Hey, Interintellects! Next week, writer and editorial director Herbert Lui will be discussing his new book on creativity, Creative Doing, in a SuperSalon hosted by startup veteran Jason Shen, who embarked on his own Creative Doing challenge.
We’re sharing an introduction from Herbert and a few of these prompts in this exclusive excerpt—check out the book for more! This book was written for entrepreneurs, freelancers, in-house creatives, hobbyists, and aspiring creators of all kinds—especially those who feel stifled by their day jobs, or otherwise blocked creatively.
The premise of Herbert’s work is that creative thinking comes from creative doing—taking a little bit of action every day. So whether you have a project you’ve been meaning to pursue, you want to deepen your creative problem-solving, or unveil your creative purpose, the 75 prompts in this book are bound to help. If you like what you read, tweet at Herbert and learn more about his work.
We hope to see you there!
—ii Editorial
Great ideas aren’t found, they’re made, through consistent creative practice. Creative thinking comes from creative doing.
Influential painter Chuck Close said in an interview for Inside the Painter’s Studio:
“Inspiration is for amateurs—the rest of us just show up and get to work. And the belief that things will grow out of the activity itself and that you will—through work—bump into other possibilities and kick open other doors that you would never have dreamt of if you were just sitting around looking for a great ‘art idea.'”
Or, as Picasso said, “Inspiration exists, but it has to find you working.”
What you’re reading in this excerpt, adapted from my book, I wish I had at the beginning of my journey, one with prompts that would encourage, stimulate, and strengthen the creative process.
My approach to creativity is to bring together the hands, head, and heart, by focusing on quantity (doing as much as you can), quality (improving your abilities and honing your taste and style), and purpose (knowing what you are creating for).
This book provides exercises to move each of these levers forward.
A lot has happened since I wrote and independently published this work—I got a chance to work with a publisher (Holloway) to expand and revise the book. It has made a difference with some readers, and my writing has reached millions of viewers. Regardless of these external rewards, the thing I’m most proud of is that I found a way to make my creative process work throughout the other commitments of my life—work, relationship, family, friends, and health.
The incredible intrinsic and extrinsic rewards of the creative process do not mean that it comes easily. Whether you’re choosing to make a vocation out of your creativity, you’re seeking a new hobby, or you’re simply figuring out how to make time for your creativity, this book will enable you to find the process that works for you. It’s something that nobody else can teach you, that only you can learn for yourself.
Work with What You Have
Artist Chuck Close describes the tendency for artists to spend years finding, designing, and outfitting the perfect space to work. Once the space is done, though, they end up selling it and building another. Close says in Inside the Painter’s Studio, “It seems more often than not a way to keep from having to work. But I could paint anywhere. I made big paintings in the tiniest bedrooms, garages, you name it. You know, once I have my back to the room, I could be anywhere. I could care less.”
Even before we start our creative work, it’s easy to find reasons to stop—it’s common to say, “I can’t create because I don’t have professional tools or the right space.” We spend hours—maybe even days—getting around obstacles that we set up for ourselves. Even for something like writing, which can involve as little as a single tool, you can stop yourself from actually working by cycling through an endless series of questions: what word processing software or notebook should I use? Where should I publish my work? If I’m deciding to set up my own blog, which software should I use? Should I be building my audience first instead of writing?
These questions are all well and good. They also have absolutely nothing to do with writing. Just put the pen on a page (or even a scrap piece of paper), and start writing.
In reality, we don’t need anything except our brains and bodies to practice our creative work. The goal is to put this reality into practice with the fewest tools possible, in any environment.
◀️⬌ Or flip this prompt: Find the Simplest Element of Your Craft
Draft, Demo, and Sketch
No creative work emerges finished. Preliminary work is rough, and often bears little resemblance to the polished, completed product released to the public.
Mozart would often start a piece, set it aside, and then pick it back up months or years later. Musicologist Ulrich Konrad called these beginnings “departure points … a delineation of intellectual places to which Mozart could return as necessary.” Each field has different names to describe preliminary creative work. In writing, a preliminary work is called a “draft.” In recording arts and software, preliminary work is called a “demo” and often used to demonstrate the artist’s or group’s capabilities and the work’s possibilities. In visual art, preliminary work is called a “sketch,” and used to assist in making the final work.
