The Pessimist’s Guide to Optimism

For, you see, so many out-of-the-way things had happened lately, that Alice had begun to think that very few things indeed were really impossible.”

Lewis Carol, Alice’s Adventures in Wonderland

For all it takes is for my paranoia to be right once, and it saves my life.

Nassim Taleb, Skin in the Game

The human condition matters, unconditionally.

It is the defining feature of your life, whether you think of it that way or not. However, like many “features,” it can be a bug if not handled well. And two significant aspects of your “human condition” are optimism and pessimism.

You’ve likely heard of some of the research on how optimism seems to be, well, optimal. For example, it correlates with better overall health, a longer life span, a stronger immune system, earning more, happier marriages, and better stress management.

And plenty of research has concluded that optimism doesn’t just correlate with these sorts of attributes; for many of them, it is the cause of the benefits.

But how about pessimism? Have you seen the research on how pessimism is, well, also optimal?

Chances are, you don’t think of pessimism as a desirable trait. After all, it generally correlates with outcomes like shorter lifespans, lower earnings, and lower overall achievement. How could it possibly be good for you?

But there are deep-rooted evolutionary reasons; a pessimistic species, one that’s more skeptical of potential sources of danger, is more likely to survive in a threatening world. But pessimism is plenty valuable in the modern world, too. For example:

  • Accuracy — As Martin Seligman, one of the foremost researchers of optimism and pessimism, has written, “[t]here is considerable evidence that depressed people, though sadder, are wiser.” For example, compared to optimists, pessimists more accurately judge their own capabilities and how much control they have in a situation, and more accurately recall past events.

Yet, of course, pessimism can lead to depression and learned helplessness.

So how can you balance optimism and pessimism? What’s a good way to manage the two?

I’ve been thinking about and researching that issue since law school. This post contains some of the themes and insights that can be gleaned in the hopes that maybe it can give you a mental model to better understand and approach the role of optimism and pessimism in your life. A list of sources containing all the information mentioned is included at the end.

A Degree in Pessimism

A good place to start examining optimism and pessimism is law school.

Lawyers are notoriously pessimistic; we’re often referred to as “professional pessimists.” But non-lawyers can learn a lot about their own optimism and pessimism from attorney-focused research.

In exploring lawyers’ high rates of pessimism, a good starting point is that this group of “professional pessimists” is not naturally pessimistic. That is, despite being one of the most pessimistic professions, lawyers aren’t naturally more pessimistic than the general population.

One of the largest studies of law students by Benjamin et al. showed that law students enter law school with totally normal, average rates of pessimism and depression.

But in the first semester of law school, pessimism skyrockets. Pessimism is so rooted in a legal mind that high levels of pessimism correlate with law school GPA.

As a profession, lawyers are 3.6 times more likely to suffer from depression than the average employed person. And this extreme pessimism, of course, spreads to other areas: attorneys are over five times as likely to develop alcohol-related problems as the general population and have the 11th highest incidence of suicide among professions.

But if law students entering law schools don’t start out that way, what gives? How do they develop such pessimistic capabilities?

Tetris and Blindness

At a fundamental level, law is about “issue-spotting,” or looking for all the ways the world can wrong. Law students are taught to be critical of everything, most importantly their own thinking. They’re taught to constantly ask questions like:

How will the other side undermine my case?”

How will the other party abuse this contract and hurt my client?

Your brain defaults and gravitates towards the thoughts that come most easily. The more you think about something, the stronger the neural paths to that thought become, and the easier (and more likely) it is for your brain to default to that mental pathway.

This is known as the Tetris Effect: if you give enough attention to an activity or thought, it deeply shapes and controls your thoughts (think: seeing shapes from a video game like Tetris after you’ve played it for an extended time). It seems obvious, but the Tetris Effect is profoundly powerful, in large part due to how easy it is to miss the subtle changes as they’re happening.

And, as Sean Achor explains in The Happiness Advantage, “[t]he problem is that if we get stuck in only that pattern, always looking for and picking up on the negative, even a paradise can become a hell.”

So law students that spend their time trying to imagine how the world can go awry end up getting stuck in a negative Tetris Effect: their brains identify bad events and outcomes to an unrepresentative degree.

In addition to the Tetris Effect, a second key part of the lawyers-as-pessimists phenomenon is Inattentional Blindness. This refers to the phenomenon that your brain is generally blind to what it doesn’t look for. That is, you tend to overlook what you don’t look for.

An oft-cited example of Inattentional Blindness is the gorilla experiment, where participants were asked to watch a video and count the number of times people passed a basketball. But halfway through, someone in a full-body gorilla suit walked through the middle of the action. The surprising finding was that nearly half of participants missed the totally obvious gorilla walking in the middle of their field of vision.

