart

In contemporary organisations, a polymath represents something specific:[3]

Multi-domain expertise: Genuine depth across 3+ business functions (not YouTube University certificates)
Execution capability: Can DO the work, not just manage those who do
Cross-pollination ability: Applies manufacturing principles to software deployment, or insurance concepts to SaaS architecture
Systems thinking: Sees the cascade effects that siloed specialists miss

Think of them as intellectual Swiss Army knives, but each tool is professional grade, not a toy.

Identifying Genuine Polymaths

Green Flags - True Polymaths:

Held successful roles across unrelated departments with measurable achievements
Solve problems using unexpected analogies that work
Get restless once they've mastered something ("Now what?")
Can cover multiple roles during crises without the wheels falling off
Ask naive-sounding questions that expose fundamental flaws
Have serious hobbies entirely unrelated to work (the CFO who rebuilds engines, the developer who's a certified sommelier)

Red Flags - Pretenders:

Heavy on LinkedIn buzzwords, light on specifics
"I could do that" without ever having done it
Defensive when pressed for technical details
Broad exposure but no resounding victories

The Business Case - Why Polymaths Matter Now

The Numbers Don't Lie

Research from MIT found that Nobel Prize-winning scientists were 25 times more likely to engage in artistic activities than the average scientist. The correlation isn't a coincidence; diversity of thought drives breakthrough innovation.[6]

In business terms:

Cost Reduction: One polymath can replace 2-3 mid-level specialists in small to medium organisations [2]
Innovation Acceleration: Cross-domain thinkers identify novel solutions by combining methodologies from different disciplines [3]
Succession Protection: Built-in redundancy across critical functions [2]
Translation Elimination: No more Chinese whispers between IT and business

The Specialisation Trap

While specialists provide crucial depth, over-specialisation creates expensive problems:

The Silo Tax: Marketing optimises for leads that Sales can't close, that Operations can't deliver
Innovation Blindness: Solutions trapped within disciplinary boundaries (why did it take a computer company, Apple, to revolutionise the phone industry?)
Single Points of Failure: Lose your only Kubernetes expert and watch your entire containerised infrastructure grind to a halt
Communication Overhead: Armies of project managers to get departments talking

The Dark Reality - Why Organisations Reject Polymaths

Tall Poppy Syndrome on Steroids

Tall poppy syndrome, the tendency to criticise, attack, or resent someone due to their success, particularly affects high achievers who stand out [4][7]. For polymaths, this amplification is exponential. They don't just excel in their lane; they excel in multiple lanes simultaneously, triggering both envy and a sense of existential threat among specialists.

The 2018 Canadian workplace study found systematic undermining of high achievers [4], but polymaths face unique challenges:

They expose incompetence simply by existing
Their suggestions feel like invasions of territory
They make specialists question their own value
They destabilise carefully constructed hierarchies

The Uncomfortable Truth About Superiority

Let's address the elephant in the room: polymaths can be insufferable. When you see solutions that others miss, spot incompetence that others accept, and fix problems that others can't even define, humility becomes challenging.

This creates a destructive cycle:

Recognition: Polymath identifies systemic inefficiencies
Intervention: Attempts cross-functional improvements
Resistance: Specialists feel threatened, push back
Frustration: Polymath becomes condescending ("How can they not see this?")
Isolation: Labelled as "difficult" or "not a team player"
Exit: Valuable employee leaves or is managed out

The Bottleneck They Create

Polymaths often sabotage themselves by becoming indispensable:

Everything flows through them because "it's faster if I do it"
They hoard challenging work while resenting routine tasks
Documentation is sparse because they'll "always be here"
They become frustrated with "incompetent" specialists who can't keep up

Research shows that sustained workplace bullying can actually change personality traits over time, with targeted individuals experiencing significant reductions in extroversion and conscientiousness [7]. For polymaths who already face systemic undermining, this creates a vicious spiral of isolation and reduced effectiveness.

However, not everyone claiming to face these challenges is a genuine polymath. The business world is full of pretenders.

Separating Wheat from Chaff

The Dunning-Kruger Epidemic

Not everyone claiming broad expertise is a polymath. The business world is full of people who've mistaken exposure for expertise, particularly in consulting, where surface knowledge is weaponised with PowerPoint.

