Why and How to be (Professionally) Pessimistic
Nobody likes a downer. There is a lot of advice out there on the importance of staying optimistic and is a sought after trait in professional settings. For good reason, too. Things are hard and if you start with a defeated mindset then the outcome becomes a self-fulfilling prophecy.
But like most of us don’t like cardio or hearing bad news, there’s a reason we should sometimes embrace the bad. Plenty has been written on optimism, I’m here to talk about the power of pessimism. Why and how you should apply it in a professional environment. In the right doses, it is healthy and helps you be both productive and prepared. Let me explain.
Primarily, pessimism is appropriate because of the reality of most people and projects that you encounter. 50% of small businesses fail within 5 years. For startups, that number is closer to 80%. Email click-through rates? 2.5%. Chance of landing any given job you apply for, 2%. Most large-scale projects come in over-budget and past-due. Construction estimates are rarely accurate. (Heck, there’s a good chance you don’t finish reading this article. A 7 minute read? C’mon)
At any given juncture in your life, you are at the confluence of increasing complexity, competition, and entropy. In general, there are more ways to mess up than there are to succeed. This is the nature of reality.
Indeed, our brains are conditioned to ignore this reality to help us overcome it. Overconfidence bias is the mother of many psychological biases and if we were more aware of this, a great many mistakes could be avoided (the Titanic and Chernobyl to name two high profile examples).
Being optimistic, or persistently overconfident as I will rebrand it, can help. There are great tales of perseverance and eternal optimism that drove success. Yet, these are exceptions where the alternative meant a great loss of life or otherwise. For every outlier tale of an entrepreneur who failed 100 times before making it once, there are dozens you’ve never heard of who exhausted their resources for little if no gain. (Can you tell I’m a thrill at parties?)
Is all this to say that you shouldn’t try? No, not at all. There’s great value in pursuing difficult tasks. I’m glad some people take on tasks against the odds. I’m here to argue that doing so with the right combination of reality and rationality can help in many ways.
A popular business practice are “postmortems” where once a project finishes the team gathers to reflect on what went well and what didn’t. That’s great.
I prefer to include the “premortem” as well. If we were to fail, what would cause it? What would the consequences be? What are the pitfalls, what are the unknowns that might trip us up? This is inherently pessimistic, you’re assuming failure, but by doing so you reveal blind spots you might not have uncovered otherwise. You might discover the project isn’t worth the effort, and that’s good to know before starting. Or, you might take a smaller-scale approach and proceed. Either way is better than assuming you’re immune to the failure that plagues most projects.
At work, “big wins” are sexy. It what your manager asks for, it’s what leadership celebrates on the all-hands or even the annual conference. However, is it not as valuable, if not more, to avoid big losses? At any company, avoiding a project that has valuable resources lost to it is key to survival. The right dose of pessimism helps avoid that.
Secondly, there’s a philosophical appeal to pessimism. One of my favorite little sayings is, “nothing is usually as a good or bad as it seems”. It helps you to stay grounded.
It’s been articulated in many ways, but can most succinctly put as “embrace the suck”. Instead of coming up with strategies to focus on the positive, training yourself to be optimistic, or ignoring the state of things, you acknowledge it and lean in.
I love Camus’s absurd heroes to approach this. It is absurd that we are placed into an existence so full of challenges and complexity, but with so few satisfying answers. Instead of viewing the world as the opposite — straight forward in which as long as you’re optimistic about the hard work you put in, everything will be fine — you embrace that you will not get external answers and work towards internal answers.
There’s a stoic appeal to the pessimistic approach. Instead of being swept up in your hopes of success that your work will bring, you work with the understanding that things out of your control can and will go wrong. You avoid the inevitable disappointment.
Work for the sake of work is enough if it’s worth it to you. History is full of examples of people who were likely pessimistic about the outcomes of their actions, but they did it anyway out of virtue and they serve as lessons to us now. Do you think the Texans at the Alamo were optimistic about their chances? Did that stop them?
Is work not full of times in which you can exercise this kind of attitude? “This very well might fail, so what? If it’s worth it to us, it’s worth trying and we won’t get bummed out when we hit the inevitable roadblocks.”
It feels good to be optimistic. But like it feels good to eat too much cake when what you need is a serving of veggies, undeserved optimism is a cheap filler for the substance of reality. It feels bad to be pessimistic about ourselves and the things we attach ourselves to, but it’s a poor reason to avoid it all altogether.
I’m not here to say you can’t be excited or confident about any of your projects. I’m here to say that you should probably be intentionally pessimistic about most things and use that to better approach the world. It doesn’t sell, it’s not sexy and it doesn’t make people like you. Nobody ever bought something because of uncertainty. But it’s the more accurate and grounded attitude that may end up making your life easier in the long run. So that’s a lot of why. What about how?
I already mentioned the “premortem” in which you go ahead and think of all the potential downfalls and plan against them.
The other way is to try to think like an investor because you are one. You choose how to invest your time, energy, social capital, etc. every day. Professional investors invest other people’s money, so they have to be smart about it.
The main way is to say “no”. Investors will say no to most opportunities that come across their desks because they know that most are not a good use of their time, much less their money. This is a pessimistic view, that almost any given venture will likely lose money.
That doesn’t mean they never invest, they invest with the belief that out of 10 ventures, 8 will either fail or just make it, and 2 will last and start to create returns. They choose those 10 with guidelines that lower the risk of their investment.
This is how you should view options at work as well. Most ideas are bad, most plans are wrong, and that’s okay! We’ll learn from them, and carry on. The purely optimistic approach would be to say yes to everything, which is surely a waste of your time and others.
Wise investors, like yourself, evaluate ideas through a lens of potential return as well as doing their best to eliminate the decision-making biases that infect us all. As I mentioned above, overconfidence bias is one that we must guard ourselves against. We underrate the likelihood of events that we don’t want to happen, and vice-versa. Investors would love to think that every venture is a good one, it would make it all so easy. That kind of thinking is pure optimism. That’s not reality, though.
So, ask yourself at any juncture, “How might I be wrong?”, “How easily could this go wrong?”, “What information do I need to say ’no’, instead of ‘yes’”?
Let this principle of pessimism guide you more often, and you will be grateful in the long-run. That much I’m not pessimistic about.
