The Road Less Stupid Book Summary - The Road Less Stupid Book explained in key points

Listen to the Intro

00:00

The Road Less Stupid summary

Name: The Road Less Stupid
Rating: 4.6 (37 reviews)
Author: Keith J. Cunningham

Keith J. Cunningham

Advice from the Chairman of the Board

4.6 (37 ratings)

18 mins

Table of Contents

The Road Less Stupid
summarized in 6 key ideas

Audio & text in the Blinkist app

Key idea 1 of 6

What’s in it for me? Reduce your risks, increase your profits, and solidify your sustainability.

No one is safe. Not even the smartest people, like you.

We all do dumb things. When we do, we all pay a dumb tax.

Sometimes the dumb tax is small, like your car seats being wet because you left the windows cracked overnight. Sometimes it’s huge, like declaring bankruptcy because your delivery system couldn’t keep up with demand.

Reducing the number of dumb things we do is the most reliable way to improve our business. In order to do that, we need to think more and optimize our thought process. That’s exactly what Keith J. Cunningham writes about, and that’s what you’ll learn to do in this Blink.

This Blink shows you how valuable it is to avoid mistakes. Then it gives you the tools you need to do just that by creating your own Thinking Time ritual and practice. If you commit to them, regular Thinking Time sessions will help you dodge the costliest mistakes, recognize the most lucrative opportunities, and provide you with multiple solutions to your problems.

The Dumb Tax

A jolt runs through the crowd as the curtain rises. He appears in the spotlight, beaming. His smile flashes as his voice wraps around the audience. They laugh at his jokes and nod at his truths. They are buying what he’s selling – the Kool-Aid.

“Just one sip, every day for 30 days, and your business will thrive,” he promises as the light catches his Rolex. “You’ll be rich beyond your wildest dreams, just like me.”

He might be rich – but it’s from selling his flashy Kool-Aid, not drinking it.

There are no secret formulas when it comes to business success; there are only bits of knowledge you haven’t learned yet. How do you find that knowledge? You think. That’s why Napoleon Hill titled his 1937 book, which has sold more than 70 million copies, Think and Grow Rich. He didn’t name it Follow Your Heart and Grow Rich or Learn the Secret and Grow Rich.

The Kool-Aid salesman isn’t the only one pushing blind optimism and quick fixes on you. You might be doing it to yourself. Sure, the idea for a new production method seemed great after that second glass of wine at dinner, but have you really thought it through? The harsh reality is many of our biggest problems began as our best ideas. As Warren Buffet said, “Optimism is the enemy of the rational investor.”

So the key to making more money, and keeping it, isn’t chasing down more smart ideas. The real key is making fewer dumb mistakes.

Imagine how much more money you might have at this moment if you could go back in time and undo any three financial mistakes. Make it a ballpark estimate, and then write it down. That’s just a portion of the “dumb tax” you’ve paid over your lifetime.

The best way to reduce your dumb tax is to develop the habit of Thinking Time. And the best way to do that is to create a Thinking Time ritual. The next three sections of this Blink will show you how to do both.

The Core Disciplines of Thinking

Productive Thinking Time sessions start with a high-value question or questions. They should help you re-evaluate a problem that has left you feeling uncertain or stuck, or a situation in which you feel overconfident or have been unrealistic in your approach.

These questions can take many shapes, but they tend to revolve around five core disciplines: Find the Unasked Question, Separate the Problem from the Symptom, Consider 2nd-Order Consequences, Check Assumptions, and Create the Machine. The disciplines are connected, and mastering all five leads to the largest dumb-tax deductions.

The King Cobras of New Delhi

During colonial times, the British were terrified of the venomous king cobras that populated the Indian city of New Delhi. To solve the problem, the colonizers offered a sizable bounty for dead cobras. The bounty system worked, but it also led to some enterprising locals setting up snake farms and breeding cobras for the bounty. When the British found out about the scam, they ended the bounty system. So, the snake farmers released the cobras into the city, and New Delhi wound up with twice as many snakes as it had before the British bounty system.

