We’ve been living in Valle de Bravo – a mountain town a couple of hours outside Mexico City – for 9 months now.

I’ve lived in 5 countries for at least 6 months each, and traveled in another 20, and I think this is the most perfect place I’ve ever encountered for an expat family to live.

It’s so perfect, in fact, that I think it can actually serve as a template for finding other great places to live around the world.

After months of reflecting on what makes this place so special, I’ve identified 13 criteria (and one bonus criterion) that create the magic. 

What’s fascinating is that these aren’t just random qualities – they work together as a system, each element reinforcing the others to create something truly extraordinary.

1. Right Distance from a Major City

A 2-3 hour drive outside a major city is the perfect distance.

It’s close enough that you can drive in for the day or the weekend, yet far enough that people can’t commute daily. This creates a rooted community instead of a bedroom suburb.

We love being relatively close to Mexico City and everything it offers, but we don’t feel like we have to go there to access people, culture, or entertainment.

I’ve also met some of the most fascinating people ever here – artists, writers, poets, spiritual guides, entrepreneurs, permaculturalists, and creators working remotely.

2. Mountain Location

The mountains are objectively a wonderful place to live.

You get milder weather, fewer mosquitos, tons of nature, and cold nights to cozy up in bed. Plus activities like hiking, horseback riding, and camping.

The mountains also keep it from developing too much and maintain the region’s rural and outdoorsy character, with that small town feel.

Valle is a world-class destination for paragliding, waterskiing, and other outdoor activities, located in one of the few mountainous, temperate regions of Mexico.

3. Water Access

A lake provides recreational activities like swimming, sailing, powerboating, and waterskiing. It also creates beautiful waterfront views.

Research consistently demonstrates that proximity to water bodies leads to higher levels of mood improvement and stress reduction compared to other natural environments. The sights, sounds, and even smell of water provide a calming sensory experience that promotes a uniquely positive state of mind.

Valle is well known for its lake. Lots of people water ski most weekends throughout the year.

4. Tourism and Wealth

This may not seem desirable, but a certain level of tourist influx brings benefits.

There’s likely to be more investment in the town, interesting people coming and going, and more amenities like restaurants, grocery stores, and paddle courts than there’d be otherwise. People are also more likely to visit you.

All the more so if it’s also a wealthy enclave. Valle has a population of around 100,000 that doubles during busy weekends, since many people have weekend houses there. But it rarely feels crowded.

5. Few Foreigners

Our main goal in moving abroad was to immerse our kids in the Spanish language and Mexican culture. I know from living abroad before that this really only happens if there aren’t too many Americans around.

Valle has surprisingly few foreigners living there. It seems like it’s kind of an undiscovered secret for Mexico City families.

6. Warm Culture

Mexico has to be one of the warmest cultures anywhere. We’re constantly surprised by how completely open and generous everyone we meet is.

Especially the families at our kids’ school, who have become our closest friends.

It’s like rewinding the clock to a time before smartphones and the Internet. People greet each other, even strangers treat you like a human, everyone knows each other, and it’s easy to make friends.

At a restaurant, if a kid is crying, a waitress will pick them up and carry them around. They’re happy to give you an extra condiment without charging you for it.

I love that we’re raising our kids in a culture that teaches them how to be warm and open, with a background level of trust between people.

7. Airport Distance

You might think you want an airport nearby, but many of the positive qualities above exist because it’s not too easy to get here.

There’s an airport in Toluca, an hour away, but it’s not international. So you have to drive to one of the international airports in Mexico City, around 2-3 hours away.

8. Low Labor Costs

The single most life-changing part of moving to Mexico has been getting full-time help.

My wife and I save probably several hours a day because our help does all the cooking, cleaning, laundry, and sometimes watches the kids.

We spend all this extra time on exercising, resting, sleeping, art, hobbies, socializing, and hanging out with the kids – all things we had much less time for living in Southern California.

We pay probably double the local going rate, and it’s still remarkably cheap for us. About $137 per week for 40 hours (or $3.40 per hour).

9. Slow Lifestyle

Part of our motivation for moving abroad was to deprogram ourselves from the work-centric life we adopted in the San Francisco Bay Area and Los Angeles.

We found it simply impossible to do this living in Southern California. As long as everyone else was work-centric, there was nothing to do and no one to hang out with!

A core part of that work-centric mindset is an addiction to speed. We found we couldn’t slow ourselves down when everything around us was trying to speed us up.

Every place has a background tempo that dictates the underlying speed of everything within it. I think the only truly effective way to change your tempo is to change your environment.

Mexico, and especially small Mexican towns like Valle, operate at a fundamentally different pace than the US. The cultural emphasis is on relationships and enjoying life rather than maximizing productivity at all costs.

10. Similar Time Zone

If you’re from the US and do business there, you’ll probably want to be in a similar time zone.

This facilitates so many things, from scheduling calls easily to not having too much jet lag when you visit home.

It’s also a bonus if you can get back to the US in just a few hours and have connections to different places within the US. This means Mexico and Central America are ideal!

11. Strategic Inconvenience

In the US, we’re constantly driving toward efficiency, which mostly means removing people from the process. This results in a highly efficient society in which everyone feels alone.

In Mexico, they just throw people at every problem. It isn’t optimized, but there are so many people around, it’s way more fun!

Resisting that drive toward efficiency and convenience is nearly impossible as an individual, and even more difficult as a family, because you seem strange for actively resisting things being too easy.

I’m happy to be raising my kids in a place where there’s still friction, still humans you “have” to deal with, where you literally can’t go it alone to accomplish anything of significance. Relationships are the central element in life.

Part of this is also having a tolerance for risk. We live in a bubble-wrapped, liability-waiver, hyper-sensitive culture, especially when it comes to children. We’ve forgotten how to let them rough it up and find out for themselves.

Paradoxically, as my wife put it, we “overvalue” life to such a degree that we end up devaluing life, by refusing to allow our kids to face its risks.

It’s very hard to intentionally expose your kids to risk, though – you have to move somewhere where the environment provides it. We love that in Mexico, kids are an integral part of every activity. They’re not in a separate world where everything is anesthetized and infantilized.

12. Good Schools

This is probably the crux if you have kids, because good schools are hard to find anywhere. I would start your whole search for a location on this basis.

Valle has several great options, including (incredibly for such a small town) a Montessori and Waldorf school.

High school is harder, and some families move to Mexico City when their kids reach that age. But there are a couple of good options and additional ones on the way as more people settle permanently in town.

13. Good Weather

This is also a good starting point for your search, as weather defines so much of daily life. Obviously you’ll want somewhere without too many extremes.

Valle has year-round spring-like weather, except for an intense rainy season from June to September. But that just gives us the perfect excuse to travel in the summer, as many families do.

14. Artistic Culture (Bonus)

I don’t consider this essential, but Valle has a wonderfully artsy vibe. It was the “Woodstock of Mexico,” hosting a huge concert in 1971 that introduced rock ‘n roll to the mainstream.

This makes it unusually rich in all kinds of art, music, dance, and even psychedelic medicine. It’s more open-minded generally than most places in Mexico, all of which we enjoy immensely.

