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Creative Doing

75 Practical Exercises to Unblock Your Creative Potential in Your Work, Hobby, or Next Career

Herbert Lui

Whether creative work is part of your full-time job or personal passion, a few simple and powerful tools can unlock a unique creative process that works for you.
120 pages and 191 links


Updated November 3, 2022
Rachel JepsenEditor
Bernice LiuIllustrator


Purpose from Process1 link

Like many people aspiring to do creative work, I wasn’t born into a family of artists, or into unearned income that would enable me to pursue my art full-time. I didn’t participate in any talent shows, I’ve dealt with years of underestimating myself, and I wasn’t taught how to be creative in school. I wrote, and rewrote, this book not because I’m a creative genius revealing a secret, but because it was the book I needed to read.

I have been obsessed with the mystery of the creative process for over a decade. Successful artists had figured out how to do great creative work. Why couldn’t I?

I sought out every chance to find an answer. In the first half of the 2010s, I pored through academic literature, biographies, and memoirs. I interviewed prominent recording artists and authors on their processes. I seized every opportunity I could to ask people about their creative processes and for detailed examples of what they did to make their work. I immersed myself in a study of each individual’s creative process itself—the observable parts of ideation, creation, and release.

Creative work sounds simple enough (“Just make stuff!”), but it can feel painful when you don’t know how to make sense of it. For many years, I experienced a version of the creative block that might sound familiar: numbness. I wrote at a media company, started an editorial studio, and supported other people’s creative projects with marketing. I felt I had to suppress my true creative urges in order to make money. I tried my best to make it work.

Because I had so little time for the creative work I wanted to do—to write and express my own ideas—I became completely attached to the results I could attain. I wasn’t practicing, I was pushing. After months and years of this struggle, I realized that I was missing a piece of the puzzle: my own creative purpose.

Finding my creative purpose involved letting go of every impulse and habit that made me successful at my work projects, and shifting my focus away from results into the process. Process is about consistently making time and energy to practice every day, rather than intensely pursuing a creative project and then burning out, falling out of love with it, and becoming resentful. It’s about creating a lot of work that meets a standard I set for myself. There’s a chance you probably feel the same way I did; that throughout each day, the thought comes to you, “I’m meant to do something, and it’s not what’s in front of me right now.” What does it mean when you find yourself creatively blocked? What if that wave of inspiration never comes, and how are you supposed to know how long to wait? What if you can’t get started, or begin but don’t finish, or are always too busy with everything else?

What’s In This Book1 link

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 is the 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.

Who This Book Is For1 link

If you’re reading this, I’m sure you’re a fan of an artist, a field, or a subculture, eager to make your contribution through remixing, interpreting, or creating something.

You could be starting your journey to creating and publishing your work online. You might be working a full-time job in a field unrelated to your creativity, and recently left or are considering leaving. Maybe you want to try a creative hobby outside of your day job.

Maybe you just know that you’ve got something to give to the world that you don’t have a chance to express right now.

Michael Saviello, a manager at Astor Place Hairstylists, was inspired to pick up his paintbrush after he saw his friend and customer Rafael Hines self-publish his book Bishop’s War by writing from midnight to 3 a.m., sleeping until 6 a.m., and going to his full-time job. He resolved to paint during his lunch hour; several months into this habit, he debuted at his local art gallery. He said in an interview with Humans of New York, “My entire life, I’d been saying, ‘I can do that.’ I always knew it. But I finally did it. So now other people know it too.”

In this book, you’ll hear firsthand from Saviello, as well as other acclaimed creatives like Shantell Martin and DJ Dahi, to get a better sense of how they do what they do. That’s the promise of Creative Doing. Whether it’s dull or torturously painful, you are experiencing a block on your creativity, and this book will enable you to unblock it, express it, and get it flowing again.

You’ll find this book useful if you are:

  • A content creator online, who wants to rediscover the joy of creativity and connection, find new sources of inspiration, refine your creative process, and deepen your craft.

  • A creative independent who wants to restore your passion, rediscover a creative outlet that isn’t commercially driven, and to work through creative blocks.

  • A creative hobbyist who wants to figure out your creative purpose, pursue creative excellence, and make time for your creative endeavors.

  • An in-house creative who wants to be more creative at work, by finding new ways to solve professional problems and apply your creative skills, developing new technical skills, and getting more comfortable with brainstorming and ideation.

You may find that more than one of these roles describe your situation. Making progress with your creative work will require you to commit essential amounts of time, at least three to five hours per week, in researching, learning, or trying to participate in a form of creativity or art. Maybe you’re already along on your journey, and are spending money each month seeking inspiration, or maintaining your software or equipment for your practice. You’re clearly interested in creative expression, and you’re now encountering some of the other challenges that come along the road—uncertainty in the quality of your work, developing your skills, finding your creative purpose.

I wrote this book to honor and support you, the emerging, competitive, and practicing creators and artists dedicated to exploring your creative potential.

How to Use the Prompts

Nine polyhedral shapes adorn the cover of this book. Mathematically speaking, there are an infinite number of possible polyhedral shapes—just as there are an infinite number of versions and variations of each piece of work in the creative process. Each new day creates an opportunity to make a new shape. It’s through making a lot of shapes that the ones you like start to emerge.

Each of this book’s 75 prompts will suggest an action, propose a new way of thinking about what’s in front of you, or tell you a story. It’s through this action, and ensuing ideas that your brain generates, that will allow new breakthroughs and insights to reach you.

The prompts are organized in nine chapters, each with a path that you can follow.

I’d recommend starting with Part I: Start the Creative Process, which will help you begin a new creative endeavor with the right mindset. You’ll put together your starting points—places where your work can develop from—and learn to let go of the expectations and outcomes you’d had in mind to open up to something even better. You’ll also learn how the creative process works through hands-on experience.

Part II: From Action Comes Progress, is all about, well, action—first, producing as much creative work as possible, then defining and practicing quality work, sharing your work, and soliciting and integrating feedback.

The prompts in Part III: Creative Purpose, will help you slow down and get back to basics, trust yourself, and have clarity of vision.

That said, these prompts can also be approached any other way. Jumping to a prompt you think will speak to where you are right now is a great idea. Prompts also reference and link to other prompts—you’re encouraged to choose your own adventure. Overall, and in any order, this book will encourage you to work within the many constraints that life presents, get other people involved with your work, improve your craft, experiment with new ideas and methods, and build a life rich through creativity, whether or not you choose to make it your full-time profession.

Here are some other starting points:

Part I: Start the Creative Process

I’ve been making music for a long time. I’ve learned a lot of stuff along the way, but I don’t let that get in the way. I don’t let that impede the process of making something new.Rick Rubin

In Orbiting the Giant Hairball, Gordon MacKenzie, who led creative for three decades at Hallmark Cards, paints the portrait of “a rotund gentleman in a $700, power-blue, pinstripe suit,” leaning on the fence and watching cows eat grass. He yells, “You slackers get to work, or I’ll have you butchered!”

MacKenzie likens this person’s ignorance about milking cows to common feelings about the creative process. He knows that cows eat grass and produce milk but has no idea what happens in between—he wants measurable evidence of creativity without honoring the invisible creative activity it takes to produce that. You might know someone who bears resemblance to the gentleman. Perhaps it’s you.

In July 2013 I published a blog post titled, “Why Quantity Should Be Your Priority.” I proposed that quantity could be a reliable tool to improve quality. The response was immediate. Musicians, writers, designers, CEOs, investors, and even professional gamers virtually nodded in agreement that repetition and purposeful development of the skill were the only way to become a master of the craft. As I write this, the article has been read over 200,000 times, shared thousands of times, and even added to a university’s coursework.

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Set Up Starting Points22 minutes, 11 links

My observation is that the doers are the major thinkers. The people that really create the things that change this industry are both the thinker and doer in one person.Steve Jobs*

You probably think about doing more creative work a lot. At a certain point, it’s time to just pick up the brush and start painting. “Many people die with their music still in them,” physician, poet, and polymath Oliver Wendell Holmes Sr. said. “Too often it is because they are always getting ready to live. Before they know it, time runs out.”

There is no right way to do creative work; the only wrong way is not to do anything. This chapter will help you get started.

Choose a Creative Operation

Whether you have grand ambitions or are simply curious to explore, it helps to begin concretely. Pick a creative operation you will explore.

If you don’t have a creative area to work in and are nervous about getting started, think about what area might expand on your existing skills. If your job involves writing, for example, and you enjoy doing that, creative writing might be an interesting place for you to start.

If you already do creative work but feel blocked, consider a new creative operation—it could be something entirely different than your usual work. This decision could be a temporary experiment, and not necessarily the medium you’re going to stick with forever.*

You could start with a community you appreciate. For example, if you regularly read a subreddit like r/startups, you could start by responding to questions or sharing business opportunities you’ve noticed.

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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.

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Adorn Your Space

Chuck Close may be able to turn his back on any room and get to work, but shutting out the world might not work for you—or not work all the time. You may not have a Parisian atelier with floor-to-ceiling windows (or need one) but there are ways to make the space you do have more inspiring and conducive to creative work.

In his biography of Leonardo da Vinci, Walter Isaacson quotes da Vinci describing an artist at work: “The painter sits in front of his work at perfect ease. He is well dressed and wields a very light brush dipped in delicate color. He adorns himself with the clothes he fancies; his home is clean and filled with delightful pictures, and he is often accompanied by music or by the reading of various beautiful works.” (In psychology, enclothed cognition covers the influence of clothes on the mind of the person wearing it.)

You can also experiment with the temperature, and be mindful of how that influences your thought process. Singer-songwriter Ester Dean says, “I always have an electric heater behind my feet, but I like to be comfortable so that I can be vulnerable.”

Because this is a book about creative doing—which means creativity in the physical world—test some things out that play with your senses, to see what affects your creative mind. Light a candle or apply some essential oils. Create a playlist of songs that pump you up, and then try music that calms you down. If your work is mostly done on the go and on the screen, you can also take some time to make your virtual environment—screen brightness, wallpapers, and software—more conducive to creative work. Whatever or wherever it is, make your environment a place you want to spend time every day.

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.”

