Thinking Time: The Process

August 5, 2022

From The Road Less Stupid by Keith J. Cunningham 

Designing a Thinking Time process that works for you will be no different than figuring out any other ritual you want to create. The time of day, the best location, and the optimum duration are all discovered through practice and experimentation until you have created a Thinking Time process that best supports your outcomes. The key here is to obsess about obtaining the outcomes and not about finding the perfect process!  

My Thinking Time is based on many years of trial and error to find the exact combination that works for me. My strong recommendation is that you start with my process and adjust it to meet your needs.  

My Thinking Time is highly ritualized. I have a thinking chair. The only time I sit in it is during my Thinking Time sessions. I have a thinking pen and thinking journal: I use them only when I am in Thinking Time mode.  

And I follow this step-by-step process to structure each Thinking Time session:  

1. A great Thinking Time session requires a great question as the launching pad. Prior to my Thinking Time session, I will create and write down a question(s) I want to think about. (In the remainder of this book, you will find examples of various Thinking Time questions I have developed and used over the years.)  

Often I create three to five questions that focus on a common thread or concern. Sometimes, during the actual Thinking Time session, I might change only one or two words in a question to see if I can get a different insight into the issue I am thinking about. For example, the original question might be: “Who is my target market?” I might change this to: “Who was my target market?” I could tweak this question to: “Who is my competition’s target market?” That question could easily change to: “If I was starting again today, what market would I target?” I could add this question: “If I wanted to double my sales, what market would I target?” This might morph into: “Why aren’t my sales double what they are right now in the market I am currently targeting?”  

Each of these questions will spark different possible ideas, insights, and answers, which is why I am doing the thinking in the first place. I am not concerned about addressing each question on my original list. I might have three questions on my page, which morph into eight, but only make it through one. That’s okay, because I am optimizing for possibilities, not completion. 

2. I clear my calendar for sixty minutes, which will enable me to think for about three-quarters of an hour and then evaluate/sort the solutions and ideas I identified in the last fifteen minutes or so. 

3. I have three possible scenarios for my Thinking Time questions: 

– Create a new question. 

– Revisit a prior question that could use additional thought. 

– Use an answer from a prior Thinking Time session as the basis for refining/fleshing out/changing the original question and searching for additional possible choices or variations on the theme. 

4. For most of my questions, one Thinking Time session is insufficient, but focusing for more than about forty minutes is the limit of my capacity to concentrate. I will usually present myself with the same question (or with a possibility created in a previous session) over multiple Thinking Time sessions (two or three is not uncommon) before I get an elegant answer that is worthy of execution. 

I often have a Thinking Time session about the machine I need to create after I have of a viable solution. (In my Thinking Time, I am totally aware of the difference between an option and a choice: An option is an idea; a choice is executable. Each deserves Thinking Time.) 

5. I close my door, turn off the phones, and eliminate all noise and visual distractions. I sit in my chair (which does not face my computer or a window), question, pen, and Big Chief tablet in hand. (I am old-school, so I always think on paper and never the computer, where too many distractions and temptations pop up.) 

6. I set a timer on my computer that alerts me when my Thinking Time has expired and keeps me from fidgeting and looking at my watch. 

7. Right before I start, I sip my water, scratch what itches, go to the bathroom, clear my throat, and then sit perfectly still. I have found over the years that my body has the power to derail my thinking and break my concentration. To optimize the thinking process, I must lose touch with my body so that my train of concentration is totally uninterrupted. During my Thinking Time, I am totally motionless except for my right hand, which is recording my thoughts.  

8. I typically think with my left hand on my forehead partially shading my eyes, which limits my ability to get distracted by looking around my office and breaking my concentration.  

9. In my Thinking journal I always have an empty dot(“.”). It looks like this:  

Question: How would I run my business if 100% of my future customers were by referral only?  

  1. ABC  
  1. XYZ  

The instant I write down an answer, I always create a new dot. My mind sees an empty”.” and assumes there must be at least one more idea.  

10. This is a creative process not intended to be filtered or judged. If I hit a blank or gap in which nothing is flowing (or my mind starts wandering), I will silently re-ask myself the question I am working on during the particular session. I might also silently ask myself, “What else could it be?” or “What could I do that would make this problem worse?” or “How would my competition solve this problem?” or “If I got fired and a new CEO took over, what decision would she make?”  

11. Ideally, I let one idea spark another tangential idea and follow that train of thought as far as it wants to take me. I remind myself that I am looking for ideas and possibilities, not perfection and absolutes. I attempt to avoid judging my ideas (which I have found is almost impossible for me, but nevertheless is my goal). The more judgment I have about an idea during the actual Thinking Time process, the less creative and more prejudiced I tend to be.  

12. Remarkably, I have found my better ideas tend to emerge during a pattern known as the “third third.” The first third of my ideas on any given day are typically the obvious ones. The second third are variations on the first third. But the last third tends to be the most robust and frequently are where the juice is found. 

13. When my Thinking Time has been successful, I’m always startled when the alarm goes off. I can’t believe how quickly the time has passed. At the conclusion of my forty to forty-five minutes of Thinking Time, I will always take at least fifteen to twenty minutes to read what I have written and capture the best ideas I have uncovered (usually no more than three). 

14. Capturing my Thinking Time ideas while they are fresh is critical to this process. The key is to connect the dots, not just collect more dots. I have a separate file in which I keep my best ideas, insights, and distinctions. These ideas can become the basis for a future Thinking Time session or might need to marinate for a few days. 

If any of these ideas are worthy of future consideration or possible action, then I schedule additional Thinking Time on my calendar. If I don’t take the step of scheduling it on the calendar, it stays on my “To Do” list and never gets implemented or addressed. (A handy tool I use for To Do lists is to identify the lingering items that keep getting transferred from list to list throughout the year and do a Thinking Time session on specific To Do items to figure out what needs to happen either to get traction or remove them from my list.) 

15. It is rare for me to have fewer than two or more than three Thinking Time Sessions in a week. (Having said this, I could probably benefit from more.) 

Fundamentally, Thinking Time is a structured process that enables me to minimize the risks, identify the opportunities, and maximize the results. That is a pretty high return for a very low-cost investment.

Sign up to receive a monthly business leader email from gunnercooke. Click Here  

This article is reprinted with the permission of the author from Keith J. Cunningham, The Road Less Stupid., Advice from the Chairman of the Board.  American entrepreneur, international speaker, and acclaimed author, Keith J. Cunningham is regarded as one of the foremost authorities and teachers on business mastery. With more than forty-five years of business and investing experience, Keith has taught critical business skills to thousands of top executives, business owners, and entrepreneurs around the world. 

In Keith’s Keys to the Vault® Business School, he has created curriculum designed to accelerate the transition from Operator to Owner and drive sustainable financial performance and business success. Through his Board of Directors program, he serves as Chairman of the Board for businesses in a wide range of industries. Keith’s latest book The Road Less Stupid is about adopting the discipline of Thinking Time which will enable you to run your business more effectively, make more money, and dramatically increase the likelihood of keeping that money. 

Keith is also the author of Keys to the Vault: Lessons from the Pros on Raising Money and Igniting Your Business and The Ultimate Blueprint for an Insanely Successful Business. 

For more information on Keith and his programs, please visit