In Search of Better Decisions: 2022 in Books

Kristen Craft
7 min readJan 8, 2023

For the past 3 years, I’ve enjoyed tracking the books I’ve read and summarizing the themes I’ve encountered. My 2020 reading list was rife with themes of connection during a year that was otherwise so devoid of it. My 2021 list was peppered with a disproportionate number of dystopian narratives and stories of trauma, which, I believe in retrospect was an attempt to sort through my own feelings about the state of the world.

This year, I explored the theme of decision making. How do we make good decisions? How can we tell if they’re good? What are the biases that get in the way of good decisions? How can we better communicate with others about the decisions we make? Like anyone, I’ve made good decisions and bad. Given that we all make millions of decisions over the course of our lives, it seems worth exploring how we can improve this skillset.

Some of the books that focus on this theme include The Biggest Bluff, Thinking in Bets, Atomic Habits, and The Cardturner. Various memoirs I read this year echo this theme as well. After all, a memoir is often an author’s attempt to gain a better understanding of their own choices and communicate the impact of those choices. In Crying in H Mart Michelle Zauner explores the decisions she made in navigating her mother’s terminal illness and death, while in All You Can Ever Know, Nicole Chung explores the decisions involved in seeking out her biological family. The following are some lessons I took away from exploring this theme.

2022 book lineup

All Decisions are Bets

We tend to think about decisions in binary terms: “the right decision” or “the wrong decision” when in reality, decisions are rarely so binary. In order to weigh the pros and cons of any decision, we need information. And yet, we never have perfect information. We must seek to do the best we can with the information we have.

As James Clear writes in Atomic Habits:

“Life feels reactive, but it is actually predictive. All day long, you are making your best guess of how to act given what you’ve just seen and what has worked for you in the past. You are endlessly predicting what will happen in the next moment.”

This reality — ie operating and making decisions amidst uncertainty — is what makes poker such an interesting corollary. In poker, you’re always making decisions and bets, based on the information in front of you while also staying aware of what info might be missing, so as to calibrate your bets according to your certainty level.

As Maria Konnikova writes in The Biggest Bluff:

“Poker, unlike quite any other game, mirrors life. It isn’t the roulette wheel of pure chance, nor is it the chess of mathematical elegance and perfect information.”

Most styles of poker present some knowns and some unknowns. Similarly, life will throw many knowns and unknowns our way. We can learn to make better decisions by being more aware of our own blind spots, communicating them to others, and developing smart systems to overcome them.

Smart Processes Support Smart Decision Making

So, how do we remain aware of our limitations and adjust our decision making behaviors? Often, it comes down to having good systems in place to navigate uncertainty. We need to get better at the process of analyzing decisions, making decisions amidst bias, and at learning from our mistakes. As Annie Duke notes in Thinking in Bets:

“What makes a decision great is not that it has a great outcome. A great decision is the result of a good process, and that process must include an attempt to accurately represent our own state of knowledge.”

A few specific processes we can use to make better decisions:

  1. Create space for “organized skepticism”: Engaging in organized skepticism means making space for uncertainty and doubt in an intentional way. I’ve long been a fan of the post mortem (assessing a situation after the fact to determine what worked, what didn’t, and what could be done differently next time.) I’m a more recent convert to the idea of the pre-mortem: talking through what might go wrong before even making a decision. When working with a team, this might mean breaking people into a red team and a blue team to run the traps on both sides of a potential decision. Processes like these help bring forth new perspectives that might otherwise go ignored.
  2. Put a probability on our own certainty: We humans love hyperbole, so it’s not uncommon for people to say things like “I’m 100% sure this is the right answer” even when we’re nowhere close to 100% certainty. Instead, create space — in your own thinking and in your conversations with others — to articulate your certainty level.
  3. Practice the 10/10/10 rule: Ask yourself “how will I feel about this in 10 minutes, 10 months, and 10 years?” We often over-index on how we feel in the moment. Taking a beat to think about your future self could help you avoid making a costly misstep.

Practice makes ̶p̶e̶r̶f̶e̶c̶t̶ ̶ improvement

There are no silver bullets in life, and these systems and process are no exception. They are frameworks that can help you improve over time. We all need to put in the work and get in our reps. We need repetition and practice when it comes to our processes of analysis, decision making, and learning from mistakes.

Our goal when it comes to practicing these processes shouldn’t be perfection, but rather, continuous improvement. Every time we approach a decision with greater intentionality, we’re investing in ourselves. As James Clear writes:

“The more you repeat an activity, the more the structure of your brain changes to become efficient at that activity. Neuroscientists call this long-term potentiation, which refers to the strengthening of connections between neurons in the brain based on recent patterns of activity. With each repetition, cell-to-cell signaling improves and the neural connections tighten.”