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Organize Your Departure Points

Every effort begins somewhere, from some idea, some element of work. The vision of this prompt is to build your own collection of elements that you can apply and combine with others, sometimes more than once.

It’s important to keep these departure points as small as possible. These days, we are blessed with technology that can store and organize all of our departure points.

For example, even though I’d written hundreds of articles in my 20s, many of the ideas—points, stats, and quotes—embedded in them were too interlinked and dense for me to move around and re-use in new ones. My solution to that was to extract the ideas and put them into index cards and Notion for my Zettelkasten note-taking system, which I learned from How to Take Smart Notes by Sönke Ahrens. Each stat would get its own separate index card.

It’s possible to do this with other forms as well. If you’re in the recording arts, you can separately save different elements of songs for easy access. If you’re in visual arts, you can work digitally and do the same by saving elements in different layers or files altogether. Be descriptive in your filename so you know what to search later. I’d highly encourage you to take even just a few minutes to set up a simple system for staying organized.

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Say Yes

If you go to an improv comedy class, you’ll see that participants are encouraged to agree to and build upon everybody else’s ideas. Comedian, filmmaker, writer Tina Fey calls this the “Rule of Agreement” in her memoir Bossypants, describing it as a reminder to:

“Respect what your partner has created” and to at least start from an open-minded place. Start with a YES and see where that takes you.

So try saying yes to every prompt or idea from others, at least once. If the need arises, you are free to make modifications and to add an element of your own to the prompt. I would be extremely happy to hear that you’d augmented one of these prompts to fit you better.

When you say yes, you train your brain to let go of your preferences and expectations, and to let go of them to work with whatever’s in front of you.

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Make Your Work a Craft18 minutes, 8 links

In writing about the sea I have learned the important truth that a writer’s subject is always far bigger and more important than the writer himself.Rachel Carson*

Writing in The Craftsman, sociologist Richard Sennett explores how culture is made. He defines craftsmanship as, “An enduring, basic human impulse, the desire to do a job well for its own sake.” A craftsperson is “dedicated to good work for its own sake. Theirs is practical activity, but their labor is not simply a means to another end.”

When a person is dedicated to doing something as well as it can be done—beyond commercial and external interests—their labor becomes craft.

The craftsperson is self-reliant and imaginative; even in the endless repetition of piano scales or in the sharpening of a pencil, the craftsperson can see ways to improve their work. A craftsperson can try new materials and apply their attention to detail and observational skills in different contexts. They work with intention at every level. They may get into a creative flow where work comes easily. But it is never mindless. Over time, the craftsperson can master the methods of a form, and then add new ones. They develop their own style and become recognizable.

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Find the Simplest Element of Your Craft

One of Shantell Martin’s most popular projects involves two objects: a black medium-width Staedtler Lumocolor marker and a white wall. Using the permanent marker, she’ll cover an entire wall in elaborate line work. She also draws murals on walls and surfaces at live shows, incorporating an element of performance art to her process.

Martin has said, “It takes a ton of work and practice to get to the point when a line is a true reflection of yourself.”

It can feel incredibly inspiring—and overwhelming—to consider a final body of work. Instead, as you’re starting out, turn your focus away from the final vision of the project and toward the simplest element of it.

In Martin’s form of visual art, each piece of her work is made up of lines. In all forms of writing, each article, book, or poem, is made up of words. In the recording arts, each bar and song is made up of notes.

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Remove Imaginary Barriers to Your Work

After years of learning and applying rules, you might live within these constraints even when they don’t actually apply to you. You’ll feel like you’re bumping into invisible walls. For me, a huge invisible wall was the traditional publishing system; I felt like I needed to have a book agent, write a book proposal, and build an audience, all before I could actually start to write a book. For years, I tortured myself with that idea that I needed the system’s buy-in before I could write a book. This fixation on being accepted by the traditional institutions distracted me from the clear vision of what was in front of me and the valuable experiences and ideas I already had.

The reality is, as I found out years later, I could’ve written a book at any time. A book can be as simple as 20,000 words strung together. If I stitched together 20 articles at 1,000 words each, which I was writing every week, I could’ve put a book together. (In the traditional book publishing world, some books are even just 11,500 words.) This is true for you as well. As soon as you’ve figured out the simplest elements of your craft, you can start creating. Elsewhere in this book, you’ll do exercises that involve finding new materials to work with—new lines, words, and sounds, for example—and more deliberately setting a mission and theme, which can be based on one specific element of your work.

Even before we start our creative work, it’s easy to find reasons to stop. We don’t have the equipment that the professionals use, we have no one following our work, and we’re unsure if what we’re trying to do is even “really” what we want to do. If you’ve let your craft get more complicated in your head—through the mystique and magic of creativity—it’s time to let them go. Don’t impose fictitious rules on yourself.

You might think you need all of that to get started, when in reality all of those resources and insights will come to you as you do the work.

Make Idle Time

The most important thing I noticed today was that only in stillness can we recognize movement.Marina Abramović

There is no universal creative process. But any creative process will involve various periods of incubation, or time spent not consciously thinking about the problem. You have likely experienced this phenomenon yourself when after hours at work spent agonizing over a problem, the solution pops into your head when you get home and take the dog for a walk. This is also known as The Shower Principle—ideas come to you when you’re doing something else, like taking a shower, doing the dishes, or working on another problem entirely.

As it turns out, even if you’re not concentrating on something or keeping busy, a different part of your brain activates and processes your thoughts. If you’re interested in the neuroscience at work here, I suggest reading Alex Soojung-Kim Pang’s Rest.

Practically speaking, we can’t actually make ourselves process things or produce creatively faster. In fact, it’s only when we allow our mind some peace and quiet that it can relax, and produce the ideas we so desire. But don’t cover your mind in Netflix or podcasts—reject media’s influence and let your brain settle down. Take a bath or long shower. Try meditating with or without an app. Go for a trail walk or bike ride. Let rest and distraction become part of your creative process.

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Make Time to Play

“Without play, only Shit Happens. With play, Serendipity Happens,” wrote David Weinberger in The Cluetrain Manifesto.

“Work which remains permeated with the play attitude is art,” wrote philosopher John Dewey.

The difference between work and play is largely intention. Play is intended for amusement, joy, and perhaps mastery, with the main intention being to continue to play. Work is intended for results, benefit, and sustenance, with the main intention being to continue to survive or provide for yourself.

We already know how to play—to do something for its own sake, to explore, to imagine. It’s just that sometimes we go without it for so long that we may forget. No wonder there are classes to teach us how to relearn this valuable skill that was squished out of us. If you need ideas, go do improvisational comedy or try a new instrument or a sport. Rent a bicycle and go for a ride. Buy a Lego set and build. Draw a cartoon. Feed your creative practice (and well-being) by making time for play.

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Lose Yourself

Let go of your external expectations. Immerse yourself in the task at hand.

Bono wrote about Frank Sinatra, “Fully inhabiting the moment during that tiny dot of time after you’ve pressed ‘record’ is what makes it eternal. If, like Frank, you sing it like you’ll never sing it again. If, like Frank, you sing it like you never have before.” This philosophy is applicable to your craft; you can pretend like it’s the last time you’re doing your work, the last chance you might be able to contribute to this piece of work. This immersion naturally lets expectations, hopes, and fears fade away; none of it matters. Treating your work like a craft will help you let go of external measures of quality and focus on what’s in front of you. Everything else is an unnecessary distraction.

Whenever a thought of comparison comes across your mind, notice it, and then let go. If you catch yourself ruminating about it, tap it away like a feather duster cleaning a glass and bring your mind back to whatever you are doing. As composer, band leader, and saxophonist Charlie Parker said, “Don’t play the saxophone. Let it play you.”

Or flip this prompt: Make Them Curious

Enjoy the Plateau

Mastering any skill, including all forms of creative work, means spending a lot of time moving forward slowly. The spurts of growth are very occasional, perhaps even rare. Instead, day in and day out, we are working. We are practicing. “At the heart of it, mastery is practice. Mastery is staying on the path,” writes martial artist and author George Leonard.

Make your practice enjoyable. Don’t obsess over improving, or whether someone else is better or worse than you in some way. Stay focused on your own skill set and craft. Perhaps it means changing your environment or schedule. It could also mean switching the routine or the sources of inspiration.

If you find yourself wrestling with metrics such as likes, shares, and comments, check out why three creators ignore the stats and some alternate ways of measuring success. You can also choose to set a mission for your work.

Relax Expectations

With vision comes expectations. We believe this project will be the one that enables us to break through. It would be weird if we didn’t—there might be less of a point in working on it. This expectation can serve as an occasional fuel, but more often gets in the way of us doing our best work. It’s where many creative blocks start.

“It’s important to keep the ideas going. A lot of times, you can’t get too worried about the results. I’m in a business where basically I get hired and fired as soon as a song comes out,” Dacoury Natche told me in an interview for this book.

Chris Kim, who produces music under the name CVRE, is known best for making songs with artists like Justin Bieber, Future, and Don Toliver. Based on his wide range of musical experiences, he observed to me, “Expectation always kills creativity. … You expect a certain result and you have to achieve that industrial definition of success that always kills the magic that could happen in the unknown.”

If you feel your expectations rising, that this project you’re working on is going to be a hit, acknowledge that there’s a chance it might also just be another project. The external measures of success might come after the next one, or the one after that. That is the beauty of consistency. You always have another shot. Another opportunity is just around the corner if you want it to be.

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Relinquish Results

Throughout the years, we are conditioned to do things well and to constantly improve. If we’re not doing that, we’re led to believe we’re getting worse. If we regress, we are failures. These beliefs are all based on the flawed assumption that progress is linear.

At an extreme, this could lead us to chase perfection. If we can’t do something perfectly, we just won’t do it. Perfectionism creates an impossible standard for us to meet. This is just one of many reasons we start procrastinating and get blocked.

In his book Surely You’re Joking, Mr. Feynman!, Nobel Prize-winning physicist Richard Feynman recalls an art class when he was instructed to draw without looking at the paper. He was impressed with the results, noticing a “funny, semi-Picasso like strength” in his work. He knew that it would be impossible to draw well without looking at the paper, so he didn’t consciously try. He writes, “I had thought that ‘loosen up’ meant ‘make sloppy drawings,’ but it really meant to relax and not worry about how the drawing is going to come out.” The solution is to do something without caring about the results.