Finding Your Own Valle de Bravo Around the World

After thinking through these criteria systematically, I discovered dozens of other towns that fit this template. Here are some of the most promising options (courtesy of Claude 4):

In Mexico

Malinalco, Estado de México 

• 2 hours from Mexico City Mountains: Dramatic cliffs, mystical pre-Hispanic sites 
• No lake but swimming holes and streams 
• Wealthy weekend enclave for Mexico City families 
• Very few foreign residents 
• Traditional Mexican pueblo culture 
• Labor costs comparable to Valle 
• Extremely slow-paced, artistic community 
• Good private school options emerging

Zacatlán de las Manzanas, Puebla 

• 3 hours from Mexico City, 2 from Puebla 
• Mountains: Pine forests, apple orchards 
• Lake: Presa de Tenango nearby Mexican tourist destination (famous for apples/cider) 
• Almost no foreign residents 
• Warm provincial Mexican culture 
• Very affordable labor 
• Traditional, family-oriented lifestyle 
• Growing educational options

Real de Catorce, San Luis Potosí 

• 3 hours from San Luis Potosí (with airport) 
• Mountains: High desert mountain town 
• No lake but stunning desert landscapes 
• Mystical/spiritual tourism, wealthy Mexican visitors 
• Few permanent foreigners despite tourism 
• Deep traditional culture Very low labor costs 
• Contemplative, artistic atmosphere 
• Alternative education options

Tapalpa, Jalisco 

• 2 hours from Guadalajara Mountains: “Pueblo Mágico” with forests
• Lake: Presa del Nogal 
• Guadalajara’s weekend retreat 
• Minimal foreign presence 
• Traditional Jalisco hospitality 
• Affordable labor 
• Outdoor-focused, slow lifestyle 
• Good local schools

Cuetzalan, Puebla 

• 3 hours from Puebla city 
• Mountains: Cloud forest, coffee region 
• Waterfalls instead of lakes 
• Cultural tourism but few foreign residents 
• Strong indigenous Nahua presence 
• Incredibly warm community 
• Very low labor costs 
• Traditional, market-town pace 
• Local schools with cultural programs

In Central America

Suchitoto, El Salvador 

• 1.5 hours from San Salvador 
• Mountains: Overlooking Suchitlán Lake 
• Lake: Lago Suchitlán (country’s largest) 
• Arts/culture destination for wealthy Salvadorans 
• Almost no permanent expats 
• Warm Salvadoran hospitality 
• Very affordable labor 
• Artistic, slow-paced colonial town 
• Emerging private school options

Gracias, Honduras 

• 3 hours from San Pedro Sula 
• Mountains: Celaque National Park 
• Hot springs instead of lakes 
• Honduran tourist destination 
• Virtually no foreign residents 
• Traditional Lenca culture influence 
• Extremely affordable 
• Quiet, colonial atmosphere 
• Local schools improving

Matagalpa, Nicaragua 

• 2 hours from Managua Mountains: Coffee highlands 
• Rivers and waterfalls 
• Nicaraguan tourist/coffee region 
• Very few expats 
• Warm mountain culture 
• Lowest labor costs 
• Coffee-farming lifestyle pace 
• Several school options

Volcán, Panama 

• 1.5 hours from David 
• Mountains: Volcanic highlands 
• Streams and rivers (no lake) 
• Wealthy Panamanian retreat 
• Some retirees but families can find Spanish immersion 
• Indigenous Ngäbe influence 
• Reasonable labor costs 
• Agricultural, outdoor lifestyle 
• Good private schools

San Agustín Lanquín, Guatemala

• 3 hours from Guatemala City
• Mountains: Limestone caves region
• River: Cahabón River (turquoise pools)
• Growing eco-tourism, Guatemalan visitors
• Few permanent foreign families
• Q’eqchi’ Maya culture
• Very affordable
• Nature-based, slow lifestyle
• Community schools with cultural programs

In the United States and Canada

Nelson, British Columbia, Canada

• 3 hours from Spokane, WA (airport)
• Mountains: Stunning Selkirk Mountains
• Lake: Kootenay Lake (magnificent)
• Tourist/wealthy enclave: Vancouver families’ mountain retreat
• Warm Canadian mountain culture (surprisingly bohemian)
• Slow, artistic, non-work centric lifestyle
• Good Waldorf school + alternatives
• Great weather (for Canada)
• Pacific Time Zone
• Missing: Low labor costs, foreign language immersion

Salida, Colorado, US

• 2.5 hours from Denver
• Mountains: Arkansas River Valley, 14ers all around
• River town (Arkansas River) rather than lake
• Wealthy outdoor enthusiast enclave
• Warm, artistic community vibe
• Deliberately slow, “simple life” culture
• Growing alternative school scene
• 300+ days of sunshine
• Mountain Time Zone
• Missing: Low labor costs, foreign culture, major language immersion

Joseph, Oregon, US

• 3.5 hours from Boise (a stretch, but worth it)
• Mountains: Wallowa Mountains (“Alps of Oregon”)
• Lake: Wallowa Lake
• Tourist destination, Portland/Seattle wealthy retreat
• Genuine cowboy/artist culture mix
• Extremely slow-paced, no chain stores
• Small but good school
• Beautiful weather, real winters
• Pacific Time Zone
• Missing: Low labor costs, foreign culture, close to major city

Sandpoint, Idaho, US

• 2 hours from Spokane
• Mountains: Selkirk and Cabinet ranges
• Lake: Lake Pend Oreille (huge, gorgeous)
• Wealthy Seattle/California exodus destination
• Surprisingly warm, outdoorsy culture
• Anti-corporate, slow lifestyle ethos
• Waldorf school + good public schools
• Four real seasons
• Pacific Time Zone
• Missing: Low labor costs, foreign culture

Rossland, British Columbia, Canada

• 2.5 hours from Spokane
• Mountains: Ski town in the Monashees
• No lake but close to Christina Lake (30 min)
• Weekend destination for Vancouver/Calgary families
• Small, tight-knit community
• Extremely slow, outdoor-focused
• Good elementary, high school requires creativity
• Snowy winters, perfect summers
• Pacific Time Zone
• Missing: Low labor costs, foreign immersion

The System Behind the Magic

Strangely enough, the mountain town I lived in for a year when I was 14 – Campos do Jordão in Brazil – meets most of these criteria as well. It’s a few hours outside São Paulo, in the mountains, a tourist destination and wealthy enclave, with a warm and inviting culture.

The year we spent abroad there was so formative for me, I think I’ve subconsciously tried to recreate as many of those conditions as possible for my kids, but in Mexico.

What I’ve learned is that these criteria work together as an interconnected system. The distance from a major city creates the rooted community. The mountains provide the natural beauty and limit overdevelopment. The tourism brings investment and interesting people. The culture provides immersion and different values.

Each element reinforces the others to create something greater than the sum of its parts.

The real insight isn’t just about Valle de Bravo – it’s about understanding what creates the conditions for the kind of life you actually want to live, then systematically looking for places that provide those conditions.

What would your criteria be? What kind of life are you trying to create, and what environmental conditions would support that vision?

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In 1997, a young hip-hop producer from Detroit named J Dilla did something that violated every rule in music: he programmed his drum machine to play “off beat.”

Not just slightly off, but deliberately off—breaking up the rigid timing that had governed musical performance in every genre.

What happened next confounded the music industry. Instead of sounding amateurish, the “wrong” beats created a revolution. They somehow felt more organic, more alive, and more expressive than anything else in electronic music up to that point.

Professional musicians couldn’t explain it. Hip-hop critics couldn’t categorize it. But listeners—particularly other producers and artists—couldn’t get enough of it.

And here’s the paradox that stopped me cold: Dilla used the most mechanical of tools—a drum machine—to create something that sounded profoundly, unmistakably human.

(I suggest listening to this playlist of J Dilla-produced songs on Spotify while reading the rest of this piece.)

I’ve been thinking about this story as I’ve watched the panic unfold around AI and creativity. Many cultural critics and artists paint a bleak picture. They warn of creative fields decimated by automation, of human imagination rendered obsolete, of a future where authentic human expression drowns in a sea of algorithmic content.

But what if they’re wrong?

