Steven Pressfield: Go From Amateur To Pro

James Altucher discusses going from amateur to pro with Steven Pressfield

Episode 197: From Amateur to Pro: How to Use Your True Potential and Win

I had a full time job. I was trying to run a business on the side. I was pitching two TV shows. And I was obsessively playing chess day and night and traveling to tournaments.

And nothing was going well. My attention was scattered. I was unhappy. I felt stuck.

One time I was talking to one of the partners in my side business, Randy Weiner. I said to him, “I’m reading this fascinating book about chess endgames.”

He said, “I don’t care about that! Why are you even looking at those books? Chess is a game for kids. You should be working at this business full-time.”

The next day I quit my job. I joined the business full time. I never played in another chess tournament ever again. I stopped pitching TV shows.

I went from being an amateur to being a pro.

Which is why I’m glad the other day I spoke to Steven Pressfield, author of “Turning Pro,” “The War of Art,” “The Legend of Bagger Vance,” “Do the Work,” and more than a dozen other great books and novels.

Sometimes it seemed like each new low was lower. And often the highs were higher. But I haven’t had a job since.

Ever since I made the decision to turn pro, I’ve been free.

It took me two years of asking before Steven finally agreed to do the podcast. I’ve read all his books twice. But I was still scared to death right before the podcast.

Steven and I spoke for two hours about turning pro, writing, how to improve, how to achieve peak performance in any field of life.

I wanted to ask questions nobody else would ask him. Two hours later I feel good about it.

Here is some of what we spoke about:

How to deal with the demons

When I join a gym, I go until I stop going. Then it basically teeters off.

I’m an amateur at going to the gym.

Every single day I write. If I don’t do it for two days in a row I feel physically sick.

But so many times I feel bad about what I am working on. Or I feel unsure if I should work on the next book. or try the next new idea.

The demons come up. I get blocked. I get frustrated or scared. Will I be a failure? Have I run out of ideas?

Steven wrote several books about these very demons.

Steven said, “Those thoughts are ‘the Resistance’.”

“Every time you want to go from a lower level to a higher level – becoming an entrepreneur, get in better shape, meditate, be an artist – the Resistance will ALWAYS attack. Every writer or entrepreneur feels the Resistance every day.”

Recognize each thought as it comes up, he said. Identify the thoughts that are the resistance. Say, “That’s the resistance.”

“There’s no way to get rid of The Resistance. Be aware of it. Say to yourself, these thoughts won’t help me achieve my dreams.”

Keep the ego out

A friend of mine started a company once. It was clearly a bad idea. But he thought it was a homerun.

This is a cognitive bias. We tend to believe that if we pour our heart and soul into someone (our personal “investment”) then it’s a good idea.

When I do something I have to constantly stop and ask if I’m smoking my own crack.

One time I made a website I thought was brilliant. It had an IQ test on it. And it was a dating site. And it would tell you if you were smart or stupid and you can then date people and know their intelligence.

I thought it was brilliant!

My six year old daughter told me, “Isn’t this kind of mean?”

My daughter refused to light my crack pipe.

Steven told me he had to make sure with his most recent novel, the autobiographical “The Knowledge” that he had to keep his ego out of it. “I had to put some distance between myself and the writing because it was about my early struggles as a writer.”

Even a porn director can be a mentor:

Steven told me about how he switched from writing bad novels to going into screenwriting, to finally getting back to writing novels.

It’s important to keep switching around, to pursue every angle of an interest. To take away a lesson from every area.

Along the way he met a director of porn movies that wanted Steven to write some scenes.

“He told me two things:

A) don’t make a sex scene just about having sex. Make sure it advances the story. Like the detective is having sex with someone and spots a clue.

B) Always have something else happening so they can cut back and forth. Like a wife is cheating with the carpenter but the husband is coming home and she doesn’t realize and the camera cuts back and forth.

That took me to a new level in my fiction writing.”

The porn director was a mini-mentor. Other writers he admired were virtual mentors. Editors, agents, other directors and writers also became mentors. Learn from everyone.

Fear of success is real

I said, “I don’t believe that ‘fear of success’ is a thing. Is it?”

Steven said, “Absolutely. In fact, maybe it’s the biggest fear people have that prevents them from turning pro.

“To be successful you have to give up a lot. There’s a lot of sacrifice. You are tied to what you dedicate yourself to, and you have to get better and better at it. There’s no stopping.”

“What did you sacrifice?”

“Everything,” he said. “I write every day. I will write until the day I die.”

I asked him again what he had sacrificed. We were sitting in his home where he lives on his own. He looked out past me, looking out at the amazing views of the Pacific Ocean. “Everything.”

