How to beat cripping insecurity, doubt and failure: lessons from Steven Pressfield

If you’re an artist, author or entrepreneur, you’ve probably heard of Steven Pressfield, author of The War of Art and more recently, Do The Work. His books have become manifestos for creatives because they rephrase the artistic life in terms of battle and violence, and help people overcome their fears, doubts and worries.

According to Steven, resistance is an “intelligent, active, malign force working against us. This enemy is intelligent, protean, implacable, inextinguishable and utterly ruthless and destructive.”

The only remedy is to kill it, squash it, battle it. Art is this constant war between our creative selves and resistance.

For every big dream, there is automatically resistance.

As Oprah points out in a 2013 interview in response to Pressfield’s idea that resistance is an active force of nature, “That’s a comforting belief. I feel a little bit of relief right now. You know why it’s comforting? Because I don’t have to blame myself so much.”

It’s not YOU who are lazy… it’s not YOUR fault. It’s resistance!

And there are practical benefits: in an interview with Jeff Goins, Pressfield says “I’m a believer in what my friend Randall Wallace calls ‘little successes.’ I always go the gym first thing, or run, or do something act that faces Resistance and wins. That psychs me up for actually hitting the page.”

Will power is a muscle that can be trained. Little successes do lead to bigger ones.

If you’re creative, but dealing with feelings of insecurity, inadequacy, stagnancy, helplessness, then Steven’s writing can give you support and encouragement. It can inspire you to take action and do the work and get shit done.

Hence its popularity.

But it can also make you fail

Steven believes that whatever you are passionate about, whatever you feel you want to do, is the right thing to do.

We are ALL artists. Everybody has a calling, and your real job in life is to figure out why you are here.

That’s the thing you MUST do, that you were put on this planet for.

Steven believes worldly success, in the form of financial gain or popularity, is accidental and besides the point, and shouldn’t be sought out for itself.

All you can do is follow your passion and keep producing and see what happens.

That’s terrible advice.

Entrepreneurs follow Pressfield’s advice and it works for them, because they are focused on developing things people want, establishing demand through a minimal viable product, doing things as quickly as possible. But it isn’t their passion. They aren’t listening to the muse. They don’t believe in an epic battle between heavenly forces, who are using them to produce a great work.

They might fail, but it won’t crush their souls.

For artists and authors, on the other hand, Steven’s advice can be devastating. Sure, on the one hand, it gets them producing. And they have to produce a lot to build up the skills. They have to write or paint badly before they can write or paint well.

But then, according to Steven, they shouldn’t do any market research, they shouldn’t care about what people will like, they should just listen to that inner voice of inspiration and keep doing the work.

Some artists and authors will get lucky and people will actually like what they’ve made (although usually because they’ve also spent some time becoming entrepreneurs and know how to market and sell their work). But many, a grand majority, will be met with failure.

By his own admission, Steven got lucky with the The Legend of Bagger Vance. As a career author, he’s learned to write pretty well and his books are well received. He’s a model of success. He’s been on Oprah. But in Do The Work, he recounts the story of The Big Crash.

“My newest book, a novel called The Profession, was done – after two years of work. I was proud of it. I was psyched, I was sure I had broken through to a level I had never achieved before. Then I showed it to people I trusted. They hated it. Let me rephrase that. They HATED it. The worst part was, they were right.”

The story has a happy ending; through a ton of revision, and several start-overs, Steven polished the novel and made it successful. Though not before suffering through bouts of serious depression: “I went into an emotional tailspin. I was lost. I was floundering.”

I think it’s important to establish that Steven’s philosophy of art comes with a couple serious drawbacks.

1) If you believe everything you are doing creatively is a spiritual gift you have been chosen to share with humanity, failure will be personally devastating.

2) You are far more likely to fail if you “write from the heart” and don’t think about things like whether people will like it.

It’s no wonder that Steven’s paradigm of art is a WAR – a cycle of bitter feelings, and emotional turntable, filled with ups and downs.

It’s no wonder he has such crippling insecurity about his art: in the Oprah interview, he says resistance is the shadow of the dream, and you absolutely can’t have one without the other. In his artistic process, there is no way to tell whether he’s working on something great or something that’s a waste of time.

You’d think that following the muse or your passion would always lead to quality work, which in turn would lead to success. But that isn’t the way it happens. Which should certainly insinuate that there is no muse, and that it doesn’t matter what you create specifically.

Even as an established writer with a huge following, Steven wasted years writing a book that people hated (before salvaging it). Sure it’s all part of the process.

Sure huge setbacks can be expected (if you do things his way) but they can also be minimized, and/or trivialized, by not taking yourself and your work so damn seriously, and by thinking about the end user.

At the heart of it, I think Steven’s way of producing art is profoundly selfish – a personal journey of creation without thinking of benefits to other people, which at the same time is absolutely dependent on other people for positive feedback, reception and financial gain. Steven (like all the rest of is) is a commercial artist. He is creating things for popular consumption, not just his own pleasure or to honor the muse.

The two kinds of failure

The first kind of failure is never starting. Giving up to soon. Not finishing the work. Art is hard. It takes perseverance, dedication, stubbornness.

If you’re having trouble getting started, Steven’s work can help give you a push, and you should totally read his books.

But then there’s the other kind of failure: When you’ve finished your life’s work, your pure passion, your one goal, the sweat and labor of YEARS, and nobody likes it.

Nobody likes it because you didn’t think about whether they would or not. You didn’t care to check whether the work would be well-received. You didn’t ask your friends, family or a support group to give you critical feedback during the development stage. You didn’t treat your art like a business and make sure you weren’t just wasting time and money developing a product nobody was going to buy. And you don’t find all this out until it’s done and you’re trying to market the damn thing and nobody will touch it.

This failure is hard to recover from; and tragically, it’s the inevitable outcome for most authors and artists who have bought into Steven’s paradigm, and even worse, it could have easily been avoided with a more pragmatic, if less inspiring and motivating, view of art.

A better model for artistic success

You can view art as violence and struggle if you want to. You can view failure as inevitable. Personally, I like success. I like it when I make something and everybody loves it. I like it when it earns me a lot of money, so I have more freedom to focus on doing what I want.

I still do what I’m passionate about, but I don’t expect other people to love it (because I didn’t create it for them). Those projects have a “cult following” but not mainstream success.

Make nice things that people like and find a way to sell them. Help other people solve problems and achieve their own goals. Keep doing this until you have a healthy passive income stream, and some serious skills (Pressfield spent 20 or 30 years as a struggling writer before he sold anything. No wonder resistance is such a huge part of his mental process).

What do you think of Pressfield’s books? Have they helped and inspired you? Do you believe in a metaphysical muse?

The 3 secrets to book marketing, and a haunted castle tour. Totally free. Get it here.

Derek Murphy

I’m a philosophy dropout with a PhD in Literature. I covet a cabin full of cats, where I can write fantasy novels to pay for my cake addiction. Sometimes I live in castles.