Lessons From the Best Books of 2016

Chris Szymansky
11 min readDec 28, 2016

I’m an avid reader, always looking for the best books to help me grow my career, abilities, and general knowledge. Here are the most significant lessons and takeaways from my favorite books of 2016.

The Only Rule Is It Has to Work: Our Wild Experiment Building a New Kind of Baseball Team

By Ben Lindbergh and Sam Miller (Goodreads)

The Only Rule Is It Has To Work details the ultimate sports fantasy for two baseball writers who had the opportunity to take over a minor league baseball team for a season. They assembled a roster using a blend of Moneyball-style advanced statistics, persuasion, and gut instinct. It’s a fascinating look into the low paying, low-budget world of the (very, very) minor leagues and the sheer amount of determination and love of the game it takes to be a part of them.

Regardless of whether you’re a baseball player or an entrepreneur, opportunities are fleeting. Embrace them, put everything you have into them, and don’t take them for granted.

In a passionate attempt to coax a player out of retirement to join the team’s roster, one of the protagonists says:

“Any of us who are in the game or work around it, you play it because you love it. You play it because it’s not golf. It’s not something that you can do until you’re seventy-five years old. You’ve got a finite number of at-bats in you — we all do. And you want to get as much out of every pitch that you can see or catch, because that is something that is fleeting and finite.

And not to add more emotion to it, but as a guy who’s thirty-four, thirty-five years old, it feels like a hundred years ago that I was playing competitive baseball. It’s something that I personally miss and wish I could’ve held on to a little bit longer.”

Playing Through the Whistle: Steel, Football, and an American Town

By S.L. Price (Goodreads)

Equal parts football story and social history, Playing Through the Whistle is the gripping output of Sports Illustrated writer S.L. Price’s five-year immersion in Aliquippa, Pennsylvania, a small city just outside of Pittsburgh that was a company town for J&L Steel for much of the 20th century.

Aliquippa is perhaps best known for its football stars, especially NFL Hall of Famers Mike Ditka and Tony Dorsett. It has also produced leaders such as Henry Mancini (winner of four Academy Awards and 20 Grammys), Jesse Steinfeld (a former Surgeon General of the United States), Pete Maravich (a college basketball Hall of Famer), scientists, authors, over a dozen NFL players, multiple MLB players, and an NHL player.

Playing Through the Whistle frames the history of Aliquippa through the lens of four different football coaches, generations of athletes, and the cultural events in each of their respective eras, including steel strikes, race riots, crime and drugs, football, and the decline of the steel industry.

Considering that Aliquippa’s population was only 27,000 people in its heyday in 1950 and has steadily declined to just over 9,000 people today, the staggering number of success stories per capita is uncommon and perhaps unprecedented.

The harsh realities of life in the steel mill and ruthless crime on the streets pushed people to better themselves and build on the generation before them, which often meant finding a path out of Aliquippa. At its core, that makes Playing Through the Whistle a story about self-made individuals who created their own opportunities, as the status quo was a dead end of crime and unemployment.

Telling the story of Tony Dorsett, Price writes:

Dorsett was running from failure, shame, even death, and lucky to have come late in the family line. Surrounded by cautionary tales, he was the only one sensitive enough to be able to read them.

The mill? Wes Dorsett told all his boys: “Come in this place, you don’t know if you’re coming out. And if you do you might be missing an arm or eye or leg. Do something for yourself.” But his brothers, at one time or another, all ended up working at J&L. Only Tony listened.

Many of those who didn’t get swallowed up by the mill got caught up in crime. Ty Law, an Aliquippa alumnus who went on to have a successful football career at Michigan and won three Super Bowls in the NFL, did a brief stint selling crack as a teenager and his mother once sold his football awards to fuel her drug habit.

The future of Aliquippa is unclear and probably murky at best. In the book’s closing chapter, some of the stars of years gone by offer a grim outlook of things to come. That said, youthful naivety breeds success in many areas of life, so it’s interesting to see that one person who expresses optimism for Aliquippa’s future is recent graduate Kaezon Pugh:

Pugh has a dream, one he doesn’t talk about much. It involves the dodgy streets of Plan 12 and the corner where his friend Tiquai died, the crumbling Pit, his mom living up on a darkened street off Monaca Road. It involves, even, all the factors that pushed his dad to pull a trigger and go off to jail.

