Writing about loss is diffi­cult. Few can success­fully describe the empti­ness one feels after the sudden death of a parent, child, friend.

And yet we try. When my mother passed away nearly twelve years ago, I started a web journal. Writing helped me process my thoughts and feelings into something concrete and more understandable.

Joan Didion described loss with quietly powerful language in The Year of Magical Thinking and Blue Nights, her memoirs about the death, in shock­ingly short succes­sion, of her husband and daugh­ter. Despite the painful subject matter, I highly recom­mend reading them (in order), both to people who have experi­enced a sudden loss and to those who haven’t. Didion captures the empti­ness of life without her husband so well—the immediate eleva­tion of once-unimportant miscel­lany to artifacts, the new strange­ness of once-familiar daily routines.

William Maxwell’s So Long, See You Tomorrow is a short, moving work about memory, family, and loss, set in a small town in Indiana. Like The Sense of an Ending, most of the action occurs in the distant past, as an elderly narrator looks back on his life. And, like Sense, So Long can be read in an evening, though I’d recom­mend allowing some time for the words to sit in your mind. Maxwell uses decep­tively simple language throughout the book; it took me some time to realize how carefully he chooses his words, and their cumula­tive effect is powerful.

I’m not sure how long a quote is too long, but I found this passage near the begin­ning of the book exceptional:

My father was all but undone by my mother’s death. In the evening after supper he walked the floor and I walked with him, with my arm around his waist. I was ten years old… Because he didn’t say anything, I didn’t either… His eyes were focused on things not in those rooms, and his face was the color of ashes…

I had to guess what my older brother was think­ing. It was not something he cared to share with me… At night we undressed and got into bed and fell asleep without taking advan­tage of the dark to unburden our hearts to each other. It strikes me as strange now. It didn’t then… What I didn’t say, across the few feet that separated our two beds, was that I could­n’t under­stand how it had happened to us. It seemed like a mistake… I had to find an expla­na­tion other than the real one, which was that we were no more immune to misfor­tune than anybody else, and the idea that kept recur­ring to me, perhaps because of that pacing the floor with my father, was that I had inadver­tently walked through a door that I should­n’t have gone through and could­n’t get back to the place I hadn’t meant to leave. Actually, it was the other way round: I hadn’t gone anywhere and nothing was changed, so far as the roof over our heads was concerned, it was just that she was in the cemetery.

It’s not fair to describe So Long, See You Tomorrow as a book strictly about loss; the plot revolves around a murder, the details of which are revealed slowly. But all of the charac­ters feel loss of some form or anoth­er—death, betrayal, separation, regret.

It’s a beautiful book. You can probably find it in your local used-book store, and on Amazon.

Atul Gawande expanded a great piece in the New Yorker from 2007 into The Checklist Manifesto, a short, compelling read about how a simple tool can help humans tackle complexity.

Most of the book explores reducing human error in medicine (spoiler: good check­lists prevent mistakes). But Gawande includes a fasci­nating chapter on the construc­tion industry where he writes:

For most of modern histo­ry… the dominant way people put up build­ings was by… hiring Master Builders who designed them, engineered them, and oversaw construc­tion from start to finish, portico to plumb­ing. Master Builders built Notre Dame, St. Peter’s Basil­ica, and the United States Capitol build­ing. But by the middle of the twentieth century the Master Builders were dead and gone. The variety and sophis­ti­ca­tion of advance­ments in every stage of the construc­tion process had overwhelmed the abili­ties of any individual to master them.

The solution? A combi­na­tion of delega­tion, commu­ni­ca­tion, and checklists.

I see many paral­lels to the computing indus­try. Thirty years ago, Steve Wozniak designed and built a complete computer by hand, the now-legendary Apple I. Today, I carry a computer many orders of magni­tude more complex than the Apple I in my pocket: the iPhone. There’s no one person who can under­stand every single compo­nent of the iPhone and how they work together, let alone assemble one from scratch.

Our solution in both hardware and software is abstrac­tion. Different special­ists and compa­nies handle different compo­nents, and agree on inter­faces between those compo­nents, much like the plumbers and electri­cians and HVAC special­ists collab­o­rate on a skyscraper.

In software, abstrac­tions have evolved at the same speed as the under­lying complex­ity, so that appli­ca­tions like the webserver Nginx and the game Minecraft can still be largely written by one person. The tools just keep improving.

The Apple iPhone SDK is a great example of an excep­tional tool: for (almost) no cost, Apple offers devel­opers a complete coding environ­ment, UI compo­nents to make beautiful inter­faces, a distri­b­u­tion channel, and payment process­ing. It’s never been easier for a team of one or two people to make great software that reaches a large audience.

Moreover, program­mers have created many varieties of automated check­lists to fight against increased complex­ity, from unit tests to full functional tests that click on buttons within an app.

Without such tools the age of the programmer “master builder” would have ended long ago. I’m curious if we’ll ever reach a point where one or two people can no longer create meaning­fully useful applications.

