Overcoming the challenge of facing a blank canvas in order to create meaningful work.

Know Your Audience

Jeff Bezos famously remarked that while most companies are concerned with how the world will be different in 10 years, Amazon focuses on the ways in which the world will be the same.

Things like fast shipping, low prices, and easy returns never go out of style. (Amazon still needs to learn that treating employees with dignity and respect also falls into that category, but I digress.)

It can be helpful to skate to where the puck is heading, but you can also expect some things about people to never change.

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My grandfather's restaurant was struggling to sell a particular wine. He tried lowering the price, but sales hardly budged. So he raised it, and it sold out in a matter of weeks.

Cheaper doesn't always mean more desirable.

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Yellowstone National Park had a problem. The bears had figured out how to get into the park's trash cans, and they needed to redesign them to prevent bears from strewing trash everywhere in search of a discarded treat.

The challenge, according to one park ranger, is that "there is a considerable overlap between the intelligence of the smartest bears and the dumbest tourists."

That (possibly apocryphal) story isn't just about the tension in designing something that balances security and convenience. It's also about asymmetry of intent. The average bear is way more motivated to get a stray orange peel out of a trash can than the average tourist is to figure out how to deposit it there.

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No matter your work, part of the key to achieving your goal is knowing the audience for it. How will people's motivations today change (or not) tomorrow? What price makes your service most desirable, while still sustaining you? And how do you balance the compromises and risks that exist in every change we seek to make?

The answers to these questions aren't always obvious — especially when trying to coexist with bears.

Be Brilliant

In the summer after my junior year of college, I spent a month studying abroad in Oxford, England. It was an immersive acting program — we'd spend weekdays in classes and have evenings and weekends for rehearsing, seeing shows, exploring the Hogwarts-esque school we were staying in, and of course, partying with our peers.

On the first day, we were each asked to prepare a monologue to present to the program's director and a couple teachers. It felt like an audition, even though the stakes were low: They simply wanted to get a sense of us as performers in order to sort us into class groups.

Though it felt like we had stepped into the world of Harry Potter, there were no magical sorting hats here.

One student raised her hand and asked if the director had any suggestions on how to prepare. His advice was concise:

"Be brilliant."

The response reminded me of the time another teacher of mine, when asked how long our capstone paper needed to be, simply said, "As long as it needs to be."

We live most of our lives without a rubric, but it's tempting to reach for the certainty of one. Often, simply pursuing excellence is good enough. There's no need to complicate it further.

But what does brilliance look like? The answer to that question is analagous to, of all things, a rainforest.

Erik Torenberg summarizes this analogy from the podcast Exponent in his post "The Death of the Middle":

In a rainforest, with its abundantly available water, sunlight, and nutrients, two types of plants thrive: the tiny, highly differentiated plants on the forest floor, and the giant trees that form the canopy. It’s hard to be in the middle.

In an ever more connected world, it becomes harder and harder to be in the middle. This is because finding the best products and services in the world to solve your problem is easier than ever.

People don't seek out things in the middle — they seek out the best in the world.

"Best" and "world" are relative, however. The grocery store down the street from me may not literally be the best in the world when compared to every other grocery provider in the world. But in this case, if the problem I'm trying to solve is "fresh eggs within walking distance," then the local mart is the best in the world for me.

If you're an illustrator, "best in the world" may mean "best painter on the Santa Monica pier creating portraits in less than five minutes for tourists."

Or if you're an accountant, it may mean "best online bookkeeping service for small non-profits looking to automate their payroll."

As a creator, employee, artist, entrepreneur — however you define your work self — your goal should be to keep redefining "best" and "world" until both things are true.

In other words, be brilliant.

H/t to Naval

YouTube Videos

YouTube had a problem. After releasing their video upload app for iPhones, between 5-10% of uploaded videos were upside-down.

The issue soon became clear: The app had been accidentally designed for right-handed users. When a minority of users rotated their phones 180º to hold in their left hand, the resulting video was the wrong way up.

Diversity comes in so many different forms, and YouTube's anecdote is a powerful reminder that having a wide range of people on your team is critical to ensuring your work is accessible by all.

We are blind to what we don't know. So to best serve those we seek to help, we must lean into expanding our awareness of how others interact with our work and the world.

