Despair or Destiny? Why Artists Live the Most Joyful Lives

Recently, I got a message from an artist friend. “Do you identify with this?” she asked.
It was a picture from Steven Pressfield’s The War of Art, page 68, titled “How to Be Miserable.” I’d read the book years ago, loved it, and recommend it to every artist I meet, but I didn’t remember this section. In it, Pressfield equates the practice of art to being a Marine—reveling in the sheer misery of creating. He says, ”an artist committed to his calling has volunteered for hell, whether he knows it or not. He will be dining for the duration on a diet of isolation, rejection, self-doubt, despair, ridicule, contempt, and humiliation. An artist has to love being miserable.”
Yikes. When I read it, my heart sank. After the hundreds—maybe thousands—of artists I’ve recommended this book to, did they read that page? I hoped they’d skipped it or it bounced off their brains. Oh Steven, Steven… what are you saying here? You're definitely being dramatic and exaggerating. Artists are signing up for a life of despair and humiliation? An artist has to love being miserable?
Into the Fire
Of course this grated on me, and I immediately rejected the idea. But then I thought about the question: Did I identify with this? I thought back to the beginning of my education in art. I traced my steps all the way back to when I was first getting started. I thought about how many times someone told me no, or how often I wasn’t accepted into a show. I thought about the dealers and publishers talking about my art as if I wasn’t even there.
“I’m not sure that color will sell,” says Joanne.
“Yeah, looks kind of dated,” says Todd.
“Let’s pass on that one and this one,” says Joanne.
“I agree, but we can try this one over here and see if anyone will like it,” says Todd.
I remembered the galleries that ripped me off and pretended they didn’t have any of my work or had never heard of me, even though I had records proving they had received everything. I knew they were trying to steal my art. I had a sick pit in my stomach about confronting them and felt despair wondering what recourse I even had.
Then there was the time an entire tent burned to the ground with all of my art in it, and every vendor sued us because our electrical outlet was damaged—even though we reported it and no one came to repair it. Our booth was ground zero for that fire. The whole experience was terrifying. Court depositions were intimidating and humiliating.
My mind drifted to the time I spent $16,000 on a booth at the New York Art Expo and was blacklisted by our ex-dealer, who tried to destroy us forever in one weekend. I remembered hiding under the display table, crying my guts out into my hands as silently as I could. Tears of injustice rolled down my cheeks as I felt the depth of that dealer’s contempt for me.
Sweetness and Struggle

I have definitely been kicked in the face, betrayed, and eaten a ton of poop sandwiches. But nothing compares to the joy and freedom of creating for a living. Nothing compares to being present when someone sees their painting for the first time and their eyes well up with tears. Nothing compares to struggling through a difficult painting and then feeling the satisfaction of conquering all your doubts. Nothing compares to the empowering feeling that you defied the odds, said “no” to all the naysayers, and stubbornly—relentlessly—stayed faithful to your dream.
There is nothing like having Monday be your favorite day. Nothing like the deep fulfillment of knowing you are truly living out your destiny. There is great reassurance in knowing your purpose is not unspent, and you said yes when others said no.
What is truly miserable, exceptionally disheartening, and utterly frustrating is watching the hours of your life tick by while doing a job you don’t care about. It’s miserable to trade time for money just to scrape by. Misery shows up in every insult a superior hurls your way, every minute spent in rush-hour traffic, every decision from the top you don’t believe in. A dead-end job is misery.
Allowing time to pass you by, marked by unpainted paintings, is miserable. Not trying, giving up, throwing in the towel—that’s miserable. Feeling hopeless and wondering what life is even about is miserable. Knowing you gave in to fear is miserable. Despair, isolation, and humiliation are found in being distant and detached from the pursuit of your dream.
The Joy of Saying Yes