The immediate goal is for you to take a very small step closer to the thing you want to do. You already know your form’s most essential element; now it’s time to build something with it. If you want to write a book, then write at least one sentence in a notebook today, building up to a daily writing practice. If you want to draw, sketch out a person or an object—don’t think too hard, just choose something in front of you and draw. If you want to make music, hum a melody into the voice memo in your phone and try to create it on an instrument or in your computer.

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Part II: From Action Comes Progress

Draw, Antonio, draw and don’t waste time.Michelangelo*

When we were children, none of us needed to be told to draw. It was practically primal. We would naturally doodle. Yet at some point, most of us stop drawing. Comedian and writer Ricky Gervais quoted Pablo Picasso saying, “Every child is an artist. The problem is how to remain an artist once he grows up.” While the popular quote remains unverified, it’s not difficult to imagine the words coming out of Picasso’s mouth. John Lennon said something similar: “Every child is an artist until he’s told he’s not an artist.”

Human beings have an instinct to create, but we are made to unlearn it, suppress it, and repress it as we grow up. Our natural-born instinct to be creative, to play, and to look at the world with wonder and limitless possibility is stifled and tamped down so we can deal with the unpleasant business of being adults. A lifetime of comments like “You can’t do that,” “That’s not how things work,” and “Do you have a backup plan?” beat us into thinking practically and logically.

While the more analytical side of our minds—the judge—is great for lots of things, we can’t count on it to think our way into being more creative. The solution is not to try to think our way out of this, but to take action and to let the brain follow. “If you want to think differently, first learn to act differently,” scientist Heinz von Foerster said.

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Make Constraints Your Canvas21 minutes, 22 links

In The Craftsman, author Richard Sennett tells the story of two houses. The first is the work of philosopher Ludwig Wittgenstein, who financed the design and construction of his house with his virtually limitless family fortune. He set out with his eye on perfection, eager to build the prototype of “the foundations of all possible buildings.” His integrity could spare no expense. Stuart Jeffries writes in the Guardian, “When the house was nearly complete, he insisted that a ceiling be raised 30 mm so that the proportions he wanted (3:1, 3:2, 2:1) were perfectly executed.”

Figure: Villa Müller by Adolf Loos in Prague-Střešovice, Czech Republic. Credit: Miaow Miaow, Wikimedia Commons.

One of Wittgenstein’s mentors and friends, the more senior Adolf Loos, had a smaller purse to draw from. When the foundations of his Villa Müller were set differently from the plan, he thickened a side wall to accommodate the change. His two choices were to adapt or to give up on the building.

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Select One Tool

Professor, author, and human-technology researcher Sherry Turkle suggests in The Empathy Diaries, “To be good at a job, you had to love the objects associated with that job.” This can also apply to your chosen creative operation. Finding an object that sparks joy could change how you operate.

For example, Big Mike’s current journey with painting started off with a canvas he found across the street from his workplace. Even if this lucky event hadn’t happened, I can imagine him buying a canvas and paints and getting started painting the same day. He didn’t let himself get stuck figuring out which paints were best, which brush to use, where he could work. His method, in his own words, is simple: “Put the paint on the canvas!”

Choosing a tool provides you with a clear idea of what you will be doing. You paint with a paintbrush. You draw or write with a pencil. Commit to this tool for a set amount of time—maybe 10 days—just enough time to see what you can do with it but not so much that you get bored.

Don’t overthink the tool just yet. Start with the simplest version of the tool, the one you already have lying around, and figure out what you need out of it along the way. As Wired co-founder Kevin Kelly writes, “Start by buying the absolute cheapest tools you can find. Upgrade the ones you use a lot. If you wind up using some tool for a job, buy the very best you can afford.”

Set a Time Limit

In 2018, the average Instagram user on Android spent 53 minutes a day on Instagram. Over the course of the year, that’s 322 hours, the equivalent of over eight full 40-hour work weeks.

Imagine what you could create with 53 minutes a day! (Especially if you’re reclaiming that time from Instagram.) Even five minutes will move you further along your creative path than no minutes at all. You can begin to reclaim time for creative work by setting yourself a manageable limit.

You can use a technique called timeboxing, which means giving yourself a set amount of time to do one thing. One of my favorite devices is the kitchen timer. I’ve bought maybe a dozen of these in my life so far, and I plan to buy dozens more. I set the timer for a few minutes—for a short workout, for a sprint through really boring paperwork, or to get started on a big creative project—and then I press start. I give myself a window to work through. After that, I can choose to stop, and sometimes I do. But many other times, I keep going.

In the professional world, a popular productivity strategy is the Pomodoro method: set a timer for 25 minutes of uninterrupted time to complete a task, take a five-minute break, then start the timer again. After three of these 25 minute sessions, the person takes a longer 30-minute break.

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Commit to a Size

The two most common dimensions we’re constrained by are space and time. If setting a time limit is timeboxing, then perhaps the space-analogous exercise can be called sizeboxing. You pick a limited size for your work and work within that.

If you’re recording music, scale down by committing to recording a song with only two instruments if you usually use more; or if you want to produce a lot of ideas, commit to writing thirty-second melodies for one week.

If you’re working with paint, choose a surface with dimensions no more than four inches by four inches.

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Do Your Work without Your Equipment

While most of the prompts in this book involve getting ideas out of your head and into the world by taking action, and creating ideas through action, this prompt is about working on an idea in your head and leaving your studio, laptop, or gear bag behind. Steve Jobs said, “Creativity is just connecting things.”

These connections come from many sources, including what you see and experience. Photographer Ivan Chow leaves the house without his camera to practice his observation skills. He says, “By taking away the need to make photos, you’re relieving yourself of that pressure to deliver. This will allow your mind to focus solely on spotting moments that are worthy of capturing. You’ll get less caught up with what’s directly in front of you and you’ll start looking a bit further to spot potential subjects and points of interest. Being a good street photographer is all about being good at observing, and that means that you already have a very good head start.”

If your chosen creative operation is photography, you might choose to take a moment out of each day to observe a location or scene that would make for an interesting photograph. What makes it stand out to you? How can you return and recreate the moment, or would it be worth capturing in different lighting conditions? If it’s music, take a long walk and play with a melody in your head—when you take away the option of recording an idea right away, you’re forced to work with the raw materials in real time, which can lead to many surprising developments.

Working without equipment can also help us stay connected to our creativity when we can’t access resources. Shawn “Jay-Z” Carter memorized lyrics during the early moments of his career, as he writes in a piece for Vibe. “When my thoughts began to crowd each other, I would go to the corner store, get a pen, and empty my head, pouring rhymes onto pieces of paper bags. But how many scraps can you fit in your pocket? I had to start memorizing my ideas until I got home, which was usually in the wee hours of the morning. Ironically, using memorization to hold on to my lines is the way I developed the writing style I use today. No pen, paper, or paper bags needed. Just point out the track and I’m all over it.”

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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.

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Choose Analog

Before he became the Grammy-winning DJ Dahi, Dacoury Natche used to play, practice, and experiment with instruments. It was how he became a musician. As he gained success in his industry, more and more of his work was done on a computer. “So much of what I was doing just felt rigid because I’m stuck within a screen,” said Natche. As a response, he remembered what he temporarily forgot—that he used to make music outside of his screen, with instruments.

Using only analog equipment—nothing connected to the internet—practice your craft. Make something. Going back to basics can be a great way to revisit why you chose this work in the first place, as Natche describes. It’s a chance for us to let go of the constraints and systems we need in order to work with technology, and to remember the simplest elements of the craft.

Complete Your Operation in Seconds

Social scientist B.J. Fogg’s Behavioral Model tells us that the more ability a task requires, the more motivation it will also require. That idea can certainly apply to creative work, which is why these prompts require minimal ability and time. This insight is key to creating habits and tapping into your discipline.

Vin Verma, who goes by the name Internetvin, has made music and written code every day for a year. One of his techniques is to find a way to create music or code in 20 seconds (writing just a single line of code on the days he didn’t have time or felt tired).

If you’re making music, your tactic could be to record a 10-second voice note of a new melody, or to write one bad line of a song lyric.

If you’re working in photography, take a still life of an object within arm’s reach.

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Never Run Out of Ideas25 minutes, 25 links

It’s tempting to believe that “ideas” are what you wait for, sitting quietly until inspiration strikes. Ideas can come down on us in this way, but more commonly, creators and artists cultivate their own inspiration by recording as many possibilities as they can come up with, generating their own idea momentum.

Not every idea has to be good—some ideas will be horrendous. But the consistent work of generating ideas, good or bad, relevant or not, is what matters in developing creative thinking. The point is to discover just how possible it is to make ideas every day, not just “have” them whenever the gods decide.

Creating acceptable ideas is a strategy that professor and author Dean Keith Simonton recommends. He writes in The Genius Checklist how the more attempts an artist or craftsperson makes, the more major works (or “hits”) they create. As a general rule, Simonton suggests that mass production of these ideas is a safer approach than focusing on a single idea and trying to make it perfect.

“Giving up on perfectionism doesn’t mean that you will not produce anything perfect, but rather that perfection will happen from time to time because of the sheer mass of output,” Simonton writes. Throughout their lives, some artists have made this prolific approach work. Famous examples include Yayoi Kusama’s 9,000 pieces, Shantell Martin’s 5,000 works, Wolfgang Amadeus Mozart’s 800 compositions, Pablo Picasso’s 20,000 drawings, and Vincent van Gogh’s 2,000 drawings as examples of this strategy.

Write Down 10 Ideas

Virgil Abloh told i-D Magazine in 2015 that he came up with 30 ideas a day. Just for fun, here’s an example of what one of them looked like:

Source: Off-White Imaginary TV on Instagram.

If you’re like me, 30 ideas will take you two hours—so I decided to start with a more modest 10.

