Artist = Entrepreneur
Are you familiar with the work of Ryan Holiday or Jack Carr?
These gentlemen are what I mean when I say “artist = entrepreneur.”
Both are excellent in their specific creative spheres. Both can handle their emotions despite any external adversity or their own internal Resistance. (I.e., the first “two brains” I cited in last week’s post.)
But where Ryan and Jack truly separate themselves from the competition is with the third brain—the mindset of the entrepreneur.
Ryan and Jack are not just writers, they are industries. In movie terms, they are studios. Both have podcasts, both have extensive speaking careers, both have massive online presences. Both tour. Both have teams to support them. Both have online stores with as much merchandise, it seems, as an old-time Sears Roebuck catalog. Ryan has an actual physical bookstore in Bastrop, Texas (outside Austin) that doubles as his office and podcast studio.
You may say (and I might myself), “Hey, I don’t wanna do that. I’m a writer. I don’t have the time to build an empire and I wouldn’t want to if I could!”
Consider this, however. The year is 2025. The world has changed. You and I can’t hope for a review of our newest novel in the New York Times. The apparatus of awareness generation that once supported writers and artists no longer exists (or at least has changed form dramatically.)
When a Big Five publisher evaluates our work and ponders bringing it out in print, its editors and sales team and marketing people ask, “What else, beyond her talent, does this writer bring to the party? Does she have an online presence? Does she speak at events? Does she do personal appearances? How will she come across on podcasts or radio or TV? Does she have a podcast herself?”
I’m not trying to discourage us, I swear. I’m only trying to point to the hardball reality of the 2025 creative world.
Each of us must be the face of our brand. We must have a brand, even if it’s the idea of NOT having a brand.
Nothing is more dispiriting than to launch a work of our best and truest art into the world and have it vanish without a trace.
We are of necessity entrepreneurs, you and I, and we have to learn, one way or another, how to represent ourselves and our work as such.
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.
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.
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.
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?"
I do not find Ryan Holiday very believable so do not examine or think about his work.
Jack Carr writes tremendous Novels. I’ve been reading them since you mentioned Jack a while back.
We have to develop our own uniqueness.
Besides when we attempt to copy greatness it tends to get diluted and sometimes we can move away from our natural self and talent.
Thanks for a timely note on what it takes to build a personal brand in the age of social media. I realize that this is sort of unrelated, but I seem to have misplaced my Strunk & White style guide. Is the prevailing trend henceforth that when referring to a hypothetical personage, say an aspiring author, the assumptive pronoun is “she”? Because that’s a trend I’ve been noticing since the recent turn of the century. What if we’re talking about a serial killer or some other type of social untouchable? Does the assumptive pronoun revert to “he”? I get confused about proper etiquette, and I know it’s considered gauche to discuss at literary cocktail parties. In case I were to hypothetically get invited to one. What about capitalizing racial signifiers like black and white? I know about capitalizing Japanese or Namibian, as they are proper names; but are “Black” and “White” now de rigueur everywhere and always? Or do we capitalize Black, but leave white lowercase in lieu of monetary reparations for long-dead ancestors? Again, I apologize if this sounds petty or facetious. I’m the kind of person who sees the fastidious punctuation and diacritical marks in the New Yorker magazine, and instantly thinks “Whew! I’m a cosmopolitan intellectual, and these people are giving me a wink and a nod that they’re cosmopolitan intellectuals too; diacriticals, even! If you know, you know…” Then, whenever I’m forced to read some run-of-the-mill publication which is less punctilious about punctuation, I fell sullied and unclean. These are some random thoughts that drift through my addled brain in the wee hours, when I really should be asleep, or else stealing some convict cadaver brains from the local cemetery on moonless nights, for Master’s experiments…
And this is why only the “sharks” make it right? Even if the work of the sharks isn’t very good, as long as they know how to sell themselves, it doesn’t matter if they turn out shite.
I wish I were a shark, sometimes. I did try. For 20 years! But I guess it was a lot like a bunny putting on those plastic vampire teeth like the kids wear for Halloween. A shark just isn’t who I am and maybe it’s time I stopped trying. All that trying made me forget that art is something I love to do because it’s FUN. It took the joy out of my painting. The practice really only became toxic when I put my entrepreneur cap on.
