The Positive Power of Negative Thinking

This guest post is by Vergil Den, author of The Stoic’s Burden.

  • A triathlete comments that training and preparation for a competition is harder than the competition itself.
  • A general creates a contingency plan against the event of an unexpected attack by the enemy.
  • An engineer tests the rudder of a plane at twice the expected normal load.

What do all of these individuals have in common? They’re harnessing the positive power of negative thinking.

In this age of positive thinking, negative thinking has gotten a bad rap. And why not? Most people would rather not think about the bad things that can happen in life. But just as positive thinking has a place in goal-setting, practical negative thinking has a place in goal achievement.

Fortune at the door

Are we prepared for what fortune has to offer us in life? Life is not like a box of chocolates—unless some of the chocolates are spoiled. We must face the harsh fact that bad things happen.

The ancients knew something about fortune. The myths of antiquity often have fortune as a central theme. The Stoics, in particular, were aware of fortune and its random, uncertain nature. They would visualize all the negative things that could befall them so they were prepared for the event, both physically and emotionally, if it were to occur.

Fortune may appear to be totally random, but a lot of seemingly random events are in our control. Why does it seem then, like they are not in our control?

Studies have shown that people often overestimate what they know and underestimate what they don’t know. Consider the following example. In 2000, Time Warner merged with AOL. At the time, the deal was the largest in history and was expected to create a company that would revolutionize the digital industry. This likelihood was heralded by both experts and non-experts a like.

In fact, this turned out to be one of the worst deals in history. If you invested in these companies at the time the deal was announced, your investment would have been nearly wiped out. What happened here? All the experts were wrong. It was a case where they overestimated what they knew and underestimated what they didn’t know. For an investor, with proper planning, this seemingly random bad event could have been avoided.

Goal achievement

So how can we apply the Stoic principle of negative thinking, and the negative thinking that we know less than we do know, and even less about what we don’t know, to help us achieve our goals? Follow these five steps:

  1. Establish your goal, and identify what you think it will take to reach that goal. This is the positive form of thinking that we all do.
  2. Then think about the worst things that could happen on your way to reaching that goal.
  3. Put a plan in place to either mitigate the risk of those events occurring or mitigate the risk associated with the impacts of those events.
  4. Modify the actions needed to reach you goals from step 1 with the newfound risk insights from step 3.
  5. Periodically repeat steps 2 to 4. This is an important step because things in life are always changing and risks evolve. What may have been adequate now may not be in six months’ time.

Negative thinking and the stock market

When we think about investing, we often visualize making lots of money. This often leads to excessive risk taking. Try this instead: visualize losing all of your money in your investments and imagine how that would make you feel. How would that impact your life and your family? If there’s a significant impact, then put into your investment strategy the proper controls to avoid this failure. For example, if you purchase an individual stock, you might consider also putting in a stop loss.

Negative thinking in business

With all the self-help business management books out there, you would be certain that to be successful all you have to do is work hard in addition to six other successful habits. This is nonsense. These books are written by those who succeeded—and produces something that’s called survivorship bias. These books are not typically written by those who actually failed.

The attributes of the successful are often the same as those who failed. For every Jack Welch, there are thousands of others with the same attributes that failed. To be successful in business, one must avoid failure. Once your business goals are set, visualize the events that could cause your business to fail. How does that feel? Now think about what you can do to avoid those failures. For example, consider the concept of tinkering and how that can help your business avoid total failure.

Negative thinking in life

None of us like to think about death. But death is an important part of life. Think about it for a moment. How does it feel? How would those you love be impacted by your death? Many people don’t anticipate death, so when it occurs (I can guarantee that it will), their loved ones are left to struggle with the loss both emotional and financially. If your death will impact your loved ones, you might consider at least a low-cost life insurance policy.

We can also apply this thinking to job-loss preparation. Most people don’t prepare for job loss, but by visualizing losing your job and the impact it would have, you can prepare. For example, it is recommended that people have at least six months in operating costs available as cash in a savings account.

The positive power of negative thinking is a check to the natural, irrational exuberance we feel when we try to attain success. Also, by thinking about the negative events, if and when they occur, the bitter taste of their impact will be lessened thanks to your planning. And if and when you finally succeed, the taste of success will be that much sweeter.

Vergil Den is a free thinker and a recovering wannabe Empty Suit (i.e., a heartless corporate executive). He now doesn’t take himself quite as seriously and periodically muses about life at

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  1. I find that “worse case scenario” thinking actually relaxes me. It makes me realize that, in most cases, the absolute worst thing that could happen when I try something new isn’t near as bad as I first thought it would be.

    It makes failure something much less scary.

  2. Virgil – It’s rare to find an article that isn’t simply a re-hashing of the same ole’ self-help advice. You’ve achieved the unique distinction of actually writing something new in a world of sameness. This was a thought provoking piece and is much appreciated!

    – The Contrarian

  3. Mike James says:

    Tim Ferris talked about this at a google ignite talk. Old news, but a good article nonetheless.

  4. Thanks for all the feedback. This is great.

    I do confess that the concepts in the article are not new as is with most articles – it is unique, however, in that it is a mash up of many ideas that are presented in a way that is digestible given the short form. Tim Ferris did discuss this at the ignite conference but although I found his talk inspiring, I was confused as to how to actually implement it. He also clearly leveraged some of the ideas from “A guide to the Good Life: the Ancient Art of Stoic Joy” that details negative visualization.

    On a separate note, there was a recent article in the NY Times on how past adversity may aid emotional recovery. It would be interesting if simply the visualization of negative event (rather than the physical experience of the event) aids in resilience – perhaps lending scientific support to Miss Britt’s comment. The article can be found at

    Vergil Den

  5. positiveness of negative thinking

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