“Tell me if anything was ever done…Tell me…Tell me…” – scribbled inside Leonardo da Vinci’s private notebook.

Leonardo Da Vinci is the quintessential Renaissance Man. He likely inspired the inception of the phrase itself. Yet in his quiet private hours, the man we call genius sat in despair of his countless incomplete and failed projects.

Da Vinci, one of the world’s most famous artist and inventor (and architect, urban planner, anatomist, pageantry designer, weaponry designer, geologist, etc.) was also a master procrastinator who questioned his ability to complete “anything.” Walter Issacson writes in his recent biography on da Vinci:

“As he approached his thirtieth birthday, Leonardo had established his genius but had remarkably little to show for it publicly.”

I love stories like these. For one, they bring genius down a level and say — hey, if da Vinci beat himself up for not completing “anything,” then maybe we all need to cool down on our own perceptions and expectations of ourselves.

Second, the way da Vinci approached his life and work is one that maybe we could – dare I say, must – adapt to future-proof ourselves for an ever-changing and uncertain world.

Becoming Leonardo

Leonardo da Vinci’s many interests and skills personifies a term I’ve learned of recently: Expert Generalist. Rather than possessing a singular skill or interest, the Expert Generalist dabbles in many disparate fields of knowledge, building up an abundant repertoire of skills and abilities.

Dilbert cartoonist Scott Adams calls this unique combination of skills a “talent stack.” To become extraordinary, Adams argues you have two paths:

1. Become the best at one specific thing.
2. Become very good (top 25%) at two or more things.

Adams’ unique talent stack – drawing, humor, business skills, and familiarity with corporate American humdrum – gave the world Dilbert.

Scott Adams, Dilbert

Da Vinci’s greatest insights and contribution were also born from his unique “talent stack” and reluctance to focus on one thing. He constantly linked two or more seemingly unrelated fields — technology and nature, pageantry and astrology, anatomy and art — to create the unique and valuable.

One example: da Vinci’s love of nature helped him invent sfumato, a technique of blurring tones and colors gradually into one another to produce softened outlines and hazy forms, eventually giving us Mona Lisa’s curious smile. Another example: da Vinci’s obsessive (and illegal) dissection of cadavers –– both human and animal –– gave him a deep understanding of bodies beneath the skin and enabled him to draw one of the most iconic works in human history: Vitruvian Man.

Issacson writes of Da Vinci’s time:

“This mixing of ideas from different disciplines became the norm as people of diverse talents intermingled.”

Da Vinci and the Future of Work

Maybe we’re entering a similar age. Maybe we’re already here.

A recent study by Upwork predicted freelancers to become the U.S. workforce majority within a decade, with “nearly 50% of millennial workers already freelancing.” Sounds crazy. But Seth Godin reminds us of what’s crazier:

“100 years ago, almost no one on earth had a job… This idea that you would go to a building where a stranger would tell you what to do all day was pretty alien. Now everyone has a job! That’s a massive shift.

…Now that we’re coming out on this other side, where the internet is changing so much of what people do. That perfect world of the 60s and 70s we grew up with with endless industrial growth is going away. And it’s being replaced with something that is completely impossible. Which is one guy, by himself in a room, can press one button and thousands of people around the world can support a project that lets me go build it for a year…and I didn’t have to take out anyone’s permission! That’s revolutionary.”

The biggest driver toward freelancing seems to be autonomy and independence – working when you want, where you want, how you want, while getting paid well to do it.

But the great opportunity with freelancing isn’t becoming a hired gun to perform a single job autonomously. It’s to become more like Leonardo: a multi-interest expert generalist with a robust talent stack, combining skills and abilities to create the unique and revolutionary. Or at the very least, being able to earn a buck in whatever ways are fashionable and marketable at the moment.

There’s a name for this: Full-Stack Freelancer. Coined by Tiago Forte in his article The Rise of the Full-Stack Freelancer, the potential of becoming a Full-Stack Freelancer lays somewhere in between salaried employment and entrepreneurship:

“Formal schooling frames our career choices in stark terms: either hyperspecialize, putting all your eggs in one basket you hope and pray will be relevant for years to come; or take a gamble on self-employment, testing your resilience and risk tolerance under extreme conditions.

Perhaps the most compelling aspect of Full-Stack Freelancing is that it offers a middle ground, with potentially the best of both worlds. It is pragmatic, recognizing that most people are generalists who want to pursue diverse interests. But it is also aspirational, recognizing that you need the flexibility to take advantage of unexpected opportunities.

A Full-Stack Freelancer does not see a black-and-white world of free agents vs. wage slaves. They are more than willing to incorporate full-time employment as one item in their portfolio, temporarily or long-term, knowing that it neither defines them nor limits them. Breaking down this barrier, we see that the full stack is available to everyone. It requires only a level of engagement with technology as producers, not just consumers. More fundamentally, it requires a willingness to grow your portfolio toward toward areas of uncertainty and discomfort, instead of only toward existing strengths.”

Maybe the future belongs not to those who do one thing well, but instead to those who connect random dots like da Vinci – creating that which does not yet exist and constantly adapting to a rapidly, forever evolving world.

And if you find yourself freaking out at age 25 or 30 or 55, with your list of half-started projects and failed ideas, wondering if “anything was ever done” – maybe you’re well on your way to becoming the next da Vinci.

Here’s the catch: we won’t know it for another couple hundred years or so.

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