Research on "illusory superiority" reveals that those claiming the broadest knowledge often exhibit the most substantial overconfidence bias. They literally don't know what they don't know.

The Litmus Tests

True Polymaths Will:

Eagerly dive into technical details
Admit knowledge gaps without defensiveness
Provide specific examples of cross-domain innovation
Be recognised by specialists in multiple fields
Show continuous learning across disciplines

Pretenders Will:

Deflect technical questions to "strategic thinking"
Use complexity to hide ignorance
Name-drop without substance
Focus on appearing bright rather than solving problems
Claim expertise without evidence

The LinkedIn Problem

Social media has made everyone a "polymath thought leader". Real polymaths rarely use the term; they're too busy actually doing the work across domains to worry about personal branding.

Survival Guide for Polymaths

The Art of Not Being Hated

Pick Your Battles Wisely. Not every inefficiency needs your attention. Focus on high-impact improvements within your official remit before venturing into others' territories.

Build Bridges, Not Empires

Frame insights as questions: "Have we considered...?" not "You should..."
Credit specialists liberally: "Building on Sarah's excellent analysis..."
Position as translator, not competitor: "Let me connect these dots..."
Document everything: Prove value through evidence, not assertion

Manage Your Frustration. Yes, you see incompetence everywhere. No, you don't need to fix it all:

Specialists have depths you might miss
Organisational antibodies exist for reasons
Your perspective is valuable, but not omniscient
Sometimes "good enough" is good enough

Finding Your Niche

Position yourself where boundary-spanning is valued:

Chief of Staff: Explicitly cross-functional
Innovation Lead: Meant to break silos
Transformation Roles: Change requires polymath thinking
Founder/Entrepreneur: Where wearing all hats is expected
Crisis Management: When standard approaches fail

When Leadership Is the Problem

When you spot incompetent leadership (and you will), strategy matters:

Document Everything: Build data-driven cases, not emotional arguments. "Project delays increased 47% under the current structure" beats "This person is useless".

Build Coalitions: Other competent people see it too. Find them carefully, through one-on-one conversations over coffee, rather than group complaints.

Leverage Your Advantage: Translate the problem into multiple languages. Technical debt can become a compliance risk, leading to customer churn and ultimately eroding shareholder value.

Know When to Leave: Some organisations are structurally incapable of valuing polymaths. Please don't waste your gifts on those who can't see them.

Organisational Playbook

Finding Hidden Polymaths

They won't call themselves polymaths. In interviews, probe deeper [8]:

"Tell me about your interests outside work"
"What's the most unusual connection you've made between different fields?"
"When have you successfully worked far outside your job description?"
Look for the engineer with an MBA, the accountant who codes, the salesperson with patents

Creating the Right Environment

Structure for Success: [2][3][9]

Rotation Programmes: Formalise their boundary-crossing
Innovation Time: Google's 20% rule works for polymaths
Cross-Functional Teams: Their natural habitat
Problem-Solving Squads: Complex challenges requiring diverse thinking
Knowledge Platforms: Capture cross-domain insights

Prevent Self-Destruction:

Require documentation (they hate it but need it)
Pair with specialists for knowledge transfer
Set boundaries on scope creep
Create succession plans for their roles
Regular rotation to prevent stagnation

Managing the Dynamics

Cultural Interventions:

Explicitly value both depth and breadth
Reward collaboration over competition
Address tall poppy syndrome in culture training
Celebrate cross-functional wins publicly
Create "safe spaces" for challenging orthodoxy

Where They Thrive: [9]

Startups and scale-ups (multiple hats required)
R&D departments (innovation focus)
Consulting firms (client variety)
Digital transformation initiatives
Turnaround situations

The Strategic Advantage

The Bullshit Detection Superpower

Polymaths are organisational bloodhounds for nonsense:

They recognise recycled failures pitched as innovations
They spot when complexity masks incompetence
They see through vendor smoke and mirrors
They identify when jargon replaces substance

In due diligence, a polymath can save millions by asking the right questions. In vendor selection, they prevent expensive mistakes. In strategy, they stop you from reinventing square wheels.