What if new technology doesn’t destroy creativity but instead transforms it in ways we can’t yet imagine?

Recently, I found an unexpected source of insight into this question—a book about the life and innovations of that same hip-hop producer: Dilla Time by Dan Charnas.

As I learned about Dilla’s career, I couldn’t help but notice striking parallels to our current moment with generative AI. Here are seven insights drawn from the early history of hip-hop that challenge today’s techno-pessimism about AI and creativity:

1. Technology can create new creative forms that humans can’t

James Dewitt Yancey—known as Jay Dee and later as J Dilla—died in 2006 at the age of 32 from a rare blood disease called TTP, but his revolutionary approach to rhythm lives on. As Charnas puts it: “He is the only producer-composer to emerge from hip-hop and, indeed, all electronic music to fundamentally change the way so-called traditional musicians play.”

J Dilla’s innovation was impossible without the Akai MPC3000 drum machine. By deliberately manipulating the timing of drum hits, he created what Charnas calls “Dilla Time”—a style that juxtaposed even and uneven time-feels simultaneously, creating a pleasurable rhythmic friction that no human drummer could physically execute.

The parallel to generative AI is clear: while many fear AI will make creative work formulaic, it might instead enable entirely new forms of creative expression—forms that humans alone couldn’t accomplish due to our cognitive or physiological limitations.

2. The most innovative uses of technology often subvert its intended purpose

Drum machines were designed with a quantizing function to “correct” human timing errors using software. 

But J Dilla deliberately subverted this function. He turned off quantization or manually moved drum hits off a mathematically precise grid, creating beats that communicated emotion through “imperfect” rhythm.

This paradox—using a machine designed for metronomic perfection to create controlled imperfection—suggests that the most powerful innovations often come from subverting a technology’s intended purpose.

The most transformative uses of AI may similarly come from those who find ways to bend the technology, introducing controlled variations that make its output more distinctively creative and human.

3. New technology can reconnect us with ancient traditions

Surprisingly, Dilla’s innovation via digital technology represented a return to older forms of musical expression. His rhythmic approach reconnected with polyrhythmic traditions from West Africa, the Caribbean, and South Asia that had been marginalized by the conventions of European classical music for centuries.

As ethnomusicologists noted, Dilla’s rhythms broke through the European frame that colonialism had forced on much of the world’s popular music.

This challenges the narrative that technology alienates us from our authentic human nature. In this case, the drum machine allowed musicians to reconnect with complex rhythms that had been all but lost to history.

Similarly, AI might not lead us into a posthuman future but instead return us to our primal roots, surfacing ancient aspects of our psychology that were repressed by industrial-age modernity.

4. Creative relationships with technology evolve from conforming to bending

Early hip-hop producers conformed their creative process to their drum machines’ limitations, trying to make audio samples fit neatly into the rigid 16-pad time grid. But Dilla took a fundamentally different approach.

As DJ Jazzy Jeff observed: “Everyone in hip-hop had heretofore been trying to cut, splice, and jam samples to accommodate the machine’s time grid… But Jay Dee did the opposite: he bent the machine grid to accommodate his sample sources, because he was focused on using those samples for their rhythmic and harmonic feel.”

This evolution from conforming to technology’s rigid constraints to bending it to human intention is instructive. The earliest AI-generated art shows creators conforming to algorithmic limitations, but as these tools develop and creators’ technical understanding deepens, we’ll see more instances of the technology being bent to accommodate our visions.

This evolution from conforming to bending seems inevitable in every creative-technological relationship. It’s not a question of if professional creators will bend AI to their will, but when and how they’ll discover the equivalent of turning off quantization in their generative workflows.

5. New technologies create new creative specializations

J Dilla’s innovation created an entirely new category of musicianship. He wasn’t a traditional percussionist but what audio technology pioneer Roger Linn called a “sequencer player”—someone whose primary instrument was the programming of rhythmic time itself through digital interfaces.

Dilla made microsecond timing variations in ways that were impossible for human drummers, creating a new art form that required a new type of technical virtuoso.

We’re seeing the same pattern with generative AI. These tools are giving rise to new creative specializations: prompt engineers, AI image directors, model fine-tuners—emerging roles existing at the intersection of human aesthetics and machine capability.

Just as many classically trained musicians initially dismissed “sequencer players” as not being real musicians, we see traditional creative professionals dismissing these new AI-adjacent creative roles.

But these new creative forms don’t replace existing ones—they expand the total landscape of expressive possibilities. They are additions to our creative ecosystem, not wholesale substitutions within it.

6. Technological innovations transform how we value information repositories

Hip-hop pioneered sampling—taking segments of existing recordings and transforming them into new compositions. J Dilla elevated this practice using sophisticated digital techniques to chop, stretch, and manipulate audio samples into entirely new sonic arrangements.

This practice made certain information repositories—warehouses of obscure vinyl records from defunct labels—skyrocket in commercial value. Producers spent countless hours digging through dusty crates searching for unique drum breaks and bass lines no other producer had discovered.

We’re seeing this same pattern with generative AI, where specialized datasets have suddenly become incredibly valuable for training and fine-tuning. Collections of information previously overlooked in the pre-AI economy now hold tremendous monetary and strategic value.

This raises profound questions about creativity itself: Has human creativity ever truly been about creating from nothing? Or has it always involved recombining, transforming, and recontextualizing what came before us in novel ways?

7. Machine innovations feed back into human creative practice

Perhaps the most powerful lesson from J Dilla’s story is how his machine-enabled innovations transformed human musicians’ techniques. 

Professional performers like Questlove of The Roots and neo-soul keyboardist D’Angelo meticulously studied Dilla’s machine-made rhythmic patterns and learned to replicate them with traditional acoustic instruments, fundamentally rethinking their relationship with music in the process.

As Charnas describes: “Jay Dee could shift a drum’s position in time by programming it, and there it would remain. But Questlove had to counteract a lifetime of physical reflexes, to retrain his body to do things and feel time differently.”

A machine-made innovation forced one of the world’s most accomplished drummers to unlearn years of muscle memory and develop entirely new techniques. The drum machine wasn’t replacing the human musician—it was pushing human creativity into previously unexplored territories.

J Dilla’s innovations extended beyond hip-hop, influencing jazz orchestration, classical composition, and mainstream pop production. His work has been interpreted by symphony orchestras at Lincoln Center and studied in university music conservatories.

This pattern suggests something important about our AI future: the most significant impact of generative AI on human creativity may not be direct replacement of jobs, but how it challenges professional creators to develop new capabilities and aesthetic perspectives they wouldn’t have discovered otherwise.

Embracing the Meta-Creativity of the AI Era

If the evolution of music production technology and electronic instruments teaches us anything, it’s that new tools don’t eliminate human creativity—they transform it, often in ways that expand rather than contract the range of human creative expression.

But this technological transformation requires a specific creative approach.

J Dilla didn’t set out to revolutionize rhythm—he simply explored the creative possibilities of his MPC3000 with extraordinary dedication and meticulous attention to detail. His daily creative routine, as described by Charnas, involved rising at 7 am, cleaning his Detroit studio while listening carefully to newly-acquired vinyl records, and then making beats from 9:00 a.m. until noon. He created them “quickly, one after the other, finished them, and then moved on.”

I find this aspect of his disciplined practice particularly illuminating for our AI moment.

This combination of structured daily practice, deep listening to source material, and rapid iterative experimentation mirrors what the most innovative creators are now doing with generative AI tools. The truly groundbreaking uses of AI aren’t coming from those who simply prompt a model to create something and uncritically accept whatever it produces. They’re coming from those who engage in a sustained dialogue with the technology, who develop deep technical understanding of its capabilities and limitations, and who have a clear creative vision that transcends the particular tool itself.

