How to Make Good Decisions without Rational Thinking

“All successful people operate by principles that help them be successful. Without principles, you would be forced to react to circumstances that come at you without considering what you value most and how to make choices to get what you want. This would prevent you from making the most of your life.” - Ray Dalio

When I was younger, I was bad at math. Growing up in this Age of Economics with folks equating “smart” with “rational” often made me feel insecure as to whether I would have the mental horsepower to make good decisions in a complex world. If I couldn’t solve a basic Sudoku puzzle (still can’t, by the way) how could I possibly succeed in the 21st century? The answer so far: good advice, hard experience, deep reflection, reading, intuition, and principles.

 The only way I’ve gotten anywhere in life so far is with this formula:

 –> 1. listen to advice from mentors

 –> 2. work hard to apply that advice in real settings

 –> 3. reflect on the experience

–> 4. repeat.

When I first started caring about my future, I was lucky to have mentors, and I took their advice as gospel. A local college student and a few successful older professionals guided me in the right direction, encouraging me to study hard, pursue projects, eat healthy, exercise, read books, and build a network. I listened, figuring: if mentors did these things and they were successful, then if I do these things I’ll be successful, too. All of the advice was pretty good, and my actions affected few people beside myself, so it wasn’t a big deal that I was much better at parts 1 and 2 of the above formula than part 3.

As life kept moving along, I continued asking for advice and found that most people were eager to supply it. After a few times misapplying good advice (my fault) and properly applying bad advice (also my fault), I learned to focus more on part 3: reflecting on my experiences. Reflection was like adding rocket fuel to the equation: it enabled me to get so much more leverage out of every bit of wisdom offered, and eventually helped me show value to mentors by sharing insights about how their advice played out in the field.

The other thing about reflection: it got me reading more. Some of the best mentors of all time–heads of state, philosophers, humanitarians, and business titans–wrote down all their wisdom. Reading quickly became a cyclical vehicle for internalizing and validating lessons I was learning from experience in the field.

These days, I’ve gotten to a point at which I’m almost always facing several complex decisions, so to ask for advice on every decision would be impossible and impractical. Seeking guidance from mentors (who, by the way, range from age 8 to 83, living to dead, in-person to remote) still helps me stay on track and ask the right questions, but part of becoming a leader is learning to take responsibility for decisions. Two tools have helped me tremendously in this regard: a) intuition, and b) principles.

Intuition. It’s the ability to channel all the internalized wisdom of personal experience into a single felt moment of directional intention. The University of Chicago taught me that I don’t naturally excel at rational thinking (or thinking, for that matter!). So instead of stumbling through tough subjects, I took a lighter course load and focused on sharpening my gut instincts outside of the classroom through writing, travel, entrepreneurial projects, and aikido. That choice has served me well, so long as I double-check my gut inclinations against principles (and still occasionally mentors, advisors, peers).

Principles. As my foundation of advice, experience, and reflection has grown, I’ve built a reservoir of personal wisdom that I can use to make decisions moving forward. I can let this sit as an electrically-charged pool of unarticulated feelings in my nervous system (intuition), or I can distill it into vertebrae of articulated thought that together form a backbone for confident action (principles). As Ray Dalio says, “Principles connect your values to your actions; they are beacons that guide your actions, and help you successfully deal with the laws of reality. It is to your principles that you turn when you face hard choices.” I took a rough hack at a few initial principles in my 31 Things I Learned in College post, and am slowly forming more. Here are two that have come in handy recently:

-Better to be in the arena than on the sidelines.

-Better to have fewer opinions and invest a lot of action behind those opinions than have a lot of opinions and invest little action behind any.

One process that has helped both sharpen my intuition and distill core principles has been Key Decision Analysis, a process designed by Ivan Mazour: “To sharpen my instincts, I keep a monthly journal of all key decisions which I make – decisions that could be truly life changing – and my instinctive reasons for why I made them. I go back only after exactly a year has passed, and I note down whether the decision was correct, and more importantly whether my instincts were right. At the end of the year, I go over all twelve months worth of notes, and search for any patterns amongst all of the right and wrong choices.”


Now read this

A Few Things I Learned in College

Recently, I’ve had the privilege of speaking for college audiences to share what I learned during my undergraduate years. I don’t think any of this stuff is super unique, but some audience members found it valuable, so I’m posting it... Continue →