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The Road Less Stupid
Avoiding the dumb mistakes that sabotage growth, profits and business success by Keith J. Cunningham
Ever wish you could take back a dumb decision?
In The Road Less Stupid, Keith J. Cunningham argues that the key to getting rich (and staying that way) is to avoid doing stupid things. He breaks down how smart people do dumb things, and how you can avoid the “dumb tax.”
SMARTEST TAKEAWAYS
Stupid Things to Avoid
1️⃣ Generalizations (which kill clarity): Sweeping statements like “they never listen to me" can blind you to critical details. Instead, Cunningham urges us to challenge generalizations with specific, probing questions. Clarity comes from drilling into the specifics, not relying on broad strokes.
2️⃣ Obsessing about Oz (instead of the yellow brick road): Many focus so much on the big end goal—“Oz”—that they lose sight of the daily actions—the “Yellow Brick Road”—needed to get there. Success is built on consistent execution, not grandiose visions. Stay grounded in the process and let the outcomes take care of themselves.
3️⃣ Faulty assumptions (ignoring risk): Assumptions are silent killers of success. Whether it’s overestimating demand or underestimating costs, faulty assumptions can derail even the best plans. Cunningham advises rigorously testing your assumptions by asking, “What if I’m wrong?” and identifying the risks before taking the leap.
Keith J. Cunningham, author of ‘The Road Less Stupid’
INSIGHTFUL EXAMPLE
Learning from Life’s Lessons
Cunningham shares a story about a business owner who expanded too quickly, ignoring cash flow and logistics. The result? A financial meltdown.
The lesson: Growth without strategy is a recipe for disaster. By practicing “Thinking Time,” this entrepreneur could’ve identified the flaws in their plan before leaping.
A QUOTE TO REMEMBER
Smart People, Dumb Things
“Smart people do dumb things. Don’t let your ego write checks your wisdom can’t cash."
BOOK FACTS
The Road Less Stupid
Publication date: December 15, 2017
Print length: 320 pages
Listening length: 11:32
Ratings: 4.8 Amazon, 4.3 Goodreads
BEYOND THE BOOK
Be Less Stupid
DID YOU KNOW?
Reflection and Thinking Time
Cunningham was one of the inspirations behind Rich Dad’s mentor in the book Rich Dad Poor Dad.
Studies show that structured reflection can boost decision-making accuracy.
CEOs who dedicate regular time to strategic thinking outperform their peers by a significant margin in long-term profitability.
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