What would a “J Dilla approach” to generative AI look like in your specific creative field?

What we should be looking for (and investing in) are not just incremental improvements in AI model capabilities, but the emerging meta-practices that leverage AI to create new forms of human-machine creative collaboration. These emerging practices might involve using AI to rapidly explore creative possibilities, to overcome specific technical obstacles, to challenge established aesthetic assumptions, or to handle routine aspects of production work so that human creators can focus on higher-level creative decisions and emotional subtlety.

The story of J Dilla reminds us that when a new technology enters a creative field, the most interesting developments often happen not at the center of that technology’s intended use but at its experimental edges—where innovative humans push it beyond its manufacturer’s instructions, bend it to their unique artistic vision, and in the process, discover entirely new dimensions of creativity.

Rather than fearing that AI will replace human artists, we should be asking more specific questions: What new forms of meta-creativity will emerge in the AI era? What new patterns of thought and creation – what new harmonies between human aesthetic intelligence and machine computational intelligence – might become possible through thoughtful collaboration?

The answer to these questions won’t come from the technology itself, but from the James Yanceys of our era—those visionary creators and artists who see in our new digital tools not a threat to human expression, but an invitation to expand it in ways we’ve yet to imagine.

And perhaps, just perhaps, that creator could be you.

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I’m proud to introduce Death Clock, a life expectancy calculator that predicts the day of your death based on 17 personalized variables.

Give it a try for free!

This is not only the first “app” I’ve ever created myself, but also my first experience with AI-assisted coding, which has become known as “vibecoding.” 

I can definitively say this was one of the most eye-opening, impressive encounters with technology I’ve ever had, and it opened my eyes to a vast horizon of possibilities that I think AI-assisted coding will open up going forward.

Here are my observations and insights based on my first few hours of vibecoding.

Finding an entry point

One of the first things I look for when trying to learn a new skill is a good “entry point.”

Simply typing the topic into Google or YouTube is not smart, as it only results in a flood of mediocre-quality, clickbait-driven results. Instead, I look for a single, in-depth piece of content or a course taught by a qualified instructor with a strong track record of quality. Ideally, there’s also an accompanying community or discussion forum associated with it, so I can see what others are doing.

All these criteria were fulfilled when I signed up for my friend Nat Eliason’s new course, Build Your Own Apps with AI. One recent Saturday morning I started watching the instructional videos while my wife and the kids were sleeping in.

The course recommends the coding program Cursor. As I downloaded the desktop app and created an account, the complex-looking interface was already starting to intimidate me. I had downloaded IDEs (Integrated Development Environments) before, but since I have virtually no technical ability or knowledge, I always felt overwhelmed and confused by the unfamiliar interface and quickly gave up.

Here’s what the interface looks like in Cursor:

As I watched Nat’s videos, it soon dawned on me how incredibly straightforward and easy it was to create functional code using Cursor, for one simple reason: it draws on the formidable powers of leading LLMs.

As I began experimenting, I found that it wasn’t necessary to interact with any part of the software except for one: the ongoing chat with the AI. Although you can directly manipulate the code, navigate around the various project files, approve or reject individual edits, and issue commands in a terminal window if you want, none of that is strictly necessary. The AI can take all the actions itself.

Building Death Clock v1

After watching the first module of the course, I decided to go right ahead and try building something I actually wanted: a life expectancy calculator. 

I’m in the midst of writing my new book, on the art and practice of completing an annual life review, and I’m finding that one of the main themes of the book is reckoning with one’s mortality and limited time on the planet. It’s quite hard to take on that longer-term perspective day to day. But at least once a year, I think it’s incredibly valuable to do so. I was looking for a way to give readers a visceral, felt sense of how short life truly is.

I can write thousands of words about mortality and its ability to put our lives into proper perspective, but no volume of words compares to the power of a personalized, interactive tool that calculates your own expected date of death. It’s the difference between generic advice and an expiration date that takes into account your own unique life circumstances.

Living in Mexico has also exposed me to a very different attitude toward death than I’m used to in the US. Instead of something to be feared and the mention of it avoided, death is a much bigger part of the culture, from the ofrendas of Día de Muertos to the ubiquity of skeleton iconography to the constant awareness of ancestors. I want to make death something that people can talk about more openly.

And lastly, I turn 40 next week, so let’s just say that mortality is on my mind

Working with the AI

I started my project by creating an empty folder, loading it up into Cursor, and asking it to “Build a web app that calculates someone’s life expectancy based on lifestyle factors.” That was it. There were no technical specifications, no feature requests, and no tech stack. Just a simple request made in natural language.

Cursor gives you the option to select which LLM you want to use, including all the leading models from OpenAI, Google, and Anthropic. I kept it on “auto-select,” which means it decided which model to use depending on the situation.

It proceeded to immediately build a full-fledged React project, which took several minutes and involved creating an entire structure of multiple interlinked files. I asked it to open the app in my web browser, and it prepared the file, which I just needed to double-click.

Here’s what that very first version looked like:

So the app now existed, but with one tiny problem: there was no way to input any personal information! I asked it to add input fields for each of the lifestyle factors, and in a couple of minutes they appeared. I put in my own information as a test, and it spit out the results:

After only about 5 minutes, I already had a functional web app! This alone is astonishing, as I would have probably needed hours to get even this much up and running on my own. I thought back to my early web design efforts using Microsoft FrontPage as a teenager in the 90s, and how that experience was so daunting that I gave up on the endeavor altogether.

I spent the next several hours adding features, which amounted to no more or less than asking for them in the AI chat window and waiting. Here’s what I changed, one element at a time:

• Added a total of 17 questions, encompassing various aspects of a person’s life that influence their life expectancy
• Added an in-line BMI calculator, based on a person’s height and weight
• Asked the AI to create a logo of an hourglass and place it at the top of the page
• Had it try out a couple of styles, settling on a muted, grey and blue color scheme
• Added some interesting outputs and observations related to life expectancy to the “results” page, based on the answers to the questions
• Added a pie chart visualizing a person’s remaining lifespan (which required Cursor to download and install a new library, which it handled on its own)
• Added a call to action to check out my website at the end
• Set up a repository on GitHub and published the app using GitHub Pages, so I can share it with others

All this took about 3-4 hours, but I would estimate around half that time was spent waiting for the AI to do the work, or for the new version to deploy, so I could view it in a browser. While all this was happening, I hung out with the kids, washed dishes, took a shower, and got some reading done. Instead of requiring an all-encompassing, immersive day of obsessive learning, which is what I would have expected, I actually had quite a relaxing, balanced day!

There were only a couple of hiccups I encountered during this project. At one point, there was a bug that would make the whole screen go blank when I clicked the “Calculate Life Expectancy” button. Cursor asked me to copy and paste the error message from the console into the chat, but before I even did that, it guessed what the problem was and proceeded to fix it by itself. Here’s what that interaction looked like:

I sometimes had to perform actions beyond just clicking “accept all,” such as typing “y” into the command line to allow it to proceed, or typing in my computer’s root password to allow it to install something, so I did have to pay a bit of attention and look out for next steps.

A few times, a new feature didn’t work correctly the immediately, and required follow-up fixes, such as this first attempt at a pie chart:

One of the most surprising parts of working with an LLM in a coding environment is that the AI has context and knowledge about many, many domains that have nothing to do with code. For example, at one point, I got stuck with the GitHub settings, so I just pasted a screenshot of what I was seeing into Cursor, and got a precise diagnosis of what was wrong, plus step-by-step instructions on how to fix it.