Maybe it’s high time I accepted that we can’t all be Mozart and that most of us really are just Salieri. I want to find the joy in my art again. I’m never going to be a superstar and that’s all right, I guess. For those of us who still have the drive to be entrepreneurs as well as artists, good for you and I wish you all the best, honest! But for me I guess I don’t want to wear the plastic fangs anymore. I guess I just don’t have it in me to be a shark.
Hey Jill, cheers to the bunnies who find fun in picking up their brushes after folding underwear. The world needs us, too.
Bravo!
Hearing the applause as a symphony👏🏻
And here is where I land. I want to write, blog, host my podcast and be a great public speaker. All of these I have made stabs at, mastered none. Brand? Just being Gigi isn’t quite enough!
True story. And it’s charming how you lump yourself in with “us.” Thanks.
Hey Steve, I’ve been an email subscriber to this blog for more than a year now, this is my first comment I just want to thank you for the support, we’re all on our separate journeys but at the same time we’re on it together
I really wanted to respond without an emotionally fueled statement, but it might not be possible. As a writer and painter, I folded my blog to find more time to finish a middle-grade book. I began a third book while querying the first book and am waiting for illustrations for the second. I’ve sent out multiple short stories and an easy reader. I have three paintings ready for an upcoming juried show. I grow a portion of my food, am part-time daycare for a grandchild, part-time eldercare for a parent, clean my own home, go to the gym three days a week, and do volunteer work. What I see from down here in the pits is an industry that wants you to do their job for a chunk of profits. In a society where many women and a few men are our society’s safety nets, there is not enough hours in a day to also become your own entrepreneur. It’s daunting, but still I persist. So if a publisher passes on my work because I do not have an already made audience, I will have to live with that. This juggler can’t see how to add one more ball to all the balls already in the air. Thanks for the vent. The laundry awaits.
“What I see from down here in the pits is an industry that wants you to do their job for a chunk of profits.”
This is the most beautifully put calling a spade a spade.
Could not agree more! How does one find the time in a busy life to do these things AND be creative? That I would like to know.
Perfect read for me today. Where can I learn more about how to represent myself. I have just published my first book. So far my advertising method has been to talk about my book and give out my book marks. I know they have created some sales..
That is very interesting. The decision is – is it important to me that what I wrote is shared with as many people as possible? Do I want my stories and beliefs and what I am learning to be told to as many as possible – and why? Because my story may resonate or be very similar to what you are going thru or thinking. And that’s enough. I just have to choose how much I’m willing to push to promote it, put myself out there and try. Thanks Steven – always love your perspective and advice. I love writing wednesdays.
Indeed … I am wondering how far I must go. And I must say that I deeply feel that those 2 guys are just way to “powerful “ for me. The energy they have, not given to all. Imho.
I find that the more I focus on going on Insta, FB, Linkd, etc they all sick my time !
But I still understand what you mean. But I feel overwhelmed.
That was well said. We are entrepreneurs by necessity. Thank you for enlightening our sometimes lazy understanding of what it takes to make it in 2025.
Exactly right. Decades ago, I went to a pitch session for Christian writers, and even there, the first question was how many followers do you have in your social media accounts. One soft spoken woman had not only followers, but she also did YouTube videos, etc. They were immediately interested without even seeing any copy. This is our reality now, and the lid cannot be put back into the box.
Yikes, Steven! I know you are right about this because I have been avoiding admitting I’ll ultimately need branding, which totally terrifies me! I do accept, thanks to you, that this terror is just another form of Resistance rearing its ugly head.
Right now, I think it would take me too long to learn how to develop the most effective, multi-platform, media presence for myself; so I’m resigned to delegate that which I cannot handle. I know there are experts out there and if reinventing that wheel is too daunting for me, I accept that I’ll have to find a branding professional for guidance.
Perfectly said. My Empire is under construction 🙂
Thank you so much dear Steve.
I can see it from two sides. On one side, those writers are also entrepreneurs and marketers. It seems to run through their veins. And to expect greatness or fame from absolutely nowhere, or worse from the commercial world, without being a marketer etc., that sounds foolish especially today.
I will also counter-argue with your encouraging thought from the war of art, that the writer is an Infantry Man. Those other candy-asses he despises. In that infantry man there is wrath, anger, threat from the war zone, failure as hell, and powerful emotions if controlled, and original, not on purpose: it is his duty, as the writer has one. Not that being a great entrepreneur isn’t original -it’s just that the entrepreneur is a salesman. I don’t know exactly where a commercial man and a pure soul interwine and where not but my heart worries.
