3 Lessons from 43 Books in 2019

Stuart O'Keeffe
8 min readJan 28, 2020

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Photo by Alfons Morales on Unsplash

I finished a lot of amazing books in 2019 — from classic works of fiction to deep dives into philosophy & incentive structures. Instead of talking about which books were my favorite or which I think were the most influential — I want to go over 3 of the lessons I’ve learned and want to keep in mind for 2020 and beyond.

If you want to see the full list of books I finished this year, they are listed at the end.

1: Fear as an awareness tactic is effective — but may hurt our decision making

Fear was a major topic of discussion across a number of the books I went through this year. A natural amount of fear can be helpful — its a motivating factor that can drive people to action and avoid negative outcomes. However, when that fear becomes too prevalent it can either drive us into making rash decisions or to becoming despondent and giving up.

In “Factfulness”, Hans Rosling raises the idea that most people are living with a negatively skewed interpretation of the world. There are many possible reasons behind why that might be — my guess is the overwhelmingly distressing articles I see every day online — but the main takeaway was that the fear and anxiety that comes from this negative world view may color how we deal with threats and resource allocation for the worse. For example — in the US, terrorism is the cause of <0.01% of deaths but accounts for >7% of Google searches on the cause of death and >30% of media coverage while heart disease makes up roughly 30% of deaths and gets <2.5% of media coverage. If we give in to fear — we may think that terrorism is the greatest threat to our nation and over-allocate time and money into addressing it. Meanwhile, we may be better off focusing on issues that are less scary — but more deadly — like heart disease. (source)

The team behind “Factfulness” has put out a quiz online where you can test your current understanding of the world — which I got primarily wrong (https://factfulnessquiz.com/)

The second takeaway I had on the topic of fear, was that it often gives way to unnecessary anxiety and feelings of hopelessness when there is little an individual can do to address the source. From another book, “The Practicing Stoic” by Ward Farnsworth, I loved the quote, “The trouble with fear, first is that it multiplies our problems… What then is more insane than to be tortured by things yet to be — not to save your strength for actual suffering…”. In today’s world, there are a lot of things that can make one afraid that seem too big to handle and sometimes becoming overly anxious about them causes useless suffering. We should try to only feel fear to the point where we can affect change then move on.

2: Power is relative to one’s dependence on others

Power — in governance, business and farm animals — was another major topic across titles. Something perhaps obvious, but that had never occurred to me, is that power is a relative state in that it only exists in comparison to others. In “The Dictator’s Handbook” by Bruce Bueno de Mesquita and Alastair Smith, rulers and entire governance structures were defined by the relative power leaders had compared to those they were beholden to. A core concept from the book was that for a leader to “survive” they needed to effectively follow only two rules — 1. Get Power, 2. Keep Power. For both rules, a leader needs supporters and the quantity of these necessary supporters is inversely proportional to how much actual power a leader has. A dictator with absolute power needs only to appease a few people (possibly the heads of commerce & military), but a functioning leader of a democracy needs a majority of the populace on their side to win elections. It follows that in a democracy, the leader has to use their power to help the greatest number of people in order to secure their vote and are thus beholden to them.

A perfect example of these power dynamics was shown in “Animal Farm” by George Orwell and its “more equal animals”. In the allegory, only the leading pigs were able to truly read & write the laws of the farm which allowed them to concentrate their power among themselves. Over time, they needed the support of fewer and fewer of the other animals until the non-pigs became “unimportant” to ruling over the farm. When the leading pigs were not beholden to the other animals, they began to act against the other animal's best interests.

On the business side of things, similarly to grow and strengthen one’s business, one needs to make sure they are not overly reliant on any one partner. In “Shoe Dog” by Phil Knight, Nike (at the time Blue Ribbon) was almost killed by their business partner and supplier Tiger. After surviving the ordeal, Phil ensured that he never relied on any single manufacturer again to prevent any manufacturer from having control over his business’s destiny. In this way he reduced his suppliers’ relative power by increasing the number of them.

3: “More Effort” isn’t always a good way to deal with a challenge

A bit of “self-help” philosophy I picked up in 2019 from books is the importance of strategically surrendering. As a somewhat restless overachiever — it's easy for me to fall back on the plan of just “hustling harder” when overwhelmed. However, while this can work in some cases (crunch time, the final stretch of a race, or working through a backlog of chores) its often way easier to instead re-evaluate what I’m actually trying to achieve.