Preliminary work is not optional, and every version of preliminary work is crucial for improving the work we’re making. This stage is far too early to demand perfection; it’s best to keep expectations low, to refrain from self-criticism, and to support psychological safety (the feeling that it’s okay to make mistakes) to allow every single detail of the idea to flow out.
One of the most fascinating properties of the creative process is, every version of a piece of work can be seen as preliminary work. While you can finish different versions and variations of a project, there doesn’t have to be a final sense of completion. Pablo Picasso said, “If it were possible … there would never be a ‘finished’ canvas but just different states of a single painting.” And here’s W. H. Auden paraphrasing a line of Paul Valéry’s: “A poem is never finished, only abandoned.”
Dacoury Natche and his collaborators worked on the song “Time” on Childish Gambino’s 3.15.20 album for nearly two years. Natche said there are multiple versions of the song, including one that sounds more like a party, and another that sounds more like a live version. He was willing to commit that time because the song held potential. He described his mindset: “Let’s just try as many versions as we can because I know this song feels like something special.”
Our goal here is to practice not worrying about whether or not something is perfect. Instead, it’s about creating one version of a project that will likely either be improved upon in the future or serve as inspiration for something else. The key is to cultivate the commitment and conviction to declare that something is done, for now.
“Anything you do is basically a demo until it comes out, or it’s present,” said Dacoury Natche. “Sometimes even if it comes out, it still can be a demo.” It’s fitting that Natche brings this up, since iterating on final products often takes place in music through remixes, samples, and covers.
It might sound counterintuitive, or even painful or scary, to your inner craftsperson to complete work in so little time that it doesn’t feel ready. That’s the whole point. Your judgment of your work may not reflect how somebody else interprets or experiences it. It’s fine to know something that you made isn’t your best, and still declare this version of it complete—or to release it to the world. The work that resonates with the most people may not be the one that you declare to be the best; still, it can make an impact on people.
This prompt requires that you focus on starting something and finishing a version of it. Think of everything you make as a demo, a sketch, or a draft. Remove all ideas of expectations and goals, and focus simply on the process and taking a draft to a state where you declare it finished and acceptable as a working version. With every end comes a new beginning. It’s only by finishing a preliminary version of your work imperfectly, that you can start a new one.
Set a 10-Day Quota
The mystique of art and creativity shines a spotlight on inspiration and creative breakthroughs. A practitioner will speak more of the power of repetition, routine, and tangible deliverables.
This is a priceless lesson that many people have paid thousands of dollars in tuition to learn. As I share in Source Inspiration, graphic designer and Pentagram partner Michael Bierut assigned a project to his students: pick an activity and commit to doing it for 100 days in a row. Bierut recalls his instructions: “The only restrictions on the operation you choose is that it must be repeated in some form every day, and that every iteration must be documented for eventual presentation.” Bierut would repeat this project in each class in the following years. One student chose to dance every day, another chose to make a poster in under 60 seconds each day, and still another made a different version of the same poster each day.
This is a reliable way to gain experience, improve your skills, and build discipline. Lindsay Jean Thomson, who facilitates the 100 Day Project, an online project inspired by Bierut’s class, told me in an interview that there is a noticeable improvement in how the projects turn out from day one to day 100. “If you sit down and do something every day, you will get better at it,” she says.
One hundred days can sound like too much of a commitment, so I suggest starting with 10. If you feel on day 10 that it’s manageable, then continue to day 100.
You have innate discipline; it might just be asleep. The daily quota will cultivate this discipline, channeling it into your creative work, until it’s strong enough to take over and it becomes a part of who you are.
For added accountability, participants in the 100 Day Project need to share their progress every day on Instagram, and Bierut’s students presented their project at the end of the 100 days. To keep yourself accountable, I’d recommend doing the same form of public documentation during this 10-day project. If you find that the work isn’t ready for you to show to all of your followers yet, find a friend or classmate who might want to share their own 10-day project with you. Now you have an accountability partner.
The beauty of this exercise is that it also encourages you to find idle time and space in your day for your creative work, helping you form creative habits that will last well after this 10- or 100-day project is complete.
