August 2

7 Essential Traits For Anyone Who Wants to Build a Career in the Arts

The Hero’s journey and the artists journey are real. They come with the promise of change, of passion, fulfillment, and self-actualization, and they come with the curse of Eden – “henceforth shalt though eat they bread in the sweat of thy face” – which mandates unrelenting toil and labor. The struggle never ends. It never gets easier – Steven Pressfield


A career in the arts is filled with perils and pleasures,  lingering in obscurity, and moments in the spotlight.  There’s no outline, sequence of steps to follow, or collection of advanced degrees that ensure a secure future and guaranteed paycheck. There are no well-lit paths or clearly marked destinations. It’s the kind of pursuit that will cause people to question your sanity and encourage you to do something more practical. 


The only good reason to pursue a career in the arts is because you can’t imagine doing anything else. 

It is by all accounts a life, not just a career, in which nothing is guaranteed, but anything is possible. To navigate such a life, a person must either possess or develop a particular set of essential qualities.


1. Patience

The fact that we can go from idea to execution in a matter of minutes has made unparalleled amounts of creativity possible. But it has also resulted in impatience and unrealistic expectations. People want opportunities before they are ready. They want the attention of an audience before they’ve earned it. They want to produce masterpieces before they’ve taken the time to master their craft. As Todd Henry said “attention for your work is not a birthright. It has to be earned.” In a world driven by access to instant validation, vanity metrics, rapid feedback loops, and frenetic shallowness, patience is in short supply.


When I started my first blog in 2009,  a book deal was the unicorn and metaphorical mountaintop for bloggers. In the years that followed, I watched many bloggers take low advances, sign with publishers who churned out books like McDonald’s churns out hamburgers, often a result of nothing more than the ego-driven desire to see their name on a book cover. In some cases, the publishers did little more than send a PDF about how to market their books. Most of them haven’t written any books since. I even know a writer who recently signed a contract, in which SHE paid the publisher.


  • Sometime in 2012, I had a conversation with a woman who helped aspiring authors get book deals. After an hour of talking, she kindly informed me that I wasn’t ready. This forced me to be patient and ended up being a gift. It gave me the time to develop the necessary habits to finish a book and ultimately led to a much more lucrative book deal.
  • Ryan Holiday had worked for authors like Robert Greene, Tucker Max, and Tim Ferriss when he was 19 years old. His second book The Obstacle is The Way didn’t take off until, almost 3 years after it came out.
  • When Dani Shapiro described her career to me, she said her first 3 novels came and went without a trace. 3 books without a trace. Imagine the patience required to persist in such circumstances. As she herself said in her beautiful book Still Writing “Who would sign up for such a life? Most days it seems like lunacy.”


The long game is a dying art. Impatience and unrealistic expectations are becoming the default narrative. The greatest competitive advantage you have as an entrepreneur is a long-term view, and the most significant competitive advantage you have as somebody who wants to build a career in the arts is patience

2. Persistence

My old roommate left an incredibly lucrative finance career to pursue his dream of becoming an actor in Hollywood. He’s been a bouncer at clubs, done telemarketing, and whatever it takes. Every year he shares an update about the Hollywood resume: “9 years and still here, 10 years and still here.” That’s the kind of persistence and grit that’s required to build a life in the arts.


Matt Damon and Ben Affleck had been working in the movie business for 10 years by the time Good Will Hunting was released. They wrote the movie to create jobs for themselves.  In a conversation with photographer Sam Jones, Matt Damon said: “if I can talk someone out of doing this in one conversation I know they’re not cut out for it because it’s so hard.”


The adversity of broken hearts, failure, and rejection, are all par for the course. Our adversity can make us break us. It can give us chapters to write or colors to paint with. As  I’ve said in my new book, it’s all material.


This kind of persistence and art that rewards its creator long after the average person quits is admired but rarely encouraged. After all, persistence doesn’t promise any guarantees of being commercially successful.  But without persistence, it is virtually guaranteed that you won’t be commercially successful. 

2. Tolerance for Uncertainty

A creative career is unpredictable and uncertain. Sometimes we don’t know where our next dollars will come from or if they will come at all. This is the case with famous movie stars, best selling authors, and anybody else who has built a career in the arts.


When we set our hopes on this life, we are staking our future on the contents of our own minds. On our ability to create and continue to create. We have nothing but this. No 401(k), no pension plan, often no IRA, no plans- god knows-for retirement. We have to accept living with profound uncertainty.  – Dani Shapiro, Still Writing

We watch our friends settle down, start chapters of their lives that we should have started by now, while secretly dreading that it’s all going to fall apart, that we’re going to end up shuffling in a robe in a nursing home, wondering why we didn’t just go to medical school, law school or some other practical societally approved career choice.


But if we were interested in a life characterized by a predictable certainty, we wouldn’t have chosen this path in the first place. Like a surfer falls in love with surfing because every wave is different, an artist falls in love with her art because every day and every piece of work is different.


4. Humility

The effort is what we control. The results are what we don’t. But any of us who have created something can’t help but think about the results. In reply to his own words about this Ryan Holiday replied: “easy to say, hard to do.”


And it is hard to do. It’s the hardest thing to do. None of us who make something for public consumption want our work to linger in relative obscurity.  Separating the effort from the results of your work is a delicate balancing act of living in the moment and keeping your eyes on the horizon. But when we lose this balance, our eyes become fixated on the horizon. We live in perpetual pursuit of a distant dream.