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Source Inspiration

One of the most difficult parts of creative work is sitting down and deciding what to actually do. One solution to that is to draw from a predefined source, each day. For example, over a decade after he first worked as a lecturer at Yale, graphic designer and Pentagram partner Michael Bierut assigned a brand new project to his students: pick an activity and commit to doing it for 100 days in a row. This project emerged from a practice that Bierut had started five years prior to the assignment, starting January 1, 2002.

Every day, Bierut would make one interpretive drawing of a photo he found in the New York Times. These drawings could take just a few minutes, perhaps even a matter of seconds. They could also be more elaborate, if he had the time. But no matter what, he never ran out of ideas—because every day the New York Times came out, he would get more. You’re free to do what Bierut did, which is to pick a source that provides a constant stream of new ideas.

You could also choose to train your attention, by taking photos of an object that you like anytime you see it in your life. Virgil Abloh observed an acquaintance taking a photo every time he saw a specific luxury handbag, which essentially trained his mind to see it during his day-to-day life. Abloh said, “If you want to find new space, if you want to get to another crescendo of design, and having your brain figure out how to aesthetically put together something, you have to do it often.” You could also do this with visual patterns, as Abloh did with diagonal stripes.

If you prefer writing fiction, you could respond to the r/WritingPrompts subreddit, which surfaces new prompts every day. If you’re more interested in nonfiction or memoir writing, you can try author and speaker Suleika Jaouad’s The Isolation Journals.

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Roll the Dice

Letting go of control, and introducing chaos into an environment, is one of the keys to cultivating creativity. If you’re ever experiencing blockage or a sense of stuckness on a decision, try opening the door to chance in order to support your creative work.

In The Travels and Adventures of Serendipity, authors Robert K. Merton and Elinor Barber quote the late Professor Salvador Luria of the University of Illinois as praising “controlled sloppiness, which states that it often pays to do somewhat untidy experiments, provided one is aware of the element of untidiness.” In any case, the idea here is to trend toward chaos, entropy, and randomness in your work—a sense of controlled sloppiness.

For example, if you’re feeling stuck on what to write, you can take a chance with a dictionary or a random word generator. In literature, there is a constrained writing movement called Oulipo. Several of their techniques are set by constraints and involve chance. For example, the N+7 technique involves creating a new poem through taking an existing poem and replacing each noun with the seventh noun after it in the dictionary. In the 1920s artistic movement Dada, a common game to manufacture inspiration involved cutting up newspapers and pulling words and sentences out of a bag.

In the board game Letter Tycoon, each player starts their turn with a limited set of vowels and consonants, with the goal of spelling out the highest scoring words. You could replicate this game by picking eight letters and write as many words as you can with the set as possible. If you’re feeling ambitious, you can even compose a poem or write a sentence with the letters.

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Do the Opposite

Whatever your routine is, flip it.

A friend once told me, “If you keep doing what you’ve done, you’ll keep getting what you’ve gotten.” I wrote this down, though I probably didn’t need to; it has continued boomeranging back into my brain throughout the years. Sometimes, in order to make breakthroughs or to disrupt our patterns, we need to flip our habits, routines, and rituals on their heads. Similar to rolling the dice, this is about opening the door to chaos to introduce new creative ideas.

Even if what you’re doing is getting you the results you want, it’s almost always worth trying something new in a small way (unless a process is in a critical stage of a project with high stakes—for example, you probably don’t want to change the way you fire up a kiln for a project you’d spent the past four months on). You’re creating an opportunity to get better results, or different ones. I discovered this saying through author Neal Pasricha’s book You Are Awesome: “Different is better than better.” Author Laura Huang writes a different version in her book Edge: “Different isn’t always better, but better is always different.”

“If you get so good at drawing with your right hand that you can even make a beautiful sketch with your eyes closed, you should immediately change to your left hand to avoid repeating yourself,” Marina Abramović quotes artist Krsto Hegedušić in her memoir, Walk Through Walls. In this case, you could try drawing for a few minutes with your eyes closed as Abramović suggests, and as Richard Feynman did. You could also try drawing with your non-dominant hand. If you like what you see, you could expand the time to an entire work session. The writer’s equivalent might be working on a piece of fiction if you’ve only ever written essays.

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Turn Problems Into Ideas

Many of these prompts have been akin to invention: making ideas and trying new things. In Let My People Go Surfing, Patagonia founder Yvon Chouinard writes about how his company doesn’t invent—it discovers. “There’s simply no time for inventing,” he writes. Instead, the company talks directly to customers and learns how they use its products. The company digitally renders new ideas, makes samples, and works to shorten the time it takes to implement these changes. From those situations, Patagonia finds guidance on how its products evolve. Of course, this involves developing an understanding of people and providing them with a solution.

Your idea can be a solution. For example, if you’ve heard a friend talk about how boring their new apartment or house is, you can paint something that gently alleviates some of that boredom or something so bold it completely shatters it. If you’re a programmer hearing someone talk about their problems with gardening, you can build a simple app to help solve them.

Focus on Connection

This prompt is about making something just for one person, someone you know, as a way of finding authentic creative expression. Productivity writer Tim Ferriss found the tone for his books when drafting an email to his best friend. Michelle Kuo, assigns letters to all of her students, whether it’s in classes at The American University of Paris or at a creative workshop for incarcerated people. She observes when people begin to write, they risk their voices sounding pretentious, because it’s common to believe “good writing” means impenetrable or abstruse. Kuo told me, “There’s something about writing a letter that allows you to discover your conversational voice, which also means your forms of speech, your idioms, your little jokes. Sometimes, it also allows the voice to be funnier, to be self deprecating, and to desire actual connection. When a person knows who their exact audience is, it gives them more consistency, so they’re not switching between different potential targets. When you’re consistent, then the reader trusts you. An outside reader trusts you.”

Kuo suggests that if you’re into songwriting or the recording arts, an equivalent to the letter could be a ballad. Bernice Liu, also known as artist Spime, suggests a visual equivalent could be a signed painting or a portrait of someone you know.

One happy byproduct of focusing on connection as your inspiration is that it may bring you in contact with other artists and aspiring creatives with whom you can continue to share work and inspiration. When teaching kids in rural Arkansas, Kuo would assign “I Am” poems, which consist of lines starting with “I am….” She writes in her memoir, “I had asked the students to tape their ‘I Am’ poems on the walls, to make them proud of their own writing. Then I noticed something surprising: They wanted to read one another’s work. Certain students—who, during my attempts at collective reading, put their heads down or slapped the head of a studious classmate, trying to keep him from ‘being good,’ as they called it—would now stand attentively in front of a classmate’s poem, tracing the line methodically with an index finger, not saying a word.”

Find New References

French Impressionist Edgar Degas once said to poet Stéphane Mallarmé that he had a great idea for a poem. “But Degas,” replied Mallarmé, “You can’t make a poem with ideas. … You make it with words.”

Words are one fundamental element of poetry and prose, and every form of creative work has its own. This prompt is about identifying or referencing an example, sample, or inspiration you’re not as familiar with, and applying it to your work. These examples are often called references—exemplary work that you can refer to as inspiration for your work.

If I’m looking for new elements to reference as an author, I would be looking for new words in the dictionary, or finding new sentence structures I could try.

If you work in film or the recording arts, sounds, scenes, and storyboards are references as well. Filmmaker David Lynch calls this “firewood,” and is constantly looking out for and stockpiling music to inspire his scenes in his films.

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Pick a Neglected Idea

Instead of shelving an idea, pick an idea you’ve put on a shelf—or simply neglected—and develop it. Write down three ways you can change the idea to make it meet your quality criteria.

In Walk Through Walls, performance artist Marina Abramović writes of an exercise where she gives her students a thousand pieces of white paper. The students write down ideas. They keep the ones they like, and trash the ones they don’t. After three months, Abramović only takes ideas from the trash cans; she calls these the “treasure trove” of the things her students are afraid to do.

Remember, each idea holds potential to be the one that changes your life. If you revisit an idea and have the sense that it’s special, don’t be afraid to commit to it.

Or flip this prompt: Archive an Idea

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Decide What Quality Means27 minutes, 37 links

Ease isn’t the goal; excellence is.Ed Catmull

There’s a difference between what you think quality and progress mean and how other people receive your work. You have to define what quality means.

Patagonia founder Yvon Chouinard, who writes in Let My People Go Surfing, “Striving to make the best quality product is the reason we got into business in the first place.” Patagonia’s definition of quality involves invention, global design, ease of care and cleaning, added value, authenticity, beauty, and the core customer’s needs.

Pixar’s former chief creative officer John Lasseter says, “Quality is the best business plan.” In his book Creativity Inc., Pixar co-founder Ed Catmull talks about the company’s definition of quality as one that highly values people—finding, developing, and supporting good people, who “in turn will find, develop, and own good ideas.”

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Form an Opinion

In 2007, Ye (then known as Kanye West) founded and ran the blog called UniverseCity. The blog became well known as a source of inspiration, connecting the worlds of art and architecture with mainstream pop culture. The New York Times called it “a masterpiece blog.”

West ran UniverseCity with the help of a small team, including graphic designer Joe Perez. Perez was responsible for supplying and researching the content, making ideas available to West to curate, comment on, and approve. Even though Perez had formally studied at the Art Center College of Design, he has likened research for the blog to returning to art school—and studying every major simultaneously. “You can say you do research every day, but when something forces you to look at thousands of images on a daily basis, the best of the best, it starts to definitely have an impact on you on a really basic level,” he says. This exposure to a vast quantity of images seems to have remained with West, who would report looking at 800 images a day several years after the blog ended.

Part of what Perez brought to the table was geographic; he had access to the Rhode Island School of Design library, where he discovered inspiration and references in books that weren’t as easily found on the internet. But looking at thousands of images wasn’t the only thing that refined Joe’s taste. There was also the thought process and dialogue that he and West developed to select and curate images for UniverseCity. Managing the blog required that both of them develop and refine opinions on the mountains of images that Perez selected.

Understand that while uninformed opinions are common, informed opinions are rare, interesting, and actually useful. Put in the work to develop and discover your opinions. Through rigorous and consistent studying, you’ll realize what your sensibilities and values are. Know the other possibilities, perhaps even better than the people who support them know it.

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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.

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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.

