The Five-Tool Designer

As someone who has managed and worked with designers for most of my adult life, I get a lot of calls from people looking to check references on someone I’ve worked with or find out from me if there are other designers they should be talking to.

When I think about the range of critique I’ve provided in these situations, the term I always use to describe the very best designers I’ve ever worked with is five-tool designer.

Five-tool player is actually a baseball term used to describe someone who can hit for average, hit for power, run the bases, throw, and field. It’s the highest compliment you can pay to a player and is generally reserved for only the most complete athletes, like Ken Griffey Jr. and Willie Mays. In fact, Major League Baseball estimates there are only 8 five-tool players in the game today.

Everyone looks for slightly different things in the designers they hire, but for me, there are five tools that stand above the rest.

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Books to Expand Your Perspective

Over the course of the last year since leaving Twitter to take some time off, I’ve managed to catch up on a ton of reading. Real reading. Actual books!

I don’t think I’ve read more than a few books a year since I was a kid, but in the last 12 months, I’ve managed to keep a healthy pace of 2 or 3 per month. Two books have stood above the rest in terms of expanding my understanding and perspective of how the world works:

  1. A People’s History of the United States by Howard Zinn.

    One of the birthrights of growing up in the United States is that you are indoctrinated at a young age with a very rosy version of America’s history: the journey of a group of people seeking freedom, discovering territory, declaring independence, drafting a benevolent Constitution, and then over the course of the next few hundred years, building America into what it is today.

    While a lot of it is true, it is written from the perspective of “the victors” (as most history is). This book takes the opposite approach, instead opting to tell the story of our country through the lens of those who’ve been taken advantage of (i.e. Native Americans, women, slaves, immigrants, minorities, the poor, and even what we think of as “the middle class”). The author admits that just as textbooks are biased in one direction, his book is likely biased in the opposite direction, but the point is to better balance our view of how America began, what our behavior has been like throughout the course of our history, and what power dynamics continue to shape our society.

    I might go so far as to say this is the most important book I’ve ever read. If we are going to get through the next few years and beyond, it’s important that everyone have a sober perspective on how we got here, and the tensions that have been around from the very beginning.

  2. Guns, Germs, and Steel by Jared Diamond

    Speaking of “how we got here”, this book rewinds the clock even further, explaining how modern humans evolved from Homo Erectus to a (mostly) intelligent species spanning every continent on earth. The emphasis is less on physiological evolution and more on the sociological advances that enabled us to live as we do today.

    There is a good amount of material on agriculture, the invention most responsible for our modern way of living, but there are also fascinating storylines about why certain groups of people ended up where they did (e.g. Africans in Africa, Europeans in Europe, etc).

    If you want to get caught up on the story of humans in a single book, this is the one to read.

What’s Next

Jason Kottke had an interesting post which linked to two reading lists from a guy named Cass Sunstein, who worked under Obama and seems like a pretty well-rounded political scholar. The first list is 5 Books To Change Conservatives’ Minds, and the second list is 5 Books To Change Liberals’ Minds.

I am going to try and read all ten, and I won’t lie: I’m not exactly looking forward to it. 176 pages from Antonin Scalia isn’t the sort of thing that gets me up in the morning. But I guess that’s the point!

To make things easier, I’m going to tackle this in machete order. Left, right, left, right, until they are all vanquished. If you’d like to do the same, I sorted them into two public lists — left and right — ordered by number of reviews. Might as well read the popular ones first.

Will report back when I’m done. Happy reading, people!

(This post also available on Medium.)

Behavioral Targeting is Getting Scary

This fascinating article about how an “election management firm” — under contract with the GOP — mined social network data and used it to bombard impressionable voters with content designed to manipulate them is thought-provoking and troubling.

Go ahead, read it first, and then come back. Also, for balance, read this counterpoint from Bloomberg doubting the data’s effect on the election, and listen to this podcast from Michal Kosinski who is the Stanford researcher featured in the article. Kosinski is unsure what effect data mining and targeting had on the election, but has plenty of fascinating things to say.

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“Is This Helpful?”

The first book I checked off my list this year was one I had heard about thousands of times since I was little but never actually read: 1984 by George Orwell.

I think what finally got me over the edge was this Reading List for the Resistance from Jason Kottke, so thanks Jason.

I very much enjoyed the book, and in a way, I’m glad that I waited until this very instant to read it. I think my younger self would have dismissed it as delusional and irrelevant, as I tend to retreat from science fiction the moment it feels implausible to me.

Reading the 1949 novel now though, at a moment in which the stiff boot of authoritarianism threatens to become part of American lives for the first time, I’m struck by how prescient it now seems.

There are a lot ideas from the book that feel more and more familiar in today’s world, but the one I can’t get away from is the concept of newspeak. For those who haven’t read the book, newspeak is a new language developed by the oppressive government that drastically reduces the amount and complexity of words in order to drastically reduce the amount and complexity of thought amongst the citizenry. The idea is, if you can remove say, 95% of words from the English language, new generations will not be able to formulate the undesirable thoughts represented by the eliminated words (think “coup”, “resistance”, “steal”, etc).