Everyone needs to be the hero in their story

“The arc of the hero” is a structure that is at the heart of every story,” Steven told me. “But it’s also the arc of your own personal story. Pay attention to it in your life.”

The ‘arc of the hero’ is from work by Joseph Campbell and, earlier, from Jung, that is the primal structure of almost every story.

It’s the arc of Harry Potter, Star Wars, the story of Jesus, and every great story you can think of.

“If someone is sitting in their office, wondering how to make use of the potential they know they have, this is their arc also.”

  • The hero is feeling stuck, but feels he/she has a destiny
  • There is a call to action. An opportunity to become better and enter a new world.
  • A mentor (real or virtual) appears to help the hero enter the new world once he chooses to do so.
  • The hero meets new allies and even enemies.
    problems get worse and worse until all seems lost
  • The hero gets what he wants
  • And, finally, the hero has to return home, a changed person, but this return home is also beset with challenges.

We enjoy movies and stories best when they have this structure.

But our lives are also stories. Make sure you become the hero of your story. You can have many stories in your life, not just one.

We all feel stuck or frustrated at some point.

Find a destiny, find mentors, meet your new friends, confront the obstacles, return home a changed person.


Now you are the pro. Now you are the hero.

Links and Resources:

Also mentioned:

  • James Buechler

    I like to read how to be the luckiest guy on the planet by James, I read it over and over and I follow the rules

  • I loved Steven Pressfield’s ‘Legend of Bagger Vance’. it was filled with deep wisdom throughout. It reminded me of Paulo Coelho’s ‘The Alchemist”.

    The Bagger Vance book (& movie) is loosely based on the Indian Hindu sacred text the Bhagavad Gita, where the Warrior/Hero, Arjuna (Juna, played by Matt Damon) refuses to fight.

    The god Krishna appears as Bhagavan (Bagger Vance, played by Will Smith), to help Juna to follow his path, as the warrior and hero that he was meant to be.

    The plot is framed around golf but don’t let that put you off. There’s so much sage advice and lessons to be learned pertaining to life and success. One thing it teaches is the art of discipline.

    When Bagger Vance describes finding your “Authentic Swing” in Chapter 11, but has more to do with finding your authentic self and how to live a truly authentic life (whatever your form of “golf” is).

    As an entrepreneur for me the essential takeaway and central lesson of Steven’s book was to TAKE ACTION.

    There is only one way to learn, It’s through action. Everything we need to know, we learn through “the journey’.

    To continue our journey demonstrates deep wisdom, because it expresses faith in the search, launching fearlessly into the void. Unfortunatley this state of wisdom cannot last, it must by nature progress to the next state. ‘Self awareness’. We realize we possess this wisdom, but we can’t read it. Some days we can’t find it at all. Our frustration mounts, we study, seek instruction, but this only leads to despair, as we cannot overcome revealing what we need by force of will. This is when our wisdom is at its zenith.

    This search applies to most entrepreneurial endeavors. And we must strive to reach our mountain through discipline, endless effort, and utter relentless commitment to achieving mastery and our goal.

  • Ted Scarborough

    James, you are truly great at sales. You write such a compelling story to go with this podcast, I have to listen. Storytelling=sales.

  • Kaysher Hamid

    I don’t know why my PC is not loading the “player” part here. Is there any Soundcloud link of this podcast?

  • James, your player isn’t working in your blog. Your developer needs to reset that code and re-embed it to test it out. I think there’s a part of the missing. :) Thanks

  • James Buechler

    What is the blog post James refers to here that he said was one of his most popular re: Buddha’s Four Noble Truths for entrepreneurs? Thanks!

  • James Buechler

    Great ideas and extremely helpful for me thank you

  • James Buechler

    And the side notes are much much much appreciated that you provide for these interviews

  • I was listening to this in the car so all of your links and notes are GREATLY appreciated! Great interview!

    • I was paid 104 thousand bucks in last 12 months by doing an online job at my house and I did that by w­o­r­k­i­n­g part-time f­o­r several hours each day. I was following a business opportunity I found online and I am so happy that i made so much money on the side. It’s really newbie friendly a­­n­­d I’m so thankful that I found out about it. Here’s what I do…

  • jRocåmaroon

    James, I know you’re pro in what you do and a very deep person with a lot of knowledge, but can you please let your guest expand more in the question you asked them instead of cutting them right in middle answering the questions yourself and introducing whole new themes.

    I believe that you’re inserting yourself to much in in the interview and not let it be about your guests. I loved your interview with Mr. Pressfield, but I had to force myself to keep listening every time you cut him up and try to give your own explanation about the question you just asked him.


    A Listener

    • I ask when I’m curious. If I don’t know something, I ask. It will be the last time in my life, maybe, I have a chance to ask. So I do.