The Ultimate Entrepreneur

If you think about it, the artist is the ultimate entrepreneur.

Virginia Woolf, entrepreneur.

She is in business entirely for herself.

She has no boss.

No mentor.

No paycheck.

No medical, no dental, no safety net.

She has no imposed daily schedule, no externally prescribed structure.

The artist possesses total workplace freedom. She can tackle any project she wants, execute it any way she wishes, take it to market in any manner she pleases.

She can write To the Lighthouse, audition for a Broadway play, compose a symphony, lay out the next Assassins’ Creed.

The artist is the ultimate rugged individualist.

She can rise to the top or crash to the bottom.

Nothing is stopping her from either outcome except her own exertions.

[P.S. This is the fourth in this series I’m calling TK THS JOB N SHOVE IT. You can see video versions of these chapters on Instagram at @steven_pressfield. I’m guessing there’ll be between 30 and 50 “chapters” when all is said and done.]

DO THE WORK

Steve shows you the predictable Resistance points that every writer hits in a work-in-progress and then shows you how to deal with each one of these sticking points. This book shows you how to keep going with your work.

do the work book banner 1

THE AUTHENTIC SWING

A short book about the writing of a first novel: for Steve, The Legend of Bagger Vance. Having failed with three earlier attempts at novels, here's how Steve finally succeeded.

The-Authentic-Swing

NOBODY WANTS TO READ YOUR SH*T

Steve shares his "lessons learned" from the trenches of the five different writing careers—advertising, screenwriting, fiction, nonfiction, and self-help. This is tradecraft. An MFA in Writing in 197 pages.

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TURNING PRO

Amateurs have amateur habits. Pros have pro habits. When we turn pro, we give up the comfortable life but we find our power. Steve answers the question, "How do we overcome Resistance?"

Turning-Pro

26 Comments

  1. Nick on July 2, 2025 at 1:40 am

    Invigorating.

  2. Kati on July 2, 2025 at 1:43 am

    Virginia was also a sad woman who killed herself…. Being an artist and entrepreneur is a meaningful way of life, but it is not the happiest one. But then, humans have never wanted happiness. They´ve always chased meaning. Eudaimonia. Otherwise, Adam and Eve would still be in the Garden of Eden, and we wouldn’t even exist. I do not personally know one happy artist or entrepreneur, and yet so many want to have what they having. It is weird but also human.

  3. Jill on July 2, 2025 at 1:58 am

    Thing is, in the real world, you’ll crash to the bottom even with your best exertions for 20, 30 years. And those of us with safety nets (i.e. a “real job”) get criticised for having them, like we weren’t “real artists”. And then those critics turn to us saying “my aunt is in the hospital and needs surgery could you find me a buyer (for my paintings) real quick” (like we didn’t have enough trouble finding buyers for our own stuff).

    It’s not fair but that’s the way the world works. Artists are the ultimate, etc. etc. but they have bills to pay and like to sleep in beds and have food to eat same as everybody else.

    • Michael on July 2, 2025 at 3:35 am

      Using your wits to get your own money is the honorable path. Most genuine artists have the intelligence to find good day jobs. The challenge is to resist the promotions up the ladder that are offered in return for your whole mind. Being too busy for your art will make you sick. Franz Kafka took a boring clerk job so he could write whatever he wanted in the evenings. Bukowski sorted mail. It’s more likely that artists who get grants and handouts (and say the right things) are more likely not to be real ones. We are all sellouts when it comes to feeding our kids. Nevertheless, all artists owe it to their work to do their best by it and get it out in the wide world. It’s not about making money, it’s about honoring your creations. Steven gives us a boost to help us keep doing this.

    • FERNANDO BERDI on July 2, 2025 at 6:03 am

      E ser empreendedor é muito mais saudável, ainda que seja muito mais complexo e temerário.
      Curioso, Steve. Tudo o que é bom é dificílimo de conquistar.
      Saudações!