This story, likely fictitious and surely exaggerated, was made famous by German economist Horst Siebert, who coined the phrase cobra effect. It shows what can happen if you ignore the third core discipline of thinking: Consider 2nd-Order Consequences. In essence, this discipline is asking you to consider the possibility that you’re wrong, and what the price of being wrong might be. Answering these three questions before you act should reveal 2nd-order consequences and help you avoid dumb taxes: One, what’s the upside of this action? Two, what is the downside? And three, can I live with that downside?

The Process

Eventually, you will discover the right time, place, and length for your Thinking Time sessions. You will find the right chair, lighting, and writing instrument. But for now, use the following blueprint to create your Thinking Time ritual, and then let it evolve over time.

Thinking Time sessions are powered by the high-value questions discussed in the previous sections. Before each session, write down the questions you want to think about. Creating three to five that revolve around one topic can be helpful. Don’t worry about answering them all – you’re trying to maximize options, not complete a to-do list.

The Importance of Thinking Time

Joe worked on the new plan for weeks, toiling alone late at night. After he finished the plan, he followed the steps diligently, never missing a day or a detail. His business hasn’t turned around yet, but the gold-plated results should start rolling in any minute.

While we can admire Joe’s diligence, chances are good those gold-plated results won’t be rolling in. Running with enthusiasm can be positive, but not if you’re headed in the wrong direction. That’s when you pay a dumb tax. Instead of toiling alone, Joe could have asked someone else to look over his plan. Better yet, he could have hired a professional. If Joe had a Thinking Time ritual, he probably would have thought of that himself.

Final Summary

The key to business success is not taking more smart steps – it’s taking fewer dumb ones. In order to avoid dumb steps and the dumb tax that follows, you must think, and a Thinking Time ritual and practice will help you optimize your thought processes.

While it probably took you less than 20 minutes to consume this Blink, getting the most out of it and a Thinking Time practice will take longer. The information in this Blink is only valuable if you actually commit to Thinking Time and then follow through on that commitment. Wanting to develop a Thinking Time practice or deciding to develop one aren’t the same as actually doing it.

Want to see all full key ideas from The Road Less Stupid?

Key ideas in The Road Less Stupid

More knowledge in less time

Read or listen

Get the key ideas from nonfiction bestsellers in minutes, not hours.

Find your next read

Get book lists curated by experts and personalized recommendations.

Shortcasts ^New

We’ve teamed up with podcast creators to bring you key insights from podcasts.

What is The Road Less Stupid about?

The Road Less Stupid: Advice from the Chairman of the Board (2018) is about avoiding the dumb mistakes that can sabotage businesses. The way to avoid these mistakes, which is usually more valuable than having smart ideas, is to think more and with more focus. Cunningham shows readers how to do this with his Thinking Time practice.

Who should read The Road Less Stupid?

Business leaders interested in minimizing risk and maximizing output
Small business owners who are looking to take the next step
Anyone struggling to find a solution to a recurring business problem

About the Author

Keith J. Cunningham is an entrepreneur, international speaker, and the founder of his own Keys to the Vault Business School. He also runs a board of directors program, where he facilitates learning among various CEOs. Cunningham’s other books include Keys to the Vault: Lessons from the Pros on Raising Money and Igniting Your Business, and The Ultimate Blueprint for an Insanely Successful Business.

Categories with The Road Less Stupid

Entrepreneurship Personal Development Management & Leadership

Books like The Road Less Stupid

The Power of the Pussy

Kara King

How to Get What You Want from Men: Love, Respect, Commitment and More!

13 min

3.6

Unreasonable Hospitality

Will Guidara

The Remarkable Power of Giving People More Than They Expect

Master the Secret Language of Charismatic Communication

15 min

4.5

Hopping over the Rabbit Hole

Anthony Scaramucci

How Entrepreneurs Turn Failure into Success

End Self-Sabotage and Demand Your Life Back

How To Make Offers So Good People Feel Stupid Saying No

How Hackers, Innovators, and Icons Accelerate Success

A Simple Strategy to Grow a Remarkable Business in Any Field

How to Think and Act Like the Most Successful and Highest-Paid People in Every Field

26 min

4.2

It Worked for Me

Colin Powell with Tony Koltz

In Life and Leadership

Toss Plan B Overboard and Unleash Your Full Potential

13 min

4.3

How Big Things Get Done

Bent Flyvbjerg and Dan Gardner

The Surprising Factors Behind Every Successful Project, from Home Renovations to Space Exploration

