On Pessimism

I’ve been a bit of a pessimist for a while now. Even publicly.

My argument then was that it was both an accurate and thus practical way to encounter the world. Basically, a lot of things are out of our control and can go wrong. Our belief that they won’t (optimism) has no impact on the outcome. We should be willing to embrace difficult emotions to interact with a more accurate model of the world. Nobody wants to feel inadequate, doubtful, or like they’re going to fail. But screw what feels nice and warm, get real. The more you engage with the world on the world’s terms, the better off you are.

A foundational belief of mine is that very few of us see ourselves or the world that clearly, and that is the root of many of our problems. To me, overly-optimistic people were not seeing things clearly. Overconfidence bias is the root of many biases and bad decisions. If you want to have a good strategy in life, you have to overcome this bias. You have to be a little more pessimistic.

A common piece of advice from therapists is that when facing difficulties you should talk to yourself like you would talk to a good friend. We can engage in some heavy negative self-talk, though if we pretend we are talking with a friend we are much more forgiving and solutions-oriented. The problem with that is that we are rarely as honest and straightforward as we should be with people we care about. When you tell people “things are going to be alright, you’re awesome, you got this” we do so more out of wanting to provide comfort and avoiding having to deal with their difficult emotions. It’s as much about soothing yourself as it is about soothing someone else. The same goes for our self-talk. Sometimes the best growth comes through confronting failures head-on.

However, after some time and thought. I need to update this belief. Here’s why:

Success can be boiled down:

Direction — what you chose to work on. Application — how you work on it. Consistency — working enough to make a difference.

To do any of that with the required energy for it to work, you have to be optimistic about yourself and the outcome. You have to believe despite the obvious reasons not to. This hurts me as someone who is trying to be as rational as possible but it’s the truth.

Direction. Are you optimistic that the direction you chose is the right one? If you’re not then it is going to be near-impossible to muster the willpower to get through whatever mountain you’re climbing.

Application. Are you optimistic that the methods you’re employing toward your goal are going to work? If not, then you need to do some more digging because otherwise, you will have a hard time following through on them. Especially when they require more effort.

Consistency. Are you optimistic that this juice will be worth the daily squeeze? If not, you likely won’t be consistent enough to succeed. To get good enough at something to make a difference in your life, you need to put the hours in. Inherent talent helps but even talent has to work hard, and the rest of us need to work harder. I hate truisms but this one is evident across disciplines.

I criticized optimists for being intellectually lazy, too. “You’re not objective or rigorous enough in evaluating yourself and the environment” was my going. Well, pessimism can be about avoiding difficult emotions to feel good, too. Pessimism is an excuse. If you find reasons for why you will fail and shouldn’t try then you don’t have to, well… try. If everything is out of our control, then we’re not responsible and don’t have to work that hard or be accountable. In any case, you’re avoiding the difficult emotion of failure or the difficulty of serious effort.

Another reason it can be lazy is in the sense that we don’t give enough things long enough to work. It’s obvious enough that success is not linear. There are either ups and downs that adhere to a line-of-best-fit that trends upwards, or there is a curved line that only sharply turns upward after things have an opportunity to compound. It takes time.

Being impatient is lazy, not looking hard enough for the positives is lazy, pessimism can be lazy.

I criticized the overly-optimistic by attaching their belief to the infamous overconfidence bias which haunts so much of our reasoning. Pessimism doesn’t get a free pass here, either. Negativity bias is everywhere, too. We are wired to look for threats. Being rational means looking past automatic reactions and bugs in our reasoning — including our proclivity to see more negative things and make a bigger deal about them.

Here is a key, though. You have to be willing to feel uncomfortable either way. Whether it is to confront a shortcoming of yourself, or by struggling towards progress. Too strong of optimism/pessimism will keep you from both. When used well, optimism helps you get through the lows of doubt that accompany struggle. Pessimism doesn’t.

