Possibility Starts With Pessimism

Possibility thinking is not the same as optimism. This is a common misconception. I consider myself an extreme optimist, yet it’s not for amateurs. Extreme optimism can lead to really poor outcomes when it’s based on denial or refusal to confront reality. Possibility thinking is a skill that requires acknowledging the possibility of the worst outcomes as well as the best. The Stoics called it premeditatio malorum, or thinking of evils in advance. This is why pessimists can gain at least as much from the discipline as natural optimists can.

I know a few extreme pessimists. I keep them in my social media feed because I find them oddly endearing, at least in small doses. These super-pessimistic friends don’t know each other, but they have a lot in common. One of the main traits that they share is that they are nearly impervious to support, compliments, and expressions of empathy, even as they complain that nobody is ever there for them. Another is that they are virtually incapable of gratitude. They are quite angry whenever anyone dares to suggest that something might be going well for them. These are dangers inherent to extreme pessimism. Alienating people who want to be your friends will inevitably shrink your pool of allies and emotional support. It also eliminates the vast majority of opportunities that other people automatically receive from being part of a more conventional social network.

Simply stop rejecting other people’s offers, and things start happening. People vouch for you. People introduce you around and you form more loose social ties. You start to make more friends and acquaintances, you start to get invited to more events. You start hearing about more opportunities, like job postings, vehicles or stuff for sale, road trips, roommates, pets that need a home, maybe even a future spouse. A crotchety, curmudgeonly person loses out on all of this. Over the years and decades, it really builds up.

Possibility starts with pessimism as soon as someone realizes that pessimism is only one of the many responses that are available. Attitudes are not set in stone. Perspectives are infinite. Negativity itself can come in uncountable forms, and one particular negative response is only one option. See?

Pessimism is a smart place to start with strategic planning. It’s just not a smart place to end.

Travel. Start with the assumption that every single thing will go wrong. Assume you’ll forget your passport and your ID, assume you’ll get to the airport without your prescriptions or your glasses, assume you’ll lose your keys and that someone will steal your wallet and your luggage will get lost. Assume that every single leg of your trip will be delayed and every connection will be missed. Assume that your hotel rooms will all be given to others and you’ll have nowhere to go at midnight. Assume you’ll show up on the wrong day. Assume you’ll get food poisoning and the flu. Assume you’ll fight with your travel companions. Assume you’ll come home to a burst pipe and an insect infestation. Pessimistic starting assumptions are part of how you learn to foresee issues and form multiple backup plans. These negative forecasts also help you learn to appreciate how special and rare it is when everything works properly. Most of all, pessimistic assumptions help to generate an attitude of acceptance instead of outrage, dark humor rather than disappointment.

Romance. Start with the assumption that your crush is a bad person with a lot to hide. Do your due diligence. Assume that this person does not share your values and is not safe to introduce to your family, friends, neighbors, or coworkers. After my early divorce, I used to say that I would never get married again without a credit report, a criminal background check, a psychiatric assessment, and a blood test. This impressed my future husband, who says this bizarre boundary meant he would get the same information from me that I was demanding from dates. It helped him to trust me. When you do find someone solid, someone who has passed all the gates, then you know to appreciate and respect this person as a worthy mate.

Finances. Start with the assumption that you’ll outlive your money by at least fifteen years. Inflation will come for you and you’ll be physically unable to work about ten years earlier than you had thought. Assume that various bad actors are out to defraud you, sell you things you don’t want or need, and trick you into paying hidden fees and high interest rates. Know that the stock market will crash, defined as a 30% decline in value, at least two or three times between now and your desired retirement date. Believe that you have an inner spendthrift, that you will constantly try to delude yourself by rounding your income up and your expenses down. Optimism is a good propellant for pursuing career advancement, but it’s probably more dangerous around the topic of money than anywhere else.

Health. Start with the assumption that all the research about longevity, fitness, and nutrition is true. Assess what you know about the individuals in your family tree and assume that their health problems will also be yours. Here is where pessimism should stop. It’s a fixed mindset fallacy that genetic tendencies are fate, carved in stone, when really a tendency is just a tendency. We have information and interventions that were not available to earlier generations, and it’s prudent to make use of it. Pessimistically assume that one day, Future You will berate Today You for not trying, for abdicating and procrastinating and passively awaiting the worst outcome. Isn’t it more pessimistic to regard Present Self as an ignorant, lazy procrastinator who avoids the necessary hard work and self-discipline, than to see a more efficient body as somewhat attainable?

There’s no particular reason why any individual person couldn’t... let’s see... go on a trip, meet a new love interest, pay off debt, start a business, or get stronger and more agile. The same person could also move to a new home, adopt a pet, study a musical instrument, or learn a new language. Why not? Really, why not? A pessimism that denies options is not realistic or pragmatic. Pessimism can be a useful tool, but it’s only one of many among a thinking person’s cognitive assets.