The prologue to Zen Mind, Beginner’s Mind1 begins with something of a koan: “In the beginner’s mind there are many possibilities, but in the expert’s there are few.”

I think about this a lot when I’m working on hard problems; I find that over a long enough time frame I actually have to use both modes of thinking to make enough progress.

As an “expert” in familiar mental terrain, being able to block out extraneous information and irrelevant details simplifies the task in front of me. I cannot advance by moving in every direction simultaneously—at some point I have to rely on my experience to pick one direction and follow it well.

No matter how well that goes to begin with, however, I eventually realize I’m dealing with things that I only think I know, and that if I continue on with the same approach I always use then my task will beat me. I need to clear out my assumptions and become a “beginner” again.

There’s a chengyu (成語 ) related to this concept: 刻舟求劍 , translating roughly as “mark the boat to find the sword”. If you drop your sword into a river, you can’t mark its location on the side of your boat to come back to later. The river, the sword, and your boat all move. Your mark is then useless; you and your sword are both lost.

But what I find interesting is how essential both the “beginner” and “expert” patterns of thinking have been for me, when we don’t often talk about them as complimentary, mutually reinforcing processes.2 That gap in discussion corresponds to something else that bothers me: an implicit assumption that everyone continues on with the same behaviors forever.


When I was on my way up / Why you ain’t see the stairs?3

I don’t normally think of myself as a “company man”, but I do think my employer (NASDAQ:GOOG) tends to be underappreciated—in a purely fiscal sense—by the stock market. Between January, 2010, and January, 2013, Google’s stock was fairly flat, being beaten by the overall NASDAQ to the tune of 12%:

The lighter blue line (on top) is the NASDAQ composite, finishing that 3 year run up 35.28% vs. GOOG's 22.92%.

In that same time, though, the company’s revenue increased from $23.6 billion to $50.1 billion, and net profit was up from $6.5 billion to $10.7 billion—that is, revenue more than doubled and net profits were close to doing the same.

When looking back at this strange phenomenon, Ben Thompson (prodded by a reader) agreed to attribute it to “shareholder rotation”, where the investors that had backed Google in its early life as a public corporation were pulling out and “value investors” who are more enticed by sheer profitability were slow to fill the gap.

The implications of that are kind of fascinating to really dig into, though: not only have the VCs that were the earliest backers almost undoubtedly sold their shares, the “growth investors” that followed them in the public market have likewise (seemingly) moved onto other bets.

Internally, meanwhile, I think Google is notable among tech companies in just how good its employee retention has been, but it’s no secret that some unknown number of employees (especially pre-IPO employees) cashed out their millions in equity and dipped. And growth in total headcount has been incredible—94 thousand employees as of the end of last quarter, vs. just 78 thousand the year before.

So the company is entire generations of investors removed from its beginnings, and it’s hard to even calculate how different its employee make up is. That’s not even getting into the big reorganization into Alphabet, Inc. , of which “Google” is now a wholly owned subsidiary. But the stock ticker is still GOOG, and the company is still “Google” in our minds, somehow. So much so that people still complain about the death of Google Reader4 like that’s got anything to do with anyone anymore.


But you learn, my God do you learn5

Back in ye olde times of 2016, I remember there was a brief pseudo-meme6 that talked about how much older Obama looked at the end of his eight-year presidential tenure, contrasting it with the youth he seemed to enter office with.

Image as seen in a New York Magazine piece .

After seeing the 19th rendition of those articles, it was easy to find the level of journalistic ambition behind them questionable, but when it was still a fresh idea it definitely scratched at a real… something, talking about a certain depth of experience that changes you, even on a physical level.

Looking back, I think what I initially liked about those articles was that they implicitly discussed the presidency as a journey, rather than as a single state of being. We have an unfortunate tendency to interact with public figures and brands as though they were somehow stateless—the events of their past, present, and future are somehow all happening at roughly the same time, with none informing any of the others.

Kevin Hart arguably got bit by this and is no longer host-to-be of the Oscars. I always wonder with stories like that, though—how much are we asking for? We want diverse comedians (or musicians/artists/celebrities) from somehow-disadvantaged backgrounds creating both edgy and insightful original content that is ultimately non-offensive? Is that really even possible? It’s hard to not feel like it’s a secular age fantasy: a leader who pushes their way from the bottom of society all the way to the top and never accrues a chip on their shoulder; Christ re-invented from first principles.7

The New Yorker did a great profile of Anthony Levandowski that actually dared to investigate the inflammatory idea that Levandowski was in many ways the pinnacle of Silicon Valley’s value system—“a brilliant mercenary, a visionary opportunist, a man seemingly without loyalty.” The traits that people valued in him—and that allowed him to create so much value, first in Google Maps and then in autonomous cars—eventually caused those people to turn on him when the scale he was working on (which implicitly includes his role and the standards he’s held to) grew beyond him. But how avoidable was that for him? How could he learn that he needed to change the behaviors that gave him so much success without some tremendous failure? Lurking in the shadow of that discussion, of course, is another to be had of Travis Kalanick and Uber as a company.

