How to Take the Road Less Stupid

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If I’m going to be honest with myself, I have to admit that many of my greatest strengths and my greatest weaknesses are often two sides of the same coin. For example:


  • I’m really good at being flexible and rolling with unexpected changes in the daily schedule… but I’m not always great at sticking with the priority tasks on the daily “to-do” list even when there are no interruptions.
  • I love creating new ideas for programs and services… but can sometimes fall victim to “shiny object syndrome,” wanting to try a dozen new things before I’ve completed the old ones.
  • And I love engaging hundreds or even thousands of people on stage or on camera because I am excited to share ideas, content and experiences that will change their lives for the better… but I’m terrible at sitting in the quiet, taking sufficient time to process and digest those experiences, or to meditate thoughtfully as part of strategic planning.


This last one is particularly challenging. Sitting still and focusing 100% of my mind on one specific problem and how to solve it (not just daydreaming randomly or letting the mind race through my to-do list while driving or making dinner) often feels self-indulgent, as though I’m not actually “working” unless I’m actively “doing” something… and somehow “thinking” doesn’t seem like “doing.”


Yet “thinking time” is a shared practice of the most successful leaders. Bill Gates, Warren Buffet and John Donahoe of Nike are just a few.


And it’s not just making the time to think that matters — it’s the quality of the question you ask that makes the difference.


One of my newer favorite books is a treasure trove of great leadership “thinking time” questions, strategies and tactics for maximizing the value of thinking time: It’s Keith Cunningham’s The Road Less Stupid.



The premise is simple: we’d all be more successful if we made fewer bad decisions, and bad decisions are frequently due to a failure to think through things sufficiently.


Does it feel like you don’t have time to “just think” about things? If so, let me ask you this: if you don’t have time to contemplate key questions, how will you ever find the time to FIX the problems you create by making the wrong decision because you didn’t think it through enough the first time around?


Put more concisely: If you don’t have time to do it right, when will you have time to do it over?


Taking time to think about challenges also gives you time to listen for that little voice inside that frequently knows better, but that we often tend to ignore. Call it your gut, your intuition, your conscience, your guardian angel… whatever it is, it often shares words of wisdom, if we let it!


Carlos Malatesta, CEO of Apex Energies, joined me on this week’s Speaking to Influence podcast , and shared a variety of experiences when he did and did not listen to his intuition, especially when communicating with people about difficult topics. In particular, he realized that his inner voice usually had great advice around timing when it comes to making important decisions.


Similarly, he shared an important insight that it’s that inner voice that often reminds him to listen to the unspoken signals about the “mood” of the moment, and how that should influence his timing.


For example, he described when he enthusiastically and impulsively decided to talk to a business partner about an opportunity even though his instinct realized that the partner wasn’t in a mental or emotional state that would allow him to hear Carlos’s idea. Not so surprisingly, the conversation ended in a yelling match. (Hmmm, how close to home does that hit?)


Listen to the conversation here or watch the video here.



Today is also National Philanthropy Day. Feeling a little extra generous in your heart but not sure how to express it? We’ve had some amazing leaders of not-for-profit organizations over the last two years on the podcast, and all of them would help ensure your generosity went directly to making a difference in someone’s life who needs you.


To refresh your memory overall, go to to see the full list and hear their amazing stories. But here are just a few for starters, in case you missed them, with direct links to their organizations:


Bringing Hope Home
Congreso de Latinos Unidos
Urban Affairs Coalition
Education Works
Foundation for the Support of the United Nations
Big Brothers Big Sisters
Chester County OIC
Women Against Abuse
The Mann Center for the Performing Arts
The Adoption Center
PA Family Support Alliance
JDog Foundation
Please Touch Museum
Alice Paul Institute


Find whichever inspires you in the moment and click the link to make your difference.

Not sure? Listen to that little voice inside. It will steer you right!

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