Jack of Many Trades or Master of Some?

In this article, we return to the topic of specialising versus generalising as a career strategy, and expand on Protagion’s previous writing to share the views of Scott Adams, Tim Ferriss, and Erik Torenberg with our readers. 

How many tools are needed in your skills toolbox?

Scott Adams is most famous as the creator of Dilbert*, the renowned cartoon starring an engineer in a business setting. Scott’s own career includes majoring in economics, picking up an MBA, and working at a bank and a phone company before becoming a cartoonist. He’s naturally a fan of MBAs, advising: “...Get a degree in business on top of your engineering degree, law degree, medical degree, science degree, or whatever. Suddenly you’re in charge, or maybe you’re starting your own company using your combined knowledge.”

Tim Ferriss is also likely to need little introduction. He’s a multiple-bestselling author and popular podcast host of The Tim Ferriss Show. His books include: The 4-Hour Workweek*, The 4-Hour Body*, The 4-Hour Chef*, Tools of Titans* and Tribe of Mentors*. He’s been referred as a polymath and believes “it is possible to become world-class in almost any skill within one year”.

Erik Torenberg is a venture capitalist and co-founder of Village Global and On Deck, “where top tech talent goes to explore what’s next”.

Read more to dive into the worlds of specialists, generalists and specialised generalists, including Scott, Tim and Erik’s thoughts on the advantages and dangers, and tips for combining skills. We briefly revisit our previous article (In Pursuit of Knowledge: Specialising vs Generalising as a Career Strategy) and conclude with a 6-minute video of Tim.

Specialists
Specialists have deep knowledge in a specific area – if you choose this route for your career, it’s important to be extremely good at what you do, and keep your skills up-to-date so that you remain relevant. Mastery takes time, and specialists can make very significant contributions to the world due to their in-depth knowledge in a particular area – for example, advances in medicine or astronomy. Specialisation can be achieved in a given location too, allowing you to be the best in a particular niche i.e. becoming successful by filling an existing niche.

Some advantages of being a specialist include expertise they can charge high rates for consulting on, and that they can allocate all of their attention and focus on their field of specialisation. They do, however, have a higher risk of becoming obsolete and their careers are likely to be more inflexible.

Scott calls this strategy “becom[ing] the best at one specific thing” but warns it’s “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.”

A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyse a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialisation is for insects.”
ROBERT HEINLEIN, Science Fiction Author, in ‘Time Enough For Love’

Generalists
In contrast, generalists have a broad involvement in a range of areas. They operate at a level of abstraction, and can be very helpful in connecting ideas and insights from specialists. Engaging effectively with specialists from different areas is one of the important roles of generalists i.e. manifesting the “unseen interconnectedness”. Tim argued in 2007 that “as technology becomes a commodity with the democratisation of information, it’s the big-picture generalists who will predict, innovate, and rise to power fastest.”

Leadership, by its nature, involves generalisation as you won’t be an expert in all the areas you are leading. In Tim’s words: “At the highest levels, you need certain... connective tissue, like communication and otherwise, to be able to thread everything together, to be a proper leader.” Leadership requires considering many different perspectives and therefore requires many different skills outside of one’s core competency, he argues.

In addition to understanding and seeing the bigger picture and making connections, generalists are skilled at transferring existing skills to new areas, and applying their knowledge gained in one field to another. This can lead to greater innovation, often a result of combining ideas. Generalists can also adapt far more flexibly to changes in their working environment i.e. having more skills helps you adapt to unexpected changes.

The real master has no tools at all, only a limitless capacity to improvise with what is to hand. The more fields of knowledge you cover, the greater your resources for improvisation.”
ROBERT TWIGGER, poet, writer and explorer in his essay ‘Master of Many Trades’

​A related advantage that generalists have is their ability to learn quickly (as they’ve practised how to learn). Tim is a strong believer that new skills can be acquired at pace, especially when one applies concerted effort, with a sense of urgency. He says that “Generalists take [their] condensed study up to, but not beyond, the point of rapidly diminishing returns”, explaining that specialists tend to “overestimate the time needed to ‘master’ a skill as they confuse mastering a skill with perfecting a skill”. While this is partly semantics, Tim is highlighting that deliberate practice can make you significantly better than the average person at something. Scott echoes this with: “Everyone has at least a few areas in which they could be in the top 25% with some effort.” They’re not suggesting 20 hours is what’s required for Tim’s definition of ‘mastery’, but we’ve shared before that you can learn a lot in even such a short time.

