How To Learn a Career Without Losing Your Personality

In Mastery, Robert Greene paints a thorough picture of apprenticeship and the power it has had to shape great creative careers throughout history. In one form or another, apprenticeship has been part of the path for masters from Leonardo da Vinci to Benjamin Franklin.

Apprenticeship sounds very rosy, but the truth is that (in its purest form) it was designed to suck – at least for the apprentices.

No room for originality

When you start out in a skill, you must often suppress many of your natural inclinations and follow the direction of the master who is teaching you – whether it’s a person or a team. Back in the old days, this basically meant being indentured to a blacksmith or a printer or a candlemaker for a decade or so. Today things are a bit different, but real learning of a career takes tremendous humility, patience, and yes – conformity.

The hardest part of a career for any creative person is probably the beginning, because it’s when our own unique personalities, perspectives, desires, quirks, and insights are least valued. No one wants our originality, and our originality can get in the way of our progress in learning from people who have “been there and done that.”

In my own work, I’ve had to change my writing style and change parts of my personality. I’ve had to suppress my own opinions, my own ego, my own credit, and my own desire to defend myself. I’ve had to accept brutal criticism and insults, revise endlessly, and wait anxiously for feedback and green lights.

All of these can be perfectly fair and good things. In fact, they’re keeping me from making deadly mistakes, and they’re showing me perspectives and skills I might never have noticed if I just want my own way. If I want to be good at marketing, I have to submit to this stage of apprenticeship.

No room for conformity

There is a “but” to all of this. Also in Mastery, Robert Greene talks about the importance of the final stage of mastery as being that bit where you finally step out and do your own thing. You take the skills taught to you by the master and use them to power your own new direction.

No one denies that we remember real masters not for their conformity to tradition but for their clever ways of breaking with tradition (while still knowing the best of the past). In my case, the world probably doesn’t need another copycat marketer following the same best practices as everyone else. If I want to be truly great at marketing (or anything else), I’ll have to bring something new to the table.

That’s what we all must do at some point. But that’s the tricky thing: what if the conformity of apprenticeship has so sapped your originality that you have nothing fresh to bring to the world?

Keep your originality alive

So, if we grant that we have to suppress our originality a bit in the apprenticeship phase, how can we keep it alive for the times when we have to become masters ourselves?

For me, the solution has been finding outlets for my creativity *outside* of my apprenticeship in marketing* I write every day, I journal, and I try all kinds of new experiences and new skills from jiu jitsu to running to volunteering to the occasional side gig. These are all release valves for any kind of originality I have to suppress in my own pursuit of mastery as a marketing apprentice.

My friend and Praxis education director T.K. Coleman found himself in a similar situation during a stint in the film industry. He got so tired of asking for permission to create his films that he started writing every day. Blogging was something no one could take away from him, and he didn’t have to ask anyone permission to create what he wanted and how he wanted. (You can get this bit of TK’s story in his interview with Isaac Morehouse on his own career and apprenticeships)

I think this sort of thing – “creating without permission” – is key in any apprenticeship or early career phase. As Greene has observed, the great masters are those who can pass through an apprenticeship with their individuality and originality intact. If you don’t want to lose these rough edges, you need to be intentional about using them outside the narrow focus of your apprenticeship.


Intellectual credit: Mastery by Robert Greene, Jordan Peterson, Isaac Morehouse, and TK Coleman, among others

*For the record, I have been lucky enough to have a *tremendous* deal of freedom within my apprenticeship, too.

Photo by Stefan Steinbauer on Unsplash

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.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.