The Value in Negative Thinking
When I was an undergrad, my roommate was someone I thought of as a pessimist. M was great company but he was in the habit of presenting the rest of us with the worst-case scenario. This particularly chafed a group of eighteen year olds when anything exciting was in the works. M’s two pennies would more often than not be a dampener. Why are you such a pessimist, we would ask. I was one of those who would be rattled by M.
I was also one of those who paid little thought to the future. Anticipating the future, especially negative outcomes, and preparing for all contingencies was not something I invested myself in. As a result, I did not build my future with forethought. I let it happen to me, (over)confident in my abilities to deal with whatever came my way. I was an uninformed optimist.
Not starting something simply because we are worried about the worst-case scenario materializing is letting pessimism hijack our decision making. But anticipating the worst outcome is not pessimism. It does not signal we are less confident in our abilities to accomplish what we have set out to. It means being clear to ourselves that we cannot predict the future. It is acknowledging the uncertainty and allowing for less favorable outcomes to co-exist in our minds with the more favorable ones. It is an admission of the role of luck and of the fact that even our best efforts may not always lead to the best outcome.
Putting time and effort into planning for something that is not what you want to happen may sound like a waste. But there is a continuum of possibilities between 0% right (100% wrong) and 100% right (0% wrong), isn’t there? When we only think positive, we seldom urge ourselves to consider the range of probabilities. We are aiming for the bull’s eye but what if we miss, and how does our choice of next move depend on how much we miss by?
Our confidence is underpinned to being right and ignoring most, if not all, remaining possibilities. This confidence is hollow. If we have planned for only one path to our destination we will be at a loss when we see that chosen path blocked. The sure-footedness that emerges from having considered a range of paths is one that helps us maintain composure when plans have to change. That confidence is bedded in substance.
It is important to make a habit of anticipating the future by thinking negative. Because if we have never learned to include a margin of safety into our plans, we won’t suddenly do so when the stakes are high. If we are not someone that checks the spare tire before a much anticipated road trip, it is not going to occur to us to consider the prospect of the best performer in our team quitting in the middle of a critical project. Without awareness, our confidence resides in our belief that only good things will happen. We are uninformed optimists, much like I was.
It is when things do not go our way that we want options. Planning for the worst outcome means admitting to ourselves how much we do not know about what is to come. That is a humbling thought, not easy to come to terms with. No wonder making a habit of planning for negative outcomes is hard.
The most volatile thing is not always something whose value fluctuates wildly. It is that whose value we do not fundamentally understand such that any deviation from its present state comes as a surprise to us. With things we do not understand, we believe the future will be exactly like the present. But we know that is not true. We see it again and again in the world.
So if you are planning a bank heist, better think negative. Or make sure you have someone like M in your crew. I know I would.
Thanks to Atul Sinha for reviewing drafts of this.