The Road Less Stupid: Advice from the Chairman of the Board

by Keith J. Cunningham

How much money would you have right now if I gave you the ability to unwind any three financial decisions you have ever made?

Thinking is critical to sustainable success in business; said another way, business is an intellectual sport.

It turns out that the key to getting rich (and staying that way) is to avoid doing stupid things. I don’t need to do more smart things. I just need to do fewer dumb things. I need to avoid making emotional decisions and swinging at bad pitches. I need to think!

most of our problems (and ensuing dumb tax) is our excessive optimism and emotional belief in magic pills, secret formulas, and financial tooth fairies.

Here it is on a bumper sticker: Emotions and intellect work inversely. When emotions go up, intellect goes down. Optimism is a deadly emotion in the business world. Warren Buffett said it best: “Optimism is the enemy of the rational investor.”

More often than not, critically thinking about what could go wrong and doing the work to mitigate those risks before taking action is abandoned in favor of comfort zones, the path of least resistance, and speed (instant gratification).

The name of Napoleon Hill’s book is Think and Grow Rich.

It’s THINK! (There are no secrets . . . just stuff you haven’t learned yet.)

You will run your business more effectively, make more money, and dramatically increase the likelihood of keeping that money if you adopt the discipline of Thinking Time.

“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

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.

strategy that is painful, slow, a...

Practice does not make perfect. Practice makes permanent.

To excel, we need a coach or an advisor

You cannot achieve a new outcome without learning something new and practicing what you learned (probably outside your comfort zone).

The people with the best life have the best choices.

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.

Suggest a series of possible Thinking Time topics and questions you can use to spark your thinking,

The book is organized into short, stand-alone chapters and designed to be consumed in a nonlinear way.

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.

Some chapters have an intimidating number of possible Thinking Time questions.

just find the high-value questions on a topic and work on those.

This is a business book for business readers, meant to educate rather than to entertain.

“Thinking Time,” which is a thirty- to forty-five-minute session of uninterrupted concentration. I start by preparing a high-value question before the actual session begins. The better the question, the more insightful and robust the answers and possibilities created.

My questions are designed to help me think about a problem or situation where I am uncertain (or too certain), stuck, or have been unrealistic in my thinking, which is usually a sign that I am about to do something stupid.

five core disciplines:

Find the Unasked Question—Create a question that will result in clarity and generate better choices. Separate the Problem from the Symptom—Identify the real obstacle that is blocking my progress. Check Assumptions—Differentiate the facts from the story I am spinning. Consider 2nd-Order Consequences—Clarify the risks and the possibility/cost of being wrong. Create the Machine—Create the executable plan and identify the resources (people and money) required to solve the real (core) problem and make forward progress.

Core Discipline #1—Find the Unasked Question

What keeps us stuck are inferior questions that produce tactical or unattractive choices.

A problem is simply an unanswered question.

(Sadly, most unanswered questions remain unanswered because the quest...

Framing the problem as a statement is always a mistake. A statement tricks your brain into thinking this situation is a fact and not a question that needs a solution.

I have a couple of tricks I use to help expand the number of possible choices. One is to frame the problem as a “How might I . . . so that I can . . .”

“How might I generate an additional $20,000/month in profits so that we can afford to invest in a new building and double our capacity?”

it helps me think about what needs to be broken vs. what needs to be fixed. A common mistake we make as business owners is to assume that the problem identified is a situation that needs to be repaired, duct-taped, or mended. My experience is that often the machine I currently have is not the machine I need.

Having the right answer is smart. Having the right question is genius.

Our job as business owners and leadership teams is to get clarity on the right question to ask before we pull the trigger.

We would all have better answers and more choices if we invested the time to design better questions and then actually allocated some Thinking Time to consider them.

Core Discipline #2—Separate the Problem f...

What you identified as the problem is actually a description of the gap. The gap is not your core underlying problem; it’s the symptom.

The symptom is what indicates something is wrong, but it does not shed any light on what is causing it to show up.

We mistakenly believe we know what our problems are because we can identify the places we don’t have what we want (the gap or symptoms).

The key to defining the root problem is discovering the obstacle (it resides in the gap) that is impeding your progress from here to there. It is the obstacle that is the problem, not the dissatisfaction with your current circumstances!

The machine that gets built addresses only the obvious symptom and does not solve the core problem or overcome the obstacle that is in the way.

Our tendency is to search for obvious answers and tactical solutions to alleviate the discomfort of the symptom.

Diet books and elliptical trainers are tactical answers and have nothing to do with understanding or addressing the core problem that is sabotaging my fitness.

“What marketing initiative should we start, or how many new salespeople should we hire, or which SEO expert should we retain to secure a page-one Google ranking?” (All tactical, not strategic.)

Confusing activity with productivity is a major saboteur of business success. Just because you’re sweating doesn’t mean it’s working.