Getting Your Relationship Sh!t Together

14 min

4.2

How to Grow Your Small Business

Donald Miller

A 6-Part Strategy to Help Your Business Take Off

16 min

4.8

The Procrastination Cure

Jeffery Combs

7 Steps to Stop Putting Life Off

16 min

4.5

The Customer Service Revolution

John R. DiJulius III

Overthrow Conventional Business, Inspire Employees, and Change the World

11 min

4.3

Listen Like You Mean It

Ximena Vengoechea

Reclaiming the Lost Art of True Connection

24 min

4.4

Impromptu

Reid Hoffman with GPT-4

Amplifying Our Humanity Through AI

A Dystopian Classic on the Dark Side of Human Nature and Survival

19 min

4.6

The Emotional Lives of Teenagers

Lisa Damour

Raising Connected, Capable, and Compassionate Adolescents

21 min

4.9

The Answer to Anxiety

Joyce Meyer

How to Break Free from the Tyranny of Anxious Thoughts and Worry

And Why Some Companies Never Give In

Unmask Your Shadow and Embrace Your Power

Lessons in Liberty from a Hospital Diary

The secrets of 40 millionaires' wealth, revealed

15 min

4.5

The Future is Faster Than You Think

Peter H. Diamandis

How Converging Technologies Are Transforming Business, Industries, and Our Lives

A Violent Satire on Modern Capitalism and Corporate Greed

Knowing When to Give It, When to Withhold It, How to Earn It, and How to Fix It When It Gets Broken

14 min

4.5

Start With Why (New Version)

Simon Sinek

How Great Leaders Inspire Everyone to Take Action

21 min

4.7

The 16 Undeniable Laws of Communication

John C. Maxwell

Apply Them and Make the Most of Your Message

16 min

The School of Greatness

Lewis Howes

A Real-World Guide to Living Bigger, Loving Deeper, and Leaving a Legacy

Escape 9–5, Live Anywhere, and Join the New Rich

The Hidden Determinants of Human Behaviour

18 min

4.2

The 7 Habits Of Highly Effective Teenagers

Sean Covey

The International Bestseller Updated for the Digital Age

18 min

4.3

The Power of Discipline

Daniel Walter

How to Use Self Control and Mental Toughness to Achieve Your Goals

14 min

4.4

The Heart of Transformation

Michael J. Leckie

Build the Human Capabilities That Change Organizations for Good

15 min

The Long View

Brian Fetherstonhaugh

Career Strategies to Start Strong, Reach High, and Go Far

16 min

4.4

Should I Stay Or Should I Go

Ramani Durvasula

Surviving A Relationship with a Narcissist

17 min

3.8

The Perfectionist's Guide to Losing Control

Katherine Morgan Schafler

A Path to Peace and Power

The 15 Most Powerful Principles for Wealth, Health, and Happiness

26 min

4.6

Love More, Fight Less

Gina Senarighi

Communication Skills Every Couple Needs

Discovering a Life Beyond the Clock

The Biohacker's Guide to Getting the Body and Mind You Want

20 min

3.5

The Science of Happily Ever After

Ty Tashiro

What Really Matters in the Quest for Enduring Love

Leading Flexible Teams To Do The Best Work of Their Lives

The Origins and Healing of Attention Deficit Disorder

24 min

4.5

The 1-Page Marketing Plan

Allan Dib

Get New Customers, Make More Money, And Stand Out From The Crowd

Cultivate mental toughness and high performance like a Navy SEAL

17 min

4.2

The Orderly Conversation

Dale Ludwig and Greg Owen-Boger

Business Presentations Redefined

11 min

4.4

People ❤️ Blinkist

Sven O.

It's highly addictive to get core insights on personally relevant topics without repetition or triviality. Added to that the apps ability to suggest kindred interests opens up a foundation of knowledge.

Thi Viet Quynh N.

Great app. Good selection of book summaries you can read or listen to while commuting. Instead of scrolling through your social media news feed, this is a much better way to spend your spare time in my opinion.

Jonathan A.

Life changing. The concept of being able to grasp a book's main point in such a short time truly opens multiple opportunities to grow every area of your life at a faster rate.

Renee D.

Great app. Addicting. Perfect for wait times, morning coffee, evening before bed. Extremely well written, thorough, easy to use.