Header image for Offscreen Magazine Interview
Photo by Martin Holtkamp

Offscreen Magazine Interview

Notes on writing, publishing, startups, life, and disconnection

Originally published by: Offscreen Magazine

In late 2017 I was interviewed by Kai Brach for Offscreen Magazine. Many thanks to him and Martin Holtkamp, who photographed me with good humor, for many hours, on a fine day in late fall in Japan for this very interview.

I’ve significantly expanded / edited these answers from the published originals.

For those randomly landing here, here’s how Offscreen introduced me (and my general about page):

Craig is a digital savant in love with the analogue. In code, design, and photography, but mostly through his writing, he explores our collective struggle to find focus in a world of perpetual distraction. He lives a quiet life in a seaside town south of Tokyo – sometimes escaping to remote writing retreats around the US – where he revels in his various creative outlets while hidden from the public eye. When he’s ready, he emerges from hibernation with thought-provoking, introspective essays, books, and talks that examine the meaning of a connected life.

[Offscreen] Let’s just get this question out of the way: How would you describe the current state of the book as a medium? If print is not dead, and ebooks are not what they promise to be, where are we headed from here?

What’s clear is that Amazon won (in the US). There is a line of arguing that goes: Amazon’s de-facto monopoly on the medium has cut short the evolution of ebooks. I don’t know if that’s entirely true, but I do know Amazon is the worst kind of company to compete against because they don’t mind burning money to grab market share. And they are able to funnel cash from, for example, their profitable AWS services into unprofitable arms, indefinitely. Good luck raising money if you’re a startup and your main competitor is Amazon. It creates a very desolate landscape.

Seven years ago, the ebook space was invigorated with young energy. Remember Nook, Kobo, or even iBooks on the then newly launched iPad? Flipboard emerged from that era, too. But now that the Kindle owns the majority of the market, these other platforms1 folded or got swallowed by Amazon. And the Kindle turns out to be a good enough solution for enough people — it sells well enough as is — which has, I believe, disincentivized its evolution. It hasn’t changed much since it launched.2 So here we are.

Kindle and non-Kindle book sales account for less than two percent of Amazon’s market cap.3 The Kindle could disappear tomorrow, and Amazon would not be materially affected. Even from a branding perspective, I don’t think Amazon = Books anymore, certainly not to younger consumers. Amazon = Prime. Prime = a 3D printer on a one-day time-delay that deposits anything you can imagine on your doorstep. Operating as a company with the best interests of shareholders in mind, it’s clear that putting money into innovating ebooks won’t carry much of a return.

Publishing is tricky. What’s the old aphorism? How do you make small fortune in publishing? Start with a large fortune. Financial returns can’t be the only metric driving a lot of publishing houses. I mean this on a philosophical level, and obviously it isn’t true across the board or between all divisions or publishers. But inside certain publishers — the best publishers — there is a sense of a respect for the medium and a recognition of its cultural importance. Maybe I’m being overly generous, but this has been the case in conversations and relationships I’ve been privy to.

I mean, you’re (Offscreen) probably not making a ton of money publishing an indie magazine, right? So why do you do it? Because you feel it in your bones. This must exist. Sadly I don’t get the impression that the publishing arms of Amazon or Apple operate under this ethos. To call iBooks a throwaway “feature” of iOS is too dismissive, but the output does not give off the impression of a thing that must exist in the world, and must exist at the highest level of grace.

But there’s a silver lining: The publishing industry is now able to relax (a bit). Seven years ago, there were a lot of question marks. Is print going to survive? Which platform should we build for? Oh my god, do we need an apps division? Now, it’s okay. There’s Kindle. That’s it. We can mostly ignore everything else. The market has spoken. Nobody wants apps. Or book trailers. And guess what? Print sales are going up again and indie bookstores are seeing a resurgence. Turns out things aren’t much different than they were ten years ago, just that — for better or for worse — we now have Amazon as the uber-ubiquitous distribution vector for print and digital.4

[Offscreen] What do you think drives a reader’s decision to go for either the printed or the digital edition?

