I want to be a Jack of all trades

I was asked recently if I think that it’s better to master one thing or be kind of good at a bunch of things. And that’s a question that I don’t have an answer to.

For me, life is about exploring my passions, and I have many. My ruling passion is writing, but I’m equally obsessed with entrepreneurship and business, technology and music, speaking, reading, painting, drawing, building, making and, well, eating.

I always used to wish that I had one driving passion, so that I could truly master it. Be the best at it. Focus only that one thing and level up repeatedly. Over time, I’ve stopped wanting that.

Because at the end of the day, I don’t necessarily do anything to be successful at it. I follow my passions because they make life worth living. I write music constantly, and every now and then I pull a DJ gig somewhere.

I paint original canvases, and I write flash fiction, probably even more than I write about creativity here on Medium. I spend my time, every spare moment that I have, pursuing the things I love.

And that’s what makes me happy. If I tried to silence any one of my passions in favor of purity and mastery, I can’t imagine that ending anywhere but total misery. That’s the kind of person I am.

I’m not saying that’s going to be right for everyone. There are people who are going to pursue mastery, and they’ll be a lot better at some things than I’ll ever be. More power to them. But if you’re not one of those people, here’s my message to you.

It’s okay to chase more than one dream. It’s okay to combine your passions, and let yourself be free. It’s okay to be a startup founder who records indie pop when she’s not writing fantasy novels about dragons.

It’s okay to be a lawyer who jams out to Black Flag and performs free verse slam poetry on the weekends and collects Sega games. It doesn’t all have to make sense.

Not everything has to be cohesive or consistent. Sometimes, you have to be human and do what makes you happy.


The old saying, if you’re a Jack of all trades, you’re a master of none, doesn’t apply in every situation. People think it does, because it’s a saying everyone knows, and we’ve just imbibed it and accepted it as the truth.

To call someone a Jack of all trades comes from an old insult — “Johannes Factotum”. Robert Greene used it to describe William Shakespeare:

“There is an upstart crow, beautified with our feathers, that with his tiger’s heart wrapped in a player’s hide supposes he is as well able to bombast out a blank verse as the best of you: and being an absolute Johannes Factotum, is in his own conceit the only Shake-scene in a country.

…the implied insult being that Shakespeare himself was a Jonny-do-it-all, a Jack of all trades and a master of none. People have been using that phrase as an insult since the 1500’s.

People will always use that insult to attack folks who have diverse interests and careers and passions. I’ve been attacked with it before, and it’ll be thrown at me again down the line. But that’s okay.

I somehow feel that if Shakespeare was a Jack of all trades, I’ll be in good company.


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I’m a writer, a speaker, and a social media entrepreneur. Appeared and published in Business Insider, Inc.com, TIME & others.

Email: jon@jonwestenberg.com

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