The Innovation Engine

Cross-domain thinking drives breakthrough innovation:[2][3],

Insurance + Gaming = Gamified risk assessment
Manufacturing + Software = DevOps revolution
Psychology + Technology = Behavioural design
Biology + Business = Organisational biomimicry

Specialists optimise within boundaries. Polymaths eliminate the boundaries.

The Future of Work

We live now in a world that can be characterised as connected, complex, chaotic, and faster than ever before. In this environment, the ability to adapt, learn, and apply knowledge across domains isn't just valuable, it's essential.[9]

AI will replace narrow specialists faster than versatile polymaths. When algorithms can diagnose better than doctors and calculate better than accountants, the humans who survive will be those who can do what AI can't: make unexpected connections across domains.

Conclusion: Reclaiming the Crown

Remember that "upstart crow" Robert Greene tried to put in his place? Shakespeare didn't just survive the attack; he became immortal. The "Johannes factotum” [9] who dared to write, act, and produce revolutionised human expression itself.

Four centuries later, we're still playing the same game. Specialists still sneer "Jack of all trades, master of none" at those who dare to cross boundaries. Organisations still push out their most versatile minds while wondering why innovation stagnates.

But here's what's different: in an era of digital transformation, where companies need to think like tech companies, and tech companies need to understand regulated markets, being "master of one" is increasingly a liability. When AI can out-specialise any specialist, the humans who survive will be those who do what AI can't: make unexpected connections across domains.

The organisations that understand this aren't just collecting polymaths like trading cards. They're building systems that leverage polymathic talent despite its challenges. They recognise that yes, polymaths can be difficult, create bottlenecks, and frustrate specialists. However, they also drive innovation, solve previously unsolvable problems, and identify opportunities invisible to siloed thinking.

For the insurance and technology sectors specifically, polymaths aren't optional extras. They're competitive necessities. The question isn't whether your organisation needs them. It's whether you're structured to recognise and retain them before your competitors do.

And for the polymaths reading this: You're not broken. You're not "too much". You're not a "Jack of all trades, master of none." You're exactly what forward-thinking organisations need, a master of integration in a world that desperately needs connection.

Find the companies smart enough to realise it. Or better yet, build your own.

References

Greene, R. (1592). Groats-Worth of Wit. Referenced in "Jack of all trades" etymology. https://www.phrases.org.uk/meanings/jack-of-all-trades.html
TD.org (2020). "Polymathy: A New Kind of Diversity". https://www.td.org/insights/polymathy-a-new-kind-of-diversity-that-could-take-your-business-to-the-cutting-edge
Qandle HR Blog (2024). "Polymath: The Hidden Superpower Every Workplace Needs". https://www.qandle.com/blog/polymath/
Medical News Today (2024). "What to know about tall poppy syndrome". https://www.medicalnewstoday.com/articles/tall-poppy-syndrome
Burke, P. (2020). The Polymath: A Cultural History from Leonardo da Vinci to Susan Sontag. Yale University Press. For book details see: https://yalebooks.yale.edu/book/9780300260465/the-polymath/ or Wikipedia's polymath entry: https://en.wikipedia.org/wiki/Polymath
Root-Bernstein, R., Allen, L., Beach, L., et al. (2008). "Arts Foster Scientific Success: Avocations of Nobel, National Academy, Royal Society, and Sigma Xi Members". Journal of Psychology of Science and Technology, 1(2):51-63. https://www.researchgate.net/publication/247857346_Arts_Foster_Scientific_Success_Avocations_of_Nobel_National_Academy_Royal_Society_and_Sigma_Xi_Members
Psychology Today (2025). "3 Signs That You're Facing Tall Poppy Syndrome". https://www.psychologytoday.com/us/blog/social-instincts/202502/3-signs-that-youre-facing-tall-poppy-syndrome
Majer Recruitment (2020). "Why You Should Hire a Polymath". https://www.majerrecruitment.com.au/why-you-should-hire-polymaths/
Kundu, A. (2021). "Future of Work and Multipotentialites". https://anupamk.medium.com/the-future-of-work-and-multipotentialites-5f11708b9e40