Book SummaryThe Road Less Stupid, by Keith Cunningham

1-Page Summary1-Page Book Summary of The Road Less Stupid

The secret to financial success is to avoid making stupid mistakes, according to Keith Cunningham. And the key to making fewer stupid mistakes is to think before you act. If that sounds easy, it’s easier said than done. In The Road Less Stupid, Cunningham discusses lessons that he learned the hard way, as well as business insights on a variety of issues, ranging from corporate culture to customer relations to risk assessment.

Cunningham is an...

The Road Less Stupid Summary Stupid Mistakes That Smart Executives Make

It’s not practical to list every stupid mistake that can or has been made in business, but some mistakes and misconceptions are common enough that Cunningham takes the time to discuss them particularly. Note that, as used by Cunningham, the word “stupid” refers specifically to things that you do or accept even though you are smart enough to know better. This contrasts with the way others sometimes use the term “stupid” to refer to a lack of intelligence.

In this section, we’ll examine these key mistakes so you’ll be able to more easily spot and avoid them.

Letting Pride Cloud Your Judgment

According to Cunningham, letting your emotions influence your business decisions will almost always result in stupid mistakes, which, in turn, will result in financial losses. One of the most dangerous emotions of all is pride because it can cause you to ignore risks or expect unrealistically easy profits.

He warns that having too much pride in your past successes can inflate your ego and give you unfounded confidence in the future success of your projects. In recounting his own greatest financial losses, Cunningham observes that one of the few good things about failing...

The Road Less Stupid Summary Avoid Mistakes by Taking Time to Think

Cunningham’s solution to the problem of making stupid mistakes is to set aside blocks of time for deep thinking that force you to confront issues and answer questions you might otherwise have failed to consider. Schedule thinking sessions at least twice a week and ideally every day.

Each thinking session is one hour long: You spend the first 45 minutes pondering questions or problems and jotting down possible answers or solutions. Then you spend the final 15 minutes evaluating the ideas you came up with and documenting any that are good enough or important enough to warrant following up on—whether in a future thinking session or as actionable business directives.

(Shortform note: In Six Thinking Hats, psychologist Edward de Bono elaborates on the process of thinking, explaining that there are six fundamental types of thinking. De Bono observes that our thinking is often a jumble of all six types and argues that you can think more coherently and productively by consciously separating them. Cunningham appears to be doing just that with his thinking sessions by dedicating the first 45 minutes to generating ideas (what de Bono...

Shortform Exercise: Start Thinking

Cunningham asserts that the best way to avoid “stupid” mistakes (mistakes you made even though you knew better) in business is to take time regularly to think deeply and rationally about the issues you or your company is facing and ask yourself thought-provoking questions. In this exercise, we’ll ask you a few questions to kick off your thinking session.

Think of the most recent mistake you’ve made that you wish you could go back and undo. If you could ask your earlier self one question to make yourself rethink the issue and avoid the mistake, what question would you ask?