The idea of “strategic yielding” came up in the book, “The Tao of Pooh” by Benjamin Hoff, when the author refers to the “Wu Wei” method of problem-solving. In this method, force is not met with force but with redirection of that energy. Many problems can be like punching a wall — the harder you hit the wall, the harder it will hit back. Take regular exercise for example — if I have to force myself to go to the gym every day and just “try hard” to get into better shape, the exercises will become a chore that I’ll end up dreading — making each subsequent visit to the gym harder. But instead, if I re-direct myself to exercise that I enjoy — like running outside instead of on a treadmill — doing it every day will be something I look forward to.

In the same vein, when just “hustling harder”, it's likely that a person won’t take the necessary time to evaluate how important the goals they are trying to achieve actually are to them. In “The Practicing Stoic,” wealth was defined as when someone “wants for nothing,” and this can mean one of two things — either the achievement of enough riches to satisfy all of a person’s desires or by simply wanting less. I loved this idea because its easy to look at social media and feel a twang of jealousy when I see someone on a yacht that’s likely more expensive than most homes. But, by taking the above idea to heart, it seems a lot cheaper and less stressful to not care about yachts than it would be to actually own and maintain one.

Related to this in “Unf*ck Yourself” by Gary Bishop, the reader is told that they should ask themselves, “Am I willing to do what is required to achieve this goal?” and if the answer is a resounding, “No!” then the reader should stop stressing about that goal. A person who doesn’t actually want to learn how to play the piano, shouldn’t feel upset by the fact that they can’t play. By discarding the goals we don’t actually care about, it becomes much easier to focus on the ones we do.

Bonus: Audiobooks are Awesome

In 2019 I hit a personal goal — the most books I’ve ever completed in a year! I was only able to get through all 43 by listening to audiobooks. I’ve mentioned this to a few people who’ve told me that it “didn’t really count as reading” but by my logic — I’ve gotten more out of books this year than any other.

Rarely am I able to find the time to actually sit down and read something, so audio was a godsend. I was able to read while commuting, working out, cooking, and just doing chores. Even if the naysayers are right and audiobooks are only 50% as effective as sitting down with a physical book — I was able to experience 4x as many books as I would have otherwise — a 2x gain for me!

~Stuart

Full List of Books (in no particular order):

Non-fiction:

  1. Buffett: The Making of an American Capitalist
  2. Meditations
  3. Bad Blood: Secrets and Lies in a Silicon Valley Startup
  4. Never Split the Difference: Negotiating As If Your Life Depended On It
  5. Not That Bad: Dispatches from Rape Culture
  6. Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future
  7. The Autobiography of Martin Luther King, Jr.
  8. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
  9. Steve Jobs
  10. Factfulness: Ten Reasons We’re Wrong About the World — and Why Things Are Better Than You Think
  11. Hit Makers: The Science of Popularity in an Age of Distraction
  12. The Dictator’s Handbook: Why Bad Behavior is Almost Always Good Politics
  13. Shoe Dog: A Memoir by the Creator of NIKE
  14. The Tao of Pooh
  15. Purple Cow: Transform Your Business by Being Remarkable
  16. Unfu*k Yourself: Get Out of Your Head and Into Your Life
  17. Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts
  18. Man’s Search for Meaning
  19. Hillbilly Elegy: A Memoir of a Family and Culture in Crisis
  20. Einstein: His Life and Universe
  21. Get Well Soon: History’s Worst Plagues and the Heroes Who Fought Them
  22. The Signal and the Noise: Why So Many Predictions Fail — But Some Don’t
  23. Ten Drugs: How Plants, Powders, and Pills Have Shaped the History of Medicine
  24. The Practicing Stoic: A Philosophical User’s Manual
  25. Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life

Fiction:

  1. Animal Farm
  2. The Sword of Destiny (The Witcher Series)
  3. Blood of Elves (The Witcher Series)
  4. Time of Contempt (The Witcher Series)
  5. Baptism of Fire (The Witcher Series)
  6. Tower of the Swallows (The Witcher Series)
  7. Lady of the Lake (The Witcher Series)
  8. Catch 22
  9. The Handmaid’s Tale
  10. Fahrenheit 451
  11. Slaughterhouse-Five
  12. The Divine Comedy
  13. Moby-Dick
  14. Dracula
  15. Of Mice and Men
  16. Crime and Punishment
  17. The Screwtape Letters
  18. The Stranger

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Stuart O'Keeffe

“The best way to get the right answer on the internet is not to ask a question; it’s to post the wrong answer.” — Cunningham’s Law; Principal at Great Oaks VC