  4. Muriel Palmer-Rhea on July 2, 2025 at 3:22 am

    Virginia was a terrified woman, whose Father locked V’s older sister in an attic apartment for defying his will that she marry his choice for her. Virginia saw life as a harsh, brutal choice and left home before what happened to her sister would crash down on herself. Setting type for her own books by hand was Freedom. Accepting a few shillings from a customer was Freedom. Leonard was older and wiser, but accepting of her choices of subject matter. Freedom!

  5. Mike Swearingen on July 2, 2025 at 3:42 am

    I like where this is going!

    • Joan Di Stefano on July 2, 2025 at 4:18 am

      You do what gives PURPOSE to your life. Everything has a cost.

  6. Eleanor on July 2, 2025 at 5:04 am

    I have recently published my first book, a hybrid memo of 22 short stories accompanied by my poems and favorite recipes. Your post today is exactly what I’m experiencing. I differ about no paycheck though . I consider the sales as “money-in- the- bank”, like a savings account. True , if by paycheck you mean no income for regular expenses. I’ve read many author’s newsletters where they talk about writing as a career. I never had a career like being employed for many years so I didn’t relate to what they were saying. But now I guess that’s what’s happening without expecting it. What’s going on about my book and writing the next one is a constant focus that I have to pay attention to every day as if I was ordinarily employed.. I can tell you the this is way more enjoyable than the employment experiences I had years ago..

  7. Kate Stanton on July 2, 2025 at 5:21 am

    Dear Steve & friends,
    I recently read something that reminds me of today’s Writing Wednesdays. To paraphrase, the five levels of being an artist:
    You make art for yourself.
    You make art & your friends like it.
    You make art then strangers like it!
    You make art then strangers pay for it?!
    Cycle back around: You make art for yourself. It helps us understand the world. We have been bitten by the bug and cannot quit. Our perception shifts. Our focus may shift. Our passion may burn out from time to time. However, every single cycle can be worthy in our hero’s journey! I’ve learned that from you, Gov.

    Kate

    • Tolis on July 2, 2025 at 5:42 am

      my dear Kate thank you. And don’t also miss the book “The Artists Way”, it may be great on your path <3

  8. Chuck DeBettignies on July 2, 2025 at 5:24 am

    “She can rise to the top or crash to the bottom.
    Nothing is stopping her from either outcome except her own exertions.”

    And it takes more exertion than we probably realize when we begin.
    Venture capitalists say that if they buy 10 companies, seven of them will be complete failures, two will break even, and one may be a winner.
    As we create, to connect and contribute to other people, it takes so much exertion to get to that creation that’s a “winner”.
    But that’s how the process works . . .

  9. Tolis on July 2, 2025 at 5:55 am

    Thank you so much my dear Steve.
    I won’t write much this time, I feel lighter.

    My thought is this: besides the entrepreneurial spirit concerning the work of art, the Writer (or creator) should also consider to let her investor spirit arise: real estate usage etc. Things that will bring money to the table but also won’t steal much time from writing and it’s implications. A Writer-Investor might have some advantages. Their disadvantage is that not all creators have such leverages. Also, I don’t mean stock exchange etc. because these systems, as I read in the nobelist Kahneman, are like playnig dice even for the pros! Statistically they actually have about the same chance of success as the amateurs, they just like the game and learn it’s implications.

    My love to you, to Diana and all creators.

    Creating is one of the best ways of living life.

