Contrary Thinking Works

Many years ago, I bought this book. “The Art of Contrary Thinking” by Humphrey B. Neill.

At the time, my wife thought I was already good enough at it and needed no further instruction. I still have both the book and the wife. Contrary thinking is not about being contrary; it is about recognizing what can be before it is.

That’s a skill that pays.

The up-to-date version

The idea came back to life a few days ago with an article in the Wall Street Journal by Andy Kessler. “Live the Contrarian Way” He points out that the contrarian way is not about arguing without effect;  “Unless you can figure out why everyone else is wrong, you’re just being a grouch.”

He draws on a thought from Arthur Schopenhauer. A thought we have all heard and perhaps not connected the dots.

“All truth passes through three stages. First, it is ridiculed. Second, it is violently opposed. Third, it is accepted as being self-evident”

That’s how the status quo evolves. The trick, of course, is to get to the truth first. He draws on Elon Musk and Mark Zuckerberg as capable contrarians. The ones who can see the potential future and act on what they see. He argues you should connect early in the second phase.

Are all contrarians right? Certainly not, but when they are right, they tend to be very right.

The first insight to a sound contrarian thought.

The status quo is wrong now or will be wrong in the near future. Once we see that idea, we know it is true. The status quo cannot remain right because things change. There are many examples of people missing opportunities because the status quo seemed so powerful. The script is that change is the only constant.

“The Americans have need of the telephone, but we do not. We have plenty of messenger boys.”

Sir William Preece, Chief Engineer, British Post Office, 1878

“We don’t like their sound, and guitar music is on the way out anyway.”

Dick Rowe, Head of A&R at Decca Records in rejecting The Beatles after an audition in 1962

“Babe Ruth made a big mistake when he gave up pitching.”

Tris Speaker, Future Hall of Fame teammate.

Learn to recognize what the status quo is and how it might change.

Where to start.

Look at institutions and practices that have served for a long time and are taken as self-evident.

  • Other than courses leading to professional degrees, do universities give you an edge in getting a high-paying job? Is the degree worth the price?
  • What aspects of AI will reduce costs in a business? Will it necessarily replace many people? If so what will those people do after being replaced?
  • Is the nuclear family dead or likely to reappear?
  • How long until public school education is reconfigured to match current societal needs and the technology available?
  • What medical diagnostic and treatment protocols will become obsolete? Replaced how?
  • What societal issues, climate change, for example, will end up being solved by gradual means? Slow-moving problems are seldom solved by early action. Better solutions evolve as technology and understanding advance.
  • How would you market a traditional religion? Marketing asks a simple question, “What is our value proposition?” The question is practical in every situation, business or institutional. It means why would someone trade something of value they have, often money, for what we offer to them as another value?

Look for new value proposition possibilities.

The bit to take away

Mark Twain gets to the kernel of truth, “Whenever you find yourself on the side of the majority, it is time to pause and reflect.” The status quo is that which everyone accepts as truth. Once you pause and reflect, look for a new truth that is beginning to emerge.

I build strategic, fact-based estate and income plans. The plans identify alternate ways to achieve spending and estate distribution goals. In the past, I have been a planner with a large insurance, employee benefits, and investment agency, a partner in a large international public accounting firm, CEO of a software start-up, a partner in an energy management system importer, and briefly in the restaurant business. I have appeared on more than 100 television shows on financial planning. I have presented to organizations as varied as the Canadian Bar Association, The Ontario Institute of Chartered Accountants, The Ontario Ministry of Agriculture and Food, and Banks – from CIBC to the Federal Business Development Bank.

Be in touch at 705-927-4770 or by email at

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