Exploration vs. Exploitation

Pixar's blockbuster WALL-E begins with 39 minutes of dialogue-free storytelling.

Imagine pitching such a non-traditional opening to the film’s producers. Pixar, fortunately, understands that the recipe for success requires a mixture of risks and safer projects.

In his book Creativity Inc., Pixar co-founder Ed Catmull writes:

We recognized that making sequels, which were likely to do well at the box office, gave us more leeway to take those risks. Therefore, we came to the conclusion that a blend—one original film each year and a sequel every other year, or three films every two years—seemed a reasonable way to keep us both financially and creatively healthy.

The company's success with this model is not an anomaly.

In his 1991 paper "Exploration and Exploitation in Organizational Learning," Stanford Graduate School of Business professor James G. March discusses the idea that organizations have two modes: exploration and exploitation.

"Exploration" refers to riskier endeavors like WALL-E that might not work. They solidify companies as innovators.

To fund that research and development, groups must also "exploit" existing successes. In Pixar's case, that means producing stories like Toy Story 4.

It's this balance between exploring new frontiers and exploiting existing discoveries that creates the engine for long-term success.

1,000 True Fans

It's possible you'll create the next blockbuster that gets seen by millions and grosses ten figures at the box office.

But if you define your success by those metrics, you're likely setting yourself up for a high chance of failure. Very few people create work that finds acclaim on that level.

It's OK if you want to play that game, but you should walk into it with eyes open.

Alternatively, you can define what success looks like on a smaller scale, and Kevin Kelly has a famous suggestion for finding it if you're a creator: 1,000 true fans.

The math is straightforward. If you can get 1,000 people every year to pay you $100, you'll make $100,000 — a comfortable living by most standards.

Of course, the numbers themselves don't matter much. You could just as easily decide that $50,000 per year is your goal and focus on getting 1,000 people to pay you $50.

But Kelly's point remains the same: If you can consistently get a relatively small number of people to pay you a modest amount of money, you can find success as a creator.

And when you consider how the internet enables finding your long tail audience, you'll find that making a living sharing your unique talents with the world has never been easier.

One Hundred Posts

This past week, I published my 100th consecutive daily blog post.

I've wanted to write online for years, but my perfectionism stood in the way: I wasn't sure what to write about and wasn't ready to open myself up to the potential criticism that comes from creating publicly.

So I hid.

But I wanted to challenge myself — to expand my surface area with the world and attract likeminded, curious people. Writing is thinking, and I also wanted to clarify my perspective by writing every day. I figured that would force me to set aside my perfectionism and help me build the habit.

Sometimes doing something every day is easier than just doing it occasionally.

So I published my first post and scheduled an event called "reevalatue blog" on my calendar for 100 days in the future. I knew I needed to commit long enough to see if the practice was worthwhile.

But I soon discovered that I didn't need the calendar reminder. The joy of creating and not just being a passive consumer on the internet soon outweighed any lingering trepidation I had.

Over the past few months, I've started to find my voice and have found that as broad as this blog is, it all ties back to a single idea:

By focusing on creating systems, we can sustainably scale our impact on the world.

My posts on system design and systems thinking started to touch more explicitly on this, and I'd like to highlight this line from the latter, because it's the current that runs through the rest of the blog:

The world is a collection of interdependent systems. And when we think holistically about how those systems interact, we’re able to bring about more meaningful change.

Your network of relationships is a system, for example, as is your wellbeing. And when we think deeply about how these interact with our work, we expand what we're capable of.

This idea extends in many different directions, so I wrote a list of the core, underlying principles that summarize the first 100 posts, which you'll find below. Each link takes you to an individual topic page, where you can read more. And if you'd like to view the full list of topics in one place, click here.


🤝 We can change our culture by leading it in a better direction.

🔎 Our work is better when we systematically understand how the world works through both a humanities and scientific lens.

📖 Changing the stories we tell ourselves and others is a powerful way to initiate the change we seek.

📈 Social progress often occurs at the intersection of art and technology, because technology enables art, and art pushes technology forward.

⚪️ Simple is better than complex because it's more sustainable.

🧠 We are more effective when we shape our perspectives through mental models and challenge our intuition through quantitative reasoning.