I’ve seen this in aspiring writers, I’ve seen it in myself, and I’ve seen it in people whose books have sold thousands of copies. There’s not a single one of us immune to the havoc that our ego-driven attachment to the results can wreak on our creative work.


Success should never determine how we show up at the page. The reality that you are very much a beginner again every time you sit down to write. What you bring with you are habits, experience, rituals, and routines. But your ego and your accolades must b checked at the door. Whether it’s winning a Pulitzer, making the NYTimes Bestseller list, or Oprah singing your praises, you must always return to the blank page with humility. The ocean punishes surfers who don’t respect its power. The muse punishes artists who don’t appreciate its gifts.


When we let success determine how we show up at the page, our ego gets a seat at the table. We create to impress instead of connect. We sand off rough edges in search of approval and validation. We mimic the people we place on pedestals in hopes of replicating their results.  It’s the antithesis of unmistakable.


It’s easy to get high on a supply of your own bullshit in a world where you can provide the world a steady stream of your latest achievements which are followed by people’s praise in the form of hearts, likes, comments, and shares. Social media causes us to overestimate our importance and underestimate the toxic impact that our ego can have on our work.


Anytime somebody mentions the words like well known or big platform to me; my response is usually “my barista at Starbucks doesn’t give a shit who I am. I’m just another schmuck buying a coffee from a girl whose job is much harder than mine.” I once saw a  podcaster in line at a coffee shop. Nobody asked him for an autograph or asked to take a selfie. They just took his order.


It’s tempting say to yourself, I’ve busted my ass for 10 years. I’ve been patient and persistent.  There’s a difference between believing you deserve something and a sense of entitlement. Driven by a sense of entitlement, it’s easy to overlook the role that luck and circumstance have played in getting to where you’re at.


I always have to remind myself there were a thousand other writers my editor could have found on Medium the day she stumbled on my article. I had parents who could afford to send me to college, and have never been in a position where I had to figure out how to keep the lights on or put food on the table. These simple things we often take for granted are in fact a form of privilege. Without humility, you can lose sight of this.


It’s easy to overestimate your importance and forget your humble beginnings when a moment in the spotlight blinds you and your ego. 

5. Discipline

 In a life and career that is inherently uncertain, discipline gives us a sense of certainty. Regardless of the money in the bank, the size of the audience or books sold, disincline and a creative practice keep uncertainty from morphing into chaos. This is just one reason I believe that professionals create on a schedule.  With creative discipline we plant seeds:

  • We show up every day
  • We practice
  • We do deep work


The fruit that results becomes our body of work. With discipline and consistency, we move into states of flow and bliss, as we start to dance on the edges of mast 

6. Focus

 One of the questions I’ve been asked more than a handful of times during interviews about my upcoming book is “what do I do if I have too many interests?” There’s nothing wrong with having multiple interests. It becomes problematic when you don’t engage in any one of them long enough to either produce a result or give you valuable data points.


When you put a magnifying glass over a piece of paper in the hot sun, it eventually catches fire. But if you lift that same magnifying glass and put it over multiple pieces of paper none of them will catch fire.  Our ability to focus is essentially the same. In 2013, my mentor had me make a list of the ways I made money:


  • Book marketing
  • Social media for a pro surfer
  • Freelance writing about online marketing


Then he said, “do you want to be doing any of these things 5 years from now.” I said no, and he encouraged me to stop doing them. Shortly after that, I finished a self-published book, launched a conference that sold out in two weeks, and finished a substantial rebrand that led to the Unmistakable Creative.


A few nights ago my friend Steve Daar and I were playing video games, and he told me about the concept of the 12 week year. The premise was simple. You pick 3 goals and focus on nothing else for 12 weeks. This forces you to be deliberate about your priorities, and it intensifies your focus.


The ability to focus on one goal for an extended period is essential if you’re serious about building a creative career:


  • Writing a book takes almost 2 years of working on the same thing every day.
  • For the leading role in a movie, you not only have to memorize your lines, but you show up to shoot and work 12 hour days for a hundred days in a row.

Great creative work, the type that you can build a meaningful career off of requires focus.

7. Love for the Work

If your sole motivation for a career in the arts is fame, attention, and validation, you will be profoundly disappointed.  A few weeks ago Oprah was having a conversation with Tom Brady in which she said the following:


Everybody wants to get rich really quick. They want to get rich through a Youtube post. Or they want to get paid. I talk to 15-year-old kids who are talking about their brand. I was telling a girl the other day “you’ve got to do something before you have a brand.” The brand comes out of the work that you do.” – Oprah Winfrey


Unless you genuinely love the work, everything I’ve mentioned above will be intolerable:


  • You’ll want to quit when it gets hard. 
  •  You’ll crack in the face of uncertainty 
  •  You’ll make choices about your work for all the wrong reasons 

When you start a creative career, you dream of the day you’ll be successful. Of seeing your name in lights, your picture on the cover of magazines, or whatever accolades that once appeared so elusive. But anyone who has become commercially successful with their creative work will tell you that the spotlight rarely lives up to your expectations. Even if it does, the sense of fulfillment you derive from it won’t last. The reward of being commercially successful with your creative work is that you get to keep doing that work.  It is an infinite game.

The real work of a creative career happens behind the scenes, out of the spotlight with nobody paying attention. Someday it might reach an audience of millions, but when it’s all said and done you’re doing the work for an audience of one.


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