I’m not sure if readers spend a lot of time consciously thinking about that choice. Personally, I think Kindle Samples are divine. I don’t buy a book unless I can read the sample. That’s my threshold. If I can’t get through the sample, I won’t buy the book. If I really like it, then I buy the physical book.

I think the return of print is in line with the other fetishizations of offline activities and objects – vinyl records, Moleskins, expensive pens, et cetera. Anything that gets you away from a screen has gone up in perceived value. All of these objects promise a context switch to a quieter mode.

But I think books are the perfect disconnected objects. They require no energy. They offer a fully immersive, quiet experience for hours or days. The medium dissolves but never becomes translucent. It’s quiet, but present. An exceptional technology.

[Offscreen] When it comes to making time for reading and writing, do you have a set of self-imposed rules you try to adhere to?

When you sit down with a book, you understand the parameters of engagement. You know how long the book is. The book isn’t changing as you read it. It’s a solid, immutable thing. You and the book are on equal terms in many ways, as least from a physics point of view. You know what’s going to happen, and the book abides by its implicit contract, which is to be a book.

However, in digital-land many spaces (apps, games) quickly turn into slithering creatures beneath your feet. You never know where you stand. Their worlds are optimized to pull you back in for one more minute, one more click. Over and over. Cascades of chemical reactions in your noggin’ tell you to keep going, just one more hit; I feel this persona of the addict very strongly when I am online or using certain apps or devices.5

That’s why I try to subvert my weaknesses, to subvert that persona. The easiest way is to turn off the internet. When I go to bed at night, the internet goes off. Phone into airplane mode. It doesn’t come back on until after lunch the next day (at the earliest). The difference in the quality of the day ahead between starting my morning with the internet on versus off is enormous.

If I wake up and touch my phone, I’ve already lost hours. Not because I’m browsing social media for hours, but because the mind has already been agitated, made unquiet, and the context switch back into thoughtfulness can take the whole morning. In other words, the addict part of my brain takes over and contaminates my ability to be contemplative. I lose the grace to dive into other worlds, the worlds of writing or programming or images.

And so much of my life is structured around rescuing that lost grace, making space for thinking. Much of what I do boils down to that. Because I’m really wimpy. Like so many of us. I’m weak when it comes to resisting the bounty of online goodness.

[Offscreen] How has the omnipresence of the internet changed the rules of becoming a writer?

The barriers to entry are lower. It’s more democratic. If you put in the legwork, you can find an audience, be a writer. A similar shift has happened in photography. Whereas thirty years ago you had to spend tens of thousands of dollars on equipment, today you can make a name for yourself as a photographer with just your mobile phone.

The flip side of democratization is that making money as a writer can be more difficult. In part because many people are willing to do it for next to nothing. In part it’s because the Ad Bucks from the old generation of publishing are gone. So much “writing” online today is incentivized and measured by clicks and volume rather than quality or nuance. Volume can be a good forcing function to produce work, but rarely leads us to a state of nuanced thought.

I’ve been reading about John McPhee’s process of writing his giant New Yorker essays thirty or forty years ago, and wow, it sounds like an alien world. The process is so slow and deliberate. At the end, he would hand in an eighty-thousand-word piece. That’s a book! Whatever structure allowed McPhee to write this way back then, it barely exists today. Unless you cobble it together yourself, or hunt it down through non-profit institutions.

[Offscreen] Was there a turning point when you realised that writing was your thing?

In 2009 I hiked up to Annapurna base camp in Nepal. Along the way I met so many kind, generous Nepalese folk. But most impactful was the bonding experience with my guide. He became like a younger brother to me. We were in tears as we parted. As we came down the mountain back to Kathmandu, ending our little adventure, I was overwhelmed. All this beauty — the mountains, the people — and yet I felt this immovable, solid lump of darkness in my chest. I was struggling to process a lot of different events in my life then, and had screwed up in a number of big ways. And so my response to all that beauty, my dumb, lazy, sad-with-a-dollop-of-self-hate response was to drink myself into a blackout in a Kathmandu hotel. It was the best response I had. I woke up the next morning with a big gash on my forehead and a distinct feeling of fluid trickling behind my ear.