So the answer I gave my friend was “no.” A deep and profound no. I don’t identify with what Steven Pressfield wrote on page 68 of The War of Art. Time in my studio—painting, creating, experimenting, trying new things, hacking away at large oil paintings, even struggling through a commission, hoping the client will approve—is all joy and utter fulfillment.
I love to paint. I enjoy every moment behind the brush. I love creating content and masterminding with my team. I love inventing new products, helping and mentoring artists, and watching them grow. Monday truly is my favorite day of the week. I rarely, if ever, take vacations. My work doesn’t feel like work. I would do it with or without the pay.
Working at the bank, waiting tables, stocking shelves at the Golden Pantry—that was miserable and lifeless. If I had never said yes to my destiny, I would still be in a job I didn’t care about. The brief and infrequent misery, despair, humiliation, or contempt I’ve experienced on my art journey pales in comparison to the misery I felt daily in a job that meant nothing to me other than a way to pay my bills.
So take up your brush! Sit before your easel and let it flow. Stop wearing the ragged, overused cape of the miserable artist. Don’t listen to Steven. There is nothing glamorous or romantic about the suffering artist. Get over it.
Life is short, and you are here for a purpose. Your life counts, and your art means something profound to this world. The art inside of you can only be created by you. Don’t wait. Don’t hesitate. This is your time to take your seat and preside over the dominion of the beauty that flows from you.
What do you think? Do artists need to love misery?
This provoked my emotions because it speaks to me in my situation So strongly I love Creating art and being social but yet I found myself not doing it as much as I want to because I have to work a schedule that seem to just take everything from me my energy my creativity etc. I don’t think a artist should have to suffer and live miserable i do think a Artist should be putting full effort into creativity and business which can bring challenges. Having a stressed free environment I think would help a artist be fully immersed in painting and prudence a Masterful work.
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Elli Milan Art replied:
My heart goes out to you. You have to fight through, being temporarily miserable to get free from your job to live with full time joy!
Dear Elli,
I’d like to drink a cup of coffee with Steven Pressfield. In my opinion he’s not taking the Marine-principle deep enough and I’d like to discuss the following with him; Marines know how to endure pain, to deal with uncertainty, to work with what they have, to go the extra mile, but all in service of accomplishing a GOAL. This makes Marines all about their why and not the journey of suffering towards it.
I’ve known a few soldiers that went into war zones. They weren’t there for the suffering! They were there to make a difference, to help, to save people. They were there because hardly anyone else would choose to be there and they chose not to look away, but to face whatever head on. And they did, That was hell (war in the Balkan area Europe). but even when they came back they wouldn’t have had it any other way. Not because of the suffering, but the lives they saved. And that’s really saying something!
Seems to me Marines have a strong enough why to endure any how, just like the soldiers I knew.
And as for artists, this applies too. There are many experiences, like you have had yourself, that are no fun. But that doesn’t automatically mean you set out to get those experiences on purpose! it simply means that your why and the upside of being an artist is so worth it. And that’s what you live and breathe.
I guess some people can’t help focussing on the negative and always try to explain why something cannot be done. It’s so sad how their survival brain is running the show. They are not very happy people too. Also, being negative attracts readers. Fear, unfortunately, still sells.
Ofcourse there are many more sides to life as a Marine, but this what mr. Pressfield states is just nonsense, so I think I’ll pass on this book, until mr. Pressfield has revised this (and maybe other) section.
Sorry if I’m too firm in my words, but this really has my blood boiling!
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Elli Milan Art replied:
To be fair, in context to the rest of the book, I think Steven Pressfield is saying exactly what you are saying. I think that’s his point. However, I’m just saying I don’t think the creative life of being a professional artist is miserable. Any offer out to an artist is what is miserable. Maybe writing is miserable while painting is not. I think artists get into a role or mindset of being a miserable wretched, broke, isolated, rejected artist is romantic. Like they are some kind of hero for it. I think page 68 feeds into this. 😊 thank you for your insights!
Absolutely not Elli! And thank you for laying out the pros and cons of your journey on a visual scale affirming the importance of converging with people in accord with one’s own path. I so appreciate your insight always!
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Elli Milan Art replied:
Thank you!!
“Artists must love misery.”
Nope. Hard pass.
After reading this Elli, I’m more convinced than ever that we don’t keep creating because we enjoy suffering — we keep creating because we love meaning more than comfort.
Yes, the journey comes with setbacks, rejection, and the occasional soul-bruising moment. But the real misery? Living a life that isn’t ours. Letting our art go unmade. Trading our gifts for “safety.”
The studio isn’t misery.
The struggle isn’t misery.
The unlived life is.
Thank you, Elli, for reminding us that joy is not the bonus of the creative life — it’s the whole point. 🎨🔥✨
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Elli Milan Art replied:
Love this! So well said!
I have been through misery already. I have strong advice…. Don’t feed it. Life is too short.
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Elli Milan Art replied:
Yes. It’s all about perspective.
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