Never Run Out of Ideas

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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.

You can write down or draw out any idea you like. If your interest is in architecture or interior design and you want to design a house, drawing it out counts as an idea. Even if you consider yourself a writer, and you have an idea for an app, write it down. That counts. If your friend has told you that the two of you should throw a party, write it down. You can use an existing reference and circle design elements you would have decided to change. You can write down a one-sentence response to something you read. What was the most interesting thing you read yesterday? What can’t you not stop thinking about? What was the coolest thing you saw yesterday? What was the most interesting thing you heard about? What is a different version of something you just made? Can you remix one of the things you saw, heard, or learned yesterday?

Write it down!

An idea can appear in point form, it can be a drawing, it can be one line, your eyes may be open or they may be closed. And you can apply whatever constraint you like to these ideas.

You may be surprised at how many ideas are forming or present in your mind all the time. Here’s an example of what one day’s ideas looked like for me, exactly as I wrote them (Canadian spellings included):

1. Sponsoring or buying a product as a way of buying into someone’s future. This reminds me of a podcast from WorkOS who had said the same thing.

2. Enterprise animals—animals that make jokes about IT sysadmin, etc…

3. My writing as a combination of Shea Serrano (because he’s so versatile he can write about anything in culture!) and … ??? See Byrne Hobart’s description of his own intersection in Marker non huckster piece

4. I add value as an idea generator (because I’ve been exposed to so many through reading)—and how I’m giving a lot away because there’s no way I can actually do all of these ideas. And that’s what Virgil [Abloh] did too, I think. You need to have the ideas to provide direction—or you’re executing them. That’s what high level means… see the book on hierarchy

5. DM interviews—just interview Twitter-famous people on DM/iMessage/Signal or over email for my blog, and let them know I also republish at Medium with 12k+ followers and sometimes at Fast Company as well. This should take no more than 30 mins on my end, and I can set up templated questions just like I do with Crossing the Enterprise Chasm. They can respond in text

6. Marketing as training your brain to see opportunity and optimism, which is what sets expectations too

7. Tourist, purist, and traveller. The value of the traveller is they bring a global perspective, a “holistic” one—they are a purist in their own way, the way of globalization. Tyler Brule is one. Virgil was one too!

8. “Best practices”—doing a lot of stuff and seeing what works and what doesn’t. Based on hypotheses, thinking, and guiding principles of course because nobody can do everything. “Allow strategy to emerge.”

9. Singapore real estate isn’t an asset, art ownership as home ownership, and a world where art is handled as an asset like real estate

10. Print the comics out in newsprint or some other unique type of paper and then take the photo. There is something curious about the screen–paper–screen transition. One of many ideas that emerged from French Dispatch.

It’s messy, practically in scribbles, and that’s the way it’s supposed to be. Seriously, you can write these ideas down wherever you like—in a napkin, on your hand, in your notebook, in a spreadsheet. I like to write mine down in my phone, or whatever pen and paper I can find, and keep track of them in Airtable, so I can search them up later. I sort them by reverse chronological order, and whenever I think of an old idea, I find it, add to it, and move it back up to the top.

You don’t need to work on these ideas right away. It’s tempting to get swept away by the chaos of inspiration, and haphazardly throw new routines and processes into the mix, but it’s important, even with new ideas, to know why you’re trying something new. Coming up with new ideas won’t matter if you’re not able to bring any of them into reality. You may find you need to write the ideas down and save them for later in order for you to truly focus on verifying one and bringing it to life.

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.

You could also prepare a set of sources. For example, before Bierut’s student Zak Klauck started doing his 60-second posters, he had put together 100 phrases (some from friends, others he selected on his own) to design from. That meant the 60 seconds could be spent working on the actual poster, not finding a source or thinking of what to do.

If you want to learn more, I’ve compiled a comprehensive list of 25 daily creative challenges at my blog.

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.

A popular improvisational comedy technique is the one word story, which requires two or more people. The goal is to tell a story by taking turns, each person adding one word at a time.

Similarly, in The Creative Habit, legendary choreographer and author Twyla Tharp shares an exercise where she throws a group of coins on a table. Based on how they land, she draws ideas from the arrangement, occasionally rearranging some of them to be in a more pleasing pattern.

Anytime you experience reluctance at leaving something up to chance, consider that Donald Glover developed his stage name, Childish Gambino, through a Wu-Tang Clan name generator. (He has succeeded perhaps in spite of the name, saying, “If I had known it was going to be something for real, I wouldn’t have used it.” The lesson I chose to take is there’s perfect vision only in hindsight, and you can make mistakes and still get to where you want to go!)

Chance plays a huge role in creativity and can be a useful generative constraint. If you want to make fewer decisions, enlist chance as an assistant. Whenever you need to make a decision, write out your options and let a coin toss, a dice roll, a results generator, or another person’s selection of multiple choice, to decide what you’ll do.

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.

If you do your creative work in the morning, try doing it for an hour or two at night. One of my high school teachers had actually recommended waking up in the middle of the night to write. Interrupting sleep is certainly not pleasant, though the creative work you produce by shaking up your routine might be worth it.

If you start your creative process with meticulous outlines and sketches (as I do!), try doing the final version as soon as possible—even in a single work session. I find the time compression equal parts stimulating and exciting. Even though I end the session dissatisfied with the so-called final draft, I often look back and realize that it wasn’t as bad as I had thought. Conversely, if you’re used to completing your work in a day, take a week, or a month, to do it.

In addition to experimenting with time, you can also find an opposing space for one work session. If you usually work in large, open spaces, try finding one that’s extremely small (channeling your inner Jackson Pollock, who worked in a relatively modest studio, or Roald Dahl’s backyard hut). Conversely, if you usually work in a small space, try working in a big place, like the foyer of a public library or even outdoors.

Creativity means walking a tightrope between consistency and chaos. Switch up your routines so that you naturally add more novelty and vitality to your work.

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.

You can find references across different crafts. For example, filmmaker Paul Thomas Anderson was struggling with a script about two fighting families, when he came across Upton Sinclair’s Oil! Anderson says, “When I read the book there were so many ready-made scenes, and the great venue of the oil fields and all that. Those were kind of the obvious things that seemed worth making a film about.” When Anderson stumbled across that reference, he was able to unblock his script which became the film There Will be Blood. The story itself deviated too far from Oil! to be called an adaptation, though its inspirations are clearly in the through-line of the film.

As you get familiar with the tools and techniques available, if you’re lucky, you might even cobble something together that no one else has tried or imagined. This is how originality actually works: not through a mythological lightning bolt of insight, but through constant bricolage, rediscovery, and remixing of references.

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.