Pessimism is Underrated

Want a better team? Get a pessimist.

I get it: nobody wants a Debbie Downer at the party. While you excitedly gush and brainstorm about the new project over crudité, you don’t want to be reminded about how recent droughts adversely affect carrot and celery production. While you daydream wistfully about the product roadmap, you don’t to be reminded that maps lead to driving, causing more CO2 in the atmosphere.

But Debbie is getting a bad rap.

Too often, group work culture is overly saturated with positivity. Positivity feels good. It feels productive to be surrounded by those who support your ideas and vision. Brainstorming takes less time. Decisions are made faster. Everything looks like it’s going to plan… until it isn’t.

Sometimes positivity oozes into toxic positivity, a newer phrase The Kids are using to describe a kind of positivity that encourages people to pretend that very real problems aren’t lurking under the surface. A positive attitude is great but not if it prevents you from seeing the truth or, at its worst, causes harm to the work or the people doing the work. And when things go off the rails, they don’t gently slide off. They tumble down a cliff.

What’s the solution? Get yourself a hardworking pessimist.

Pessimists keep you honest. You say the project can be done in six months, but the pessimist will crunch the numbers and remind you that the last similar project took a year. You may not like the honesty, but you’ll love when the expectations match the results.

Pessimists keep you challenged. The room may be filled with wide-eyed ideas of grandeur, but the pessimist will remind you of the limitations you must consider and the obligations you must meet. Great things happen when you’re pushed to creativity, but terrible things happen when you forget your limits.

Pessimists keep you focused. While salivating over the prospect of big and meaningful change, the pessimist will remind you what matters and help you manage the resulting scope creep. Everyone will appreciate this when the deadlines begin.

Too often, pessimists are overlooked as valuable contributors and shouldn’t be. Put aside your pride and remember that the pessimist isn’t here to make you look and feel good. The pessimist is here to push things from good to excellent.