The Five Lessons I Learned from The Road Less Stupid

road less stupid

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There’s another road that you can take to achieve success. It’s The Road Less Stupid – the road of more critical thinking and fewer mistakes.

The Road Less Stupid is a book that helps empower business owners to be successful. It has a different approach on how to make it big, and offers a unique insight into why so many people make bad financial decisions.

The author, Keith J. Cunningham, emphasizes the need for thinking, planning, and minimizing risk to achieve and sustain success.

I recently finished reading the book, and want to share some of the valuable business lessons with you. You can apply these smart lessons to your own business, no matter how big or small… And it’s not just about making great choices. It’s also about making fewer dumb mistakes as you plan ahead.

Smart Business Lesson #1 – Stop Paying the Dumb Tax

You can learn from mistakes, but you can’t turn back time and correct them… So you have to ask yourself, “What lesson can I learn from this?”

You have to pay the dumb tax when you let your emotions get the best of you when making business decisions.

You can see this happen all the time. Giant corporations have fallen because of it. Take Polaroid, for example… The company backed nostalgia over innovation and failed to capitalize on the digital photography market. The result was a decline into irrelevance.

Emotions and intellect don’t always go hand in hand. Critical thinking is not the same as emotional thinking. Emotional thinking often prevents you from seeing all the risks, and critical thinking helps you to take action when the time is right.

Smart Business Lesson #2 – Culture Is About More Than Silly Gimmicks

As the business owner, you are its leader. You are the one who creates the company culture – and doing that right is very important.  

Good business culture involves accountability and working in unison. It involves open lines of communication and well-established rules. It’s also about understanding the need to compromise in certain situations, like when priorities change. 

Most importantly, respect is not earned with gimmicks. Respect and mutual trust take time to build. Both are usually the results of an open culture with clear rules and goals.

Smart Business Lesson #3 – Master the Five Core Disciplines of Thinking

There’s a discipline to critical thinking and making better business decisions. As The Road Less Stupid explains, the principles of the discipline are as follows:

  1. Find the unasked question 
    • You do this by formulating a question that offers clarity – that’s how you get better answers and better choices
  2. Separate problems from symptoms
    •  Identify the real reason you’re not progressing as planned
  3. Work with facts and check assumptions 
    • Because unexamined assumptions lead to bad decisions
  4. Consider consequences 
    • Figure out the upsides and downsides of your decisions. What are the risks involved for your company? Can you bounce back if the worst happens?
  5. Create the right system  
    • Figure out how to go from point A to B efficiently – develop a system that bypasses or removes the obstacles in your path

The discipline of critical thinking is about taking more steps. It means tackling one problem at a time with careful planning, instead of going with what seems easiest at the time.

Smart Business Lesson #4 – Spend Some Time Thinking About the Information You’ve Absorbed

At the end of every chapter, Keith Cunningham says: 

“Now go think about it, you will thank me later.” 

It’s not just about taking things as they are and reacting quickly to fix a problem. It’s important to think things over, even if that means you take a bit longer to reach a decision. Chances are, you’ll make a better decision once you’ve had time to think.

Nobody can understand a complex business issue in a few minutes, even a business owner like yourself. I’ve learned the hard way that patience is necessary for scaling a successful business.

This is what the discipline of critical thinking is all about. Think about every detail before you make a decision. That’s how you find errors in judgment and properly weigh the risk/reward ratio.

Smart Business Lesson #5 – A Symptom Is Not the Same as a Problem

I really like this concept, and feel that it deserves a deeper explanation. To give an example, let me ask you a couple of questions: 

Why isn’t your business where it should be? 

If you answered, “I don’t have enough profits” – then then you have a problem in your thinking. “Not enough profits” is a symptom, not a real problem. Sure, it shows that something’s wrong – but it doesn’t indicate what.

This is a common misconception, because people easily associate problems with things they don’t have. In this instance, however, the problem is actually the obstacles that are preventing you from making enough profits. 

Do you see the difference?

Think of the gap between where you are and where you want to be as a river… One that you have to cross to get to the other side, on your way to your business goals. This is something you have to figure out before making any business decisions. It may take a while, but it’s worth doing.


So what’s the moral of The Road Less Stupid? Don’t just focus on making lots of good decisions… Focus more on making as few dumb decisions as you can. That’s how you avoid paying the dumb tax.

You can scale your business and maintain success, just by making fewer mistakes than others – and you do that by training your critical thinking.

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