Diversity of intellectual playgrounds breeds confidence instead of fear of the unknown, and breeds empathy with the broadest range of human conditions and appreciation of the broadest range of human accomplishments”
TIM FERRISS

However, Erik warns of the dangers of being a generalist in a Twitter thread: “The problem is it's easy to lie to yourself & say that you're a generalist when in reality you've tried a bunch of things and you've flaked out when things got hard and tried something else. It's easy to do this repeatedly & say ‘But I'm a generalist’… One way to be a generalist is just quit whatever you're doing as soon as it gets difficult, but that's also a way to fail at everything you do. You want to be at least great at one thing, and then apply that lens or skill to other categories.” Flaky generalists can be perceived suspiciously by specialists who may question what value they are adding, and they can suffer from a lack of job security (as their mediocre general skills may not easily translate outside their current business relationships).

Specialised Generalists
In reality, the distinction is not as stark as those two ends of the spectrum i.e. for those interested in varied areas, there is another option than simply resigning yourself to being a ‘master of none’. 

This option is that of a “specialised generalist” who combines two or more valuable skills. Generally speaking, the rarer the skills combination, the better, provided they are valuable to others who are willing to pay for the combination i.e. the more successful you can be. Scott explains in a 2007 career advice article: “Capitalism rewards things that are both rare and valuable. You make yourself rare by combining two or more ‘pretty goods’ until no one else has your mix”. He also advises that “at least one of the skills in your mixture should involve communication, either written or verbal.”

Being a generalist with depth is sometimes referred to as being a ‘T-shaped’ i.e. you know a lot of things in the horizontal but are also an expert in one of them – the vertical bar. And, Scott effectively advises adding more vertical bars i.e. ‘π-shaped’ or ‘stool-shaped’ or more. Your horizontal knowledge allows you to connect ideas and share across disciplines, and your vertical bar(s) give you depth of insight in your specialist areas.

Erik argues for depth in at least one area: “Scott Adams’ strategy – find the intersection of 2-3 things you’re best at even if you’re not best at any – is good as a plan B, but not plan A. It’s advice that will make you slightly above average, but not excellent. Switch paths if unfruitful, but do try to be great at something.”

Generalists can work towards becoming a Specialised Generalist by picking one of their areas and going deep in order to gain vertical knowledge in that area. Once they have depth there, they can choose another area and repeat to gain specialist knowledge in that next discipline. In contrast, pure specialists can extend their horizontal knowledge by beginning to explore other areas and learn new skills to spot similarities or opportunities in other disciplines.

Combining skills
When considering your handful of skills to combine, choose ones which are rarely combined by others (so that you stand out from the competition), especially where they are valuable together i.e. they boost one another. Ones you have a natural competitive advantage in (such as a passion for, or innate talent in, the subject) are a strong place to start. And, consider both skills and domain knowledge e.g. computer science skills in a law context, or public speaking in a finance context. 

Scott’s combination of skills which helped him reach such success as a cartoonist included his drawing skills, his humour / ability to write jokes, and his business and marketing skills (like listening to the feedback from his cartoon’s readers on what was resonating for them). Perhaps Dilbert is Scott’s example of a specialist, while his pointy-haired boss may just be a generalist?

Trying things out, or dabbling, is useful when looking to narrow down your areas of focus, but don’t try to master thousands – spreading yourself out across multiple skills will dilute your depth too much. During the experimentation process, Tim emphasises that we should keep the skills and relationships we gain during our failed experiments and use them towards our future success.

Multipliers for your core skills
Tim talks too about gaining proficiency in add-ons which multiply your core skills. These act as an “Archimedes lever” he says, and can involve communicating the outcomes of your deep knowledge to lay people. The three add-ons he suggests are: public speaking, writing, and negotiating.

​A personality perspective
Personality wise, specialists are probably detail-oriented and more conscientious, seeking to develop solid skill in their chosen area(s). They are more likely to be strong on the S (Sensing) dimension in the Myers-Briggs view of the world. Generalists are, in contrast, more likely to be N (iNtuitive) and have higher openness within the Big 5 dimensions. This helps to explain why they experiment in different fields and keep learning to prevent boredom.

For our readers interested in revisiting our previous work on this topic, we discussed the career distinction between being (i) a manager and generalist and (ii) a technical/functional specialist in “In Pursuit of Knowledge: Specialising vs Generalising as a Career Strategy”. It that article, we explored the advantages of expertise, including how it is relative to others’ knowledge in the environment we’re in. We discussed the choice of skills to specialise in, the importance of ongoing learning, and the application of depth vs breadth to working in the consulting industry.

We end this latest article with a 6 minute video in which Tim discusses “Should I specialise or should I be a generalist?”, a question he often gets from his listeners. In some ways, it is a refresh of his 2007 essay arguing that generalists were making a comeback and that specialists were limited by “self-inflicted one-dimensionality – pursuing an impossible perfection”. In the video, he argues for being a specialised generalist instead, mirroring how his views have developed further in his books over time, and also been influenced by his conversations with his podcast guests, including Scott Adams, who was a guest in 2015. 

What’s your take on a specialist vs generalist career strategy?​

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