This is part of the reason why a bias to action is so important in life and in our decision making processes. Some of the most powerful leaders and companies have relied for decades on the power of “high-velocity decision making” and with good reason. We can only learn from our mistaken decisions if and when we actually make a decision.

Gaining Comfort amidst Uncertainty and Mistakes

There’s power in seeking to rise above our own biases (of which there are so many!) Most of the decisions we make will be tinged with uncertainty, and many of them will turn out to be wrong. It behooves us to acknowledge our uncertainty and our mistakes. We’re all outcome junkies: we like to assume responsibility for our positive outcomes, and we like to blame bad luck when we fail. But blaming bad luck for a poor decision robs us of the opportunity to fully learn from our mistakes.

So, here’s to more uncertainty and mistakes in 2023! A strange thing to seek out, perhaps, but what if we viewed them instead as opportunities? And, really, we can’t do much to avoid uncertainty, so it feels like a worthy cause to try to become more comfortable in their midst.

Note bene (since I’ve always been the type of person who’s always liked to include many “P.S.”s in my letters)

This post doesn’t touch on the many incredible works of fiction I read this year. Some of my favorites from 2022 include Circe, The Prophets, French Exit, The Gunkle, Lessons in Chemistry, and The Island of Sea Women. So many of my favorites were recommended to me by beloved friends and family members. I’m deeply grateful for the feeling of connection I experience when I read something that a loved one suggested. Thank you to all of the people who’ve shared their book recommendations and analyses with me in 2022.

My 2022 Reading List:

  1. Seveneves by Neal Stephenson
  2. Call Me by Your Name by Andre Aciman
  3. Zone One by Colson Whitehead
  4. A Grain of Wheat by Ngugi wa Thiong’o
  5. The Girls’ Guide to Hunting and Fishing by Melissa Bank
  6. Circe by Madeline Miller
  7. Piranesi by Susanna Clarke
  8. How the Word Is Passed by Clint Smith
  9. Ghost Wall by Sarah Moss
  10. The Maidens by Alex Michaelides
  11. Wintering by Katherine May
  12. Crying in H Mart by Michelle Zauner
  13. All You Can Ever Know by Nicole Chung
  14. The Prophets by Robert Jones, Jr.
  15. French Exit by Patrick DeWitt
  16. The Rose Code by Kate Quinn
  17. The Anomaly by Hervé Le Tellier
  18. Harlem Shuffle by Colson Whitehead
  19. Ariadne by Jennifer Saint
  20. The Guncle by Steven Rowley
  21. How to Stop Time by Matt Haig
  22. The Art of Gathering by Priya Parker
  23. The Invisible Life of Addie LaRue by V.E. Schwab
  24. Cackle by Rachel Harrison
  25. Malibu Rising by Taylor Jenkins Reid
  26. The Last Thing He Told Me by Laura Dave
  27. The Paper Palace by Miranda Cowley Heller
  28. The Biggest Bluff by Maria Konnikova
  29. Thinking in Bets by Annie Duke
  30. Cloud Cuckoo Land by Anthony Doerr
  31. A Court of Thorns and Roses by Sarah J. Maas
  32. A Life’s Work by Rachel Cusk
  33. Lessons in Chemistry by Bonnie Garmus
  34. Verity by Colleen Hoover
  35. Miss Iceland by Auður Ava Ólafsdóttir
  36. Daisy Jones & the Six by Taylor Jenkins Reid
  37. The Hare by Melanie Finn
  38. I’ll Show Myself Out by Jessi Klei
  39. Homeland Elegies by Ayad Akhtar
  40. A Court of Mist and Fury by Sarah J. Maas
  41. The Candy House by Jennifer Egan
  42. No One is Talking about This by Patricia Lockwood
  43. I Love You but I’ve Chosen Darkness by Claire Vaye Watkins
  44. Admissions: A Memoir of Surviving Boarding School by Kendra James
  45. A Court of Wings and Ruin by Sarah J. Maas
  46. The Island of Sea Women by Lisa See
  47. Under the Volcano by Malcolm Lowry
  48. The Cardturner by Louis Sachar
  49. A Boy and His Dog at the End of the World by C.A. Fletcher
  50. Sea of Tranquility by Emily St. John Mandel
  51. Girl, Woman, Other by Bernadine Evaristo
  52. Atomic Habits by James Clear
  53. From Here to Eternity by James Jones

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Kristen Craft

Early-stage startup advisor at Silicon Valley Bank, parent, reader, Bostonian