Can Jacks of All Trades Become Great?

James Walpole/ February 4, 2019

As part of my Charity:Water campaign, I’m writing blog posts for people who contribute $25 or more to bring clean water to 23 people. You have a word/topic/question you want me to riff on? I’ll (probably) write it. One donor asked me to write about whether jacks of all trades could become really great. 

Interested in supporting – and getting your own blog post? You can still donate to the campaign (100% goes toward clean water, not fees). We’re less than $200 away from the goal!

Jack of all trades, n. “a person who can do many different types of work but who is not necessarily very competent at any of them.”

Being neither great nor a master of anything, this is just a guess on my part. But my intuition, learning, and observation give me the answers of both “yes” and “no.”

No – insofar as greatness requires mastery, it won’t be possible to become really great at any one skill. Specialization is the path to skill. It should be pretty obvious that you won’t become a great artist on the scale of Michelangelo if you spend equal parts of time dabbling in driving race cars, growing Christmas trees, and hunting elk.

Of course, (maybe because I haven’t been convinced of my *one thing* yet( I have yet to take this advice. I am a dabbler/dilettante extraordinaire, and while I intellectually recognize the need for focus, I have defended generalism and broad interests.

As usual, the truth of the case is probably more complex than a “yes/no” option will allow.

There is after all one thing you *can* master as a jack of all trades: creative problem-solving, or entrepreneurship.

Great creativity comes from synthesis, and being interested in many things, you’ll be exposed to many of the world’s places and occupations. If you pay attention, you can find:

  1. The pain points/problems of a place or industry or thing 
  2. The way one place or industry or thing can solve a problem for another

Bringing those together is the essence of what great problem-solvers and entrepreneurs do.In fact, these things would be hard to master if you *weren’t* a jack of all trades. There is a kind of specialization going on here after all: you’re honing the meta-skill of synthesis.

Generalists typically only need to know the broad outlines of a problem and an opportunity to do the great part of the work and initiative to solve it. As Robert Kiyosaki observes in Rich Dad, Poor Dad, wealth creators don’t have to be the “smartest [people] in the room.” They know to surround themselves with specialists who can help them execute on a problem-solving endeavor. And their generalism has given them just enough know-how to find those right people and vision to lead them.

As a jack of all trades, you will also have what Steve Jobs called “the lightness of being a beginner,” and the kind of naïveté to the “established way of doing things” that might just let you discover something new.

So, yes, jacks of all trade can be great. But there are constraints.

You must not be a generalist because you set out to be one. You will probably do better if you become a generalist not through some planned curricula of “well-roundedness” but through a series of powerful interests. Your obsession is a skill that will help you achieve.

You must also not be a jack of all trades because you hop from skill to skill or focus to focus. “Quitter” energy will never be an advantage. If instead your breadth of experience has required courage, toughness, and commitment, you can consider it an asset to your success.


Photo by rawpixel on Unsplash

Intellectual Influences: Too great to count, but Isaac Morehouse on entrepreneurship, Isaac and Dan Sanchez for thoughts on the value of being obsessed/not well rounded, Jordan Peterson on the psychological traits of founders, Robert Greene on mastery (see Mastery), and others cited and not cited here.

James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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