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Visit the Greats

“If you have writer’s block, you’re not reading enough,” says poet Nikki Giovanni to author Mason Currey. In order to improve your output, you first need to improve your input. Experiencing other people’s work is the best first step to understanding what quality might even mean in your field. Everyone who is making something, right now, has been inspired by someone else.

I’m personally not a huge fan of lists. But, if you don’t have any references or places in mind, start with the greatest-of-all-time lists for your field. For example, if you’re making music, you could look at Mojo’s Top 100 albums of all time, or perhaps just of the last decade. If you have no idea where to start, look for your favorites in the list, or start at the top and work your way down.

Pay attention to what you notice. Dacoury Natche first notices the beat on a song, not the lyrics. Michael Saviello steps right up to the painting and starts looking at it. Don’t worry too much about what to do. Just try, and you’ll know.

Besides making time to experience art, look into the lives of artists. Dive into their creative processes and their perspectives on their craft. Read their biographies. Study their heroes, too. Know the bar that your heroes set for themselves, and set your own in that direction as well.

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Study the Craft

Select a piece of work you love or that is revered in your field. Study it. Answer this question: “What makes it great?”

Write down the first thing that stands out to you about the piece of work. Then, write down the second thing. And the third thing, and so on, until you don’t notice any more unique things. Then, read someone else’s commentary on the work—or if none exists, just call a friend and ask them what they notice about the piece. What do they experience that you didn’t? What interests them? What’s the difference between what you noticed and what they noticed?

For example, if you’re a writer studying an article you really like, write down the first 20 lines that interest you, and compare them with the first 20 lines of the piece. Or compare your 20 lines with 20 lines that another writer identifies, or perhaps 20 lines that an editor identifies.

In software, there’s a method of testing called rubber duck debugging. The method is simple—you explain to a rubber duck what your code is supposed to do and talk it out line by line. You can tell it what you plan on doing next as well. The rubber duck, in this case, doesn’t need to be for debugging; it can be the listener to your experience of a piece of art. If you’re shy and don’t want to explain yourself to a friend yet, try it with a rubber duck.

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Copy a Classic

Michelangelo was a highly-skilled forger, and selling a counterfeit sculpture would actually impress the buyer and earn him his first patron. Vincent van Gogh copied Hiroshige, Paul Gauguin copied Édouard Manet, Paul Cézanne the Old Masters. Ye (the artist formerly known as Kanye West) re-created many hip-hop songs from the 90s to teach himself how to produce music.

Figure: “Flowering plum tree, after Hiroshige” by Vincent van Gogh, 1887. Credit: Niels, Wikimedia Commons.

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Imitate a Classic

To imitate is to represent, reinterpret, or reproduce the style and vision of someone else’s work. To copy is to try to make an exact duplicate. Imitation is not superior to copying—both have their place. You might need to imitate before you know how to copy exactly. For example, if you were to re-create a song you really liked, you might need to find the right instrument, drumkit, or sound file, and figure out what the layers sound like. But to imitate, you find your own way to recreate the original.

When I asked Dacoury Natche how he learned to make music, he spoke of imitating as a way to refine his own technique as he was first getting started. There will be things that you don’t know how to do yet, and that’s the point. When you don’t know something, do whatever you can to replicate it. As producer Chris Kim pointed out, the search for the answer and attempts to imitate or reproduce the original often provide more interesting results than recreating the original idea in the precise steps of the original creator.

Remix a Piece

When Dacoury Natche and I met, Kazakh music producer Imanbek’s remix of SAINt JHN’s “Roses” was at the top of our charts. I was on a road trip a few days prior and heard it at least twice an hour.

While the original artist SAINt JHN released “Roses” three years prior, it was the remix that was picked up on social media and broke through to mainstream radio stations, bringing the original with it. Essentially, the original served as a demo for a much more popular remix.

Remixing is at the heart of popular music. DJ Kool Herc sampled the best part of songs and hip-hop emerged as an art form. Hip-hop is one of the best examples of creativity involving mainly combining ideas. As Maria Popova writes in The Marginalian, “I frequently use LEGO as a metaphor for combinatorial creativity—if we only have bricks of one shape, size, and color, what we build with them remains limited; but if we build with pieces of various shapes, sizes, and colors, our creations will be infinitely more interesting.”

And before all of that, there was shanzhai (山寨). Before DJ Kool Herc, or combinatorial creativity emerged as a key component to creative work, there was shanzhai. While the term shanzhai is usually used today to describe counterfeit products (think of fake Nokia phones, the Motoloba, or Harry Potter and the Porcelain Doll), the word is built on a philosophy of creativity, “The Chinese idea of the original is determined not by a unique act of creation, but by unending process, not by definitive identity but by constant change.”

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Obsess over Details

Obsession is one of the core aspects of craftsmanship. Detail, perfection, and progression are all fruits of obsession, an absolutist view on the correctness, integrity, or honesty of something. These traits often provide a breeding ground for great work.

“The details are not details—they make the product just like details make the architecture. The gauge of the wire, the selection of the wood, the finish of the castings—the connections, the connections, the connections,” writes designer and architect Charles Eames. You could also make the case that a creative work is nothing more than a sum of details.

Author Robert Caro writes of his obsession with research in Working: “Whatever it is that makes me do research the way I do, it’s not something I’m proud of, and it’s not something for which I can take the credit—or the blame. It just seems to be a part of me.”

We, too, must cultivate an obsession with our work. For me, in my writing, it’s about rigorous fact-checking and correctness. It’s about speaking in my voice, and doing the work it takes to figure out what that even means. Sometimes, it’s merely about a headline or, more likely, a lede—where I constantly tweak it to try to make it better. Other times, it’s about finding a fact or verifying an apocryphal tale to support a point.

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Communicate Your Work16 minutes, 6 links

As long as you’re comfortable walking your truth, no one will ever beat you at being you, either.Curtis “50 Cent” Jackson

When you visit a museum or gallery, you’ll notice that each piece of art is usually accompanied by an artist statement. Each art show is accompanied by ephemera like brochures, as well as an audio guide. Curators know even the most accessible artwork can’t speak for itself to everyone; they need to provide context.

You may encounter a similar experience at a restaurant: a staff member presents the food, explaining the story behind a recipe, or where a key ingredient was sourced. The restaurant might even open up the kitchen, making every operation visible.

We see more value in things that were created through some effort, evidence that the creator really cares. When we show our process to people, we give them a chance to appreciate the work more, and to establish the value of the work we’re presenting.

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Create Your Own Market

When Vincent van Gogh died, he was not a well-known artist. His brother, Theo van Gogh, died six months later, leaving his widow, Johanna van Gogh-Bonger, the mission of promoting her brother-in-law’s work. She inherited 200 of van Gogh’s paintings, which were worth so little at the time that she was advised to get rid of them. Perhaps Van Gogh-Bonger’s mission was as much fueled by love and duty as it was an understanding of the work’s potential. Although the general public didn’t appreciate it yet, many artists admired Van Gogh’s work but didn’t have the money to pay for it.

Van Gogh-Bonger started a boarding house in Bussum, then a small village 15 miles from Amsterdam. She would meet people and form working relationships with them. She worked tirelessly with dealers, galleries, and museums, embedding herself in the art world. The work paid off and Van Gogh-Bonger coordinated 20 exhibits of Van Gogh’s work in a decade. She also published her collection of letters between the Van Gogh brothers, which added to Vincent’s reputation and drove up the value of his work. Eventually, she successfully placed his work in museums, and the market had gained the initial momentum it needed.

Some markets seem to emerge naturally, but others are made. In this case, Van Gogh-Bonger dedicated a significant part of her life to making a market for Vincent van Gogh’s work. Even though Van Gogh’s work was already complete, the reputation, awareness, and value of it weren’t set in stone yet. Vincent van Gogh wasn’t recognized as an artist until after he died, when his sister-in-law Johanna van Gogh-Bonger did the hard work of communicating and promoting Van Gogh’s genius.

In an interview with the writer and designer Debbie Millman, artist Shantell Martin says, “Create your own opportunities and do that by using what you have access to.” She recalls her journey, moving away from a fanbase, contacts, and early success in Japan to continue her art career in New York City. She practically started from scratch, sleeping on friends’ couches and meeting new people, in a city abundant with competition. It seemed like everyone else was also an artist.

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Set up Surfaces

It’s tempting to see your work as either complete or incomplete. Perfect or crap. But there are many different stages of your work and, accordingly, many virtual and physical places you can store your work. This is essential to taking action and releasing work regularly. You’ll need to prepare spaces to incubate the work you don’t feel so good about, the work that hasn’t reached a stage that you can call acceptable.

A surface can be any place you’re performing or storing your work. One surface could be private, like a folder or a box that no one else will see. Another surface could be semi-public, one that you show to people you trust. Still, another surface could be entirely public, ready to show the world.

Set up at least three different surfaces—one for storing your works in progress, one for sending to other people for feedback, and one for displaying your finished work. You can choose how visible each surface is. You can set up more, if you like. Vin Verma started his own surface, which he calls Futureland, to track his daily routines and creative activities. He has grown it into a network of digital journals, where people can either publicly or privately track their own progress on their projects.

Take Someone Behind the Scenes

One of the simplest ways of communicating value is showing the effort that actually went into the work. That might involve literally showing the process of making it, though it might also be more biographical. You may ask yourself, and answer, questions like:

  • When did you first get the idea for this piece of work?

  • How did the idea start?

  • What did you see throughout this process?

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Make Them Curious

If people had the attention span to sit for a few hours with your work, then certainly it would speak for itself. But, they don’t. Still, if they were curious to learn more, or knew how to help you, they would. If you experience a reluctance, hesitation, or fear of telling people about your work, it’s even a greater reason to try. The more reluctant you are to talk about your work, the more potential you’re blocking up.

Derek Sivers writes in Your Music, Your People, that when people ask you about your work, giving a boring answer is rude. I wouldn’t go that far, though I would agree that even just a minute of preparation could help. Sivers writes, “Before the conference, come up with one interesting sentence that says what you do—including a curious bit that will make them ask a follow-up question.” He gives the example of, instead of saying “I’m a bassist,” introducing yourself as “Bassist of the Crunchy Frogs—the worst punk bluegrass band ever. We’re headlining the showcase tonight. Our singer is a pirate.”

