The Optimist’s Telescope: Thinking Ahead in a Reckless Age
By Bina Venkatamaran
Riverhead Books, 2019

I first heard about this book from Ms. Venkatamaran’s presentation at the Long Now Foundation’s fabulous series of seminars about long-term thinking. Of all the Long Now seminars I’ve heard in the last few years, this was one of the most directly related to long-term thinking. The subject of this book is described as “how we can plan better for the future: our own, our families’ — and our society’s.”

As suggested by this description, the book is organized into three parts, focused on the individual and the family, businesses and organizations, and communities and society. Each includes examples of initiatives that have helped people overcome the pressures of the “here and now” towards decisions that serve them better in the long-term. (Ms. Venkatamaran discusses several of these examples in the seminar linked above, which serves as an excellent primer to the book.)

The final chapter synthesizes these insights into a list of more concrete strategies for acting with the long-term in mind:

1. Look beyond near-term targets
2. Stoke the imagination
3. Create immediate rewards for future goals
4. Direct attention away from immediate urges
5. Demand and design better institutions

It’s up to the reader to map these to his or her situation. (It’s just as well — expanding on each would’ve made the book too long.)

One of the ironies of our time is that we’re facing existential threats that require long-term action (e.g., climate change), all the while suffering from ever-shortening attention spans. With its many examples and stories, this book is an engaging antidote to the malaise. (If you’re not up for reading it, but interested in the subject anyway, do listen to Ms. Venkatamaran’s Long Now seminar.)

Buy it on Amazon.com

Shoe Dog: A Memoir by the Creator of Nike
By Phil Knight
Simon and Schuster, 2016

In the early pages of Shoe Dog, Phil Knight notes:

Front runners always work the hardest, and risk the most.

This pithy observation summarizes the story to follow. It’s the story of Mr. Knight’s life, and it’s the story of Nike — the two are inseparable. It’s a story of hard work and risk.

Among the things risked: reputations, relationships, money (mostly other people’s), and careers. They’re all on the line, offerings to turn an insight into a material fact. The insight is precipitated by Mr. Knight’s passions (as a college track and field runner) and his astute observations of changing conditions in global markets. He starts a company to distribute athletic shoes from his parent’s house in Oregon. His aim: victory. Competitive sports is a metaphor — and often more than that.

Almost inadvertently, he assembles an idiosyncratic team of managers, each a colorful character in their own right. The story follows this crew as they try to grow their small company. They face many obstacles: unreliable suppliers, nervous bankers, unscrupulous competitors. They also face their doubts. What have we done? Are we too far over our heads this time? Are we good enough? Mr. Knight and his collaborators have flaws and insecurities, but they’re all are committed to the cause.

Still, there’s no master plan. They’re making it up as they go along, one decision — one crisis — at a time. It’s an organic process, perhaps the result of Mr. Knight’s management style, which is summarized by a quote from General George S. Patton that appears several times in the book:

Don’t tell people how to do things, tell them what to do and let them surprise you with their results.

The book is organized chronologically, one chapter for every year from 1962-1980. This structure could be boring if not for the fact that Nike faced existential crises almost every one of those years. Although the company is still thriving today, 1980 seems like a good stopping point: it’s when Nike went public. Ostensibly, this turned it into a different company than the one described in Shoe Dog. A coda (“Night”) brings the story up to the present. It includes revelations that cast the rest of the book in a different light.

Shoe Dog is the best book I’ve read on the experience of being an entrepreneur. The book is enlightening, inspirational, and heartbreaking. Mr. Knight is an excellent writer; Nike’s story reads like a well-crafted novel. If you work with entrepreneurs, or aspire to be one, you owe it to yourself to read it.

Buy it in Amazon.com

Many people take time during the holidays to look back on the past year. Reading is a big part of my life, so around this time I usually re-visit the books I’ve read during the year and highlight the ones that stood out. I share these lists in case you’re looking for book recommendations for the holidays. (Note these aren’t necessarily books that were published during the past year — this just happens to be when I got around to them.)