    • Kenny Ford on July 2, 2025 at 6:51 am

      Greeting Tolis. I think life itself is creativity!!! And yes, I’ve spent many a times at a crap table, and the dice really don’t care if your an amateur or a pro.. So long as they’re in your hands when the dice are ready to get smoking hot at the table… Would you consider athlete’s artist??🤔

  10. Jackie on July 2, 2025 at 6:34 am

    I always had a day job shadowing the artist jobs. To work with raising a family, I took jobs with a cleaning company, worked in greenhouses, unloaded trucks, anything where I could be present for family on weekends and evenings. I wrote and painted before work and when everyone went to bed. When the day job start time changed to 6am, I woke at 4am. to write. To do things my way, takes a tremendous amount of effort to not quit. I mention this because some days the only thing that keeps me going is the phrase from The Handmaids Tale; NOLITE TE BASTARDES CARBORUNDORUM.
    Don’t let them grind you down either. Keep to the task. Great week wished to all.

    • Chuck DeBettignies on July 2, 2025 at 1:51 pm

      I salute your “finding a way” and being true to yourself.

  11. Joe Jansen on July 2, 2025 at 6:36 am

    I’m reading the recently published biography, Cooler Than Cool: The Life and Work of Elmore Leonard. Even while working his day job/real job as a copywriter at Campbell-Ewald ad agency, cranking out promotional copy for Chevy cars and trucks, he was up at 0500 every morning to write for two hours. Part of his deal with himself was that he had to write a paragraph first before putting on the coffee.

    At 0700, helping with breakfast for the kids, then a stop at church to attend mass, then at his ad-agency desk by 0900. Every day. He published five novels and 30 short stories under this regimen.

    That feels entrepreneurial.

    https://www.amazon.com/Cooler-Than-Cool-Leonard_A-Biography/dp/0063306867

    • Joe on July 2, 2025 at 12:01 pm

      Continuing to read this Dutch Leonard biography and reminded of something that touches on a topic that people often struggle with: this tension between “art” vs “commercialism.”

      Elmore Leonard starting by publishing Westerns because there was an active market for those stories. In the late 1950s and early 1960s, the market for Westerns dried up — and he shifted to crime novels.

      He became widely recognized as a master of the craft, and so might be taken as one example that art and getting paid are not incompatible.

  12. Tolis on July 2, 2025 at 6:41 am

    A small comment: I didn’t see on IG your posts on the new subject, I just got to your profile and the last video posted is that of the young kangaroo.

  13. Maureen Anderson on July 2, 2025 at 8:05 am

    The common theme seems to be defining what you most want — and what you’re willing to give up to get it.

    Many years ago a friend told me she took another job that didn’t make her heart sing because she wanted a nice life. Which made me think, “I’m glad I got that out of my system. I want an interesting life.”

    I love seeing the different approaches to that, here!

  14. Laurie on July 2, 2025 at 8:48 am

    This is a conundrum for me. I want to paint what I want and yet I feel the constraints of the art world if I want to sell work.

  15. Sha on July 2, 2025 at 9:08 am

    Beautiful. We are free. Even bad outcomes are not as harsh as never giving it a go. Life is good. Go for it!

  16. Ken Williams on July 2, 2025 at 1:21 pm

    As usual, you wrote this for me to read at this exact moment. I love this. This is the most scared and happy I’ve ever been…doing things on my terms. I decided two nights ago to write the book I’d like reading. To hell with everything else. You
    are my muse, Steven Pressfield.

  17. Stella Kevin on July 2, 2025 at 4:41 pm

    Wow, this post hits hard—it unpacks gaslighting in relationships with such clarity and empathy. That part about how it erodes your confidence?

  18. harish kotian on July 2, 2025 at 8:24 pm

    This hits so hard. Total freedom sounds like a dream, but it’s also terrifying. No safety net, no fallback just you, your work, and the will to keep showing up. Respect to every artist out there living this reality. 🔥💯 Definitely following this series it’s real talk we need more of

  19. Kevin Kermes on July 3, 2025 at 2:01 am

    I couldn’t agree more. My colleague and I were drawing this parallel jsut the other day in a conversation.

    I’d go a step further that the establishment (corporate) doesn’t want you to fully access this artistry. When you realize you true creative power and license, the idea of a job and a role become limiting to your potential.

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