Exploring the Overlap

One of my favorite forms of media is the comic strip. When I was a teenager with way fewer responsibilities, I used to consume dozens of webcomics per day. I’m glad that Instagram has ushered forward a comic strip renaissance.

What I love about the comic strip is the simplicity of its form – it organizes a simple punchline across a few simply drawn panels. There is a limited amount of time and space to develop a plot and most comics aren’t that complicated because illustrators need to produce them at an efficient clip. My favorite comics survive on the charm of its drawing style and the efficiency of its wit.

What’s interesting to me is that although comic strips are essentially a combination of humor and art, the best comic writers tend to be neither great comedians nor great artists.

Dilbert, which chronicles the foibles and mundanity of modern office life, is recognized as a pioneer of the comic strip medium. Dilbert was created by disgruntled office worker Scott Adams and has grown to become one of the most successful comics of all time.

I am not a big Dilbert guy, but the creator is still a certified legend.

On the topic of career advice, Adams posted the following on his blog back in 2007:

If you want an average successful life, it doesn’t take much planning. Just stay out of trouble, go to school, and apply for jobs you might like. But if you want something extraordinary, you have two paths:

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

The first strategy is difficult to the point of near impossibility. Few people will ever play in the NBA or make a platinum album. I don’t recommend anyone even try.

The second strategy is fairly easy. Everyone has at least a few areas in which they could be in the top 25% with some effort. In my case, I can draw better than most people, but I’m hardly an artist. And I’m not any funnier than the average stand-up comedian who never makes it big, but I’m funnier than most people. The magic is that few people can draw well and write jokes. It’s the combination of the two that makes what I do so rare…

Scott Adams via Dilbert.Blog

The Monotony of Mastery

Mastery of a singular skill certainly has its allure, but now that the concept of deliberate practice is commonplace, it will only be more and more annoying to compete with the crazy disciplined people, particularly those who are willing to cast aside meaningful relationships, well-roundedness, and having fun more than once a week.

Perhaps instead, the way we should pursue extraordinary careers is to embrace our unique skills and explore those areas of overlap.

When you compete with others within standard confines, you tend to be evaluated on singular metrics or well-established frameworks, which I find less frequently rewards having a creative mix of skills. I learned the hard way that it’s incredibly difficult being the best employee in finance, but what if I were to combine my knowledge of finance with my interests in writing or teaching?

In school, we are evaluated on marks, which often rewards diligent studying and memorization. Then perhaps we graduate and become evaluated on how efficiently we can make PowerPoint slides, which I think rewards your ability to play Spot the Difference.

More experienced roles often still just reward people based on a specific metric: investment returns, sales targets, patients per day, satisfaction rate, etc. A systemic approach to career – particularly at the junior level – seems to rob us of the value of having a diverse, generalist skill-set.

Working hard to master a skill makes perfect sense if you enjoy your job. Specialization is absolutely critical to succeed in repeatable, linear arenas. The fastest sprinter will win the 100m dash. The outcome with the highest return is the best for the fund. I am a big proponent of focused training and I understand that consistent discipline is at the heart of improvement.

But I think that focused mindset falls apart when applied to looser questions and more ambiguous circumstances, which resembles life way, way more often.

In kind environments, where the goal is to re-create prior performance with as little deviation as possible, teams of specialists work superbly. Surgical teams work faster and make fewer mistakes as they repeat specific procedures, and specialized surgeons get better outcomes even independent of repetitions… When the path is unclear – a game of Martian tennis – those same routines no longer suffice.

Range by David Epstein

A key tenet of Adam Smith’s foundational Wealth of Nations is that the economy grows as people pursue more specialized labor. Industries flourish when people become more specialized and seek out incremental slivers of productivity and expertise.

Since 2000, the percentage of Americans with a Bachelor’s degree increased from 30m to 48m and those with a Master’s degree increased from 10m to 21m. It is logical to seek higher and higher education to develop an edge and become more specialized.

But, if you’re like me and you don’t have a true career passion, working in a system that primarily rewards productivity and strict domain expertise can feel horrible and pointless.

My fascination with entrepreneurship and more general leadership positions (and product management to a much lesser, uninformed extent) largely stems from the fluidity of the role and the diversity of skills you get to use. I am starting to think that the human personality is too complicated and erratic for people to neatly enjoy doing a single function for the entirety of their lives. I do not think a perfect job exists – each of those roles certainly have their downsides, but the trade-off is alluring.

The goal is not to attain these specific jobs in and of themselves, it’s more about finding structures and environments that allow us to explore our unique skills. I identify my unique skills and interests to include writing, critical thinking, teaching, honoring time commitments, and having large calves. I found that my office job generally only rewarded my punctuality.

Jessica Livingston, the founding partner of Y Combinator, echoes the thoughts of Dilbert creator Scott Adams. Livingston discusses how perhaps a better approach to our careers involves exploring our different strengths, weaknesses, quirks, and interests to “grow the puzzle around us”.

You are a jigsaw puzzle piece of a certain shape. You could change your shape to fit an existing hole in the world. That was the traditional plan. But there’s another way that can often be better for you and for the world: to grow a new puzzle around you. That’s what I did, and I was a pretty weird-shaped piece. So if I can do it, there’s more hope for you than you probably realize.

Jessica Livingston via Founders at Work Blog

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