I would say Kalanick, Levandowski, and Hart (as well as however many other examples) were all hit by the forces of churn. They succeeded, (and kept succeeding!) but the world kept changing, and even while they changed as people, it wasn’t fast enough or complete enough to avoid getting knocked against the steel-drum-wall of public opinion.

But no amount of bad PR can kill a man. [citation needed]

Love you then they hate you then they love you again

As I’ve worked as an engineer over time, I’ve started to develop a sense for when things are just going wrong in the code I’m writing.

I’ll be trying to fix some basic compiler errors that I introduced with another simple addition I made, but fixing those starts to chain into problem after problem. Being able to stop working at that point, and completely re-evaluate what I’m doing, is maybe the most important skill I have as a programmer. It’s also the one that takes the longest to develop.

When writing, I notice something similar: if my thesis just doesn’t work, I can actually get a fair bit into supporting it before I realize what’s going on. Even creative writing can hit the same wall.

The key to what makes that kind of recognition a skill is that you have to have the strength to actually abandon all the work you’ve done to that point. The novice—or even the journeyman—will try to press their luck and see how large their castle of sand can get.

In the language of Zen Mind, Beginner’s Mind, the “expert” is someone who, upon feeling this nagging sensation, convinces themselves that they have the talent to turn a bad premise into a good one. They find themselves in a hole and hope to dig it into a tunnel instead of just climbing back out. That kind of expert is then worse than a beginner, because they can often take a whole expedition with them on their fever dreams of finding daylight.

Unfortunately, I’m not sure there’s any way to get past that precarious “expert” stage other than to get there and have it all fall apart on you. As far as I can tell, you just have to dig yourself into enough holes before you truly understand that your shovel is not a ladder.

Painting by the excellent Carty Sewill as part of
the book 1/3 .

Google’s engineering teams have what we call a "postmortem culture" based in the idea that mistakes are 1. Expensive 2. Inevitable 3. Something that can be learned from

After we really fuck something up, we write up a “postmortem” examining how it all happened and what we could do to avoid such catastrophe in the future. If said fuck up was truly epic then the postmortem has a high likelihood of being circulated across the company to make sure everyone reads it, since those were the most expensive lessons to… acquire.

There is a real sense in which this library of postmortems is something of a “moat” for the company, as we’ve made an incredible number of mistakes that others would likely have to repeat if they were going to chase us in a core competency.

At least, it would be, if it weren’t for the fact that a lot of people try to take all they learn from Google and apply it elsewhere, at other companies that they either join or start themselves. And there are a lot of people joining Google all the time who might fuck up without having had the time to find the exact, perfectly-relevant-to-their-situation postmortem.

And that’s not even including all the new, never-before-seen challenges we are all always facing with each new day, because the world keeps changing.

Living in churn

We are living in a world dominated by churn.

The world is a dynamic system filled with dynamic people—people who then make the world more dynamic.

We’re governed by the habits and approaches that were the hardest for us to learn; we try to replicate the most hard-won successes and avoid the most costly failures we have personally experienced.

Why then, is it so rare for us to talk about those almost-but-definitely-not cyclical patterns of learning when we try to make sense of the world?

A favorite podcast of mine (Retronauts) talks about the history of video games, and in their episode about the Nintendo DS they talked about how everyone struggled to envision a system with two screens, pointing out that there was a pretty obvious parallel that someone should have made the connection to.

"Oh! It's just like the old two screen Game & Watch."

  1. Zen Mind, Beginner’s Mind by Shunryu Suzuki. Published October 10th, 2006 by Shambhala Publications. ISBN 9781590302675 [return]
  2. Sam Altman is maybe an exception-that-proves-the-rule here. His New Yorker profile comes to mind, which featured Patrick Collison comparing the YC showrunner’s thinking to the prize claw machine. “It roams around but has the ability to plunge very deep when necessary.” [return]
  3. PG to Mo’ county, we definitely do all know about him.
    LoveHate Thing by Wale, ft. Sam Dew.Track 2 on The Gifted, released 2013-06-25 by Maybach Music Group and Atlantic Records. [return]
  4. There’s a crushing irony when an early retrospective got an interview with one of the project’s creators, but felt obligated to then include a link in that retrospsective out to said creator’s new and completely unrelated start up. [return]
  5. Not actually a C.S. Lewis quote [return]
  6. My polite term for highly reproducible lite-news content, I guess? [return]
  7. There’s an irony in it for me as a bisexual man in NYC. I look around and what I see as the more pressing concerns for the queer community are the self-inflicted ones that we’re really on our own to address, but no one wants to bring up the number of people talking about Tina that have never in their lives listened to Ms. Turner’s music. [return]