But it also goes beyond software. At one point, I asked Cursor to tell me how robust or evidence-backed a question about income level was, and in seconds, it pulled in an academic paper that examined exactly this question. It still had to simplify the correlation between income and life expectancy into a multiple-choice question, but knowing there was at least some validity to this question gave me the confidence to move forward.

I kept assuming I would hit a roadblock and have to switch to a “real” LLM to do more serious research, planning, or structuring of questions. But that wasn’t the case: the LLMs that Cursor is drawing on are exactly the same ones you’d have access to via ChatGPT or Claude, so there’s no need to leave.

That also means that Cursor can do design work. I asked it to create a visual style reminiscent of the blocky, 8-bit graphics of early Nintendo games, but with a death-themed, macabre look. It instantly understood the assignment, using red and black to convey the right feeling:

I decided that look wasn’t quite right, so I had it pivot to a cleaner, more modern style. Here’s what that interaction looked like, replacing probably hours of work:

The ability to pivot on a dime like this and effortlessly try out a completely new direction is astonishing. Small experiments and whimsical curiosities can be indulged and tested without expending significant time or effort.

My 4 takeaways from vibecoding

This first experience of a few hours of vibecoding left me with 4 takeaways:

• Learning to code is now optional
• The new bottleneck is how you spend the time that’s saved
• Software is the new frontier of book publishing
• We’re entering a more impressionistic era of creation

Learning to code is now optional

Over the years, I’ve considered whether I should build an app many times. I live in the world of tech and software, and in many ways, the ability to create a new software tool is the pinnacle of agency in that world.

Yet every time, I’ve decided not to pursue building an app, either because I lacked the time to learn it myself, or didn’t want to spend the thousands of dollars it seemed to require to even build something basic.

But now, in a matter of hours and at almost zero cost, I can build something that’s genuinely useful. I didn’t learn anything about coding, but I think that’s overall a good thing. Learning can be fun and is certainly useful, but it isn’t always inherently good or necessary.

Why should the ability to leverage software be limited to those willing to spend months or years studying arcane details of technical implementation? Why should someone’s vision or mission require them to know the low-level details of how a webpage gets rendered? And now, nearly all of the details are “low-level.”

Learning coding is now optional, but I think AI tools will also make it easier to learn to code for those who decide they want to. At any point, you can bring in context from any part of the codebase and ask the AI to explain it to you at any level of detail you want. You can even have it explain things outside that environment, such as the many external systems and interfaces you’ll need to get a full-fledged website working.

This is such a remarkable level of accessibility for a technology that was previously very hard to use, and it’s difficult to predict how the world will change when everyone can wield the power of software.

The new bottleneck is how you spend the time that’s saved

It’s so fast to create and edit code this way that the bottleneck starts to become how fast you can move your mouse, the speed of your internet connection, how long it takes to deploy a new build, the speed of refreshing the page, etc.

I predict we’ll see a variety of efforts to speed up every little step involved in coding, the same way that factories once invested millions in reducing the time it took to switch a production line from one activity to another, as that became the bottleneck.

But more broadly, the true limiter on the quality of software that people will be able to produce using Cursor and similar tools is how they spend the time that AI frees up for them. 

You could spend it chilling by the pool or watching TV, but you have to remember that everyone else is also having all their time freed up, so the level of competition will increase like a rising tide. Many web apps that people will build this way are hobbies, or experiments, or complements to other projects. Still, many will have some kind of competition or alternative, and the only way to compete effectively will be to invest the time saved in new dimensions of quality.

Maybe you spend that time exercising and meditating, so that you can ground yourself and bring wiser, more holistic decision-making to the AI. Maybe you spend it reading and researching, so the knowledge underlying your app is richer and more nuanced. Maybe you spend it hunting for obscure sources or offline archives, so that you can incorporate context that the LLM doesn’t already know. Maybe you spend your time talking with potential customers, so your choices more accurately reflect what they want.

All of these are valid choices, and they will all become important dimensions of competition and quality, even more so than they already are today. The true scarce resource continues to be the time and attention of other people, and I only expect the battle for that attention to keep heating up.

Software is the new frontier of book publishing

One of the domains I’m most excited about applying these new tools to is book publishing. Books have changed so little over time, and increasingly suffer in comparison to other, far more interactive and engaging forms of media.

I don’t think bemoaning this fact and lecturing people on the importance of reading is helpful, but I do believe interactive web apps like this could make a tremendous difference. What if, every time you finished a book, or even a single chapter, you were presented with a link to a free, interactive, personalized web app that directly applied the ideas you just read to your own situation?

Instead of trying to guess how to apply a book’s ideas, or get upsold to a course, or have to get expensive support from a coach or consultant, you would have a self-serve piece of software you can immediately engage with.

The value of a book is that the author has taken an extraordinary amount of time to research and think deeply about an important issue, topic, or skill. That’s a rare thing in our hype-driven online world of disposable headlines. But that same slow-moving, timeless quality makes it very difficult for books to recommend or prescribe any given form of implementation. There’s just too much variation between individuals to offer a one-size-fits-all solution, and long publishing timelines mean that any solution printed in the pages of a book is likely to be obsolete by the time it hits the shelves.

This is a way to combine the best of both worlds: to deliver the timeless, wise, holistic wisdom of books, accompanied by a suite of personalized, customizable, up-to-date digital implementation tools, accessible in one click or tap. This is how you save the culture of reading – not by resisting change but by embracing it. I plan on making extensive use of this approach in my next book.

We’re entering a more impressionistic era of creation

One of the most continuously surprising aspects of AI-assisted vibecoding is how brief, imprecise, informal, and vague my instructions can be, and still be understood. I could almost always just say “Fix this” with a screenshot, or “Make this look better,” or even just “Improve the question,” and AI would figure it out.

This is so different from past technologies that require you to be extremely exact, specifying what you want with mathematical precision. Even a single wrong character in a codebase of thousands of lines could result in a catastrophic error.

My unclear instructions often resulted in better results, because the AI would misinterpret my intentions and make improvements I hadn’t even thought of. Some of the best ideas came from the AI, either because I asked it for ideas or because it contributed them spontaneously as it guessed what I was trying to achieve.

Like the transition in painting style from the Realism of the mid-19th century to the Impressionism of the late 19th century, driven by painters’ desire to capture changing qualities of natural light, fleeting moments, and spontaneous experiences using quick, expressive brushwork rather than carefully finished compositions, we’re going to see a similar transition in software design.

Interestingly, what sparked the transition back then was technology – the advent of photography meant that scenes could be captured with nearly perfect realism, which devalued that ability by humans. Human artists pivoted in reaction, exploring a new frontier of perception, novel color combinations, and everyday life.

I think we’ll soon see our technological creations becoming much more impressionistic, based on ambiguous premonitions, subtle feelings, or vague notions that we can’t fully articulate. We’ll see people create various kinds of software as artistic expressions, or to capture a fleeting memory, or to convey a single message. Software will become its own mode of creative expression for a much wider range of people now that the price of entry has plummeted to near zero.

4 tips for using Cursor

Despite my lack of commitment to learning anything in particular, I found that I did end up learning a few things about how to work effectively in Cursor:

• You don’t have to deploy a new version with every new feature you build, as that takes a few minutes. But it’s a good idea to do so anytime you get a major new feature working, as you’ll be able to “roll back” to that point if you mess up anything in the future.
• It’s always helpful to bring in the relevant context to any interaction with the AI chat. Cursor makes this very easy by including an “add to chat” button both in the code window and in the terminal, which are the two places you’d want to draw on for context
• Pasting screenshots into the AI chat is remarkably helpful, as it allows the AI to see exactly what you’re referring to. Often, you don’t even need to say anything – the AI understands what’s working as soon as it sees how it’s appearing.