Without further preamble, here are five books I enjoyed and learned from in 2019:

Design Unbound: Designing for Emergence in a White Water World by Ann Pendleton-Jullian and John Seely Brown. A map for pragmatic design-doing — not for making products and services better (or even better products and services), but for operating at a higher, more systemic level: that of social, economic, ecologic transformation. Buy it on Amazon.com (volume 1/volume 2) or see my book notes.

Design by Concept: A New Way to Think About Software by Daniel Jackson. A compelling argument for the importance of conceptual modeling in software design. It includes clear examples and an actionable framework for defining such models. (The book is billed as a “prepublication draft”; I’d love to read the “final” version.) Buy it on Amazon.com.

The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of The Walt Disney Company by Robert Iger. A memoir/leadership manual from one of the great business leaders of our time. Mr. Iger took the job of Disney CEO at a troubled time for the company; he revived its fortunes by skillfully implementing a clear, compelling strategic vision. Buy it on Amazon.com or see my book notes.

Churchill: Walking With Destiny by Andrew Roberts. Makes the case that Churchill — flaws and all — was the right person at the right time to (literally) save the world. What’s more interesting is that he knew this, even from an early age. (At 16 he predicted he’d save England from an invasion.) He was also hilarious. Buy it on Amazon.com.

Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed, by James C. Scott. A treatise on the relationship between top-down and bottom-up organization frameworks. Argues that states seek to simplify social structures to make them more “legible.” (I.e., easier to measure and manage.) This impulse has led, in the most extreme cases, to disastrous top-down “high modernist” schemes. The book is engaging, disturbing, and mind-changing. Buy it on Amazon.com.

The Everything Store: Jeff Bezos and the Age of Amazon
By Brad Stone
Hachette Publishing, 2013

In a 2013 interview, Charlie Rose asked Amazon’s founder, Jeff Bezos, to define his company. “I would define Amazon,” he replied, “by our big ideas, which are customer centricity, putting the customer at the center of everything we do, and invention.” The Everything Store traces the story of how those ideas — which have been at the core of Mr. Bezos’s vision for Amazon — created one of the great entrepreneurial success stories of our time and transformed the way we shop.

But customer-centricity isn’t the only value that has led to Amazon’s success. Ruthless execution — another central value, and one that the book doesn’t shirk from describing — has allowed Amazon to move faster, smarter, and more aggressively than its competitors. The company’s ability to move quickly has allowed it to exploit strategic advantages it gained due to thinking long-term, another central value.

Alas, Amazon’s relentless pursuit of customer satisfaction has often come at the expense of other actors in the ecosystem, especially employees and vendors. The company’s negotiators don’t aim for win-win, and work-life balance is anathema. The book describes a demanding environment that selects for a particular type of employee, one that’s fully committed to — and willing to make personal sacrifices for — the company:
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The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of The Walt Disney Company
By Robert Iger
Random House, 2019

In the early 1980s, Disney was in trouble. Its movies weren’t resonating with the public. It had invested a lot of money into a theme park – EPCOT Center – that wasn’t meeting expectations. Having lost touch with public tastes, Disney had become a target for corporate raiders, who were looking to buy the company to dismantle it. It was a sad time for Disney fans and shareholders.

It seems hard to believe, given that Disney is now the largest and most powerful entertainment company in the world. The change in the company’s fortunes can be attributed mostly to the leadership of two men: Michael Eisner, who was Disney’s CEO from 1984-2005, and Bob Iger, who succeeded him. Now the latter has written a leadership guide in the guise of a memoir that explains how he did it.

I’m wary of most corporate leader memoirs – especially if they’re in the entertainment industry. These folks are often masters of public relations, and their memoirs tend to be carefully crafted to burnish their public images. These books often come across as being in service to their authors’ egos. Mr. Iger’s book is the opposite. He often discusses how keeping his ego in check has been essential to his leadership style. He’s frank about his mistakes and gracious in sharing the praise for his successes.