“Which means improvement over the long term has to be interrupted by short-term adversity. Pain, regret, trudge, and bullshit is the fuel for advancing and the cost of admission you have to pay to enjoy the benefits of any long-term improvements.” — Morgan Housel

Here are my caveats to both pessimism and optimism. As with many things in life, it’s not the case that one end of the spectrum is the best one, and choices are highly context-dependent. We have to find the right balance, and know when which one is best used.

Amos Tversky — someone who smart people call one of the smartest people they’ve ever met — was famous for saying “Pessimism is stupid because you suffer twice. Once when you worry about the bad outcome, and once when it happens”. So I say, don’t worry, but prepare.

Pessimism and anxiety go hand-in-hand, and anxiety is mostly relieved through action. It’s okay to be pessimistic, as long as you are course-correcting. And yes, that course-correction can be as simple as saying “I see a bad thing coming, but I trust I can handle it”. Of course, you can prepare and course-correct in any number of ways. Another reason to be a bit more optimistic, you have options.

As someone who admittedly carries a lot of self-worth in their perceived intelligence, I liked to associate optimism with salesmanship and aloofness. I’m okay with the statement “Everything’s going to be great!” if you could explain why. That kind of naive optimism otherwise stunk of Tony-Robbins-style-evangelism where people flock to feel better about themselves. So my caveat with optimism is that it has to be earned.

Earned optimism does not mean citing “your gut” or making some loose comparison (you’re not Steve Jobs). However, there are many sources from which it can be earned. You can have optimism in a proven process, like with a diet or exercise program. You can have optimism built from the past, “I’ve done this before”. You can have optimism in the forecast. “Nothing is certain, but with careful consideration of the environment, I think this plan is going to work.” Sure, it does help to have pure faith when the going gets tough, but faith buttressed with facts is all the better.

The ultimate test of any life-philosophy is to take a step back and ask yourself, “Okay, how is this working for me?” Reflection is always good.

The answer for me was, “not well”.

I was using a sour, pessimistic attitude to excuse me from caring about things, from trying too hard, from starting anything or taking risks. What had happened was that after having so many set-backs in my career, I had lost my “locus of control” and was settling into a toxic attitude of “learned helplessness”. Defending pessimism was my rationalizing to settle into a comfortable mindset. Nothing was my fault, and I couldn’t do anything about it.

Take it from me, not a good place to be.

“Pessimism is stupid because you suffer twice. Once when you worry about the bad outcome, and once when it happens” — Amos Tversky

I’ve listened to Tim Ferris talk recently about the model of “expanding the surface area of luck”. I like this visualization. The more you put yourself in potentially serendipitous situations, the “luckier” you are going to be. There’s another part to luck, though. If your eyes are not looking for opportunity, and your mind doesn’t have the courage to pursue them, then you’ve missed it as if it weren’t there in the first place. Too much pessimism prevents you from looking and acting, because why bother? However, with optimism comes the energy to act on luck.

That “locus of control” bit is important. The belief that you do have control over things is a key to success in work and relationships, and mental health it turns out. So, despite all that can go wrong and is out of your control, it’s important to believe that you can handle it. Mark Manson puts this dichotomy well when he says that “You should be an external pessimist and an internal optimist”. Expect things to go bad, back yourself to get over them.

“I am an optimist. It does not seem too much use being anything else”. — Winston Churchill

For your own sake, you have to choose, almost irrationally, that your idea will work, your marriage will last, your skills are special, your work will pay off, etc. As always, it’s good to test and update your beliefs but you need to at least start as an optimist. Otherwise, you’re doing yourself and others a disservice. Plus, you get to feel better about yourself and the world.

There are some people who it favors to be a pessimist. Wise investors, for example, will be skeptical of stories that other investors and CEOs are telling to know when to short a stock. For the rest of us, though? It pays to be an optimist. So that you will see opportunities, back yourself to take them, put in the right effort, and rebound from adversity, you simply have to be.



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Thomas Sloan

Thomas Sloan

Hi. I’m Thomas. I like to think about thoughts, and then write for clarity. Not everything here is a fully formed belief. Let’s talk :)