The Dilemma of being a Generalist

The age-old question persists: is it better to be a generalist, possessing a wide range of knowledge and skills, or a specialist, with deep expertise in a specific area? Both sides have passionate advocates, and the "right" answer often depends on the context. I want to dive deeper and explore the nuances of each side.

The Case for Generalists: Thriving in a "Wicked" World

The book Range by David Epstein makes a compelling case for generalists, arguing that they are particularly well-suited for today's complex and rapidly changing world. The core of the argument hinges on the distinction between "kind" and "wicked" learning environments:

• Kind Learning Environments: These environments have clear rules, consistent patterns, and rapid feedback loops. Think of chess or golf, where the rules are fixed, and the consequences of actions are immediately apparent.

• Wicked Learning Environments: These environments are characterized by unclear or shifting rules, incomplete information, and delayed or ambiguous feedback. Much of the modern professional world falls into this category.

Range asserts that generalists thrive in wicked environments because their breadth of knowledge allows them to adapt to ambiguity, connect seemingly disparate ideas, and navigate uncertainty more effectively.

The Generalist's Learning Advantage

Generalists often embrace learning methods that, while initially feeling slower and more challenging, lead to deeper and more durable understanding:

• Interleaving: Mixing different topics or skills during study, rather than focusing on one at a time.

• Spacing: Revisiting material after breaks, rather than cramming.

Match Quality and Exploration

"Match quality" refers to the alignment between an individual's abilities, interests, and their chosen field. Research suggests that exploring different areas before specializing often leads to higher match quality and better long-term career outcomes.

Innovation and Problem-Solving

Generalists are often better equipped to:

• Synthesize knowledge from different domains, leading to innovative solutions.

• Make more accurate predictions due to their broader perspective.

• Adapt to novel situations and abandon ineffective approaches more readily.

The Rise of the Generalist in the Post-Pandemic Workplace

The O.C. Tanner Global Culture Report highlights a trend: the increasing demand for generalists in the modern workplace. The report emphasizes that the "fluid" and "unsure" nature of the post-pandemic world favors individuals with a diverse skill set.

Google's hiring practices are cited as an example. They prioritize hiring "smart generalists" who can adapt to changing company needs, rather than individuals with narrow, specialized expertise.

The Downside of Generalism (and a Counterintuitive Truth)

Despite the apparent advantages, the O.C. Tanner report also reveals a less rosy reality: many generalists feel unsupported and undervalued. Their contributions may be less visible than those of specialists with clearly defined roles and accomplishments.

However, a 10-year study of 17,000 executives found that over 90% of CEOs had broad management experience. These future CEOs often made seemingly lateral or even "backward" career moves to gain diverse skills, ultimately propelling them to the top.

This highlights a crucial point: Optimizing for short-term gains (e.g., prestige, immediate recognition) can undermine long-term development. The path of the generalist may be less linear and less immediately rewarding, but it can lead to greater success in the long run.

The Perils of "Generalist Disease": Chasing Breadth and Prestige

Many individuals, in their quest for career success, fall prey to what can be termed "Generalist Disease." The hallmark symptom is optimizing for optionality at the expense of genuine passion and deep expertise.

Symptoms of Generalist Disease

• Chasing Breadth: Seeking exposure to as many industries and functions as possible, without developing deep expertise in any.

• Chasing Prestige: Prioritizing impressive-sounding titles and company logos over meaningful work.

Fields like consulting, banking, private equity, and more recently, product management and venture capital, often attract individuals with Generalist Disease. Top MBA programs can also exacerbate the condition.

These paths often create an illusion of progress. Your resume looks impressive, your parents are proud, and you might be making good money. But genuine fulfillment and long-term career satisfaction may remain elusive.

After accumulating several impressive lines on your resume, the promised "amazing options" often fail to materialize. You may feel stuck, trapped in a cycle of superficial breadth.

Goal Seeking: From Generalism to Specialization

A wise professor once offered this framework:

• First 10 years: Learn what you want to do.

• Next 10 years: Become great at it.