My flight back to Tokyo was that afternoon. I went straight to the ER to get an MRI. Thankfully everything was alright but I knew those demons needed to be addressed. This weird, tumultuous internal strife or angst or whatever it was was holding me back. I was certain of this, although I was not certain how to fix it. How is it that a man can stand before so much beauty and want to die? How do you deal with a feeling like that? My response was to excavate the heart. Dig, look closely. That’s all I could do. I felt very constrained. I didn’t have any archetypes or mentors that I could look towards. Excavate and write. Excavate and run. I started running marathons then.

I didn’t write about that full experience head-on, though. The world still felt too brittle for that. I wrote about the mountains. I wrote in the guise of a camera review. Along the hike I had been using the new Panasonic GF1 camera. This camera and the photos I shot became a big online essay. It took me months to write and edit and design that piece, but when I finally published it on my site it took off in a way like nothing else I had worked on.

Through affiliate links in that single post I sold enough of those little cameras to pay for two or three years of living.6 But more importantly, psychologically, for me it was a major turning point. I remember crying from the response. It was so positive and additive. The feeling of transmuting however small a portion of that garbage in my heart into something that was not self-destructive but instead instructive and inspiring to others. That was a hell of a moment. I thought: Something is happening here that hasn’t happened before. Keep digging.

A few months later I published Annapurna Moonrise. And then after that, I published another essay called Books in the Age of the iPad just before I got on a plane to New York. By the time I landed, it had been picked up by the New York Times and I had two non-fiction book offers in my inbox.

[Offscreen] Wow, what a flying start to a new career!

I wouldn’t wish my journey to that point on anyone. It was a pretty shitty (a self-imposed kind of shitty, an of-the-own-mind kind of shitty) journey, and in hindsight, there were definitely easier roads which I chose not to take for whatever reasons. It was not an overnight success story. It took me seven years of book making to be able to think about writing that post about books. And even then, six-months of actual writing and editing and rewriting to complete it. The response I got turned out to be an important external validator. Of course, I had to almost kill myself to finally start working on it.

There’s a mean fallacy in the world: that all you need to produce big, meaty pieces of work is internal gumption. “Pull yourself up by the bootstraps!” they say. “The onus is on you to make your life better!” et cetera. You see this bandied about by political nudniks when talking about down-and-out folks, folks in low-income situations, folks who’ve turned to drugs. It’s one of the meanest and laziest ways to frame the world. Sometimes you feel so small, and the room you’re in so suffocating that you want to drink yourself into the ground. Sometimes that spot in the dirt is the softest, coolest place you might have in your life.

Locking yourself into a room for weeks or months to get your thoughts out is tough. It’s lonely. It’s dark. That’s why even a smidgen of external validation can be powerful – not as the sole purpose of working hard but as a nudge that says, “You’re not crazy. You’re on the right track.” This applies to everything in life, not just “art.” Past successes become future archetypes of hope. When you are inevitably stuck in a rough patch and start doubting yourself, you can look back at some of those achievements and go: “OK, at one point, I knew what I was doing, so let’s keep going. Let’s have faith in this thing I’m working on now and hope this one works out too.” Love, books, children, paying your bills, whatever.

[Offscreen] Some time after writing those essays you took on a design role at Flipboard, but you eventually went back to being independent so that you could focus on writing. Was working for a tech company not what you expected?

