The Power of Pessimism

I was watching one of my favorite shows last week, Shark Tank, when the sharks noted what an entrepreneur was lacking: self-doubt. She was overly confident and sunny about her prospects. The sharks said a little self-doubt, and fear that you aren’t going to make it, can be keys to success. The ability to see a potentially bad outcome keeps entrepreneurs on their toes, at their best.

Some leadership and executive development emphasizes the importance of positive thinking, but I prefer optimizing pessimism. I’m a natural pessimist, and it makes me better prepared than I would be if I were an optimist. It drives me to save money, to reach out to more sources for articles than others would (knowing many will fall through), and pushes me to consider possibly disappointing or upsetting outcomes, so when they happen I’m mentally prepared.

I found an article from The Atlantic last year that resonated with me: “The Power of Negative Thinking.” The author, Elizabeth Adler, writes that it’s been found that even the communication style of negative-thinking people tends to be sharper than that of optimists, and us pessimists also tend to be more fair-minded: “Compared with cheery moods, bad moods have been linked to a more effective communication style, and sadness has been linked to less reliance on negative stereotypes. Feeling down can make us behave more fairly, too. People who saw sad video clips before playing an allocation game were more generous with their partners than those who saw happy clips.”

The challenge is nurturing enthusiastic, upbeat employees, who also happen to be pessimists. That’s hard because when you sense the possibility for danger and bad outcomes, you tend not to be as cheerful. I’m not a cheerful person, but I think cheerful pessimists exist. To be cheerful pessimists, employees must be able to manage their neuroses—a feat I’ve personally never been able to pull off. The ideal employee would be one who can calmly think through all the outcomes of a situation or decision—good and bad—plan out possible needed responses, and then put the thoughts away until the outcome is determined. 

Rather than encouraging optimism, maybe the better lesson is in how to engage in the kind of gloomy, frightening thinking necessary to be well prepared, without becoming neurotic and anxious. Providing guidance on anxiety management techniques could help; it also could help to have a sounding board inside the office so people can talk through their fears. Having at least one other person who would share in the bad outcomes (should they occur) also can be helpful. The most anxiety-ridden employee is the one who has thought through every conceivable bad outcome, has prepared, and then is left alone in experiencing the impact of the outcome. Are any of your work groups structured so that, rather than a group, it’s essentially one person who does all the work and assumes all the responsibility? Aside from logistics, that setup isn’t a good idea from a mental health perspective. 

Another great asset of pessimism is it enables an employee to set expectations with executives and customers. The pessimist can have a realistic, honest conversation about how a project, or new product rollout, likely will go. He or she can say, “We’ve worked hard, and are hopeful, that A, B, and C will occur, but it’s also possible, despite our best efforts, that X, Y, and Z will occur.” Executives and customers will appreciate the honesty. They won’t be happy with a bad outcome, but the blow will be blunted because it won’t be a total surprise. It’s much worse to present a project or product as a sure thing, and then have a minor mistake or flaw create a huge disappointment.

It’s a pessimist who would be smart enough to say, “Let’s under-promise and over-deliver. Let’s assume everything won’t go as planned, and build in leeway for ourselves, so if everything does go our way, we will have exceeded our customer’s expectations, and if everything doesn’t go our way, we will have at least met their expectations.” How much worse is it to be optimistic that your project or service will be perfect, promise perfect, and then find customers disappointed when you were off by just a little?

It’s great to have pessimistic financial managers in a company—the kind who don’t assume the money will keep rolling in at the same pace that it’s been rolling in, and so, stow money away for the coming down times, and have a fund squirreled away for surprise emergencies and debacles. 

And did you know optimists may be poor time managers? A friend from years ago mentioned that to me to explain why she was always running late. As she slowly blew her hair dry while reading a magazine, she said she always thinks she has more time than she really does. 

What roles at your company are best staffed by pessimists? Is there any employment circumstance in which it’s better to be an optimist? In life in general, pragmatically speaking, is it better to be an optimist or pessimist?


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