Death doesnt exactly make for uplifting bumper stickers or catchy memes. Much less does it lend itself to a subject like creativity. Especially if youre looking to write a bestseller.
So its more than a little unusual that death runs like an undercurrent not only through Ryan Holidays most recent book, Perennial Seller: The Art of Making and Marketing Work that Lasts, but through his larger body as well. (As proof, you can buy a memento of your demise on his website, The Daily Stoic.)
Yet somehow, sell is precisely what Holiday does.
Over the last five years, his books have moved over 500,000 copies, in more than 25 languages, and sales are accelerating. Whats more, thats just the tip of the iceberg. His creative agency, Brass Check, advises clients like Google, James Altucher, Neil Strauss, and Tony Robbins
So, why this morbid fascination?
Because death killing three things in and about ourselves lies at the core of long-term creativity and success.
1. Kill your excuses
Unlikely as it sounds, Holidays roadmap to perennial selling begins with a third century BC philosophy known as Stoicism. As Holiday told me:
The essence of Stoicism begins with making the distinction between what we control and what we dont control. This seemingly small thing is actually an enormous form of power and direction, he said. The Stoic doesnt look out at the world and try to change it; they try to change themselves to orient themselves to be the best person they can in that world.
Far from the stone-faced killjoy its often presented as, Stoicism has a long and illustrious history in entrepreneurship. From the ancient Roman conqueror Marcus Aurelius, to statesman and inventor Benjamin Franklin, right through to Shay Carl whose Maker Studios was acquired by Disney for half a billion dollars.
In true Stoic fashion, when Tim Ferriss asked Carl in Tools of Titans what phrase hed immortalize on a billboard, Carl responded: YOU ARE GOING TO DIE!
For Holiday, Stoicism means taking responsibility for life, rather than letting life dictate the terms:
When I was at American Apparel, it was often chaos. As a marketer, what that creates in you is a sense that the job is in the response. As in, Ok, this happened and what are we going to do with this? What can we do with this tiny bit of space and tight deadline? How can we turn our small budget to an advantage? he said. On a personal level, If this person is going to be up in my business, trying to attack me, what can I learn from the situation? What skill can I use this as an opportunity to practice?
Its always a question of: What are you going to do about it? he added.
Abdicating our responsibility is tempting. More so when the challenges of life are genuinely unfair.
However, to adopt a fixed or victim mindset robs us of the very power we need to face those challenges. Great art has always used pain and injustice as fuel, not just in the creative process but to thrive.
2. Kill your ego
For anyone familiar with Holiday, this point will come as no surprise. Holidays fourth book Ego is the Enemy focused on this imperative.
Still, its a subject Perennial Seller returns to because ego the hardwired desire to pursue our passions, satiate our desires, and ultimately serve ourselves is death if we want to sell to more than an audience of one.
In the book, Holiday explains, When I work on a project with clients, but particularly with my own writing I start by acknowledging a blunt but important truth: Nobody cares about what I have made. Humility is clearer-eyed than ego and thats important because humility always works harder than ego.
In the case of creatives, this can seem profoundly counterintuitive. After all, art is self-expression, right? Yes and no:
Successful creative work by definition requires satisfying an audience. Onanism is not a good artistic strategy. No one wants to buy that. If you don’t know whats going on in the lives or heads of other people, it is extraordinarily hard to make something that helps them or they enjoy.
The same is true for passion. Just because you’re excited about it doesn’t mean other people are. I felt I had to write a book about Stoicism that was my calling. But I didn’t write it in a way to please myself. I sat down and thought long and hard about how to best translate something I was passionate about into something that would benefit other people.
Killing your ego and abandoning the self-centered drive to create for me, doesnt mean selling out. Far from it. As Jeff Goins explains in Real Artists Don’t Starve, You can make money making art, and you dont have to sell out to do it.
The real issueas Goins, Holiday, and countless artists have insisted throughout timeis to fight ego with the relentless question, To whom am I adding value?
3. Kill your timeline
Relieving ourselves of egos burden doesnt mean that creative work isnt a deeply fulfilling, satisfying, and rewarding endeavor. Certainly, it is.
Just not in the manner or on the timeline we normally expect.
The creative process, Holiday noted, is all sacrifice. If the creative process is only fun, I suspect youre not pushing yourself or pushing deep into material that challenges you.
Its funny one of the knocks I have gotten has been for popularizing Stoicism, but people dont understand that the decision to write about and talk about this thing that I love and that fascinates me was not without sacrifice, he said.
I can tell you, no one in New York publishing was particularly excited about a book about an obscure school of ancient philosophy. A close friend predicted The Obstacle is the Way would sell 5,000 copies and be a huge mistake. But it was the book I wanted to write. Scratch that, I had to write it which is really the only reason to tackle any creative project. Because you cant not, he said.
Even more vital than sacrifice, however, is another mortal thread. One that takes us right back to where we began:
Theres a Napoleon line I learned from Robert Greene, Space I can recover; time. never. Of course, Seneca would say that its not that we dont have a lot of time, its that we waste it, Holiday said. Creators spend far too much time talking about what they will do and actually doing little of it. You could die tomorrow, man, are you going to be glad to put off working on your masterpiece for a day?
To kill your timeline isnt about throwing out your schedule. Instead, it means adopting a new orientation towards time itself, one that lives beneath the reality that time is limited so dont waste it talking about work. Get to work.
Death, creativity, and selling
The greatest obstacle to making work that last does not lie outside us. It does not depend on getting the right lucky breaks, cultivating the right relationships, or sidestepping the right pitfalls.
All of that matters, but the greatest obstacle lies within. Namely, our excuses, our egos, and our timelines.
At the risk of closing on a clich, perhaps Steve Jobs another man influenced by Stoicism and the desire to make something that outlasts life put it best:
Remembering that Ill be dead soon is the most important tool Ive ever encountered to help me make the big choices in life. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose, he said. You are already naked. There is no reason not to follow your heart.
Aaron Orendorff is the founder of iconiContent and a regular contributor at Entrepreneur, Lifehacker, Fast Company, Business Insider and more. Connect with him about content marketing (and bunnies) on Facebook or Twitter.
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