My 2021 Reading Journey

2021….. what’s another year?

This year was a journey, with some detours and layovers I’d rather forget. With Covid continuing to release new, better versions of a previous edition at a faster rate than Taylor Swift, it’s safe to say that there really wasn’t a reason to disable my self-titled “consumption mode” that I re-kicked into gear last year.

2021 marked my (and a lot of the world’s) first full year working remotely and that turned into being very remote for me as the year wore on. This inspired some of my reading choices with a lot of the learnings being reinforced from an outcrop of rock in Croatia where I deployed a 2 month-long project to production at around 3am local time. One of my best sleeps of the year followed.

The year of the Ox also corresponded with my first full year of having a kindle. Having moved again this year, this time a little further afield, now I even more-so appreciate the weightlessness of the digital format. There are a plethora of subscriptions that can tie in with Kindles, but my personal favorite is Readwise. I’ve used it to revisit highlights daily, and it’s a key element in reinforcing the learnings from books that would otherwise be lost from my short term memory shortly after finishing the Acknowledgements. I just wish I made the move to Kindle much much sooner, as lugging three 40l boxes filled with books into a U-haul storage locker certainly ain’t fun!

Making friends on the R/USTravelBan subreddit was something I hadn’t exactly predicted heading into the new year. Having played Russian Roulette with the joy that is America’s Visa system, I undoubtedly lost and my character respawned back home in Galway. Making the journey back into the US was for a joyous occasion but wasn’t without its trials and tribulations. Following a lot of planning and spreadsheets, I landed in Dubrovnik, Croatia from where I’d attempt to make it back into the US. While there I tested the methods of my most recent readings and started to knock down the thick dominos which were the chapters of Antifragile.

Antifragile is probably a good antonym for how I was feeling as I closed my kindle and disembarked from the plane headed towards CBP at JFK in New York. As Michael Lewis puts it in ‘Boomerang’: “You can tell a lot about a country by observing how much better they treat themselves than foreigners at the point of entry.” Safe to say I wasn’t in the easy, free-flowing lane that welcomes American’s home, but my inner desire to improve upon negotiation tactics for next time did light a small fire inside me that I eventually tended to later on.

Planes, trains, automobiles, multiple layovers and delayed flights gave me a great excuse to catch up on reading throughout the year. Moreover, I finally put together a booklist this year to create some more reliability and structure in my selection process. Now when I tell people that I’m adding their recommendation to the list, one does now actually exist, in place of storing it across scrap pieces of paper or across random notes on my phone.

This is my second attempt at documenting my yearly reading journey, and following some great conversations with folks after last year’s edition, some of you will find your great and welcomed recommendations on the list. I hope you enjoy my collection below and I can’t wait to do it all again next year with a little help from my friends!

Now onto the books themselves

My year was bookended (Boomerang aside) by two of the most tweeted-about books of the last 18 months. That was followed by a return to fiction, which when I return, I often ask myself why I ever leave. This helped cover up and occupy some of those dark, cold Chicago days where there is more feet of snow on the pavement than cars on the road around the neighborhood.

Whilst “Drive to Survive” on Netflix was re-kindling my youthful love of Formula 1, (which spanned from occasional Sunday’s watching a grainy POV of Schumacher to attempted recreations of the speed on the Playstation 2), I needed some basketball history back in my life as the regular season drew to a close. The story of the Lakers dynasty is one that examines the Shaq-Kobe relationship, how the Lakers won despite Kobe’s attitude/glory-hunting/personality and just some great stories about some of the role-players that helped them to multiple Final’s appearances.

“..the more contexts in which something is learned, the more the learner creates abstract models, and the less they rely on any particular example. Learners become better at applying their knowledge to a situation they’ve never seen before, which is the essence of creativity.”

— David Epstein, Range: How Generalists Triumph in a Specialized World

“Until everything topples, we have no idea what we actually have, how precariously and perfectly it all hangs together.”

— Blake Crouch, Dark Matter

“In my experience, those who have the greatest respect for the rules also take the most enjoyment in breaking them.”

— Lucy Foley, The Guest List

Shaq on Isaiah Rider:

“This is no lie; ... He lived in the team hotel, which was right here. And the back door of the gym was right here- facing the hotel. Yards apart. Mother-fucker didn’t come to practice for three straight days because of a flat tire.”