Although I studied many entrepreneurs, and their ideas were fascinating and self-improving, I must distance my work from entrepreneurship -damn, I don’t want to- on one thing. It is not logical. That thing is, as much as I can express it, the difference between creating and gaining. Damn. If my creating self is influenced by my gaining self, or even lead by it, then I must give the people *what they want*. On the other hand, if my creating self has walls that let nothing in, except inspiration and work and my life’s drama and canvas, then I give the people *what I am*. And what I am is so complex and unique that it can’t kneel under the banner of what “they want”. Nor of what they don’t want.
It’s me. So it’s life.
P.S. I can’t see comments here these last two posts. It’s ok, I think I’ll continue commenting even if ghosts read my thoughts.
This is a very interesting subject to discuss and, as seems often the case, a difficult one to find balance in. If anyone hasn’t read it already, I would highly recommend reading Scott Alexander’s “Meditations On Moloch”(do a Google search). A brief summary description: how competitive systems trap individuals and societies in destructive patterns, even when everyone acts rationally. Alexander uses the metaphor of Moloch to illustrate the need for better coordination and structural change to avoid collective ruin.
Yes, the competitive nature of commerce can provoke new creative ways of doing things but, again, at what cost and what are you ACTUALLY creating? Even if you have a “team” handling the complexities of modern communications, it’s hard not to think that your simply creating a self-perpetuating, self-supporting system in and FOR itself, without actually creating anything new (or honest). Every time I watch a Youtube video, I am reminded of the time and effort put into writing, lighting, recording video and audio properly, editing, publishing etc…and I am often left thinking: WHY? And the answer I’m often left with is this: Because everybody else is doing the SAME THING.
I’m all for creative pursuit and for financial “stability” but, again, finding BALANCE in it all is very challenging. We are all very fortunate to have the “Tyranny of Choice” but I would strongly suggest that we’ve all become far too competitive and everything has gotten completely homogeneous and, quite frankly, the antithesis of what the War of Art suggests. I don’t want to sound trite, but it’s complicated.
It’s also a lot easier in this day and age to self-publish.
So there’s that.
Not everyone has the desire nor energy nor money to do what Ryan or Jack do. In fact, I’d argue they’re pretty singular cases.
Few want to hear speeches from nobodies building their “personal brand.” And unless they’re already flush with cash or collateral, starting businesses like bookstores isn’t realistic for everyone.
Ryan started from a college dropout and all of this came from him over decades.
This post reminds me of being an acting student in Chicago in the 90’s. Everybody and their brother was starting a theater company to emulate the Steppenwolf Theater Company, whose alumni included Gary Sinise, John Malkovich, and others. The thinking was “they started a company in a basement, then got famous in Hollywood. We’ll do the same thing.”
And so there were about 400 theater companies in the city. Of course the truth was the Steppenwolf members never intended to get famous, it was lightning in a bottle. That particular phenomenon has never been replicated since.
I suspect the “author as podcaster/speaker/brand” thing is like Steppenwolf in the 90’s. Now that the model has been proven, the next thing is already happening, somewhere in a basement.
May I offer what I hope is hope (!) for people who find this post discouraging?
Whether it’s in person or on a podcast or even an eMail, every so-called marketing opportunity is another chance to strike a chord — the same way you do with your writing — and it’s only separate from your so-called real work if you decide it is. It can be as much fun as working on a novel if you allow for that possibility.
Every morning, I realized only recently, I practice a little standup routine with my husband when he joins me for coffee. I’m fresh from a good night of sleep and the dreams I had, the caffeine, and whatever’s been swirling around in my head since the last time we talked. He never knows what we’ll be talking about, only that by the time we finish — and you can ask — he’ll be laughing so hard it hurts.
It feels like I’m practicing for something, but I don’t know what. (And Etaoin, to your point, I give myself demerits for “ums” or “ers” and tangents. If I go for elegance in so-called normal life, I won’t have to don a Superman cape when the stakes are higher.)
If I’d succeeded, or was on my way to succeeding, at what Steve talks about in this post you wouldn’t have to go to my site to find out who I am. You’d already know. But you know what? I’m still having fun and I’m still learning a lot. Every day. The reward, at least for me and at least right now, is in the work. It has to be! Yet from what I hear, that’s also the endpoint. Truly successful people can’t imagine retiring because they love what they do.
I’m going to keep this comment handy to remind myself what I just said! I hope it will help me, the same way I hope it will help you.
