Thinking Time – By Keith Cunningham

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

“I insist on a lot of time being spent thinking, almost every day, to just sit and think. That is very uncommon in American business. I read and think. So I do more reading and thinking, and make less impulse decisions than most people in business. I do it because I like this kind of life.” – Warren Buffett

The idea of writing a book about Thinking Time (which I am hoping was not my third-best idea) has been in the making for decades. It started over twenty-five years ago (shortly after I paid a gigantic dumb tax), when I began tracking and recording the critical skills, tools, and insights I learned the hard way and which I have found are necessary to be sustainably successful. In the process, I have developed several core beliefs that have molded my thinking, actions, and results. Here are the critical few that are relevant for this book:

There is no such thing as a natural business Owner. Successful business owners and entrepreneurs are not born with an innate set of skills that produce business excellence and success. Great business owners work hard, practice, study, test, think, correct, and practice some more. None are infallible or perfect, but all are committed to excellence and mastery of the game.

Attempting to win the game of business by trial and error is about the stupidest way to learn anything. Trial and error is a “Pin the Tail on the Donkey” strategy that is painful, slow, and expensive, and it rarely succeeds. If I wanted to call you on the phone, I could consult the phone book for your number, or I could start randomly dialing numbers in the hope I would one day stumble onto the right combination. By then, of course, I would have forgotten what I wanted to talk to you about.

Running the wrong direction enthusiastically is stupid. It does no good to practice the wrong thing. Practice does not make perfect. Practice makes permanent. To excel, we need a coach or an advisor to watch our swing and provide candid advice about what we are doing wrong and how we can do better.

If you want to do better, you must get better. People do not do better because they want to do better; they do better because they get better. You cannot achieve a new outcome without learning something new and practicing what you learned (probably outside your comfort zone). A commitment to mastery (improving) is essential for excellence.

The people with the best life have the best choices. People with a lousy life have lousy choices. If I want to improve my life, I need to create better choices.

Here it is on a bumper sticker: You will pay the dumb tax if you ignore these principles or you will pay to fix the problem. Either way, you are writing a check. One happens to be far smaller than the other.

The Road Less Stupid is designed to accomplish two primary objectives:

Provide a structure/process/skill set to enable you to create a successful Thinking Time ritual that, if applied, will result in a significantly reduced dumb tax. The Thinking Time process I have developed and used over the last twenty-five years is described in the first couple of chapters.

Suggest a series of possible Thinking Time topics and questions you can use to spark your thinking, grow your business, make more money, and ultimately avoid doing something stupid.

The Road Less Stupid is a direct result not only of my experience of owning and running businesses but also, more importantly, from working closely with founders, CEOs and business owners in an intimate Board of Directors environment. The topics I am writing about are the most common issues I have encountered with our clients and Board members, regardless of their company’s size or industry. I think you will find the majority of these topics, lessons, and questions are relevant to you as well. The book is organized into short, stand-alone chapters and designed to be consumed in a nonlinear way. Your understanding of each chapter is not contingent on having read the prior chapters. Open this book to any chapter, start reading, and you will get my drift fairly quickly.

Most chapters will require less than five to ten minutes to read, but the insights you will get from your Thinking Time sessions (which I explain in the chapter “Thinking Time: The Process”) will change the way you run your business and do your job. Use my Thinking Time questions as a springboard for either creating additional questions or for your actual Thinking Time session. If your business is anything like mine, revisiting a question in future Thinking Time sessions is a particularly good idea. Things tend to change at an astonishing pace; yesterday’s answers rarely solve tomorrow’s problems. (See the chapter “The Only Constant in Business Is . . .” if you have any doubt.)

Some chapters have an intimidating number of possible Thinking Time questions. I left all of them in each chapter so that you could have a wide range to choose from. You do not need to address each and every one; just find the high-value questions on a topic and work on those. A few are better than none.

Sometimes, I have used the same question in multiple chapters. I don’t mind repeating a question if it adds value to the current Thinking Time topic. Any of the proposed questions will help you get optics (insights) on areas in your business that need prioritization and work.

This is a business book for business readers, meant to educate rather than to entertain. Wrestling with and candidly answering my suggested questions in your Thinking Time sessions will enable you to minimize taking irrational risks and making stupid decisions (which inevitably results in an unnecessary dumb tax) and to maximize creating more robust choices and business success.