It was everything I expected. Working with Marcos Weskamp and the team at Flipboard is one of the highlights of my life. They were outstanding humans and outstanding designers and engineers. I’ve never been in a room with more talent. And all of us were moving in synchronicity, with aligned goals, during the headiest time of digital publishing, the iPad fresh, infinite possibility with a nearly infinite budget — nothing was constrained except for our imaginations. Truly. A once in a millennium moment in an ancient industry. And we spent some acid-trip like adventures exploring bizarro interface tendrils that never made it out into the world. I learned a lot. I learned how vital a strong mythology was for leading a company, for raising a huge sum of money. You need product, you need market-fit, but you also need a helluva story. It was all a high. And I have gratitude for everyone on the team.

We launched Flipboard for iPhone and instantly — boom! — had millions of new users. But I didn’t feel my heart move. Not an inch. It was just an observation, a truth. You have to acknowledge these truths. It came with no judgment. My heart didn’t move. I loved the people and the work, but the object, the artifact, did not move my heart. By that point in my career I had worked on enough projects that had moved me to understand what was happening. I had archetypes to lean on.

Simultaneously, as we made the app I made a meta-book about our making of the app — the design detritus, the engineering commits — and presented that to the team. Jesus, my heart moved a mile. It was difficult not to cry. I realized in that moment that scale is secondary to grace or movement.

Does affecting one hundred lives turn you on? A thousand? A million? A billion? Why? What does it mean to have a positive impact on a life? How intimate does that connection need to be? Understanding your scale — the scale that moves you — is critical to understanding with whom and how you should work, how you should live.

I spend a lot of time making time, and then protecting that time. And through it all I fill my days with work based around return on investment. I don’t mean that coldly or even financially. I mean that in the context of — and I recognize this sounds a little crazy — respect for life itself. We are alive. We have consciousness. We are capable of a great understanding and empathy via creative and intellectual output.

So I ask myself regularly: Am I maximizing this so-called respect for my being alive or not?7 Does my work pay dividends in making me more empathetic, more curious, kinder, smarter? And the best way I’ve found to say ‘yes’ to this somewhat ridiculous question is to ask if the work, my day to day, moves my heart. And I’ve found the most reliable way to get there is by putting what’s in my head into words. Codifying an experience in a way to multiply the impact of that experience.

Example: My Kickstartup essay. The Art Space Tokyo Kickstarter project was a good experience, but the real return on investment of time-in to impact-out came in taking all of the campaign knowledge and packaging it and giving it to the world. For a couple of years I got a book a week from folks who read that essay and kickstarted their project. That’s a tremendously encouraging signal!

In the end I’ve found that understanding how you define respect for life itself is a really good organizing function for thinking about how to live, how to spend your days.

[Offscreen] And even the absurd amounts of money offered to a talented person like yourself didn’t make you think twice about leaving?

I walked away from a lot of money. I spent my 20s living on about $20,000 a year. So to suddenly get a Silicon Valley salary plus options was like walking into Willy Wonka’s minting factory of gold coins. It didn’t make any sense. Nothing was real. A man in a full-body sleeping bag suit — his tiny face engulfed by that puffy thing — came up to greet me from a ping pong battle in the basement of a nearby Palo Alto startup. He had raised $41 million. It was unclear what his app did. (The company soon folded.) I felt this was not good for my soul. It was just an intuition. But I felt whatever edge I had built up in my 20s around work and life-philosophy was being whittled down by the environment. Obviously that’s a very privileged thing to be able to say. But that’s what it felt like.

So I moved back to Japan. A cynic would say I was hiding from the “real” world. Maybe. But that presupposes monetary valuations as a proxy for realness. There is no nexus of disproportionate wealth in Japan like there is in San Francisco. In Japan it’s easy to rub shoulders with people doing incredible work that may not pay a lot, but is additive, adds a significant cultural positive to their town, city, or country, draws from a historical context, is tempered by a position of humility. Here, the cost of living isn’t very high. I don’t need a giant paycheck every month to cover my base expenses. I don’t spend four thousand dollars a month to rent a tiny apartment in an apocalyptic neighborhood.