You can check out Cursor with a free trial at https://www.cursor.com. I signed up for the paid version for $20 per month to build my first app, though you’ll have access to a lot of functionality for free. I recommend their “getting started” documentation to learn about the basic features, which are more than enough to allow you to build your first simple app.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

In the early 1700s, Central Europe faced a crisis: the forests were running out.

An explosion in mining, shipbuilding, and early industry had devastated old-growth forests that had stood for many centuries. Meanwhile, the population was exploding as well, creating demands on forests that clearly couldn’t be sustained for long.

The kingdoms of Prussia and Saxony decided to apply the emerging methods of science to the problem, developing what would eventually become known as Scientific Forestry. In order to maximize timber production for the state, forestry officials turned their wild and messy woodlands into outdoor timber factories.

They began by meticulously cataloguing every tree in the forest by species and size. They analyzed growth rates and wood quality to identify the most productive species, settling on Norway spruce to yield the maximum volume of timber per square foot. They then cleared the existing forests and turned them into monocultures – endless rows of evenly spaced, identically sized spruce.

What had once been an impossibly complex tangle of diverse kinds of vegetation – oak, beech, fir, and countless others – became a “planned forest.” It was the biological equivalent of a spreadsheet, with straight rows of trees laid out in a precise geometric grid ready for bureaucratic regulation.

At first, it worked beautifully. Forestry officials could now predict with extreme accuracy the exact yield of every patch of forest. The new plantations produced more lumber, at a faster pace, to a more precise standard. Harvests came in on schedule and in uniform sizes ready for sawmills. Logging boomed and the revenue flowed into state coffers.

But something strange began to happen after the second or third generations of trees were planted. The first generation had flourished in the absence of competition for soil and nutrients, but in the following generations, those same ecosystems collapsed, with dramatic production losses of 20-30%.

In order to make the forest more productive, the underbrush had been cleared of smaller trees, bushes, and shrubs. That underbrush had fertilized the soil with decomposing leaves and wood; without this undergrowth, the soil soon became depleted. The disappearance of fungi, worms, and insects caused pollination and soil aeration to crash.

Pests like the pine looper moth and bark beetle raced through identical strands of trees, encountering no obstacles or predators. Storms damaged vast swathes of the forest, toppling over the shallowly rooted spruces like “bowling pins.”

It turned out in retrospect that the messy diversity of the forest had been the source of its resilience. When stresses such as storms, disease, drought, fragile soil, or severe cold struck, a diverse forest with its full array of different species of trees, birds, insects, and animals was far better able to survive and recover. A windstorm that toppled large, old trees would typically spare smaller ones. An insect attack that threatened oaks might leave lindens and hornbeams unaffected. The rigidity and uniformity of the system meant that failures were not small and contained but systemic. 

By the late 19th and early 20th century, forest plantations had become “a pale shadow of their previous ecological richness.” After all the effort and resources invested, the forests of Central Europe were now producing less timber than the wild forests they had replaced. All these changes culminated in what Germans grimly came to call Waldsterben, or “death of the forest.” 

The supposedly “scientific” management of forests led to ecological problems so severe that multiple generations of restoration ecology have been needed to restore the previous diversity in insects, flora, and fauna. Germany continues to struggle with the lasting effects of monoculture forestry to this day, most recently in 2018 due to the mounting effects of climate change.

This story is recounted in James C. Scott’s Seeing Like a State, and in his book, Scott notes that far from being a unique or isolated incident, scientific forestry was one incidence of a far broader movement, which he dubs Authoritarian High Modernism. 

Across many facets of the modern world, from urban planning to public health, from transportation infrastructure to online social networks, we’ve sought to “rationalize” and “optimize” the messiness and complexity of the world. From the way we organize our cities and homes to how we manage the economy, all the way down to the systems and routines we create for our personal productivity, we’ve tried to impose rational order on complex systems based on a narrow vision of efficiency.

In this piece, I’ll argue that the results of that effort have been disastrous, and it’s time to return those systems to their natural, messy state.

An optimal level of mess

I first read the story of scientific forestry in a blog post by Venkatesh Rao in 2014. It was a paradigm-shifting moment for me. I saw in myself much the same attitude as 18th century German forestry officials – an unquestioned belief in order, reason, and systematic thinking.

I had always believed that anything I wanted to achieve in life was to be found on the other side of “getting organized.” My assumption was that there was one “best” path to achieving any goal, which was to follow a highly specific, structured, step-by-step plan with objectives and metrics. It was the “one true way,” as universal and unquestioned as my childhood religious faith.

Yet, in my early 20s, I began to run up against the limits of my blind faith in order. I began to see more and more examples of how it failed – in my own life, the lives of my friends and peers, and even in the business world and in society. The pitfalls and weaknesses of highly ordered, rationalized systems started to become ever more glaring, especially in a world that seemed to be changing faster and becoming more ambiguous and uncertain.

What if, I began to wonder, the costs of being neat and organized outweighed the benefits? What if there were hidden advantages to being messy, informal, loose, and even chaotic?

Last year, I picked up a book called A Perfect Mess: The Hidden Benefits of Disorder, by Eric Abrahamson and David H. Freedman, that finally addressed my longstanding question. Their striking conclusion after studying dozens of disciplines was a strong affirmative yes: that “moderately disorganized people, institutions, and systems frequently turn out to be more efficient, more resilient, more creative, and in general more effective than highly organized ones.”

They argue instead for an attitude toward organization that takes into account its costs, by asking yourself: Will more effort spent organizing be worth what it costs me in time and other resources? They suggest that there is an “optimal level of mess” for any given person and every given situation…and that it is just as common for people to err on the side of overorganization as underorganization.

This assertion is akin to heresy in our productivity-obsessed world. And for me personally, as someone who’s dedicated my career to teaching people how to be more efficient and organized, it felt like the portal to a hidden, subversive world.

The surprising benefits of disorder

This may seem counterintuitive, but you can think of “mess” not as simply the absence of order – like a vacuum of nothingness – but as a phenomenon in its own right, with its own qualities.

You can even conceive of mess as a valuable resource you can draw on or a strategy you can proactively apply when needed.

To understand when and where we might want to employ messes, we need to identify its unique benefits. Abrahamson and Freedman suggest six of them: flexibility, completeness, resonance, invention, efficiency, and robustness.

Messes are flexible in that they can adapt and change more quickly, more dramatically, in a wider variety of situations, and with less effort than would be required by highly ordered, formal systems. 

For example, the messiness of a jazz ensemble enables improvisation, as any musician can shift at any moment to address any other, whereas a symphony orchestra has to play the music as written. Neat systems struggle to fight off randomness, and when randomness inevitably leaks in, the system is thrown off.

Messes are more complete (or comprehensive) since they can comfortably tolerate an exhaustive array of diverse entities. 

Neat systems tend to whittle away at the diversity of their elements (as we saw in 18th-century German forestry). As another example, Thomas Edison tried any and every material in his quest to invent a workable lightbulb with a long-lasting glow, without regard to elegant theories as to why they might work. His approach to experimentation was wide-ranging and messy.

Messes are resonant, as in they facilitate surprising connections between overlapping, heterogenous elements. 

Alexander Fleming happened upon the discovery that led to the invention of the first antibiotic, penicillin, because his lab was notoriously messy. A small, ragged circle of mold had invaded one of his petri dishes, but the staphylococci culture it contained seemed to steer clear of the mold, his first clue that the bacteria couldn’t tolerate it.

Messes facilitate invention by randomly juxtaposing many elements in unexpected, unconventional ways. 