If I were talking about my book, for example, I wouldn’t say, “I’m an author,” I’d say something like, “I’m the author of Creative Doing, a book that debunks the biggest lie in creative thinking. It has 75 prompts to make the reader more creative. It’s the only book with a shape as a mascot.”

Or flip this prompt: Lose Yourself

Sell Out

Some people are like, ‘Oh, yeah, just sell out and do pop music.’ So you !@#$ing do it, then! It’s not easy.Abel Tesfaye, The Weeknd*

When Will Smith decided he wanted to become the biggest movie star in the world, he worked with his business partner James Lassiter to examine a list of the ten top-grossing movies of all time. In his memoir Will, he writes, “It was crystal clear: Ten out of the top ten films of all time had special effects. Nine out of ten had special effects and creatures. Eight out of ten had special effects, creatures, and a romantic storyline. (We would ultimately discover that all of the top ten movies were about love, but we didn’t notice that back then.)”

When Smith was approached with a $10 million offer to star in 8 Heads in a Duffel Bag, the analysis made it clearer that Lassiter and Smith should say no. And when Smith was approached to appear in Six Degrees of Separation, he and Lassiter said yes to a much smaller offer of $300,000—and set the foundation for Smith’s career as a movie star.

In this prompt, take something popular, identify elements and patterns, and infuse them into your own work.

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Get Feedback27 minutes, 18 links

While our earliest steps might involve making things for ourselves, we also must eventually show someone else our work. The goal isn’t validation, recognition, or business. Rather, the fact that we know someone else will experience it will enable us to figure out and further refine what we’re trying to say.

It’s almost as if there’s a compulsion inside us—perhaps personified by the judge—that really wakes up when we know that somebody else is watching. This compulsion will enable us to take our work to the next level.

Experiment Your Way to Something Big

Science for me is very close to art. … Scientific discovery is an irrational act. It’s an intuition which turns out to be reality at the end of it—and I see no difference between a scientist developing a marvelous discovery and an artist making a painting.Carlo Rubbia*

In 2014, while she was working at Google, Sarah Cooper found an old note. Years earlier, she had seen a colleague make a strong impression in a meeting with a completely nonsensical Venn diagram. She wrote down “How to look smart in a meeting,” with a note to herself to draw Venn diagrams. She added another nine parodical observations, and published her first post on Medium. She said, “It was just really—to use the cliché, it was low-hanging fruit for me to be able to finish it, especially since I was in a ton of meetings at the time anyway.”

Cooper eventually migrated these blog posts to her own parody blog, titled The Cooper Review. A year prior, she’d started a parody of Cosmopolitan, called oolalove!, and made videos on YouTube. She illustrated by tracing photos she took of her friends. She made a calendar. For a short while, she even made memes. Millions of people read her work at Medium and The Cooper Review, leading her to a three-book deal.

Cooper’s willingness to try new things and see how they work out is crucial to her success. So is feedback.

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Release Your Work

When you release your work, you show the world—and yourself—that you are worth the space. You declare it. You get used to sharing your work, even if it’s not your best, or if it’s not perfect. You tell yourself, as Lindsay Jean Thomson said, “I have a right to be here. I have a right to create. I have a right to be seen and appreciated.” In addition to building your confidence, releasing your work can produce interesting tangible outcomes—whether it’s new opportunities, feedback, or lessons you learn about yourself.

Now that you’ve put some work together, it’s time for you to release something. Make it the main focus of your day. If you are releasing your work on a social network, just upload your work, release it, and then go on Airplane Mode. Do something else, so you’re not worrying about how it performs.

It might feel natural for you to seek validation, especially early on if you’re uncertain of your work, but the residue of the data will take up a lot of attention. And if it falls below your expectations, then the feedback (or lack thereof) might feel discouraging. It’s more fruitful to spend the time enjoying yourself, at least.

I’d encourage you to reward yourself after you release your work, regardless of how other people receive it. If you’re anything like me, releasing your work will be scary and involve checking your phone or computer a dozen times an hour to see if anyone liked it. This could put you into an unproductive headspace. After all, we don’t control how other people receive our work—only if and how we release it.

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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.

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Find New Contexts for Your Work

I’ve been writing online for years. With the best of intentions, friends would suggest that I start a vlog, or a podcast. It used to bother me, but now I take it as part of a vast feedback channel. Instead of starting a vlog or podcast myself, I look for people who work in those areas and try to get my work out to them. Rather than repeating my work or reading it out loud, I prepare and improvise points from my writing into a more conversational format like an interview. I also keep my eyes open for visualizations that might better convey my message.

It’s in making the work more portable that I’m able to put a portion of it out for feedback. The simplest version of this is getting feedback on names—which ones did a friend remember? Or, which concepts or ideas from an interview stood out to listeners or readers?

Chris Kim is obsessed with these different areas, which he calls contexts. It’s important to him to find new contexts for his work. For example, he’s interested in building in a more modular way—saving melodies in their own track, saving drums on another, and sharing these individual elements with people to get their perspectives.

Similarly, when Louis Vuitton menswear designer Virgil Abloh was working with his team on designs, he wouldn’t be able to do it in person, so one of his team members would have to take photos or create digital versions so that everyone else could provide feedback through WhatsApp. They transferred the item of clothing from the context of the physical world, into the context of an image on WhatsApp. When producing a song, you need to listen to the track in your car, through your headphones, and through all the speakers you can.

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Be Specific when Asking for Feedback

When author Derek Sivers wrote every day for a month, he realized that there wasn’t enough time to take his writing to the standard he preferred and that he was emailing this subpar writing to tens of thousands of readers. He found it taxing to write something to his own standard every day, and he worried that he was emailing his audience too frequently. He stopped publishing every piece he wrote, only to release it publicly when ready.

You don’t need to release your work to everyone for it to be complete. Sometimes, you might realize that a version of it is complete—but you’re dissatisfied with it, or you want a second or third perspective on it. In situations like that, you can release it to a small group of friends or peers to get their feedback.

Asking for feedback on creative work is an incredibly difficult task. For starters, your family and friends will have an instinct to protect your feelings. Most acquaintances or strangers won’t know you well enough to share. And how do you know what, and whom, to trust?

The first step is to clarify your intention when asking for feedback. You decide how to ask, whom to ask, and how you know whom to ask, when you decide what you’re interested in finding out. Some starting points:

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Release in a Lab

Typically, creative work takes place in what psychologist Fabra Robin Hogarth calls a “wicked learning environment.” These are environments that involve many variables, which make correlations and causations difficult to form. Predictions are very difficult to clearly make.

In this case, you want to release your work in a kind, closed, learning environment. This prompt calls for you to show your work to 10 different people. Ask 10 of them the same questions, and you’ll start to see patterns. If you’re uncertain of which questions to ask, try this ABCD framework from novelist Mary Robinette Kowal:*

  • What’s Awesome?

  • What’s Boring?

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Share Your Intention

On occasion, an intention—a reason, or a purpose, or even just a hypothesis—can be enough to get an idea started. When you share your intention, you give the other person or people a chance to make sense of it, which refines it and provides a space for it to grow.

It can help to be clearer with how you’re asking someone to support your intention. I remember once introducing two friends over coffee, and one was sharing a vision of setting up a dome installation during a film festival and making a request for the other’s expertise with cameras. I left in awe of my friend’s informal presentation and vision.

Perhaps the request isn’t supporting an end result, but for support during the process. For example, “I’m planning on writing for 100 days, and I’d love your support because I’m trying to be an author and it’s going to be hard!” You might also make a request more specifically for accountability, or for feedback, or just general moral support.

Setting your intention and action in the right direction will help create momentum. Communicating that intention and showing people your work will get others involved. Given enough time and space, someone will see it and suggest a way they can contribute. Don’t limit your vision to your work to yourself. Invite family and friends, friends of friends, and acquaintances to experience your work, and allow them a chance to understand and further your intention.

Discard Some Feedback

Early into his career as a designer at Adobe, Andrei Herasimchuk had designed and programmed a prototype over the weekend and a few days into his workweek. One of the product managers, who had worked at Adobe for a while and was well liked by the team, stopped by Harsimchuk’s cubicle.

After a question on how long this took, they said, “While I certainly applaud your effort, I must say that you really don’t need to go to this length. You’ll have to do this all the time for all the products going forward. These screenshots you have here are plenty. It’s all we’ve ever done before, so there’s really no need to spend this kind of time on a prototype.”

Herasimchuk identifies the point when things went wrong, which is when he accepted the product manager’s feedback blindly, “Um… Ok. I guess. If you think so.” He never built another prototype while working at Adobe. His coding skills would dull over five years, and he missed a chance to make coding a part of Adobe’s design culture.

Listening to other people’s feedback is important—for certain. But as it turns out, they just might not understand your work. Or, they might not have been deliberate and thoughtful about your situation. If that’s the case, it would be terrible for you to limit yourself because of one person’s off-handed comment about your work or your process.

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Part III: Creative Purpose

Creative expression involves physical, mental, and emotional contributions. I like to represent these as the hands, the head, and the heart. The prompts in this book so far have helped you align your hands and your head. Beginning with the hands means focusing on practicing creative work. With your hands, you focus on quantity over quality, creating many average successes and total failures, learning what works and what doesn’t. By making many things, we let our expectations of each one melt away. We accept the truth that in order to make something great, we must start with the courage to make and release many ordinary things. The hands don’t have an ego. The hands don’t compare. The hands don’t wonder what they don’t know. They learn by doing, they test and experiment and try. And by putting our trust in our hands, whatever unworthiness or intimidation we feel in our heads and hearts is quieted, and our creative confidence grows.

As we progress in cultivating a hands-focused creative process, we’ve also developed expectations and a growing sense of what “quality” means to us and our work. Maybe we’ve defined what we want to create by trying many things, studying the creators, works, and stories that came before us, and speculating on what may come after us. Our studios bear a close resemblance to scientific laboratories. We’ve begun to deliberately choose our style and direction, and decide how to practice our creative operations.