🔨 When creating something, work smarter not harder to make it good enough, then iterate to make it great.

❤️ Eliminate distractions to free up space for the more meaningful things in life, like your relationships with others and yourself.

So I'm doubling down on publishing daily for the forseeable future, and can't wait to see what the next 100 days bring.

As always, thanks for reading.

Special thanks to @EmmaGZRoberts for reviewing this list of principles for me.


One of the best ways to fuel creativity is to add constraints. It's a lot easier to face a blank page when you have a prompt than it is to simply be told to draw anything. Having a deadline helps too.

Sometimes, seemingly impossible constraints can produce great work.

Beethoven famously composed his best music completely deaf. Here's Arthur C. Brooks writing for The Washington Post:

In the last decade of Beethoven’s life (he died at 56), his deafness was complete, so music could reside only in his imagination . . . During that period, Beethoven wrote the music that would define his unique style, change music permanently and give him a legacy as one of the greatest composers of all time.

[ . . . ]

Deafness freed Beethoven as a composer because he no longer had society’s soundtrack in his ears.

So if you're struggling to create something, don't be afraid to add restrictions.

Those limits might set you free.

As Long as it Needs to Be

In my final semester of high school, I enrolled in an alternative program known as Senior Year Project. It was a self-directed research project designed to give students the opportunity to pursue a topic of our choosing.

Rather than snooze through the final months of school, we got to go out into the world and explore an area we were passionate about. At the end of the semester, we presented our research to a group of faculty who gave us a simple pass/fail.

Before being let loose, we participated in a series of classes designed to help us hone our research skills and set our expectations for the project.

One moment from those classes stands out to me to this day: a student raised their hand and asked how long the final paper needed to be.

Our teacher simply responded, "As long as it needs to be."

When pressed for more specifics, he refused to relent, encouraging us to simply follow our curiosity, define a thesis statement, and write a paper that sufficiently defended the thesis. No more, no less.

It was such a radical answer to a question we had asked teachers so many times. After years of receiving specific parameters for our work, we were asked to simply "make something awesome."

The opportunity to work on a project where we had a say in defining our success, rather than scraping together something that would pass arbitrary measures, was empowering.

It was a powerful reminder that in the real world, the number of pages you write doesn't matter.

It's the impact they have that counts.

Craft and Care

In the mid 1900s, sales of cake mixes were lagging. The boxed mixes had recently been introduced, but the product simply wasn't taking off.

One day, someone at General Mills had the insight to take the dried eggs out of the mix.

As the story goes, sales immediately started to increase. All of a sudden, people felt ownership over the final product, and adding their own eggs assuaged people of their guilt over not making their family a "real" cake.

The problem with the story is that it's mostly not true.

For starters, cake mixes simply taste better when the eggs are added fresh. Plus, an overall decline in formal exposure to cooking, coupled with a shift in home economics courses to using prepackaged mixes, solidified their popularity.

But the story has staying power, because it speaks to some underlying truths about craft and care.

The Ikea effect is the cognitive bias associated with placing a higher value on something you've crafted yourself, rather than purchased fully formed. The effect is named, of course, after the sense of satisfaction you get from assembling your own flat-pack furniture from Ikea.

When we're involved in the creation of something — even if our involvement is simply adding water and an egg, then baking it — we tend to like the final product more.

There's also something intangible at play in the cake mix story. All else being equal, we enjoy a cake made from scratch more than one from a box, because we know how much more work went into the former.

A cake made from scratch by someone who cares about you is more than just sugar, butter, and flour.

It's also got another ingredient that you'll never find listed on a box.

Great Ideas

So many great ideas tend to seem early because the adjacent possible is only just coming into view.

The iPhone, for example, was a spectacular leap forward on the surface. But it was really the product of incremental progress in lots of different areas, ranging from batteries to chip miniaturization, storage, touch screens, carrier negotiations, software, and more.

In fact, Apple was so quick to combine the advances in all these areas into something revolutionary, Blackberry executives couldn't believe it was real. And even once they came to terms with the fact that it really did work as advertised, they didn't see it as a threat to their business.

This is one of the reasons why sometimes it's so important to start things before you feel ready.

The rest of the world may not know it's ready either.


Reflections on creating systems to sustainably grow your impact on the world.
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