“My plans? If I ever make it, I want to talk to all the big celebrities that came from around here and together we’ll just rebuild Aliquippa,” Pugh said that night in October. “Make it new. Get it to start feeling, like: I’m home again. I would love that feeling. That would be the best — to have everybody who’s made it out come back and just . . . enjoy ourselves. Like a family again.” A winter’s chill was already in the air.

He let the idea marinate a moment; a shaft of light spilled from the living room window onto the darkened porch, enough to see Pugh nod and smile. “I think it can happen,” he said. “I’ll make it happen.”

Shoe Dog: A Memoir by the Creator of Nike

By Phil Knight (Goodreads)

I couldn’t put down Shoe Dog by Phil Knight, the co-founder of Nike.

After graduating from college, Knight had a “crazy idea” to start a shoe company. He traveled to Japan and boldly negotiated a business deal with Onitsuka to distribute their shoes in the United States, even though he had yet to form a company. With the Onitsuka deal in hand, Knight launched Blue Ribbon Sports, which he slowly grew from a couple thousand dollars to over $2 million in sales, consisting almost entirely of selling Onitsuka shoes. When Onitsuka conspired to cut off Blue Ribbon, Knight steered his company to manufacturing its own shoes, which it called “Nike.” The name Nike, for the Greek goddess of victory, came to one of the company’s executive team members in a dream. Had that not happened, the shoe would have been called “Dimension Six.”

Shoe Dog is a compelling read, weaving together tales spanning Japanese partnerships, cash and credit issues, attracting top athletes to wear Nike, the death of Steve Prefontaine, a lawsuit against Onitsuka, expansion into China, inventory issues, a standoff with the U.S. Customs Service, and an IPO. Knight doesn’t hold back; the book is raw and honest even when it covers his personal failings and character flaws.

While Nike is seen as an unqualified success today, Shoe Dog provides a striking look at how the business was precariously close to collapse on many occasions.

After telling the staff of Blue Ribbon that Onitsuka had cut them off, Phil Knight looked around the room at the shocked and concerned employees at a staff meeting before saying:

“What I’m trying to say is, we’ve got them right where we want them.” Johnson lifted his eyes. Everyone around the table lifted their eyes. They sat up straighter. “This is — the moment,” I said. “This is the moment we’ve been waiting for. Our moment. No more selling someone else’s brand. No more working for someone else. Onitsuka has been holding us down for years. Their late deliveries, their mixed-up orders, their refusal to hear and implement our design ideas — who among us isn’t sick of dealing with all that?

It’s time we faced facts: If we’re going to succeed, or fail, we should do so on our own terms, with our own ideas — our own brand. We posted two million in sales last year . . . none of which had anything to do with Onitsuka. That number was a testament to our ingenuity and hard work. Let’s not look at this as a crisis. Let’s look at this as our liberation. Our Independence Day.

“Yes, it’s going to be rough. I won’t lie to you. We’re definitely going to war, people. But we know the terrain. We know our way around Japan now. And that’s one reason I feel in my heart this is a war we can win. And if we win it, when we win it, I see great things for us on the other side of victory. We are still alive, people. We are still. Alive.”

This passage is reminiscent of Paul Graham’s How Not to Die essay, where he said “So I’ll tell you now: bad shit is coming… The odds of getting from launch to liquidity without some kind of disaster happening are one in a thousand… So don’t get demoralized.”

Knight circles back to the same theme several times throughout the book, repeating a quote from Nike co-founder Bill Bowerman:

“The cowards never started and the weak died along the way — that leaves us.”

To Pixar and Beyond: My Unlikely Journey with Steve Jobs to Make Entertainment History

By Lawrence Levy (Goodreads)

In To Pixar and Beyond, Lawrence Levy, the first CFO of Pixar, tells the story of his recruitment by Steve Jobs and his subsequent work to get the company on sound financial footing, release Toy Story, have an IPO, and negotiate a favorable deal with Disney.

It’s an excellent read, packed with lessons about Pixar’s innovation and interspersed with Steve Jobs’ trademark tenacity. It serves as a complement to 2014’s Creativity Inc. by Pixar co-founder Ed Catmull.