The prompts in this final section will work to align your heart with your head and hands. Our hearts provide us with the spirit and energy we need to keep our hands and heads adapting. When we work with our hearts, our creative process takes us deep into ourselves, and we start to make sense of the parts of our lives we forgot or didn’t notice before. We start seeing why things happened, what drives our obsessions, and what makes us who we really are. It’s in finding, connecting with, and expressing these deep, universal, truths that we create opportunities to build deep connections between ourselves and someone else. External expectations like reception, competition, and logistics fade away. Only completing the current phase of the exploration matters. In opening our hearts, our heads and hands will follow, and we tap into the deepest level of creative doing.

Get Out Of Your Own Way30 minutes, 17 links

Throughout the book, we’ve already alluded to breaking imaginary barriers, relaxing expectations, and losing ourselves. At this point in the journey, we will embrace letting go; to be gentle with ourselves and to seek a harmony with the creative process. In What is Tao?, Alan Watts describes a skilled carpenter saying, “Let the saw do the work, let the teeth do the cutting.”

We’ll learn to break the habit of force and discipline, and to accept and embrace how the work turns out, even if the outcome doesn’t fit in with what we were expecting or preferring.

Stop Obsessing

As powerful as it is, obsession can also be a troubling occupation of the mind. Left unchecked, it also causes obstacles, or even causes projects—and people—to eventually self-destruct. Obsession can raise a standard so far beyond acceptable that nobody can meet it, creating a creative block. Many people become slaves to their obsessions, caving in to the impulse to push for perfection. Sometimes, if they’re lucky, this results in a complete piece of work. Many other times, though, it causes the work to self-destruct.

The Pixar team, inarguably masters at the crafts of storytelling and animation, also face the over-obsession challenge. Sometimes, people on their team spend days or weeks on a detail that none of the viewers ever actually see. In the 2001 blockbuster Monsters Inc., there is a three-second segment where Boo knocks over a stack of CDs. Pixar artists created a CD cover, as well as a program to change rendering for each of over 90 CDs, for a three-second segment. It was a level of detail that very few, if any, viewers would notice. “Clearly, something in our process had broken—the desire for quality had gone well beyond rationality,” writes Pixar co-founder Ed Catmull in Creativity Inc.*

We can practice loosening the grip obsession can have on us in the creative process. In practice, this means declaring something that you feel is acceptable—but incomplete—to be done. If it’s not acceptable, scope it down by omitting the incomplete details.

If you really can’t bring yourself to do this—if only it were so easy!—set a timer for 45 minutes to complete the omissions and transition the rest of the work together, and declare the work done after the timer goes off. Save and title this version of the work.

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Know Your Stage

In 1926, London School of Economics co-founder Graham Wallas published The Art of Thought, in which he described a four-stage creative process. The first three stages were adapted from physicist Hermann von Helmholtz, and Wallas’s descriptions are in quotes:

Preparation: “the stage during which the problem was ‘investigated … in all directions’”—think about exercises, rituals, and routines that stimulate your mind.

Incubation: “not consciously thinking about the problem”—this is about consciously letting go of the problem and relaxing your mind. It might involve going for a walk in nature, or relaxing in a shower.

Illumination: “the appearance of the ‘happy idea’ together with the psychological events which immediately preceded and accompanied that appearance”—the eureka moment, where an answer comes to you, either quietly or striking like a bolt of lightning.

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Identify Your Bottleneck

In his 1984 business fable The Goal, Eliyahu M. Goldratt wrote about how any improvements or optimizations made to a single process are an illusion, unless they’re at the bottleneck. This is often the slowest step, or the weakest link. In their book Diaminds: Decoding the Mental Habits of Successful Thinkers, Mihnea Moldoveanu and Roger Martin describe this constraint as a “rate-limiting step,” and illustrate it with the example of the flexion hip joint, which gets in the way of even the fastest sprinter from being even faster.

This idea applies to your own creative process. It’s important to take a critical eye to your work and assess which part of the process is limiting you. If you’re not happy with your results, it’s easy to blame an absence of audiences or an unfavorable algorithm. But both of those are lagging indicators of high potential creative work and the promotional work that activates the potential.

Here’s a list of questions you can ask yourself to see which stage you’re getting stuck in the creative process, at the preparation, incubation, illumination, or verification stages:

  1. If it’s a struggle for you to come up with enough ideas, expand your preparation phase. Find more references and spend time studying them and distinguishing between the ones you like and don’t like, and why. (See Visit the Greats.)

  2. If you find you’re coming up with a lot of ideas, but none are resonating, expand your incubation phase. Give your brain more time to rest and relax. (See Make Idle Time.)

  3. If you find you’re missing breakthroughs, pay more attention. Write each breakthrough down whenever you feel your mind making a connection, whether it’s a small one or a big one. Don’t distinguish or edit what your mind is telling you. (See Write Down 10 Ideas.)

  4. If you find that you don’t have enough time and energy to make acceptable work, redefine what quality means to you at this point in your life. In all likelihood, you have to assess how much time, money, energy, and other resources you have to verify—edit, polish, refine, design—and lower the fidelity and scope you are shipping your ideas with. (See Complete Your Operation in Seconds.)

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Be Obvious

This prompt actually emerged as my own reflection, as I was identifying my bottleneck. For example, I’m fairly practiced at writing ideas down, but I have a difficult time choosing one to start writing. I realized through listening to myself that one of the blocks I face as an author is, “I don’t want to write this, it’s too obvious.” This feeling of a lack of originality is a challenge that I’ve seen other writers face as well.

For me, I came across a few sources of consolation. First off, I saw a tweet from marketer and software engineer Patrick McKenzie assuring the reader, “You radically underestimate both a) how much you know that other people do not and b) the instrumental benefits to you of publishing it.” McKenzie also linked to New Science executive director and blogger Alexey Guzey’s writing about the value of unoriginality, “Because it helps in the process of discovery and in the process of supporting underappreciated ideas.”

I also noticed how a handful of “obvious” ideas other people had made an impact on me and my friends. For me, two examples were author Seth Godin’s “Talker’s Block”—which asks why writer’s block exists when nobody gets talker’s block—and Roy Bahat’s “Forwardable email,” which suggests that readers shouldn’t ask for an email introduction, and instead make a request for someone to forward their email along.

I grew to appreciate that what was obvious to me might not be so obvious to someone else, and might seem original and—more importantly—useful.

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Embarrass Yourself

We choose creative work not only because we love it; we also have good taste. Naturally, as we start making creative work, we see the distance between what we call good and what we’re making. The fear dawns on us: What if we make something bad?

This is the gap between taste and ability that everyone starts with. As broadcaster and producer Ira Glass says, “It’s only by actually going through a volume of work that you’re actually going to catch up and close that gap. The work you’re making will be as good as your ambitions.”

The quantity of work is essential. We’ll make mistakes, pretend we know what we’re doing, say the wrong things, imitate people, and find new ways of working that we swore we’d never do.

We need to set the expectation with ourselves that we will probably look foolish as we make our early work. In fact, we need to lean into it and accept it.

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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.

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Archive an Idea

Choose an idea to put away. Don’t look at it again for at least six months. This prompt is particularly useful if you’re struggling with developing an idea; get out of your own way and let time do the work for you by archiving it.

The late Intel chief Andy Grove writes of a simple rule in High Output Management: “All production flows have a basic characteristic: the material becomes more valuable as it moves through the process.” That’s because more time and energy have been spent on the material to make it a final product.

One implication of this idea is the earlier you stop working on something, the fewer resources you waste. For example, if I’m coming up with a pitch, a quick Google search could tell me if someone else has written about the thing I want to write about. If someone has, in exactly the way I wanted to write about it, then I can easily shelve the idea in its current state, as it’s not acceptable to me. If I didn’t come across the prior coverage until later in my process, I’d have to give up the idea after hours spent researching and writing (which has happened before).

Sometimes, a challenging idea may be worth producing. But it takes clear discernment and deliberation to decide if that’s the case. A safer strategy could be to simply shelve the idea, and revisit it again in six months—perhaps time will be your ally and your subconscious mind will conceive of a new way to reframe your idea.

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Praise Your Own Work

What would you think about your work if you didn’t know your own intentions or disappointments?

Too often, our uncertainty of our work leads us to be critical of ourselves. We say things to or about ourselves that we never would accept other people saying to us, nor that we would say about others. “I believe that unless combated, self-hate is easy to develop and nearly impossible to shed,” writes Donda West in her book Raising Kanye.

However, we also have the ability to choose and take action. We can flip that tendency on its head. Be your own greatest supporter.

This prompt isn’t just about making ourselves feel good, it’s about nurturing and developing your own talent, recognizing progress, understanding what’s working in what you do, and identifying where you excel. When you do this, you can then focus on improving other aspects of your craft, or drawing out what’s truly special about your talent.

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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.

Find Your Comfort

To take risks and get out of your comfort zone has practically become a virtue of modern life. This book is no exception to that, with prompts on releasing your work, getting feedback, and exploring your own creative capacity.

As your journey continues, you might find that finding a ritual, prompt, or environment that makes you comfortable can support you in exploring your art and maintaining your creative process. Finding your comfort means noticing when you get into the groove with the work, and potentially developing warm-up routines to support that.

Michelle Kuo says being relaxed during the creative process is really important. “It’s not pure relaxation, it’s like relaxation plus a little bit of tension,” she says in an interview for this book. “I was taking these singing classes. I really adored my singing teacher, and she used to say this thing that always stuck with me, which is: to hit the high notes you have to be relaxed. Most people tense up when they see a high note coming, but actually to hit it, your breath needs to be relaxed.”

Finding your comfort could also mean acknowledging your own progress. “The more I’ve been painting, I don’t know if I’ll be getting better, but I get a lot more comfortable. When you’re a lot more comfortable, I think you are getting a lot better,” says Michael Saviello. “Your technique is improving even though you don’t know it.”

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Know Your Why15 minutes, 18 links

If you don’t stand for something, you’ll fall for anything.Unknown

Have you ever wondered why the comic strip Calvin and Hobbes only exists on the printed page? Unlike Snoopy or Mickey Mouse, there are no blockbuster movies, no Netflix specials, and certainly no stuffed animals. Nobody even knows what Calvin’s or Hobbes’s voices sound like. That’s the result of a deliberate decision that the cartoon’s creator Bill Watterson made to not license out his work.

