half empty glass, negative thinking, inversion
The ancient Stoic philosophers like Marcus Aurelius, Seneca, and Epictetus regularly conducted an exercise known as a premeditatio malorum, which translates to a "premeditation of evils."

The goal of this exercise was to envision the negative things that could happen in life. For example, the Stoics would imagine what it would be like to lose their status in society or to be abandoned by their spouse or to have all of their worldly possessions stolen.

The Stoics believed that by imagining the worst case scenario ahead of time, they could overcome their fears of negative experiences and make better plans to prevent them. While most people were focused on how they could achieve success, the Stoics also considered how they would manage failure. What would things look like if everything went wrong tomorrow? And what does this tell us about how we should prepare today?

This way of thinking, in which you consider the opposite of what you want, is known as inversion. When I first learned of it, I didn't realize how powerful it could be. As I have studied it more, I have begun to realize that inversion is a rare and crucial skill that nearly all great thinkers use to their advantage.

How Great Thinkers Reverse the Status Quo

The German mathematician Carl Gustav Jacob Jacobi made a number of important contributions to different scientific fields during his career. In particular, he was known for his ability to solve hard problems by following a strategy of man muss immer umkehren or, loosely translated, "invert, always invert."

Jacobi believed that one of the best ways to clarify your thinking was to restate math problems in inverse form. He would write down the opposite of the problem he was trying to solve and found that the solution often came to him more easily.

Inversion forces you to consider aspects of a situation that are often hidden at first glance. What if the opposite was true? What if I focused on a different side of this situation? As author Josh Kaufman writes, "By studying the opposite of what you want, you can identify important elements that aren't immediately obvious."

Great thinkers, icons, and innovators think forwards and backwards. They consider the opposite side of things. Occasionally, they drive their brain in reverse. Art provides another example.

One of the biggest musical shifts in the last several decades came from Nirvana, a band that legitimized a whole new genre of music—alternative rock—and whose Nevermind album is memorialized in the Library of Congress as one of the most "culturally, historically or aesthetically important" sound recordings of the 20th century.

Inversion is often at the core of great art. Humans are heavily biased to continue the status quo, which means the artists and innovators who stand out are often the ones who overturn the standard in a compelling way. This is why many groundbreaking artists create work that shatters the status quo.

This strategy works equally well for other creative pursuits like writing. Many great headlines and titles use the power of inversion to up-end common assumptions. As a personal example, two of my more popular articles, "Forget About Setting Goals" and "Motivation is Overvalued", take common notions and turn them on their head.

Great art breaks the previous rules. It is an inversion of what came before. In a way, the secret to unconventional thinking is just reversing the status quo.

Success is Overvalued. Avoiding Failure Matters More.

This type of inverse logic can be extended to many areas of life. For example, ambitious young people are often focused on how to achieve success. But billionaire investor Charlie Munger often encourages them to consider the inverse of success.

"What do you want to avoid?" he asks. "Such an easy answer: sloth and unreliability. If you're unreliable it doesn't matter what your virtues are. You're going to crater immediately. Doing what you have faithfully engaged to do should be an automatic part of your conduct. You want to avoid sloth and unreliability."

Avoiding mistakes is an under-appreciated way to improve. In most jobs, you can enjoy some degree of success simply by being proactive and reliable—even if you are not particularly smart, fast, or talented in a given area.

Similar examples exist in personal life. If you can simply manage to stay out of jail, avoid marrying the wrong person, and not go into debt, you'll already be far ahead of many folks and save yourself a lot of pain and anguish along the way. Sometimes it is more important to consider why people fail in life rather than why they succeed.

The Benefits of Thinking Forwards and Backwards

Inversion can be particularly useful in the workplace.

Leaders can ask themselves, "What would someone do each day if they were a terrible manager?" Good leaders would likely avoid those things.

Similarly, if innovation is a core piece of your business model you can ask, "How could we make this company less innovative?" Eliminating those barriers and obstacles might help creative ideas arise more quickly.

And every marketing department wants to attract the right customers, but it might be useful to ask, "How can we alienate the wrong customers?" A different point of view can reveal surprising insights.

Project Management

One of my favorite applications of inversion is known as a Failure Premortem. It is like a Premeditation of Evils for the modern day company.

It works like this:

Imagine the most important goal or project you are working on right now. It could be a business project, a goal for your family and work-life balance, or a health goal. Whatever it is, bring it to mind. Now fast forward six months and assume the project or goal has failed.

Tell the story of how it happened. What went wrong? What mistakes did you make? How did it fail?

This strategy is sometimes called the "kill the company" exercise in organizations because the goal is to spell out the exact ways the company could fail. Just like a Premeditation of Evils, the idea is to identify challenges and points of failure so you can develop a plan to prevent them ahead of time.


Most people want to get more done in less time. Using the inversion you could ask, "What if I wanted to decrease my focus? What are ways I could distract myself?" The answer to that question may help you discover distractions you can eliminate to free up more time and energy each day.

This strategy is not only effective, but often safer than chasing success. For example, some people take drugs or mental stimulants in an effort to increase their productivity. They might work, but you also run the risk of possible side effects.

Meanwhile, there is very little danger is leaving your phone in another room, blocking social media websites, or unplugging your television. Both strategies deal with the same problem, but inversion allows you to attack it from a different angle and with less risk. While there may be adverse side effects from seeking success, there is very little risk from preventing failure.


Marie Kondo, author of the blockbuster best-seller The Life-Changing Magic of Tidying Up, uses inversion to help people declutter their homes. Her famous line is, "We should be choosing what we want to keep, not what we want to get rid of."

In other words, the default should be to give anything away that does not "spark joy" in your life. This shift in mindset inverts decluttering by focusing on what you want to keep rather than what you want to discard.

Consider the Opposite

Inversion is counterintuitive. It is not obvious to spend time thinking about the opposite of what you want.

And yet inversion is a key tool of many great thinkers. Stoic practitioners visualize negative outcomes. Groundbreaking artists reverse the status quo. Effective leaders avoid the mistakes that prevent success just as much as they chase the skills that accelerate it.

Whatever problem you are facing, always consider the opposite side of things.