Before Levy’s arrival at Pixar, Steve Jobs was writing personal checks to fund the company. Levy guided Pixar to financial sustainability, which required cutting side initiatives like making commercials and selling software tools. Levy also understood and embraced the fact that Pixar could not afford to lose its culture. He walked the fine line of addressing the business’s bottom line and fostering innovation, saying:

I had long been fascinated by why Silicon Valley existed at all. My work with new businesses left me mystified as to why giant companies with enormous resources and seasoned management teams allowed tiny start-ups to eat into their markets.

Why hadn’t IBM, which led the computing world for decades, or Xerox, which invented the graphical user interface, not themselves become Microsoft and Apple? Years earlier, why hadn’t the railroads become airlines? More important to my present task, today, why wouldn’t Disney become Pixar? If Pixar succeeded at all, wouldn’t Disney, the king of the animation hill for more than two generations, want to claim computer animation for itself?

The answer was that it definitely would. What would stop it? The answer, I believed, had to do with one thing: culture. Culture is the invisible force on which innovation depends. We like to pin the mantle of invention on individuals, not circumstances. We anoint heroes and tell their stories. Yet innovation is a collective undertaking.

Whiplash: How to Survive Our Faster Future

By Joi Ito and Jeff Howe (Goodreads)

Whiplash, as the title suggests, is a whirlwind tour through technologies that are revolutionizing the way we live and work.

Ito and Howe frame these technologies as nine principles, many of which are contrary to the way that traditional businesses operate and think.

In fact, innovative thinkers often fail to see the larger potential for their idea. Companies apply technology and improve on it incrementally, but the environment around them changes exponentially.

The Lumière brothers, who invented and pioneered projected films, saw their creation as a novelty. “The cinema is an invention without a future,” they said. Ito elaborates:

In failing to comprehend the significance of their own invention, the Lumières put themselves in excellent company. Some of our most celebrated inventors, engineers, and technologists have failed to understand the potential of their own work. In fact, if history is any guide, it’s those closest to a given technology who are least likely to predict its ultimate use.

Samuel Morse saw telecommunications as an “electric toy.” Thomas Edison invented the phonograph, but it took many years for other innovators to realize the application of “playing music,” which in turn created the recording industry. In 1977, Ken Olson of DEC said there was “no reason for any individual to have a computer in his home.” And Microsoft CEO Steve Ballmer stated that there was “no chance that the iPhone is going to get any significant market share.”

These miscalculations are all rooted in the fact that comprehending the big picture is difficult. As Ito says, “our technologies have outpaced our ability, as a society, to understand them.” We’re a product of the current environment and often can’t comprehend how to think about something beyond our immediate frame of reference. He elaborates:

Our brains, at least, remain largely the same organs that believed the automobile to be a passing fancy, or for that matter, that fire was just a technology for keeping us warm and producing interesting shadows on the cave wall…

Long periods of relative stability are followed by periods of violent upheaval triggered by a rapid change in external circumstance, be it political revolution, the rise of a disruptive new technology, or the arrival of a new predator into a previously stable ecosystem. These transitions — evolutionary biologists call them “periods of speciation” — aren’t pretty.

There’s a strong case to be made that we’re going through a doozy of a transition right now, a dramatic change in our own ecosystem. It is, in short, a helluva time to be alive, assuming you don’t get caught in one of the coming cataclysms.

Lessons

Pour passion and creativity into everything you do and don’t take it for granted. (From The Only Rule Is It Has to Work)

Work hard and chart your own course. Naive thinking can remove preconceived limitations on how you approach things. (From Playing Through the Whistle)

Focus on “why” and “what,” and trust your team to figure out “how.” Challenges are inevitable, approach them with candor and belief in the overall mission. (From Shoe Dog)

Innovation is the lifeblood of successful companies. Find ways to make this part of your culture. (From To Pixar and Beyond)

Think bigger and look outside of your immediate frame of reference. Are you building a feature when you could be building a system? Are you making a product when you could be making an industry? (From Whiplash)

Summary

That’s it! 2016 was a great year for books.

I only included my five favorite books published in 2016, but there were several honorable mentions. I also read some excellent books published in previous years. And I still have numerous highly recommended books from 2016 to read.

Hopefully, you found these inspiring or have some new ideas for reading material.

--

--

Chris Szymansky

CTO at Fieldguide (https://fieldguide.io). Prev. engineering and product at Atrium and JazzHR.