The end result is something of a pidgin. Very basic sentences, using a tiny subset of words, representing the minimal amount of thought necessary to keep the wheels of the totalitarian society running.

It strikes me that many of our communication channels today — while not being created with any sort of negative intent — may have ended up with similar properties:

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⇗ How American Politics Went Insane

"Neurotic hatred of the political class is the country’s last universally acceptable form of bigotry."

If you're interested in how the American political system got to where it's at today, this is a great catch-me-up. I had never really considered the importance of middlemen, hierarchy, pork barrel spending, and other elements of what people disdainfully refer to as "the machinery of politics" when it comes to actually getting things done in Washington. We want to replace establishment insiders because we aren't happy with their effectiveness, but there is a very good chance inexperienced outsiders will be much, much worse.

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⇗ A Self-Driving Car Ethical Problem Simulator

Via Jason Kottke comes this thought-provoking exercise challenging you to apply your own morality to difficult "trolley problem" scenarios that self-driving cars will have to deal with the moment they hit the streets. In other words, when a self-driving car must make a decision to kill (either its own passengers or pedestrians), what criteria should it use to make that decision?

Please go through the exercise yourself before reading any more of this post, as I don't want to poison your answers with my own.

Ok, all done?

There are no objectively right answers to this problem, but my strategy was as follows: First, I disregarded all demographic differences between humans. I don't feel comfortable assigning different values to men, women, the elderly, kids, athletes, criminals, obese people, etc. There was one question where I did have to use this as a tie-breaker, but that was it... and it still didn't feel good. Then, I optimized for saving people who were doing nothing wrong at the time. In other words, pedestrians who crossed on a Don't Walk signal were sacrificed pretty consistently. Then I optimized for greatest number of human lives saved (pets were toast... sorry pets). The hardest question came down to a scenario where you had to pick killing four innocent people in the car vs. four innocent pedestrians. For this, I chose to spare the pedestrians, as those who choose to take a vehicle seem like they should bear the risk of that vehicle more than those who made no such decision.

The summary page at the end is interesting, but it can also give false impressions. For instance, even though I explicitly disregarded demographics, it showed me as significantly preferring to save people who were "fit" and people who were "older". Depending on your strategy, some of these conclusions may be enlightening, and some will just be noise from a small data set. Also, don't forget to design some of your own. Here is the hardest one I could create, based on my own decision-making criteria.

Tough stuff, but it's good to get people acclimated to these dilemmas now, because although no technology can eliminate traffic deaths, self-driving cars will probably greatly reduce them. Curious to hear other strategies if you have them. Jason's, for instance, were different than mine. Also, can I just say that I love the idea of pets "flouting the law by crossing on a red signal?"

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⇗ My Distraction Sickness — and Yours

Andrew Sullivan goes deep on his own experience trying to rid himself of the digital distractions that have taken over our attention spans. Lots of great thinking and food for additional thought here. It seems like there are two camps on the issue of hyper-connectivity: one is that this is the new normal while the other is that it's unsustainable. I tend to be in the second camp, and when I think of the products I really want to build in the future, most of them are squarely aimed at giving people their time and attention back so they can live better lives in the real world.

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Shipping vs. Learning

“What did you ship last quarter?”

“When is this going to ship?”

“Real artists ship.”

The verb “ship” has a long history in the software development world and before that, the physical world. In the physical world, it originally meant “to transport something on a vessel”, and in the software world, it meant “to press a tape/disk/CD and send it out to consumers”. Since then, it has come to simply mean “release”, and even then, usually not in any sort of final form.

Everyone inside tech companies loves shipping. It’s the culmination of a lot of hard work and creativity from designers, engineers, PMs, researchers, and any number of other people, and when it’s good it puts a dent in the universe. It is no wonder then that so much of the machinery of tech organizations is centered around shipping.

But should it be? Especially given how much shipping itself has changed in the last couple of decades?

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⇗ Why Do We Judge Parents For Putting Kids At Perceived — But Unreal — Risk?

As a card-carrying non-parent, one of my favorite questions to ask parents (for some reason) is at what age they will feel comfortable leaving their kids alone for very short periods of time. The answers often surprise me and are a lot more conservative than when I grew up in the 1980s. This article goes deep on why that is. The bit about the "availability heuristic" is what I had previously suspected, but the additional finding about people conflating their own moral judgement with perceived actual risks is fascinating. I wonder what other issues in society this conflation occurs with.

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⇗ Fractured Lands: How the Arab World Came Apart

The product of 18 months of reporting, Fractured Lands is one of the best explanations you will read about the current state of the Middle East. The storytelling style is unconventional, weaving the personal journeys of several people together into five distinct time periods, but it works and it's definitely worth your time.

The most interesting thing I learned is that the three nations most devastated by the Arab Spring are all nations the West helped create in the early 20th century: Iraq, Libya, and Syria. The power dynamics of those and other regions mentioned in this piece are fascinating and extraordinarily precarious.

The one thing I was surprised made no appearance in Fractured Lands is the role of global warming in the escalating conflict in Syria. For a great look into that angle, make sure to check out Yonatan Zunger's piece on the subject.

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