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How Being Pessimistic Can Help You Succeed

Thinking of the worst-case scenario can not only help you appreciate what you have, but help you be more prepared for challenges.

How Being Pessimistic Can Help You Succeed
[Photo: Flickr user Tuncay]

I’m an eternal optimist. I seek out the upside in any situation, sometimes to the chagrin of my coworkers. Once in Brazil, the hotel we were staying at had a bed bug outbreak. While my American colleagues panicked, I reminded everyone that while we had bed bugs, at least we were together, and on the beach in Brazil! I’ve never seen a group's collective anger turn so quickly.

What makes me optimistic and positive, however, isn’t naïveté or ignoring problems and living in a bubble. In fact, I’m an incredibly positive individual because I practice negative visualization. Seems counterintuitive, but as recent case studies and the ancient Stoics show, thinking negatively can make you more appreciative in your personal life and successful in your professional pursuits.

In his 2009 book, A Guide to the Good Life: The Ancient Art of Stoic Joy, author William Irvine describes negative visualization as the activity of imagining your life without the comforts you currently possess. "The easiest way for us to gain happiness," he says, "is to learn how to want the things we already have."

Irvine's argument is that we should not take things for granted. Once we become used to our environment, we lose the appreciation and love for the miracles that happen in everyday life. So, we must fight against this "hedonic adaptation" and aim to see every instance, every moment as if we were seeing it for the first time.

Try it. Imagine your life without your job. Imagine your life without your siblings. How much more would you appreciate these things if just for a moment you contemplated their absence from your life? This may sound depressing. But as Irvine elaborates, while we should contemplate such misfortune happening to us, we shouldn’t worry about it.

"Contemplation is an intellectual exercise, and it is possible for us to conduct such exercises without it affecting our emotions."

It’s like being a doctor. He/she knows and is aware of all the ailments that can strike the human body. But they don’t live in hypochondriac fear of being stricken by sickness. They’re simply aware and know that they could happen. Try something today, or tomorrow. As you go about your routine of eating breakfast, going to the gym, and getting into the office, imagine what your life would be without the things we do daily and take for granted.

  • "What if I didn’t have this nourishing food to eat?"
  • "What if I didn’t have the health to go to the gym every day?"
  • "What if I didn’t have a job or couldn’t work?"

Of course contemplating every action you do isn’t scalable. But pick a few moments in the day, try it, and see how each moment becomes more special and new again.

By coming face to face with our worst fears, we’ll see we can survive the ordeal. Think of the first time you fell in love and the first time you had your heart broken. Part of the fear of a breakup is we think we will never get over it. But as anyone who’s ever gone through heartbreak will tell you, you’ll survive and become more resilient. And that’s the aim of Seneca’s exercise: to teach resilience by bringing you head on with your biggest worries.

Do A "Premortem" On Big Projects

This exercise can be applied to business as well. A "premortem," as Gary Klein explained in the Harvard Business Review in 2007, "begins after the team has been briefed on the plan. The leader starts the exercise by informing everyone that the project has failed spectacularly. Over the next few minutes those in the room independently write down every reason they can think of for the failure—especially the kinds of things they ordinarily wouldn’t mention as potential problems, for fear of being impolitic."

The idea is to anticipate and prepare for factors that may impede the success of a given project. In preparing our sales goals for 2015, our team ran through a similar mental exercise. We asked ourselves: What will prevent us from hitting our targets? We talked about understaffing, fluctuating currencies in Latin America, and inadequate sales support. With those possibilities in mind, we structured our targets and planned for those possible outcomes. We obviously hoped they wouldn’t come up. But if they did, then we were prepared.

A premortem isn’t a long and elaborate process. All you have to do is gather the stakeholders of a project and talk open and freely about what can go wrong. We do ours over an hour or two every few months or when a new project is on the horizon. In the grand scheme of things, it’s a small time investment, but the payoff can be big.

As Tyler Tervooren writes:

There are no guarantees when you’re taking on a big, risky project. Sometimes things will go wrong that you didn’t—or even couldn’t—anticipate. But taking a few hours to go through the pre-mortem process is a wise investment for any project that’s important to you.

Once you’ve done it, you can go to bed each night knowing all your bases are covered. Don’t underestimate the value of peace of mind.

I’m all for positive thinking and an optimistic outlook on life. But the paradox is that to truly attain the two, one needs to become comfortable with negative visualization. In your personal life, it helps you become appreciative. And in your professional pursuits, it prepares you and curbs most surprises.


Eric M. Ruiz is a writer and strategist for Waze, the GPS and navigation app that was acquired by Google in 2013. A native of Modesto, California, Eric now resides in New York City. Follow him on Twitter at @EricMartinRuiz.

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