• Final 10 years: Make an impact and make money.

While not a rigid timeline, it highlights an important truth: generalism is not the ultimate goal; it's a means to an end. It's a tool for exploration, for discovering your true passions and aptitudes.

Ultimately, you need to specialize to build real leverage and achieve significant impact. This requires the opposite of maximizing optionality; it means deliberately removing options from the table.

Early in your career, chasing breadth and prestige can be beneficial. It allows you to explore different paths and opens doors to opportunities you might not have otherwise considered.

The "Explore/Exploit" Trade-Off

Recent research by Dashun Wang and colleagues further supports the value of exploration. Their study of artists, film directors, and scientists found that a period of broad exploration consistently preceded a "hot streak" of high-impact work.

• Explore: Trying new things, seeking new knowledge, experimenting.

• Exploit: Leveraging existing knowledge and skills to maximize results.

The key is finding the right balance. However, in our pursuit of early success, we often rush into "exploit" mode, neglecting the crucial "explore" phase.

Curtailing exploration can be particularly detrimental in a world of rapidly evolving technology, where continuous learning and adaptation are essential.

However, the value of breadth and prestige diminishes rapidly. The kind of breadth gained in fields like consulting is often too superficial to be truly informative. And prestige becomes a tool employers use to retain insecure individuals in jobs they don't genuinely enjoy.

If you find yourself in a traditionally generalist career path, be mindful of the point at which your learning shifts from genuine exploration to mastering the specific job itself (e.g., becoming a specialist in consulting, not a specialist in the industries you consult for). For many, this turning point occurs around the 2-3 year mark.

Chasing Aptitude and Enjoyment: The Path to Mastery

The antidote to Generalist Disease is to chase aptitude and enjoyment.

• Aptitude: Identify areas where you have a natural talent or a knack for learning quickly.

• Enjoyment: Find work that you genuinely enjoy, work that you're willing to invest significant time and effort into.

When you find the intersection of aptitude and enjoyment, you create a powerful compounding advantage. You'll naturally get better at the work, which will lead to greater enjoyment, further fueling your improvement.

This path often requires trading a steady, linear career trajectory for one that is initially more volatile. You might need to take seemingly lateral or even "downward" moves to explore different areas and find your true calling.

Hard Pills to Swallow: The Price of Finding Your Path

Two major obstacles often prevent individuals from escaping Generalist Disease:

1. The Willingness to Take "Steps Back": You must be willing to make career moves that may appear less prestigious or less lucrative in the short term in order to gain the experience and knowledge needed for long-term success.

2. The Grind: Once you've identified your area of focus, you need to embrace the "craft"—the unsexy, repetitive, and often tedious tasks that are essential for mastery.

Examples:

• Leaving a prestigious private equity job for a less glamorous role at a startup.

• A product manager spending countless hours talking to customers and collaborating with the engineering team, rather than acting like a "mini-CEO."

• A strategy professional immersing themselves in data and customer feedback, rather than just pontificating from on high.

The Best of Both Worlds: Long-Term Rewards

Taking a non-linear path, embracing the grind, and focusing on aptitude and enjoyment can be initially unsettling. But ultimately, it leads to greater happiness, fulfillment, and, often, even greater conventional success.

It's worth noting that the principles of deliberate practice, as outlined by Anders Ericsson in Peak, are most readily applicable to fields with well-established rules and clear paths to mastery (e.g., chess, music, sports). Many modern professions, including those in business and technology, are less structured, making the application of deliberate practice more challenging.

In conclusion, the generalist vs. specialist debate is not about finding a universally "right" answer. It's about understanding the trade-offs, recognizing the different phases of career development, and making intentional choices that align with your long-term goals and aspirations. Embrace exploration, be wary of Generalist Disease, and ultimately, find the path that allows you to combine your aptitude and enjoyment to achieve lasting impact.

PS: The answer that I am leading to is a T-shaped person - deep expertise in 2-3 areas and broad expertise in many more. With the advent of Gen AI - the broad expertise is democratized and what is going to stand out is experiences.

References

Range by David Epstein