This is not about being austere for the sake of austerity, but it circles back to the question: Am I’m giving time and focus to activities that I feel help cultivate a deeper respect for the short time we may have? Making sure my fixed cost of living is as low as possible immolates the issue of doing certain jobs just to pay for a particular lifestyle. Living in a country with good health care means that you don’t have to worry about bearing the expense of treatment if tragedy strikes. These details add up. They collude to create space for thinking about and exploring the world, a space which feels non-negotiable in the quest to be present and reflective.

[Offscreen] You regularly disappear to ‘writing retreats’ and you spend weeks or months in a remote location working on a book or essay without much contact to the outside world. It sounds like a pretty radical way of removing distraction.

To explain what these retreats are: They’re writing fellowships funded by endowments to private, non-profit institutions. You submit complicated, onerous applications and gather letters of recommendation and then hope that a panel of judges selects you. If you get in, often everything is paid for.8 They give you lodging and a studio to work in. It’s mainly for writers, but there are also photographers, painters, composers, et cetera.

There’s often little internet access. They involve living with a piece of text or story and being gifted the time and space to explore a depth of work very difficult to access in everyday life. These retreats are powerful because they surround you with deep-time people doing deep-time things in refreshingly non-commercial contexts. You don’t ask, “What are you working on?” You ask, “How many years are you on?” Your fellow Fellows have been working on books for years, decades. Suddenly your five year project isn’t quite as crushing as it was a few days prior.

There are no analytic KPIs. You can take a lot energy from that. These retreats give you a support network. They make you feel less mad, less foolish and they remind you that there is value to the work you are doing, that success can be measured in different ways. In some ways they point back to that McPhee mode of writing — slowly and deliberately on a time scale aligned with the human mind.

These retreats become powerful tools in the fight for creating and maintaining a space for thinking.

[Offscreen] In one of your essays you describe going offline for such a long period as a privilege. Does that mean that in the future going offline will be a luxury that only rich people can afford?

The default expectation today is “always available.” The systems we created are so frictionless that we haven’t noticed how insidiously over-engaged we are. Step by step we’re optimizing ourselves to “maximum” productivity without defining or thinking about “productivity” on a human scale. The digital world abstracts. One could argue most problems contemporary society faces are problems of over-abstraction. As an employer with a global workforce, you have no idea where your employees might be or what they might be doing, so you expect them to answer immediately. The concept of downtime is elusive.

So yes, it’s already a great privilege to be able to say ‘no’ to that system.

[Offscreen] Do you see a possible future where this trend is reversed?

Not anytime soon. Not without intervention from the government. (See: France regarding Amazon, overtime, email after hours, etc.) These flaws are connected, in part, to the structure of public markets. Time scales are too short relative to the impact of the technologies being created, too focused on numbers: growth of users, growth of engagement, growth of revenue. Human pain is too abstract to be represented in spreadsheets. There are no implicit ethics baked into the markets, few incentives for companies to think about non bottom-line metrics.

So you need to be proactive in protecting yourself. Unplug your router once a week. Go offline for the weekend. Remember what that feels like. I know this may sound hyperbolic, but it’s difficult to understand how powerful it is until you have done it a few times. You have to bridge the intellectual and experiential gap. Intellectually, you may intuit getting a different quality of work done by going offline.9 But to experience and understand the benefits you have to be disciplined enough to repeat an act a dozen times. Then you begin to recognize the nuanced changes in the way you think, your insights into problems, and the shift in quality of the solutions you come up with. Whether it’s writing, programming, or design, a quiet mind is a fertile space for thinking. I find network disconnection greatly aids in creating that kind of mind.

I wish more people were afforded the opportunity to experience this. But it boils down to the power of archetypes: Much in the same way diabetes can be normalized within a tribe, so too can infinite connectivity.

[Offscreen] You seem like a person that’s very excitable about new technologies, but you’re also deeply curious about traditional craftsmanship and an obsessively detailed, slow creative process. Are those contradicting interests?

I am a skeptical optimist! You simply cannot ignore technology whole-hog if you wish to have a conversation about our purpose on this planet.