The Checklist Manifesto can be found at Amazon and elsewhere.

After living in New York for a year and a half, I miss San Francis­co’s excel­lent used bookstores. I feel lucky to work just half a block from The Strand, but there’s something about a small bookstore’s curated selec­tion of used books that makes browsing more fun.

I was working in SF last week when I happened into Aardvark Books one night after dinner. Aardvark boasts a great “re­cent arrival­s” section, just a few shelves long but brimming with excel­lent, inexpen­sive reads. I randomly picked up a hardcover copy of John McPhee’s Uncommon Carriers, based mostly on its excel­lent cover art and a vague recol­lec­tion of having read some of his work in theNew Yorker. (It helped that some bookstore employee wrote in pencil on the first page, “Pretty good!”)

It was a lucky find. Uncommon Carriers explores freight trans­port and the people who work Ameri­ca’s trucks, barges, ships, planes, and trains, day and night. This might sound boring at first glance, but McPhee’s writing is strangely hypnotic and enthralling.

One piece in particular, Out in the Sort, kept me up late last night. The piece begins with a detailed descrip­tion of a lobster-catching opera­tion in Newfound­land, and uses the lobster compa­ny’s trans­port needs as a segue into a decon­struc­tion of how UPS operates. Describing their world­wide hub in Louisville, Kentucky, McPhee writes:

This labyrinth, which outthinks the people who employ it, is something like the interior of the computers that run it. Like printed circuitry, seven great loops, each a thousand feet around, are super­posed at right angles above other loops… Unending sequences of letters and small packages zip around these loops, while the larger packages follow one another on the belts, each package tailgating the one in front of it but electron­i­cally forbidden to touch it… Collec­tively, the loops are like the circuits in the mother­boards among the inter­face cards of a central processing unit wherein whole packages seeking specific airplanes are ones and zeroes moving through the chips.

There’s too much to glean from the piece (and from the book) for a short blog post, but I’ll pick a few tidbits. We learn that UPS employs college students to deal with “ex­cep­tion­s”—­pack­ages that require human inter­ven­tion. When the company experi­enced diffi­culty hiring enough students, it founded and endowed a college of its own, Metropolitan College, in concert with the Univer­sity of Louisville and other local schools. UPS employees also service Toshiba laptops on-site, and keep the largest supply of Bentley parts in the world. McPhee’s great writing and sense of humor keep everything interesting.

There are hundreds of other fasci­nating details. If you have a New Yorker subscrip­tion, you can read Out in the Sort on newyorker.com. If not, I managed to find a copy online, which you can download from Mediafire while it lasts. Either way, if this sounds at all inter­esting to you, you should find a copy of Uncommon Carriers. I know I’ll be looking for more McPhee titles next time I hit a used bookstore.

…when you are young, you think you can predict the likely pains and bleak­nesses that age might bring. You imagine yourself being lonely, divorced, widowed; children growing away from you, friends dying. You imagine the loss of status, the loss of desire—and desir­abil­i­ty… What you fail to do is look ahead, and then imagine yourself looking back from that future point. Learning the new emotions that time brings. Discov­er­ing, for example, that as the witnesses to your life dimin­ish, there is less corrob­o­ra­tion, and there­fore less certainty, as to what you are or have been. Even if you have assid­u­ously kept record­s—in words, sound, pictures—you may find that you have attended to the wrong kind of record-keeping.

Sense of an Ending is a short and wonderful book, a slim 180 pages readable in a single sitting. There’s much to savor, though, and like Marilynne Robinson or Alice Munro, Barnes chooses every word carefully and precisely. Highly recommended. Amazon

“The tendency to see patterns in randomness is overwhelming…”

Daniel Kahneman’s Thinking, Fast and Slow made many “best of 2011” lists this year, and deservedly so. Plenty of books on the system­atic faults of the human mind have made the rounds, from Ariely’sPredictably Irrational and its followup to Nassim Taleb’s Fooled by Randomness and The Black Swan.

Fooled by Randomness was a great book marred by the pompous­ness of its author. In fewer words (and with much less ego), Kahneman covers similar terri­tory in more depth and backed by better research:

How many good years should you wait before concluding that an invest­ment adviser is unusu­ally skilled? How many successful acqui­si­tions should be needed for a board of direc­tors to belive that the CEO has extra­or­di­nary flair for such deals? The simple answer to these questions is that if you follow your intuition, you will more often than not err by misclas­si­fying a random event as system­atic. We are far too willing to reject the belief that much of what we see in life is random.

I will do my best to remember the above quote whenever I jump to conclu­sions about a startup, an entre­pre­neur, even an A/B test.

There’s too much in the book that’s applicable to anyone starting a business, or inter­preting analytics from your website, or trying to make rational decisions. Instead of quoting from every chapter, why not just check it out for yourself? (No affil­iate link, I promise.)