◀️⬌ Or flip this prompt: Do the Opposite
Make Something You Won’t Ever Show Anyone Else
In Minor Feelings, poet Cathy Park Hong writes, “We say we don’t care about audience, but it is a lie. Poets can be obsessed with status and are some of the most ingratiating people I know. … A poet’s precious avenue for mainstream success is through an award system dependent on the painstaking compromise of a jury panel, which can often guarantee that the anointed book will be free of aesthetic or political risk.”
All too often, considering an audience gets in the way of creative work. It’s not an easy habit or thought pattern to break; even if you think you’re not making for an audience, you’ve gotten into the practice of it. The key is to practice making something you’ll never show anyone else. In doing this, you’re gaining valuable feedback from yourself.
One of Dacoury Natche’s collaborators, Donald Glover (who makes music as Childish Gambino) has talked about the importance of making work that you won’t show anyone else. Glover says, “Making songs now that I know aren’t going to be heard by anybody else, it is an interesting thing. Because I think you have to do that now as an artist. I really do. Because you start to manipulate your work based on other people, which is fine depending on what you’re trying to do.”
It’s only once you’ve gotten in the groove of making things you won’t show anyone else that you’ll make something truer to what you want to make, that enables you to find the stories you want to tell, that are worth taking risks for, and eventually to find your creative purpose.
◀️⬌ Or flip this prompt: Take Someone Behind the Scenes
Create a Quality Rubric
I’ve developed a definition of quality for all kinds of work I create. When assessing the quality of an article idea, for example, I look at timing, societal impact, counterintuition, action steps, and prior coverage. I discovered these attributes through noticing what ideas were accepted and rejected, through patterns I noticed in what I liked to read, and through papers I read. I refine the meaning of these words often, based on feedback from editors.
Criteria can be fluid; for me, they’re almost like rubrics, where I consider each of these factors, and I write down guiding questions to help me evaluate or test an idea. They also help me formulate the idea and position it.
For example, if I was looking at prior coverage, I would want to figure out how often this idea has been written about before, and in what ways. Do I have anything new to offer? Can I connect the big idea with a different small event, that’s more timely and relevant? Or is there an event that I can connect with a new idea?
I often write these questions down in second person, as if a writing coach were sending them to me. When I review each piece before I’ve decided that it’s done, I often also go through each of the criteria to make sure I can check it off.
As you develop your capabilities and perspective, you may find that list of questions getting longer. For example, in Let My People Go Surfing, Patagonia founder Yvon Chouinard writes of his own list of criteria to evaluate potential product ideas: Is it functional? Multifunctional? Is it durable? Does it fit our customer? Will people be able to repair it? Is the product and line simple? Is it an innovation or invention? Is it a global design? Is it easy to care for and clean? Does it have any added value? Is it authentic? Is it beautiful? Are we just chasing fashion? Are we designing for our core customer?
As a starting point, choose a creator in your field that you admire. Learn more about their process, through their own memoirs and interviews, or through other people analyzing their work. Be mindful of the standards that start jumping out at you.
You might also see whether the creatives you admire have written about their own quality criteria, as many have: The 20th century poet W.H. Auden put out his criteria for major poets, Robert Caro shows some of his thought process in his book Working, and Mary Robinette provides feedback for editing articles. If you want to emulate author, programmer, and entrepreneur Derek Sivers, he shows you how. The same with Y Combinator founder Paul Graham. You could also study any other writing you like, and learn how you can improve.
Practically speaking, I’ve found that the best time to strictly apply these standards of quality is in the verification stage of the creative process. I’m interested in completing the idea and making sure it’s polished enough for me to be satisfied with. However, I deliberately do not apply these standards to my generative work, like writing in a journal or notebook, if I’m just taking a note, or writing a blog post for fun. At those stages, I’m still exploring and discovering what I have to say on a topic. The idea is too fragile to go through this process. It still needs to be nurtured and developed.
Define Acceptable
Once you’ve defined what quality means to you, you can also define what is acceptable: the minimum bar for quality, a passable mark. Not complete, certainly not perfect, but acceptable for you to declare that it’s done.
When you choose to make something acceptable, rather than perfect, you reduce the expectations and ensuing pressure that could block your creativity. You complete your work, stay motivated, knowing another opportunity is just around the corner, which provides another chance to make something interesting.