There are laws that govern, or can explain, the accelerated rate of technological advancement. But within those accelerated spaces you don’t have to ‘move fast and break things.’ That’s not an immutable law of technology. You can move slowly and with great consideration from a point of strong ethics and equanimity. It’s important not to conflate “move fast and break things” and technology itself.

That said — and this will sound contradictory — in terms of creating a culture of investigating ideas and the impact of technology, I think Silicon Valley is a rigorously optimized system, and on a whole has been a net positive for intellectual exploration.10

There are obvious issues with venture capitalism. In the blind rush for multiplying itself, it can breed overly abstract, overly complex, weaponizable platforms, like we’ve seen in recent years. But it’s intellectually lazy to point at a 150-million-dollar smart juicer and lump an entire industry under the same umbrella.

Although, we do need to revisit ethics in the Valley. Technology operates on too grand a scale now to be without strong philosophical underpinnings, to be simply market driven. Obama summed it up well: social platforms have to be recognized not only in capitalistic contexts, but as “public good” entities since they affect so much of life.

In my opinion, the most exciting technologies are quiet. They’re in the background. We forget about them. They don’t pull on your attention, and they’re not necessarily consumer-facing.

I think often and fondly of Bret Victor’s lab in Oakland. He’s been exploring – with admirable determination – new modes of physical computing. And he’s doing so by using really boring technologies: a constellation of networked cameras and projectors smartly deployed. That’s interesting. Bret and his crew made a magic bookshelf. They are concerned with the real world. They are concerned with accessibility and connection. I think many of the philosophies of quietude and disconnection and silence not only can be applied to technology, but should be. Must be. Technology and quietude are powerful partners.

And yet! I believe quick iteration is a powerful tool outside of the shark tank of incurious consumer tech. Quick iteration — obliterating unknowns — is an effective way of working through ideas. One of the biggest threats to any creative project is allowing the potential for the thing to subvert your ability to make it. It’s easy to be seduced by the world of potentiality. A book is always greatest before it’s written. You are intoxicated by what it can be. That’s very dangerous. You want to kill those seductions as quickly as possible, and one way to achieve that is fast iteration.[^iteration] Make known the unknown; murder your fantasies.

Finding balance can be tough, but not impossible. Create quiet spaces, understand motives, but iterate quickly on a local level to understand every nook of your problem space.

[Offscreen] So the release of the latest iPhone model doesn’t get you excited?

I recently saw the remains of a human who self-mummified. That was a strange and moving and dark but oddly hopeful thing to see. That was exciting. I like complicated excitement. The iPhone is a very complicated thing to get excited about. The fundamental qualities of the object as a tool feel like they hit a plateau in the third or fourth generation. And it’s such an easy thing to be cynical about. But, damn, the iPhone touches so many lives. Small incremental changes can have an outsize impact. You have to pay attention. You must acknowledge the iPhone. It can’t be ignored.

What’s noteworthy is not any specific new feature, necessarily, but rather the trickle down effect of the device’s economies of scale. How does the commodification of components within the iPhone affect academic research? What does it enable in developing countries where those third or fourth generations are now affordable? We can lean on the greed of the market to gain insights into the world and (potentially) improve the lives of the other 99%. It’s one of the few ways to justify the horrors of many contemporary economies of scale.

[Offscreen] Going back to your writing, one concept that pops up regularly is the idea of things – whether real or intangible – having clear ‘edges’. Can you explain what you mean by that?

You could even describe my obsession with going offline as an attempt to give my life edges. Having a bounded mental space over which I have control. (Or a stronger illusion of control.)

Books are the lowest-hanging example when discussing “edges.” With a physical book, you can touch the object; you literally feel the edges. There are certain affordances to the object itself because of those edges, physical and psychological; you know what you’re getting into. Digital books and magazines tend to be more nebulous. In the early years of the medium, navigation happened across two axes. So you were doubly lost. Now most navigation happens across a single axis but that doesn’t mean the affordances are any better, or the ability for someone to “touch” a digital book and have an understanding of its parameters is any better. If you want to jump to page eighty and you are on page thirty, good luck ever getting back to page thirty.