— Jeff Pearlman, Three Ring Circus

As the days brightened, I wanted better bang for my b̶o̶o̶k̶ buck so I returned to the principle of the Lindy effect, basically the principle that the older something is, the longer it’s likely to be around in the future. Zero to one is one of the books that I return to every couple months and always come away with a new take or something that’s relevant to me in the moment. Deep Work has some strong principles and takeaways, but it’s really a book that would likely be better enjoyed if reduced to a 10-page/Blinkist summary.

“Unless you have perfectly conventional beliefs, it’s rarely a good idea to tell everybody everything that you know. So who do you tell? Whoever you need to, and no more. In practice, there’s always a golden mean between telling nobody and telling everybody — and that’s a company. The best entrepreneurs know this: every great business is built around a secret that’s hidden from the outside.”

On hiring for a startup: “..then promise what no others can: the opportunity to do irreplaceable work on a unique problem alongside great people.”

— Peter Thiel, Zero To One

“To produce at your peak level you need to work for extended periods with full concentration on a single task free from distraction. Put another way, the type of work that optimizes your performance is deep work.”

— Cal Newport, Deep Work

The couple weeks leading up to mid-July coincided with me moving states and then eventually back to Ireland where working remotely was going to mean something a whole-lot different than being just a 10-min commute from the office. Basecamp are thought-leaders when it comes to a plethora of business topics and from their books it’s clear to see why. My brain’s compute cycles were consumed with thoughts on company culture, project planning and prioritization throughout the summer. That might not sound enthralling, but that food for thought nourished some of the questions that had been eating away inside me and helped me hone-in on some of my work-related principles.

“Whenever you can, swap ‘Let’s think about it’ for ‘Let’s decide on it.’ Commit to making decisions. Don’t wait for the perfect solution. Decide and move forward.”

“Clear writing is a sign of clear thinking. Great writers know how to communicate. They make things easy to understand. They can put themselves in someone else’s shoes. They know what to omit. And those are qualities you want in any candidate. Writing is making a comeback all over our society… Writing is today’s currency for good ideas.”

— Jason Fried & David Heinemeier Hansson, Rework

“A quality hour is 1 × 60, not 4 × 15. A quality day is at least 4 × 60, not 4 × 15 × 4.”

“But it’s a mighty thin line when you’re trapped in an ASAP chamber. All chat all the time conditions you to believe everything’s worth discussing quickly right now, except that hardly anything is. Almost everything can and should wait until someone has had a chance to think it through and properly write it up.”

“When we present work, it’s almost always written up first. A complete idea in the form of a carefully composed multipage document. Illustrated, whenever possible.”

— Jason Fried & David Heinemeier Hansson, It Doesn’t Have To Be Crazy At Work

“One of the secret benefits of hiring remote workers is that the work itself becomes the yardstick to judge someone’s performance. When you can’t see someone all day long, the only thing you have to evaluate is the work. A lot of the petty evaluation stats just melt away.”

— Jason Fried & David Heinemeier Hansson, Remote: Office Not Required

The sole book I picked-up and was unable to finish during the year was “Seeking Wisdom: From Darwin to Munger”. A book deep-rooted in first principles, but it’s a long, long tough read, especially when your sole means of consuming it is via a dodgy PDF and when your confidence is shook following an hour of reading to see that your progress bar is barely up one percentage point! Antifragile, is another heavy read, but it’s the culmination of a lifetime of thinking by the “anti-fragalista”, Nassim Taleb. You will come away with a new vocabulary after reading it, but more importantly the mental models explained will not only help you better understand the hows and why’s of daily life, but understand how to make yourself more “antifragile” to all that life can and will throw at you.

“Systems subjected to randomness — and unpredictability — build a mechanism beyond the robust to opportunistically reinvent themselves each generation, with a continuous change of population and species.”

