Takes / Personal Growth
A jack of all trades, master of none, but oftentimes better than a master of one. Exploring why I believe strategic generalists are in a position to outperform specialists in today's complex world.
Investment Banker Turned Entrepreneur
In a world that increasingly rewards specialization, I've found myself questioning the conventional wisdom. The phrase "jack of all trades, master of none" has been used as a cautionary tale for centuries, warning against the perils of spreading oneself too thin. But what if this wisdom is outdated?
After spending years in investment banking, then pivoting to entrepreneurship and startup acceleration, I've observed something fascinating: the most successful people I know aren't specialists in the traditional sense. They're strategic generalists who understand how to connect disparate domains.
This isn't about being mediocre at everything. It's about understanding the marginal return on learning and recognizing when depth in one area yields diminishing returns compared to breadth across multiple areas.
Every skill follows a learning curve, but not all curves are created equal. The first 20% of learning any skill typically yields 80% of the practical value. After that, the marginal return on additional learning decreases dramatically.
Consider coding. Learning the basics of Python might take 3 months and enable you to automate tasks, build simple applications, and understand data analysis. Becoming an expert Python developer might take another 3 years, but the additional value you gain is often marginal for most business applications.
The strategic generalist recognizes this pattern and deliberately stops at the "good enough" level in most areas, then moves on to learn adjacent skills that compound their existing knowledge.
Here's where it gets interesting. When you understand multiple domains at a "good enough" level, you start to see patterns and connections that specialists miss. You become a translator between different worlds.
In my experience building startups, the most valuable insights often come from applying frameworks from one industry to solve problems in another. A marketing strategy from consumer goods can revolutionize B2B sales. A financial model from investment banking can optimize a SaaS business.
This cross-pollination of ideas is where breakthrough innovations happen. It's also where strategic generalists have their biggest advantage over specialists.
Think of your skills as a portfolio. Just like in investing, diversification reduces risk and increases potential returns. But unlike investing, in skills, you can actively choose what to learn based on strategic value.
The key is to identify skills that:
For example, learning basic psychology might take 6 months but enable you to understand customer behavior, negotiate better deals, and build more effective teams. The ROI on that learning is massive compared to spending 6 months perfecting your Excel skills.
Here's how I apply this framework in practice:
This approach has allowed me to build a diverse skill set that includes financial modeling, product design, marketing strategy, and team building. None of these skills are at an expert level, but together they create a unique combination that's highly valuable in the startup world.
In today's complex, interconnected world, the ability to connect ideas across domains is becoming increasingly valuable. While specialists will always have their place, strategic generalists have a unique advantage in:
The key is to be strategic about your learning. Don't just learn random skills. Build a portfolio of complementary abilities that work together to create something greater than the sum of their parts.
Remember: it's not about being mediocre at everything. It's about being good enough at the right things to create unique value through the connections you can make.
Investment Banker Turned Entrepreneur