Edges ground us. Without clear edges we don’t feel like we’re in control.

[Offscreen] As more and more virtual experiences enter our lives, do you think this need for edges will increase? Is the current craze about vinyls, printed books, and artisanal crafts more generally a reaction to the lack of edges in the digital space?

Absolutely. Whether we acknowledge it consciously or not, we’re returning to quietude, to focus, to having something we can put our hands around and understand in totality. A sensible contract between us and object.

It’s unlikely we will ever understand a system like Twitter — a jumble of intellectual horrors and excitements. If you live in that world – which a lot of us do, for many hours of the day – you suddenly want to spend a lot of money on a beautiful axe and go outside to chop down a tree. I don’t think that’s a coincidence. In chopping, you understand the parameters of what you’re doing. Or if you want to make bread — guess what? You can definitely learn everything there is to know about making a simple loaf of bread. You understand what you opted into in a way that so much of the online world doesn’t allow.

It even applies to building websites. Many of us feel a sense of responsibility to continue a web project forever. I think more web stuff should end. Finito. Put an end date on it. I was reading an article by someone in the publishing industry on a popular blog that existed from around 2005 to 2012. One day she put a post up saying, ‘So this is the last one! I’ll keep the archive up but comments are closed. Enjoy!’ That’s beautiful. I love that. It’s important to recognize that a finish line is not an indication of failure.

[Offscreen] While you’re based in Japan, you still spend quite a bit of time in the US. What is one thing you enjoy most about each country that you miss when you are not there?

In my life, America is three locations: New York City, the Bay Area, and Asheville in North Carolina. For all the easy-to-list flaws of today’s America, it is — overall — a hopeful country. You have to believe this. It’s a sad country (if only because the potential is so great, the shooting of itself in the foot so blatant), yes, but hopeful. And I appreciate the general ambition and risk-taking attitude of Americans.

I go to New York for the people. I love the people of New York. I have conversations in New York I couldn’t have anywhere else in the world. A full spectrum. Life-affirming in their non sequiturs: the standing in line conversations. The coffee conversations. The whiskey conversations. It’s a wonderful mess of a city; international, holistic, inspiring.

When I’m in the Bay Area — talking to researchers and long-term focused investors — I feel suffused by a sense of aspiration that’s hard to find anywhere else.

Asheville is just a gem. Small, knowable, with clear edges, great food, exceptional food, very good beer, kind people, interesting history, design history, historical architecture, all surrounded by mountains and rivers and valleys and hikes for days.

Compared to the Bay — because of the way companies are structured — there is less so-called “disruptive” thinking in Japan, and as result there can be less risk-taking embedded into its startup culture. It’s slowly changing. But comparatively, it’s a risk-averse startup culture.11

Japanese culture respects craftsmanship. There is a “living national treasure” award decreed by the imperial family, given to craftspeople. The specific language is that it is for “important intangible cultural properties.” What a great thing to recognize — intangible cultural properties.

Jiro (from Jiro Dreams of Sushi) became a national treasure before he got his stars. Part of this respect and acknowledgment of craftspeople is connected with hierarchy. And fundamentally, if you have strict hierarchy, you have a more difficult time “disrupting.”

Before you become a shokunin — craftsperson — you’re a deshi, an apprentice. Let’s say you want to make pickles. You can’t just start making pickles. You first have to go through your multiple years of pickle training before you can make your own.

This is a good thing in an “Am I maximizing respect for life?” kind of way. If a core component of “respecting life” is increasing one’s understanding of the world, disavowing the self-lie of understanding is a great step one: I am, therefore I know nothing.. This system forces you to learn from someone with deeper knowledge. But most importantly you are forced to admit your ignorance. Eventually you can push on the edges of your craft, be disruptive, but first you must understand the origins of what you’re trying to disrupt. You feel this philosophy — this sense of humility — often in Japan.