“Antifragility equals more to gain than to lose equals more upside than downside equals asymmetry (favorable) equals likes volatility. And if you make more when you are right than you are hurt when you are wrong, then you will benefit, in the long run, from volatility”

“Good systems such as airlines are set up to have small errors, independent from each other — or, in effect, negatively correlated to each other, since mistakes lower the odds of future mistakes. This is one way to see how one environment can be antifragile (aviation) and the other fragile (modern economic life with “earth is flat” style interconnectedness). If every plane crash makes the next one less likely, every bank crash makes the next one more likely. We need to eliminate the second type of error — the one that produces contagion — in our construction of an ideal socioeconomic system.”

— Nassim Nicholas Taleb, Antifragile: Things That Gain from Disorder

Who doesn’t love the dramatic hostage negotiation scenes in movies, but as Chris Voss explains, these are far from the typical cases that negotiators actually have to deal with. Most negotiations, whether it’s over a business deal or the safe return of a kidnapping hostage, actually take weeks or more, and Voss breaks down the tactics to be used regardless of what domain you play in. If that domain happens to be Startups, Horowitz’s book is a must read. One that has been on my list (stack of post-its) for years, it didn’t disappoint. It really drove home the importance of communication within the Org-structure, key principles in hiring and training, buying into the mission of the company and how the role of CEO is frequently jumping on the least deadly-looking grenade/trying to steer the ship out of a situation that looks hopeless (Suez Canal / WFIO).

“The goal is to identify what your counterparts actually need (monetarily, emotionally, or otherwise) and get them feeling safe enough to talk and talk and talk some more about what they want.”

“‘No’ is not a failure. We have learned that “No” is the anti-“Yes” and therefore a word to be avoided at all costs. But it really often just means “Wait” or ‘I’m not comfortable with that.’ Learn how to hear it calmly. It is not the end of the negotiation, but the beginning.”

— Chris Voss, Never Split The Difference

“People always ask me, “What’s the secret to being a successful CEO?” Sadly, there is no secret, but if there is one skill that stands out, it’s the ability to focus and make the best move when there are no good moves. It’s the moments where you feel most like hiding or dying that you can make the biggest difference as a CEO.”

— Ben Horowitz, The Hard Thing About Hard Things

The Oxygen advantage was one of my favorite books from 2019 because it opened my eyes to the importance of breathing techniques and just breathing in general. “Breath” covers less of the actual methods and instead more of the origin story and developmental history behind the techniques. Nestor himself kicks-off the book with a crazy experiment he and another pulmonaut took part in, and it’s safe to say it would scare you from ever breathing with your mouth open again.

Less scary, but equally important in everyday life, the “Psychology of Money” succinctly summarizes the key elements with which we should be using to understand ourselves as humans, not spreadsheet-driven fintech AI, and using that to develop our own core-principles when it comes to money. Everyone has a different perspective on the world, and in understanding that, the book drives home the need to deterermining what your core values, time horizons, tolerances for risk each are amongst others, so that you can help yourself figure out what financial game or lack thereof you’re actually playing.

Lastly, when it comes to finance and playing games, it’s safe to say Europe and beyond were doing both whilst highly leveraged until the “arse fell out of it” as my Mam would say. The whole story of Europe, including Ireland (mea culpa) growing to be a massive ticking time-bomb throughout the 90’s and into the 2000’s is another thriller delivered by Lewis.

“They gathered two decades of data from 5,200 subjects, crunched the numbers, and discovered that the greatest indicator of life span wasn’t genetics, diet, or the amount of daily exercise, as many had suspected. It was lung capacity.”

— James Nestor, Breath: The New Science Of A Lost Art

“..the foundation of, “does this help me sleep at night?” is the best universal guidepost for all financial decisions.”

“Become OK with a lot of things going wrong. You can be wrong half the time and still make a fortune”

“Use money to gain control over your time, because not having control of your time is such a powerful and universal drag on happiness. The ability to do what you want, when you want, with who you want, for as long as you want to, pays the highest dividend that exists in finance.”

— Morgan Housel, The Psychology of Money

“What happened was that everyone in Ireland had the idea that somewhere in Ireland there was a little wise old man who was in charge of the money, and this was the first time they’d ever seen this little man,” says McCarthy. “And then they saw him and said, Who the fuck was that??? Is that the fucking guy who is in charge of the money??? That’s when everyone panicked.”

— Michael Lewis, Boomerang