References for Better Decision Making

Russ Roberts includes this story in  Wild Problems:

Persi Diaconis was agonizing about a decision whether or not to move to Harvard from Stanford. He had bored his friends silly with endless discussion. Finally, one of them said, “You’re one of our leading decision theorists. Maybe you should make a list of the costs and benefits and try to roughly calculate your expected utility.” Without thinking, Persi blurted out, “Come on, Sandy, this is serious. (As quoted in this book review)

It is one of many stories throughout Roberts' insightful book around how to make difficult life decisions such as whom to marry, where to live and what profession to pursue.  These decisions don't have natural feedback loops. There is no way to experiment with counterfactuals.  As a result, the typical toolkits we employ for decision making (cost benefit, scenario planning, regret minimization) don't apply.

I enjoyed Roberts' book and the advice provided:  focus on principles, not pleasure;  find beauty in making long-term commitments that adhere to your principles.  

Perhaps because I am myself making several significant life decisions currently, I found myself picking up several books in this genre.  It's a tricky subject: every author needs to find some what to rationalize a decision framework that discards rationality.  Here's what I want to remember about this work:

Quit by Annie Duke - advocates for much greater experimentation in decision making. If costs are low, you should vary decisions to get more data on what works or doesn't work for you.  Even when costs are high (as in Roberts' Wild Problems) framework, she argues we have many biases that prevent us from change, so should tend to favor decisions that take on more change, such as quitting.  (Duke also wrote the terrific How to Decide with many tools for better decision making, including in group settings.)

This Could be Our Future by Yancey Strickler.  Strickler adds to this discussion a great framework for breaking out of selfish, hedonistic tendencies we all are at risk of in decision making.  He proposes evaluating a decision in a 2x2 Bento Box framework.  What are the implications of the choice for:

Since reading the book, I use the mental model regularly. I like how I am considering my own self interest in every square, not trying to shoehorn in other objectives and goals. But, the four squares each put a very different frame on my self interest, which pushes me to consider the decision more deeply.  

Happier Hour by Cassie Holmes.  I read this more because the sub-title was on 'beating distraction' which is a problem I find myself running up against more often these days.  But the book also provides simple tools for making better decisions with respect to time. I did the exercises, and found it helpful to go through the process of asking myself where I find greater fulfillment within my days.   Just writing down at the end of the day where you found happiness had the impact of shifting how I spent my time. As she writes, the days turn into weeks and the weeks years, which result in different long term outcomes from a simple task.

How Will You Measure Your Life - by Clay Christensen.  The book I have returned to most in this genre. Less about specific tools and decision points, and more about frameworks for leading a fulfilling life.   Christensen's application of his jobs to be done to a marriage and parenting continues to support me in major decisions.   Christensen puts significant weight on identity rather than incentive.  Looking introspectively at how you define yourself, and also understanding the decisions of others through how they define themselves, to understand a decision.  As I get older, I connect more with this view than the standard 'show me the incentive and I'll tell you the outcome' view of the world.

So Good They Can't Ignore You -  by Cal Newport. While not explicitly about decision making in the general form, this book provides a great framework for career decision making that applies more broadly.  The title references Steve Martin (whose Born Standing Up is terrific in this genre also).  Develop skills first. These skills can later open up options in a wide variety of fields, so you then marry passion with work.  The generalized point is good decisions result from previous work. If you don't have desirable options today, consider the possibility of delaying the choice, putting in more work, and getting to a point where you have better choices to select from.  

Money and Love: An Intelligent Roadmap for Life's Biggest Decisions by Abby Davisson.  This book I actually haven't read yet. It comes out January 10th, but I have pre-ordered.  Davisson tackles the problem from the vantage point of balancing heart and head.  It also seems to recognize for many of us, major life decisions are made within a marriage / long term partnership, which creates its own dynamics.  I'm looking forward to reading it, and want to remember it here.

The Knowledge Project by Shane Farnum. I've listened to this podcast on and off for the past five years. While the link here is to a specific piece on better decision making, I recommend the podcast as a whole, and many of the conversations.

Here's what I conclude.  

• There are a number of globally helpful systems and recommendations to improve your decision making with respect to day to day choices.  Read Annie Duke, Cal Newport and Shane Parrish for these tips and tricks which can be implemented universally.  
• As you move to large 'wild problems' of long term importance to your life such as whether to become a parent or marry a spouse, the best you can hope for is a framework for how to guide your thinking.  What resonates in this work will be personal to you, and even to a time in your life.   Some approaches are more academic (Christensen and Holmes), some philosophical/behavioral economics (Roberts and Duke) and some intuitive (Strickler).   Returning to these books over provides helpful reminders and continued guidance for making better long term decisions but they won't provide a simple how to guide.

At my current moment in time, the point around consistency with identity resonates with me.  As does the aspirational self.  Making a decision that is consistent with both my internal monologue for who I am, and also with whom I aspire to be in the future.  Journaling, walking, and talking to my family and friends are helpful tools in the discernment process to tease out which path is most consistent with these goals, which isn't always clear.