It’s a bitter pill Steve hands us this week, and I’m sensing from several of the comments I just skimmed that some of his loyal followers—fellow brother & sister “warriors-in-art”—are wrestling with the stark reality Steve presents here: This subject happens to cut to the core of what I myself am dealing with as a writer without a Substack, who reviles Meta, who resents having to have an Instagram page, and who rails against succumbing to the algorithm—The world has indeed changed, and there’s no getting around it. We either evolve or our work will sit in a notebook or on our laptops until we shuffle-off the mortal coil & is found by those who survive us like Kafka’s stories & Dickenson’s poetry.
I, for one, do not wish my work to suffer that fate.
Guess it’s time to register a domain name on GoDaddy, “suck it up, buttercup” & start building my brand—Dammit, Steve, how do you always seem to know exactly what I need to hear to light that fire under my arse?
The fact that countless great writers were never published because they didnt have any hustle is a real bummer.
Then there are all the artists and innovators that lived and died in factories and farm fields because of circumstance.
We dont all get to start on the same line.
Another example of how “and also” can be good
And how sometimes “either or” can be just the wrong approach.
It’s a personal decision, and admittedly finding my “and also” with my books is my resistance. Writing producing not easy, but I got it. Doing branding promotion etc is Resistance in spades. Crazy, because I spent 35 years in for profit management.
So many want a piece of you for retainers
Invest or not, that is the question SP.
Well if you believe your story or work can change worlds, would we not shout it from the mountain top? I think belief is key.
I’ve heard this before and resisted this, much like the notion that this is work, work, work, discipline, work, work, but the muses have dragged me over that hurdle and I’m seeking their strength in this next phase.
Thanks again Steven.
Great post Steven. I have been to Ryan Holiday’s Painted Porch Bookshop many times and have hired Ryan to speak at an event for a corporate client of mine. We’re neighbors in Bastrop. He’s awesome and has come a long way. He’s grown his niche organically, it took a long-time and he’s managed to scale up by being consistent and creating content that acts as an extension of his books. His social media skills and production value have improved over time because he does the work consistently. Each video or podcast gets a little better due to practice. As a solo musician I have learned that a band is a brand. you have to have the mindset of an entrepreneur if you want to make a living off of your art, music, writing etc. and some of that requires getting out of our comfort zone and in front of the camera It’s a lot of pressure to take the plunge of commiting to our art as our business and day job but it’s also a lot of fun and spiritually rewarding knowing you get to work on your art everyday. Once I committed to my art full-time (and left a full-time job) my audience grew as did the opportunities to earn from my art. I still face resistance when i have to make promo videos / reels for my tours and releases but i try to learn a little each day and publish “something” knowing that these incremental gains compound over time. I just look the harder work of social media content, merchandising and such as creating bonus material for my fans, as an extension of the published work (book, album, painting etc).
U Turn-
School just ended for the year. Wanted to thank you for the sweet comment to those who could not attend the course. Could not bail on job but hope to be able to sign up for another one of there is one.
Also wanted to post my own mean-spirited received comment adding to the old Master Booger-Resistance.
Sitting contentedly in a public space drinking coffee and working on a ms. Think it was Barnes & Noble. Man at adjoining table leans over and asks,”What are you doing?”
I explain that I’m completing a book chapter. He eyes me doubtfully and says, “Yeah…so have you ever even been published?”
I answer briefly that I have had a lot of local success but always hoped to write a book, and after a long time searching, had found a subject that I thought would make a successful book.
He stands up and eyes me with definite contempt this time and says triumphantly, “Nah… if you were ANY good at all you’d be rich by now.” And makes his exit.
Zing. Mission accomplished. I’d be rich how as opposed to drinking coffee in Barnes and Noble? Would I be at Starbucks or another overpriced coffee joint instead our friendly B & N ?
My question, group, is whether writing alone is enough? Is it only worthwhile if you hit the jackpot? The fraction of writers who get six figure advances seem to have skewed the dialogue forever. If you are not one of those, you have no worth or purpose, I think he meant to say.
Steve, i have always wondered…you gave up so much to wrote,, in that concrete house in the woods. You absolutely deserved success if there is any justice in the world. But, if you had not made it, would you think it had been a waste of time, a bad decision to try ? Is the future cleaning windshields in Times Square. Ah, the pain…thanks for the great blog posts. Keeps me going.
This is such a feel-good share.