Unleashing the Power of Thinking Time: Highlights from Keith Cunningham’s “The Road Less Stupid”

Jul 20, 2023, Written by Sue Miley

I love my morning time.  I have a beautiful view of the sunrise from my back patio.  It is so serene, yet morning is also when I have the most clarity and focus.  So once the sun rises and there is enough light to see, I usually jump into a morning routine of journaling, prayer, and/or reading.

Although I am not willing to give up God’s most beautiful gift of morning peace, and four days a week, I also go to the gym to work out; I have found it worthwhile to dedicate one morning per week to Thinking Time.

I read Keith Cunningham’s book, The Road Less Stupid, on a client’s recommendation.  It is packed with business insight and process suggestions.  It is not for the faint of heart, though.  He hits you right between the eyes with all the “stupid” business decisions or actions we have probably done at some point in our business ownership journey.  The title of the book sort of gives the directness away.

One essential thread throughout the whole book is to spend time just thinking.  

Once I get to work, I jump into the hectic pace of doing.  I see client after client, and I am trying to respond to others’ needs in between.  Amidst this busyness, the art of deep thinking often gets overlooked, leaving little room for introspection and thoughtful decision-making.  Renowned entrepreneur and investor Keith Cunningham emphasizes the importance of carving out dedicated “Thinking Time” to make smarter, more strategic choices that lead to success. 

What is Thinking Time Coined by Keith Cunningham?

Thinking Time is a deliberately scheduled period where you create a quiet, focused environment to contemplate essential aspects of your life and business.  It’s about stepping away from the day-to-day grind and dedicating time to think deeply about your goals, challenges, opportunities, and strategies.  Cunningham suggests that we should view Thinking Time as a precious investment in our future, as it allows us to make better decisions and avoid costly mistakes.

The Structure of Thinking Time

Cunningham outlines a practical approach to structuring Thinking Time, helping us make the most of these reflective sessions:

  • Schedule Regularly: Treat Thinking Time as an indispensable appointment with yourself.  Block out a specific time on your calendar, whether weekly or monthly, and stick to it with discipline.  Since morning time is when I am the most focused, and before work, no one is looking for me to distract me, it makes the perfect timing for me.  What works best for you?
  • Create a Distraction-Free Zone: Find a peaceful and quiet space to focus without interruptions.  Turn off all electronic devices, close the door if inside, and permit yourself to immerse in profound reflection.  (Of course, some of us must allow room for our lap dog.  My issue is that I have two lap dogs, yet only one lap.)
  • Ask the Right Questions: During your Thinking Time, ask pertinent questions addressing your most significant challenges and opportunities.  This process encourages you to dig deeper and gain insights that might not be apparent during the hustle of everyday life.  If you get the book, The Road Less Stupid, you will find a plethora of questions at the end of every chapter.  But, when you start to drill down, the questions become more and more relevant to your business and circumstances.
  • Take Notes: Keep a journal or notebook handy during Thinking Time.  Write down your thoughts, ideas, and conclusions to refer to and track your progress over time.

Strategic Thinking

One of the main objectives of Thinking Time is to engage in strategic thinking.  Cunningham suggests that strategic thinking goes beyond mere problem-solving; it involves identifying patterns, trends, and opportunities that can shape your long-term success.  I have owned my own business for over 15 years now.  And I am proud that we have stayed in the same strategic direction.  But, spending the extra time just thinking about our strategic growth let me out of my box and out of my comfort zone.  But continued growth doesn’t occur when we become stagnant.

Risk Management and Decision Making

Thinking Time also allows one to analyze potential risks and make informed decisions.  Rather than relying on gut instincts or reacting impulsively, take the time to weigh the pros and cons, assess possible outcomes, and develop contingency plans.  Ask yourself, can I live with the worst-case scenario?  This methodical approach to decision-making significantly reduces the likelihood of making costly mistakes.  There are also tools to assist in risk assessment, which I love.  They are simple ways to look at issues that only need a pen and a piece of paper.

Building the Thinking Muscle

Like physical exercise, Thinking Time helps build the “thinking muscle.” The more you engage in deliberate and focused thinking, the better you become at it.  Over time, you’ll find that your ability to analyze complex situations, connect ideas, and make wise choices improves significantly.  I can’t dedicate as much time yet as Keith Cunningham, but hopefully, some of the breakthroughs that arise from my “thinking time” will provide space for more of it.

The book has so much more than just the process of thinking time.  But, thinking time is a universal lesson we can all use regardless of what type of business, what stage our business is in, or what issues we face.

A Common Strategic Issue Most Business People Could Contemplate During Thinking Time

Towards the beginning of the book, Cunningham talks about most companies wanting to get from Point A to Point B, but there is an obstacle stopping them from getting there.  Our core issue isn’t the gap between Point A and Point B, it is the issue or problem stopping us from closing the gap.  This is an example of a strategic issue that we can focus on in our thinking time.  Why are we really not at point B?  What is the real obstacle keeping us from getting there?  If we don’t really understand the obstacle, we may choose solutions that don’t solve the core problem.

You’ll Thank Me Later

The only thing better than enjoying the beautiful sunrise with my cup of coffee and my two wiener dogs is enjoying the sunrise and having a breakthrough, light bulb moment that arises from incorporating Thinking Time into my morning practice.

For more, get the book!

As Keith Cunningham would say….

You’ll thank me later.

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Sue Miley

Sue Miley MBA, MA, LPC helps small business owners build successful businesses on a foundation of Christian values. After 20 years in business, and 10 years as a Christian counselor, Sue uses a combination of faith, business and psychology to help clients in business and in life.

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