Neatness tends to limit novelty and the unexpected and sweeps them aside as aberrations when they do occur. A sobering example: a major reason modern terrorists are so hard to fight and defeat is because they are constituted by loose, constantly shifting, non-hierarchical, i.e., messy groups.

Messes are efficient, able to accomplish goals with a modest consumption of resources. 

Consider the “productivity” of the wild forests before scientific management took root – they produced immense value for a wide variety of human and non-human species, despite the complete lack of an organizing scheme. Neatness tends to require a constant expenditure of resources just to maintain itself.

Messes are robust in that they tend to weave together and interlace many disparate elements, making them more resistant to destruction, failure, and imitation. 

For example, competitive runners benefit from “inconsistent” workouts that mix up the speed, length, difficulty, frequency, and inclination of their running routines, leading to muscles that are more adaptable. Mixed-breed mutts are often hardier than purebred dogs thanks to the random interweaving of genes from their unlike parents. Neat systems, in contrast, tend to be more brittle and more easily disrupted or copied.

Later in the book, Abrahamson and Freedman introduce a seventh benefit: messes can be fun!

Consider the joy of sorting through antiques and doodads at a flea market, browsing a stack of random magazines, or spelunking through a messy collection of notes and finding something you didn’t even know you were looking for. Messy situations inherently include many qualities we find enlivening and interesting: surprise, delight, exploration, and discovery.

Adding disorder to a system can make it more effective

It’s one thing to believe that messes have some intriguingly positive qualities in theory. It’s quite another to realize those benefits in real life.

Let’s get one level more concrete and look at practical ways we can use the benefits of disorder in our daily lives.

Specifically, let’s see how disorder can make for more creative environments, allow information systems to contain more information, make the human brain smarter, enhance one’s personal productivity, and allow us to make more consistent progress on our projects and goals.

Disorder makes for more creative environments

In his book, Where Good Ideas Come From, Steven Johnson highlights many surprising examples of how disorder has led to new ideas and inventions throughout history. In his research, he found that innovation is often driven by “the collisions that happen when different fields of expertise converge in some shared physical or intellectual space.”

Perhaps the most classic model for such a space is the eighteenth-century coffeehouse, which Johnson notes was the hotbed for Enlightenment-era innovations that transformed our world: everything from the science of electricity to the insurance industry to modern democracy itself. 

Sigmund Freud famously hosted an intellectual salon on Wednesday nights in Vienna, where physicians, philosophers, and scientists came together to discuss the emerging field of psychoanalysis. The legendary Homebrew Computer Club in 1970s Silicon Valley was made up of a ragtag group of amateur hobbyists, teenagers, entrepreneurs, and academics, who together somehow sparked the personal computer revolution.

Berkeley psychology professor Charlan Nemeth began investigating the relationship between noise, dissent, and creativity in group environments more than thirty years ago, and her research offers a clue as to why noisy cafes and amateur hobbyist clubs might have fostered so much creativity: she found that “good ideas are more likely to emerge in environments that contain a certain amount of noise and error,” ranging from mock juries to corporate boardrooms to academic seminars.

Maybe the best environment for our creativity is not sitting in a minimalist cafe, wearing noise-cancelling headphones, with an all-consuming focus on a tiny screen. Maybe there are times we’d be better served by immersing ourselves in randomness instead.

Disorder makes for more information-rich systems

Steven Johnson, in his book, introduces the field of Descriptive Complexity Theory, a branch of information science that has found that the more randomness in a system, the more information it can hold.

This may seem paradoxical, but imagine the case of two professors: one with a perfectly tidy, neat office with not a paperclip out of place, and one with a messy office full of personal items strewn all over the place. Which one provides you with more information about what kind of person the professor is? Clearly the messy one, since too much neatness and order tends to hide away the idiosyncratic details that distinguish one person from another.

Now imagine a digital notetaking app such as Notion, Obsidian, Tana, or Evernote. You might imagine that perfectly organizing your notes app – with neatly formatted text, seamless folders, comprehensive tags, and uniform headings – might allow you to fully maximize the potential of your knowledge.

But then again…maybe not. Maybe it is the very messiness that we tend to despise that makes our notes personal, intimate, and unique to us. A perfectly organized set of notes could belong to anyone, whereas a messier collection might contain all sorts of hidden clues about your unique desires and interests.

Disorder makes for smarter brains

In a 2007 study on the brain activity of children, neuroscientist Robert Thatcher and his team found that there was a correlation between the IQ of individual children and the amount of time their brains spent in “chaotic mode” (in contrast to “phase lock,” which is a more ordered and focused state of mind).

Every extra millisecond spent in chaos added as much as twenty IQ points, whereas time spent in phase lock was correlated with reduced IQ. Their conclusion is astonishing: the more disorganized your brain is, the smarter you are likely to be.

It turns out that the human brain relies on disorder for its basic functioning at multiple levels, from the processing of raw sensory data to the interplay of abstract ideas. Our brains evolved to navigate a messy world, and perhaps when we insist on organizing its activity, we rob it of that essential ability.

Consider how too much silence in a group dinner can be uncomfortable. Or that kids can knock out homework in a noisy home. Or that jiggling a telescope can help an observer’s eye pick up a faint celestial body. We are designed to thrive in chaos.

Disorder makes for higher productivity

Jane Jacobs, the famous urban planning theorist, noted a similar phenomenon at work in the design of cities. 

She noticed that planners had a tendency to substitute superficial visual order for true functionality. In other words, whether a neighborhood “looked right” became more important than whether it worked for its inhabitants. The assumption seemed to be that if an arrangement was visually pleasing, that automatically meant it would function well.

I see this tendency run amok in the personal productivity space as well: people tend to love visual order, manifesting as pleasing symmetry, clean lines, perfectly squared little boxes, and severe minimalism. Yet all too often, this order and elegance comes at the expense of functionality – Does the thing actually work? Does it work sustainably for the long term? Does it fit how your mind works? Does it provide more value than it requires in upkeep?

It’s far easier to make something superficially pretty than to answer such questions. It’s much easier to compulsively switch to a different app that promises to instantly sweep aside the digital disorder than to figure out what we’re truly trying to accomplish. It’s much easier to organize things than to decide which of those things actually matters.

No doubt some situations call for a more structured approach – think of checklists used by an operating surgeon or an airline pilot. But most of us don’t face such high-stakes situations in our daily lives and would benefit from less formal tools.

Disorder helps you make progress

We normally think of “organizing” a collection of physical, visual, or digital elements, but it also applies to how one structures one’s efforts, including goals and projects.

In Tim Hartford’s book Messy, he found in his research that the top scientists tend to switch topics frequently: “Over the course of their first hundred published papers, the long-lived high-impact researchers switched topics an average of forty-three times.” 

We are normally taught that in order to achieve something great, we have to focus maniacally on a single pursuit. Yet by cultivating a variety of projects at different stages of fruition, leading scientists clearly gain four benefits:

1. Multiple projects cross-fertilize, with the knowledge gained in one sometimes unlocking key insights in another.
2. Diverse pursuits provide variety that captures our attention, whereas a single-minded pursuit can become monotonous and boring.
3. Each project provides an “escape” from the others, giving you something to turn to when you face an impasse, instead of it becoming a crushing experience.
4. Turning our attention away from a project gives us a chance to process it subconsciously, which some scientists believe is an important key to solving creative problems.

This last benefit was designated by the philosopher Søren Kierkegaard as “crop rotation.” One cannot use the same field to grow the same crop indefinitely. Eventually the soil must be refreshed by planting something new or simply giving it a break.

This agricultural metaphor brings us back full circle to James C. Scott’s ideas in Seeing Like a State, where he makes an intriguing observation: “The rule seems to be that the more rigid and exclusive is the specialist’s boundary, and the stricter the control within it, the more disorder rages around it.”

