Road Less Stupid: Summary and Actionable Steps

Iskandar Kurbanov
3 min readMay 16
Photo by Diego Jimenez on Unsplash

This is a summary and actionable steps for each chapter from the book The Road Less Stupid: Advice from the Chairman of the Board.

Chapter 1: The Dreaded Dumb Tax

Summary: Making emotional and optimistic decisions without proper thinking can lead to financial losses. Most people’s current financial situation represents their best thinking. Smart people do dumb things when emotions override intellect.

Action: Implement the discipline of Thinking Time to minimize dumb decisions. Schedule regular thinking sessions and prepare high-value questions beforehand.

Chapter 2: The Discipline of Thinking Time

Summary: Structured thinking sessions can help identify opportunities, minimize risks and maximize results. Thinking Time requires a great question as a launchpad.

Action: Create a ritual for regular Thinking Time sessions. Experiment to find the process that works best for you.

Chapter 3: The 5 Core Disciplines of Thinking

Summary: Certain disciplines like finding the right question, checking assumptions, considering risks and creating a plan are key to minimizing “dumb tax”. Separating the real problem from the symptom is critical.

Action: Practice the 5 core disciplines in your Thinking Time sessions — find the unasked question, separate the problem from the symptom, check assumptions, consider risks and create a plan.

Chapter 4: Thinking Time: The Process

Summary: Following a structured Thinking Time process can make the sessions more effective. Process elements include clearing your calendar, preparing questions in advance, setting a timer and taking notes.

Action: Experiment to find the Thinking Time process that works best for you. Vary the duration, location and time of day until you settle on an approach.

Chapter 5: Mmm…Kool-Aid

Summary: Conventional wisdom and one-size-fits-all solutions often fail. Be skeptical of experts and their predictions. Focus on your situation and think independently.

Iskandar Kurbanov

Software Developer | Programming Instructor and Shopify Consultant