There is also a pervasive feeling of collective empathy in Japan. That empathy manifests in the national health care system and investments in infrastructure. Everyday I feel my tax dollars touch my life. Whenever I ride my bike I feel the smoothness of well-maintained roads. Take even, for instance, the state-run fitness centers: Each time I go to the gym, I pay only two dollars. That’s it. No membership fees. No antagonistic contracts. These gyms are everywhere. Two bucks and I’m able to make myself healthier. Me and a bunch of old folks working out to Eye of the Tiger. I know I’m paying for part of it in the background through taxes. But anyone in the neighborhood – whether they pay a lot of taxes or a little – have access to these affordable oases. A gym with machines sometimes curiously made of wood from a bygone era of exercise. But loved. Respected. Always well-maintained. I think that’s not only cool, but damn graceful. It’s a place that can move the heart.


  1. Readmill, I gaze in your direction with a tear in my eye.
  2. Of course it’s gone through a slight physical evolution — from that amazing 1960s space-age thing, to a slim keyboard travel computer, to a small slab, to an even smaller slab. But everything inside — the experience of the books, the interface, the typography, the design affordances — those have largely remained the same. It took Amazon almost a decade to implement hyphenation. That’s a seriously deflating timeline.
  3. US publishing industry net revenue: ~USD$30B; Amazon market share for book sales: ~50%; Amazon market cap: USD$701B; Amazon net rev from book sales: ~USD$15B = ~2% of market cap.
  4. The digital book revolution happened everywhere except in the final object of books themselves. The funding, production, marketing, and distribution systems are nothing like they were ten years ago. And yet, that nugget of wood that pops out the other end looks mightily similar.
  5. This quality of lightness, of ever changingness is also where the web / digital spaces get their power. How it’s wielded defines the contract. A shifting narrative within the context of an agreed upon pact can be a beautiful, moving, affirming thing.
  6. One of the reasons I’ve lived and continue to live in Tokyo/Japan is that the cost of living is inexpensive relative to other big cities. In my 16+ years of living here I have never paid more than $800/mo for an apartment in central Tokyo. If you decouple your measurement of “success” in life from material accumulation, you can quickly overcome the “active pain” threshold that Epicurus talks about and enter the “freedom” state. Cultivating a taste for a low cost of living is probably the most important life hack to owning your destiny.
  7. How do you even ask yourself this question? I have some simple heuristics. Some more or less concrete than others. In reflection on a past year, I often ask: Did I acquire a new skill? Did I feel challenged in my craft or life choices? Did I push myself out of my comfort zone? Did that struggle result in a better understanding of myself or others? Did I make material progress on a big project? Answers to those questions can sometimes be hard to quantify. One of my favorite quantifiable heuristics is to maximize the number of days I spend with people I love and respect and whose work moves my heart. It’s both a superficial and yet poignant metric. In essence I’m trying to “collect” good people in the way someone may acquire a stock portfolio. The greater number of people near to you for whom you have deep respect strengthens archetypes. Stronger archetypes means being shown more paths for life potentialities. Life potentialities writ clear before your very eyes demystifies them and means a higher chance of success that you, too, will be able to realize those potentialities. I’ve found the best way to increase these people in life is to work hard, be kind, empathetic. Good begets good, amplifies good, inspires diligence.
  8. Although I usually donate the amount of money my living in Japan would have cost at the end of any free residency.
  9. Of course, it depends on the work, but even work contingent on a net connection can usually be chunked into online and offline portions, and when offline, you can collect research notes for followup when you’re back online.
  10. Just be aware of scale — fast is good at small scale with low-impact, especially good when you’re just working alone. But fast and reckless at large scale is ignoring the responsibility that comes with scale.
  11. This isn’t necessarily a bad thing! And there’s more than a whiff of imperialism when Silicon Valley folk come over and try to make Japan more disruptive or try to force incompatible cultural values down the industry’s throat. That many don’t see this as imperialistic is worrying.

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