Knowing what acceptable means to you helps when you’re deciding whether or not a creative work—or a version of it—is actually done. You might double check to see if all the parts of your work pass your standard. In my line of work (writing) that means I’ll edit my draft three times before it’s done. I check it for grammar, voice, tone, and flow. Similar to a factory line, though, it’s best to also add in other stages to check the work’s quality, so there aren’t any unpleasant surprises at the end.
This can literally be a series of sentences that enable you to communicate when something is done. For example, the GitHub team published the philosophies that drove their decision making in a document known as The Zen of GitHub, which includes this quality check: “It’s not fully shipped until it’s fast.” If you want to declare something as fully complete at GitHub, you need to make it fast, probably meeting a maximum of some predefined set of milliseconds.
As I heard from recording artist and amateur bodybuilder Kim Jong-kook, the workout doesn’t end at the gym: “You’re only done after you eat.” He said, “Some people don’t eat after working out to lose weight. You have to eat to build muscle. If you don’t eat, it’s just labor.” In other words, if you want to declare your workout acceptable, you need to be as mindful of how you nourish your body—with the quantities and types of macronutrients you need—as you are of what exercises you do.
For me, I check if my idea is acceptable as a pitch, before I even write it up. Pitches for my articles are acceptable when I’ve explained to myself and the reader why the idea is well timed, what it means to society, what people may misunderstand about it, what people can take away from this story and apply to their lives, and how few people have covered it before. If the pitch fails in some way (for example, if a lot of people have covered it before), the pitch does not pass, and it is not acceptable. I’m happy, as I didn’t need to spend time writing the entire story out only to realize this—I didn’t try to make it perfect before I made it acceptable.
Make a Risky Version of Your Work
One of the best things you can do with and for your creative practice is to get outside your comfort zone and exercise your capacity for creative risk. Think of it like the director’s cut of a film. As Marina Abramović wrote in Walk Through Walls, “I always question artists who are successful in whatever they do. I think what that means is that they’re repeating themselves and not taking enough risks.”
“Safe” means creating something you’re most familiar with, that is, your “style.” Making something risky might mean dialing your style up to the maximum, or flipping it to be the complete opposite. Or it might just mean doing something completely out of the blue—that exceeds my capacity for suggestion.
For example, my friends told me that writing without quotes makes for better writing. This had paralyzed me for a bit—until I decided that I’d eventually just create two versions of this draft of the book, one with no quotes and one with all quotes. Similarly, I’d been stuck on structure, until I realized that I could just create a different version of the book with a completely different structure, perhaps a more essay-related format. I had no idea when I released this how it was going to look—and that was okay. That was how it was supposed to be.
Creative rituals, routines, and themes make it easy to get into a creative groove. But ease isn’t the goal, excellence is.
A certain degree of risk is a necessary ingredient in tapping into, and feeding, the chaotic energy of creativity. The risk could result in something original, which pushes the previously self-imposed boundaries of your work and pushes you to perceive or express yourself in a new way.
⬌ Or flip this prompt: Find Your Comfort
Accept Imperfection
One powerful antidote to over-obsession is accepting that imperfection is the essence of nature itself. The Japanese philosophy of wabi sabi embodies this theme. Author Beth Kempton translates the two words in her book, Wabi Sabi: Japanese Wisdom for a Perfectly Imperfect Life: “Wabi is about finding beauty in simplicity, and a spiritual richness and serenity in detaching from the material world. Sabi is more concerned with the passage of time, with the way that all things grow and decay and how aging alters the visual nature of those things.”
With the understanding of the etymology, Kempton describes the concept the two words convey:
“Wabi sabi is an intuitive response to beauty that reflects the true nature of life.
Wabi sabi is an acceptance and appreciation of the impermanent, imperfect, and incomplete nature of everything.
Wabi sabi is a recognition of the gifts of simple, slow, and natural living.
Wabi sabi is a state of the heart. It is a deep in-breath and a slow exhale. It is felt in a moment of real appreciation—a perfect moment in an imperfect world.”
We must accept that each imperfection is not a failure; rather, in wabi sabi fashion, each one makes the piece perfectly imperfect. Otherwise, obsession becomes a prescription for failure. An expectation or obsession for quality does not necessarily always result in it.
If you liked these prompts, you can sign up for the Supersalon, and learn more about the full version of Creative Doing, available at Holloway (digital) and Amazon (print).