In other words, you can’t really ever eliminate disorder; you can only move it around. So perhaps the greatest cost of creating a highly organized environment is that everything just outside its borders – which includes the rest of your life, your body, your family, other people, the natural environment, and human society generally– becomes flooded with externalities for the sake of that perfect system.

Practical takeaways for your productivity

So what does all this mean for our personal approach to order and organization?

Here are some actionable takeaways I can offer based on the findings and examples above:

1. Don’t feel guilty about putting off organizing

The authors of A Perfect Mess note that there’s an advantage in putting off organizing: it’s more efficient to organize a larger batch of items all at once than to do it a little at a time. 

This is known as “batch processing,” and I tend to save it for my weekly, monthly, and annual reviews, when paradoxically, the more stuff that has piled up, the better!

Don’t feel guilty about postponing your organizing to a later date, or only doing it occasionally, because in the meantime, you’re benefitting from all the advantages of mess I highlighted above.

2. Notice and embrace the odd, eccentric ways you tend to organize

Many people say they don’t have time to get organized, but in reality, they are constantly engaging in a wide variety of ingenious organizing strategies. Our propensity to seek shortcuts, find the path of least resistance, and expend as little time and energy as possible to achieve an outcome are some of the most reliable ways to find little tips and tricks that may seem eccentric or odd but work for us.

Abrahamson and Freedman present multiple examples of how most people, since they aren’t aware of the ways they naturally stay organized, tend to misjudge how a technology system might help them. They assume that the laid back, informal methods they already use are suboptimal and that they need a piece of software that only adds a lot of burdensome formality.

3. Satisfice instead of maximize

One of the subtle implications of the ideas in this piece is that we don’t ever truly have control. If we try to fully organize our surroundings, we fall into the traps and pitfalls noted above. If we instead accept the messiness, then we don’t have full control over it either.

What’s left then is to accept the reality: that we are all careening through a chaotic void, with at most brief moments of stability and fleeting periods of agency. Instead of trying to order and control our lives, we can use this inherent randomness as an excuse to satisfice, which has long been recognized as an essential ingredient for happiness.

As Nicholas Nassim Taleb puts it, “Having some randomness in your life can actually increase happiness: it forces you to satisfice, instead of maximize. Research shows that those who live under self-imposed pressure to be optimal in their enjoyment of things suffer a measure of distress.”

Living in the balance

It’s all a balance, all masculine and feminine, yin and yang. When the benefits of order start running out, it’s time to switch to disorder. And vice versa – when disorder starts careening out of control, try adding a little structure to the problem. 

There are no “right” ways that work universally in all situations; only tools that work better or worse depending on the job.

It’s not that order, reason, and efficiency are bad – it’s that they are sometimes extolled as inherent virtues when, in fact, their opposites can be just as valuable and useful.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.

I spent 2 years serving as a Peace Corps volunteer in Eastern Ukraine from 2009 to 2011. I lived in the town of Kupyansk, a couple hours outside Kharkiv, near the Russian border. It was one of the greatest experiences of my life, teaching me so much about myself and life and the people and culture of Ukraine.

Kupyansk is now on the frontlines of the Russian invasion. The streets I walked every day have been decimated, the bridge into town destroyed, and my old students scattered across Ukraine and abroad, or sucked into the vortex of fighting.

When I landed in Kyiv in September of 2009 to begin my service, the country was at peace. It was a fledgling democracy, having gained its independence in 1991 after the collapse of the Soviet Union. At 18 years old, the country was young, which meant naive and unsure of itself, but also deeply hopeful and optimistic about its future.

The word “Ukraine” means “borderlands,” and the land has indeed always been at the crossroads of many frontiers: between East and West, between Russia and Europe, between the Slavic world and the Latin and Germanic worlds, between Orthodox Christianity and Western Christendom. The sweeping, flat, fertile plains that make it an agricultural breadbasket have always beckoned to conquering armies from every direction to try their luck.

This identity of being in-between, of being at the periphery, gives Ukrainians many of their gifts, from their warmhearted hospitality and multicultural mindset, to their peacefulness and spirit of international cooperation. It makes them humble, grateful, creative, and bold. 

It’s also led to tremendous suffering. The Holodomor, the Soviet Union’s equivalent to the Holocaust, killed between 3.5 and 5 million people in a directed genocide and forced collectivization from 1932-33. The Crimean Tatars, a Muslim people who populated the Black Sea shore for many centuries, were forcibly removed from their homes by Stalin in 1944, loaded aboard sealed-off cattle trains, and transferred almost 3,200 kilometres to the barren, remote reaches of Uzbekistan. It’s hard to imagine such tragedies happening anywhere else but the edges of a “great” empire.

I had wanted to serve in the Peace Corps since I was a teenager when a friend of my parents had told me the stories of his service in the 70s. It sounded like the perfect scenario to me: lots of time in an exotic foreign location, immersed in a new culture, learning a new language, and serving people in need. This combined most of my main interests at the time, and I leapt at the opportunity.

When I arrived, I was so determined to put all my energy into serving and teaching that I decided I wasn’t going to write about my experience while I was there, which I now consider a grave mistake. I had been blogging about my travels in South America for about a year at that point, but still saw writing as an optional indulgence, not an essential way to document and understand my life, as I do today.

I did, however, make a video out of all the short clips I took on my iPhone 3G during my time there. It was my attempt to capture the spirit of my experience there – to commemorate the memories of the most exhilarating, and also most challenging, two years of my life.

14 years later, that video is also a record of what life in Eastern Ukraine was like before the wars. It feels like a snapshot of the final days of a beautiful experiment in Ukrainian independence, now undermined by the Russian invasions of 2014 and 2022.

I’ve decided to share it publicly as a small testament to what was lost. As one more piece of evidence that Ukraine once thrived, that Ukrainians know what kind of country they want to build, and could build it again if given the chance by the wider world.

In the US, we have a president and administration who have essentially switched sides, from this innocent nation struggling to defend its freedom and its rights, to Putin’s Russia, an aggressor toward so many countries on its borders and beyond. It’s the most evil act I’ve ever seen from my country, a betrayal of everything we claim to stand for, and I’m ashamed to have anything to do with it.

My hope is one day Ukraine will have independence, peace, and stability again. It deserves it, its people deserve it, and the world will benefit from it being secure, autonomous, and self-determined, not a vassal state under the thumb of Moscow like it’s been for so much of history.

If you want to help me donate directly to Ukrainian relief organizations, my book is now available in Ukrainian (Запасний мозок) and Russian (Создай свой «второй мозг»!). Here are direct links you can use to purchase it in various formats:

• In Ukrainian in Ukraine: on Rozetka and Yakaboo
• In Russian in Ukraine: on Zakupka
• In Russian in Russia: on Ozon and Yandex
• As an ebook in Russian everywhere: on Litres

I’m donating 100% of my royalties from both languages to non-profits and relief organizations in Ukraine forever, totaling $10,000 USD so far. And of course, I encourage you to donate directly if you’re able. Now that they’ve been abandoned by their main champion, the U.S., they need it more than ever.

In many ways, the origins of my work with Second Brains, digital organization, and productivity can be traced back to my time in Ukraine. It was the first time I taught “life skills” such as how to define goals, make project plans, gather resources, and execute on a timeline. There is a direct link between the community service program I created during my service, known as Projects Bring Change, to the central role of projects in all my teaching.

I hope this is one small way I can return the blessings that Ukraine and her people gave to me, and perhaps teach another generation of Ukrainians what it means to succeed with their goals in this uncertain and volatile time.

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