“You’re a square peg trying to fit into a round hole” is a metaphor often used to describe individuals who don’t neatly fit into predefined roles or categories within an organization. While companies may claim to value diversity of thought and versatility, their structures and processes often favor those who can be easily classified as “one of these” or “one of those.” This approach, they argue, simplifies designing specific career pathways, streamlining hiring, and managing talent. However, it leaves those who excel in multiple areas—without being confined to a single specialty—struggling to find their place.
Contrary to the outdated notion of the “jack of all trades, master of none,” these multidimensional individuals bring unique value that organizations often overlook.
The truth is, innovation often happens at the intersection of skills—the generalist who understands technology and business, the marketer who grasps data and storytelling, the leader who can strategize and execute. Yet, instead of leveraging this breadth, companies often see it as a lack of focus.
This article explores the challenges faced by versatile professionals and why companies should rethink their rigid frameworks to embrace the “square pegs” who don’t fit neatly into round holes.
The Corporate Obsession with Specialization
In today’s fast-paced, highly structured corporate world, specialization is king. Companies often seek individuals who can be slotted into specific roles—data scientists, project managers, software engineers, or marketing specialists. Job descriptions are meticulously crafted with narrow skill sets in mind, and career progression is frequently tied to expertise in a single domain. This focus on specialization is driven by the belief that it fosters efficiency, clarity, and measurable outcomes. A software engineer writes code, a marketer drives campaigns, and a financial analyst crunches numbers—each role neatly defined, each pathway clear.
But what happens when someone doesn’t fit this mold? What about the professional who can code and craft compelling marketing strategies? Or the manager who excels at both technical problem-solving and stakeholder communication? These individuals, often described as “square pegs,” possess a breadth of skills that don’t align with the “round holes” of traditional corporate roles. Instead of being celebrated for their versatility, they’re often viewed as anomalies—too difficult to categorize, too complex to fit into a predetermined career track.
The phrase “jack of all trades” is frequently misapplied here. Historically, it referred to someone who dabbled in many areas without mastering any. But the square pegs I’m describing aren’t dilettantes. They’re individuals who are good at many things — not just passable, but genuinely skilled across multiple domains. They might be the engineer who can lead a cross-functional team, the designer who understands business strategy, or the analyst who can translate data insights into compelling narratives. These professionals don’t lack depth; they combine it with breadth in ways that challenge conventional corporate structures.
The Struggle of the Square Peg
Being a square peg in a round-hole world comes with real challenges. First, there’s the issue of recognition. Performance reviews and promotion criteria are often designed for specialists, rewarding those who deepen their expertise in a single area. A versatile professional might excel in multiple aspects of a project—say, by contributing to strategy, execution, and communication—but their contributions are often undervalued because they don’t fit neatly into one category. Managers may struggle to articulate their value in terms of traditional metrics, leaving them overlooked for promotions or raises.
Second, square pegs face constant pressure to “pick a lane.” I’ve heard this advice countless times: “Focus on one thing to advance your career.” While well-intentioned, it ignores the reality that some people thrive by leveraging their diverse skill sets. Forcing them to specialize can stifle their creativity and limit their potential. Imagine asking a professional who excels at both coding and user experience design to abandon one in favor of the other—it’s not just a loss for the individual but for the organization that could have benefited from their unique blend of skills.
Finally, there’s the challenge of belonging. Square pegs may struggle to find mentors or advocates who understand their value and can champion their growth.
The Value of Versatility
Despite the challenges, square pegs bring immense value to organizations—especially in today’s complex, rapidly changing world. Businesses face multifaceted problems that require creative, cross-disciplinary solutions. A professional who can bridge gaps between departments, translate technical concepts for non-technical stakeholders, or adapt quickly to new challenges is a tremendous asset. For example, during a product launch, a square peg might contribute to technical development, marketing strategy, and customer feedback analysis, ensuring a more cohesive and successful outcome.
Moreover, versatile professionals are often natural innovators. Their ability to draw from multiple domains allows them to see connections and opportunities that specialists might miss. In industries driven by disruption—think tech, healthcare, or sustainability—these individuals are uniquely positioned to drive progress. They’re the ones who can pivot between roles, learn new skills on the fly, and bring a holistic perspective to problem-solving.
The rise of agile methodologies and cross-functional teams further underscores the value of square pegs. In environments where collaboration across disciplines is critical, professionals who can wear multiple hats are invaluable. They can act as glue, holding diverse teams together and ensuring alignment across different functions.
Rethinking the Round-Hole System
If square pegs are so valuable, why do companies struggle to accommodate them? The issue lies in outdated systems that prioritize predictability over potential. To unlock the full value of versatile professionals, organizations must rethink their approach to talent management. Here are a few steps they can take:
- Redesign Job Roles for Flexibility: Instead of rigid job descriptions, companies should create roles that allow for fluidity. For example, a role like “innovation catalyst” could encompass responsibilities across strategy, execution, and communication, giving square pegs a clear place to thrive.
- Rethink Career Pathways: Traditional career ladders reward specialization, but companies can create alternative pathways that value versatility. This might mean promotions based on impact across multiple areas rather than mastery of one.
- Foster a Culture of Collaboration: Square pegs shine in environments that encourage cross-functional collaboration. By breaking down silos and promoting teamwork, companies can create spaces where versatile professionals feel valued and supported.
- Celebrate Diverse Contributions: Performance evaluations should account for the unique contributions of multidimensional professionals. Metrics like “cross-departmental impact” or “problem-solving versatility” can help quantify their value.
- Provide Mentorship and Advocacy: Square pegs need mentors who understand and champion their unique strengths. Leaders should be trained to recognize and nurture versatile talent, helping them navigate their careers within the organization.
Embracing the Square Pegs
The phrase “square peg in a round hole” is often used as a critique, implying that the individual needs to change to fit the system. But what if the system is the problem? In a world that demands adaptability, creativity, and collaboration, the square pegs—those who are good at many things—are not misfits but trailblazers. They challenge organizations to evolve, to rethink rigid structures, and to embrace the power of versatility.
For those who identify as square pegs, my advice is this: Don’t let the round-hole world diminish your value. Seek out environments that celebrate your multidimensionality, whether it’s a startup, a smaller more entrepreneurial organization, a forward-thinking company, or a role you carve out for yourself (this will be the subject of a later article). Advocate for your unique contributions, and don’t be afraid to push back against the pressure to “pick a lane.” Your ability to bridge gaps, connect dots, and adapt to challenges is a superpower—one that organizations desperately need, even if they don’t yet realize it.
And for companies, the message is clear: Stop trying to force square pegs into round holes. Instead, redesign the holes—or better yet, embrace the pegs as they are. By doing so, you’ll unlock a wealth of talent, innovation, and potential that can propel your organization forward in an ever-changing world.
This article was inspired by two enlightening conversations with incredible leaders yesterday and is dedicated to my amazing colleagues.