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Strategic design: Eight essential practices every strategic designer must master
By Giulia Calabretta, Gerda Gemser, and Ingo Karpen
BIS Publishers, 2016

Design isn’t just good for making better things, it’s also good for making things better. In other words, design can be both tactical and strategic. Many designers come to the field with a tactical mindset, and as they grow in their careers find themselves drawn towards higher-level challenges that add greater value to their organizations. This book offers frameworks that allow them to transition to a more systemic and strategic practice.

At the core of the practice is the alignment between three core domains:

The premise of this book is that successful strategic design solutions emerge at the intersection of what is desirable from a customer/user perspective, viable from a business perspective and feasible from a technological/organizational point of view. Blending and aligning these three very different facets for an optimal intersection is not an organic process, and so needs to be managed explicitly.

As promised in the title, the book offers eight practices that are central to achieving this alignment:

1. Defining and articulating a clear vision
2. Co-creation and prototyping
3. Assessing the current circumstances (e.g. ownership, visioning) in the organization
4. Shedding light on the design process itself
5. Creating alignment through storytelling
6. Evaluating feasibility
7. Evaluating viability
8. Building lasting design capabilities in the organization

There’s a chapter focused on each, all authored by different teams of practitioners and academics. While this variety of voices could be a liability, in this book’s case it’s a strength, since the various authors present a range of case studies (mostly from Europe) that illustrate the practice highlighted in each chapter. It makes for a rich and actionable compendium of key strategic design practices.

Buy it in Amazon.com

Digital Minimalism: Choosing a Focused Life in a Noisy World
By Cal Newport
Portfolio/Penguin, 2019

When people ask me about resources to help them make better use of digital technologies while avoiding distractions, I refer them to Cal Newport’s work. His previous book, Deep Work, argues that social media has a negative impact on our ability to do meaningful work, and argues for leaving it outright.

His most recent book, Digital Minimalism, takes a more nuanced — and in my opinion, practical — approach, one rooted in a philosophy of use for digital technologies:

as is becoming increasingly clear to those who have attempted these types of minor corrections, willpower, tips, and vague resolutions are not sufficient by themselves to tame the ability of new technologies to invade your cognitive landscape—the addictiveness of their design and the strength of the cultural pressures supporting them are too strong for an ad hoc approach to succeed. In my work on this topic, I’ve become convinced that what you need instead is a full-fledged philosophy of technology use, rooted in your deep values, that provides clear answers to the questions of what tools you should use and how you should use them and, equally important, enables you to confidently ignore everything else.

Instead of doing without digital technologies altogether, Mr. Newport proposes that we embrace digital minimalism,

A philosophy of technology use in which you focus your online time on a small number of carefully selected and optimized activities that strongly support things you value, and then happily miss out on everything else.

He compares the approach to how the Amish people embrace new technologies. Many people assume that the Amish are against all tech. That’s not the case. Instead, they have a very thoughtful approach to new technologies that considers their impact on the community as a whole.

This requires trading off conveniences, but these conveniences often come at the expense of healthy social relationships. Mr. Newport describes the relationship between offline and online interactions as zero-sum: digital communications hamper our ability to communicate with people in physical space. Clearly we want to optimize for the latter.

Rather than quitting cold turkey, Mr. Newport proposes what he dubs the Digital Declutter Process:

1. Put aside a thirty-day period during which you will take a break from optional technologies in your life.
2. During this thirty-day break, explore and rediscover activities and behaviors that you find satisfying and meaningful.
3. At the end of the break, reintroduce optional technologies into your life, starting from a blank slate. For each technology you reintroduce, determine what value it serves in your life and how specifically you will use it so as to maximize this value.

He also offers a useful heuristic for going off particular technologies and apps:

consider the technology optional unless its temporary removal would harm or significantly disrupt the daily operation of your professional or personal life.

In all, this is a useful and practical book. It’s my new go-to recommendation for people looking to be more effective amidst digital distractions.

Buy it on Amazon.com