Watterson’s former business partners (the staff at a syndicate responsible for putting Calvin and Hobbes in the newspapers), estimate that tens, if not hundreds, of millions of dollars could have been made should Watterson have licensed Calvin and Hobbes. But for years, Watterson fought not to, and eventually won out.

At least partially, the decision was practical; Watterson said, “No one cartoonist has the time to write and draw a daily strip and do all the work of a licensing program.” But the refusal to license his work was a philosophical stance as well. In Exploring Calvin and Hobbes, Watterson wrote, “The artist gets to decide what his own creation is about and stands for. If licensing fits your vision of your creation, wonderful, go nuts. But I reserve the option of saying no for my own work. If I don’t like licensing, I should be allowed to refuse it. That’s all it was.”

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Set an Intention

Each of us has an impulse to make excellent things, to tinker, and to seek fulfillment and reward. We may also feel a need to express ourselves in order to gain a sense of comprehension or fulfillment. We want to tell our stories, like we have for hundreds of years, to make something that has a chance of lasting beyond our finite human lives, as well as to make a bid to connect with other people. We may also be driven by a deeper mission or through-line, to support or honor something or someone. We may want to give back to our community, or to find more fulfillment and reward in our jobs.

As you move forward, gaining momentum, you’ll face countless obstacles. You will need to do a simple, but very difficult, thing, which is to set an intention for your work. This transcends practice, technique, and experiments. What are you doing, and why are you doing it?

If we don’t make time to reflect on why we are creating, then political, economic, and social incentives all have a way of seeping in and causing us to make decisions based on their values. As Watterson said, “Selling out is usually more a matter of buying in. Sell out, and you’re really buying into someone else’s system of values, rules and rewards.”

The solution I propose here is an intention—your own position on what you want to do. In order to do that, you need to have an idea of your purpose as well. I know there are plenty of books out there that talk about how to do this, but my opinion is they complicate the whole matter. Nobody, no framework, no prompt, can figure out why except for you, so the only thing left to do is for you to do it and trust that you’ll figure it out along the way. Or as Ethan Hawke says, “There is no path till you walk it.”

Set a Mission

Commercial success and acceptance are both outside of your control. Aiming at those goals would be like trying to aim at the wind, instead of trying to ride with it and have it fill your sails.

Rather than succeed commercially, set out to do something for yourself. It could be as simple as trying to have as much fun as possible. As renowned record producer and recording artist Pharrell Williams says, “As long as I concentrate on the fun, it usually turns out cool. It’s when I become too worried about how it has to be, that’s when God spends a lot of time chuckling at me.”

Maybe you are setting out to express or expose some sort of truth, or to discover it, and to figure it out. Or you’re just trying to refine your techniques. Whatever it is—make it an internal mission, and not an external one.

Another way to say this is to develop a through-line for your current project. The through-line is at the heart of your project. In his class for Skillshare, author and restaurateur Eddie Huang likens a through-line to a thesis, and describes the through-line for his restaurant Baohaus driven by the truth, “No one would kick you out, call the cops, or serve you shitty 7-Eleven pressed Cubans.”

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Ignore the Stats

Everyone creates for different reasons; some of us might do it to be seen, read, heard, or felt. And while this deep connection can be incredibly rewarding and meaningful, the pressure of increasing expectations, social engagement, and sales that often represent it can crush the joy out of creativity.

Before author Mason Currey published his Daily Rituals series of books, he says in an interview with me, “I had, literally, 12 readers for like a year and a half. It was just my coworkers and my family.” His first book, Daily Rituals: How Artists Work, has now been reviewed over 17,000 times on Goodreads.* When I asked artist Shantell Martin—who has 250,000 followers across YouTube and Instagram—about her analytics, she said, “I don’t pay any attention to that stuff.”

“The most important thing I can tell you is to relish writing in obscurity,” author Michelle Kuo said to me in an interview. “I feel that I was the happiest as a writer when I was in hiding, when I was invisible, when I was secretly writing, stealing away portions of time at work, or writing on scraps of paper, or forming sentences in my head on the commute. That was a time before I had published really anything and before I even thought my writing would become a book, I was just trying to organize or to create order in my emotional life.”

Kuo recalls focusing, instead, on simpler metrics: “​​Am I writing?” “Am I showing up?” “Am I discovering something new about these experiences or about this world?” “Am I having new encounters alone?” These types of qualitative metrics, more grounded in the process than the outcome, will enable you to get back to what really matters: your creative work. Remember to enjoy the plateau.

See the Vision

Martial artist George Leonard quotes Arnold Schwarzenegger in his Mastery: “All I know is that the first step is to create the vision, because when you see the vision there—the beautiful vision—that creates the ‘want power.’ For example, my wanting to be Mr. Universe came about because I saw myself so clearly, being up there on the stage and winning.”

Picture the final version of your project, or the specific accomplishment you want. You can put it all on a vision board, collaging images of your vision together. Or, you can write it down in your journal. You can also make it more formal and concrete, writing it down as a press release like the Amazon team does.

Align your energy all towards the same goal. Aim it. And then fire. Or, in Zen fashion, forget about the goal, and let the unconscious deal with it.

Keep Moving Forward

Most people overestimate what they can do in one year and underestimate what they can do in ten years.A popular saying*

Donald Glover was a screenwriter for 30 Rock and played the beloved character Troy on Community, and his work has since earned him several Grammys, Golden Globes, and Emmy awards. Glover is a polymath. When he released his first official album as Childish Gambino, Camp, a critic at Pitchfork gave it a scathing review and a score of 1.6/10.

It’s not difficult to imagine how I might feel in such a situation—disappointed, embarrassed, and discouraged—at such a public rejection of what I had worked so hard on. And yet, whether it was due to his commitments or his drive, Glover kept moving forward with his music career even though he experienced so much success as a writer and comedian. It would have been easy to quit and stick to his comfort zone, but he didn’t. He said, “I don’t even really understand what I’m doing. I don’t. And I don’t think anybody great understands what they’re doing, hopefully. I don’t think they do.”

Dacoury Natche, who has worked with Donald Glover on his album 3.15.20, spoke to me in an interview for this book about his beliefs that great prolific work is fueled by inspiration and a connection to culture. Mixtape runs in hip-hop are a great example of this, whether it’s Lil’ Wayne’s Dedication series, 50 Cent’s pre-debut mixtapes, or Gucci Mane’s many mixtapes. Natche’s point reminds me of musicologist Neal Zaslaw, who writes of Mozart’s work, “Mozart did not compose because he was inspired, although inspiration may be why he composed so well.”

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Independent inquiry is needed in your search for truth, not dependence on anyone else’s view or a mere book.Bruce Lee*

For me, the most valuable thing about creative doing is reiterating the role of action in thinking. We learn not only by thinking, we learn by doing. We set ourselves from the paralysis of analysis by taking action, which is something we knew as children and learn to stop doing as we grow up. If we want to be more creative, we need to reconnect with our inner instinct to make and be open to introducing some chaos into our structured lives.

Perhaps the ancient Roman civilization understood this. Their god Janus, whose domain involves time, beginnings and endings, and transitions, has a head with two faces. The creative process is, similarly, two sided. It involves structure and chaos, freedom and constraint, and spontaneity and consistency. Of course, it also involves both creative thinking and creative doing. To neglect one is to neglect the other. At the end of this book, I hope you get to restart your creative journey, if you haven’t already. Spending more time on creative doing means improving the clarity and quality of your creative thinking.

It’s in creative doing that we rediscover the joy of making for its own sake, find new sources of inspiration, and work through creative blocks. We also learn and apply the practical skills of carving time and space out of each day to make, creating safe spaces for people to brainstorm and come up with ideas, and find ways to solve problems old and new.

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Acknowledgments1 link

Everything around you that you call life was made up by people that were no smarter than you.Steve Jobs*

Each opportunity to create provides us with a chance to become a part of something much larger than ourselves. Sometimes, creativity can even feel like a force channeling into us from the heavens, history, space, the infinite beyond. As recording artist Pharrell Williams said, “We don’t make much happen when it comes to creativity. We’re just antennas and transistors. We’re speakers. We’re just lucky to get the transmission.”

I wrote Creative Doing at home, mostly locked down during the COVID-19 pandemic. I’m still grateful that I had a chance to make it happen, and I couldn’t have done it alone. Writing this book indeed allowed me to become part of something larger than myself. There are a lot of people who contributed to my creative doing:

First and foremost thank you Bernice for your support, inspiration, and for being a great partner. Thank you also for creating a beautiful cover of this book, discovering the original concept, and other much appreciated and unattributed guidance.

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More About the Artists3 links

Mason Currey is the author of the Daily Rituals books, featuring brief profiles of the day-to-day working lives of more than 300 great creative minds. If he didn’t start the genre, Mason definitely popularized public interest in routines, which I’ve found to really benefit my creative process.

Alex Kallaway is the lead developer at Jiffy. He started the #100DaysOfCode challenge, a must-try for anyone wanting to refine their programming skills.

Chris Kim (CVRE) is a multi-instrumentalist, producer, songwriter and sound designer whose work has been used in tracks by artists like Justin Bieber, A Boogie With Da Hoodie, Future, Juice WRLD, and Don Toliver. Rob, Vinny, and Chris started Good Karma.

Michelle Kuo is an Associate Professor in the History, Law, and Society program at the American University of Paris, and a visiting professor at National Taiwan University. She is the author of Reading with Patrick, based on her experiences teaching English in the heart of the Mississippi Delta at an alternative school for kids who were expelled from other schools and returning to work as a tutor in a county jail after graduating from Harvard Law School. Michelle’s writing has changed my life and it will change yours too.

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Summary Graphics9 links

The tactics of this book are summarized here. Feel free to save or share these!

Infographic for Part I: Process

A collection of the tactics covered in Part I: Process. Graphic is available for download and may be shared freely, with attribution to Herbert Lui and Holloway.

Infographic for Part II: Action

A collection of the tactics covered in Part II: Action. Graphic is available for download and may be shared freely, with attribution to Herbert Lui and Holloway.

Infographic for Part III: Purpose

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