Why? Simple: they weren’t looking for it.

Their brains were focused on other things. This is Inattentional Blindness; your brain tends to be functionally blind to things you don’t look for.

And this blindness isn’t just visual; it applies to your brain’s ability to spot concepts, character traits, ideas, and other features of the world around you.

So, if you combine the Tetris Effect with Inattentional Blindness, you get:

(1) Your brain defaults to whatever you give the most mind space to, and

(2) Your brain is significantly blind to everything else.

These are also the mechanisms behind med student syndrome, where med students suddenly believe they have every disease they study because, well, those diseases are all they’re thinking about.

These underlying phenomena make it possible to change how your brain utilizes optimism and pessimism. But before exploring the tools that enable you to change them, a quick discussion of how optimism and pessimism relate is warranted.

Towards Optimism

The connection between law and pessimism occasionally leads to the question:

Does being optimistic or happy make you a bad lawyer?”

But this question assumes that optimism and pessimism are binary, or part of a spectrum. However, the research on the two traits isn’t entirely conclusive. One study of 852 pairs of twins, for example, concluded that “optimism and pessimism are at least partially biologically distinct, resulting in two distinct psychological tendencies.”

That is, to at least some degree, optimism and pessimism are separate traits. It’s not entirely accurate to think about them as “either-or” traits or part of a spectrum.

So, no, being happy doesn’t make someone a worse lawyer. Similarly, cultivating pessimism won’t necessarily make you less happy.

Building on this, you’re better off thinking about the two traits as separate skills that can, and ideally should, be cultivated separately. They’re similar, for example, to verbal and mathematical skills; being good with words doesn’t necessarily mean you’ll be bad with numbers, and vice versa.

Chances are you’ve probably cultivated one of the two more than the other (i.e., you identify as an optimist or pessimist), whether intentional or not. But if optimism and pessimism aren’t completely connected, you shouldn’t put yourself in one camp or the other.

So, now that you know you can cultivate each separately…how exactly can you do so?

Cultivating Optimism

Permanent, Personal, Pervasive

Interestingly, one of the most effective ways to strengthen your optimism is to focus on how you respond to bad events. Martin Seligman’s decades of research have concluded that the key distinguisher between an optimistic or pessimistic response is whether someone believes an event is (i) permanent (i.e., happening forever), (ii) personal (i.e., happening to them specifically), and (iii) pervasive (i.e., happening everywhere in one’s life). Optimists see bad events as impermanent, impersonal and isolated, but they see good events as permanent, personal and pervasive; pessimists are the opposite.

As per Seligman’s research, you can alter your “explanatory style” (i.e., how you explain which events are personal, permanent and pervasive) by using the mnemonic “ABCD:” Adversity happens, you respond with Beliefs, and those beliefs become Consequences, but you can Dispute the beliefs.

So when bad things happen, pay attention to and dispute your negative responding beliefs. Two key ways you can dispute beliefs are by (1) finding evidence that counters them and (2) considering alternative, more optimistic explanations.

Don’t Ruminate, Act

Rumination is a big contributor to pessimism. Rumination is the process of obsessively analyzing something (aka, “paralysis by analysis”). When combined with thinking about bad events (whether actual or possible), it becomes toxic. Allowing your thoughts to be excessively negative will trip you into the negative side of the Tetris Effect and Inattentional Blindness.

If you find yourself ruminating, two of the best salves are: (i) take action and do something (whether related to the problem or not); and (ii) plan time to think or write it out later.

Gratitude Journaling

Gratitude journaling is an effective way to counteract the Tetris Effect and Inattentional Blindness, as well as general pessimism and depression. UC-Davis researcher Robert Emmons’ has been a key figure in studying the effects of gratitude journaling, and you can read his pointers for effective journaling here.

One study by Emmons and Michael McCullough showed that found that people who wrote down five things they were grateful for once a week for ten weeks experienced significant increases in optimism, happiness, and reported fewer health problems. And it has staying power; another study by Martin Seligman found gratitude journalers were less depressed and happier than a control group at one-, three- and six-month follow ups.

Play to Your Best Self

Your Basic Rest and Activity Cycle (“BRAC”) (or ultradian rhythm) refers to your body’s natural cognitive ups and downs throughout the day. Generally, you’ll be least optimistic at 4 PM and 4 AM, and most optimistic in late morning and early evening, though, of course, the exact timing varies by person. This explains, for example, why you may feel excited about something at one time in the day, and unmotivated about it later. It’s why there’s much wisdom to recognizing the difference between “I’m burned out with X” and “I need sleep.”

So, to handle your BRAC and ultradian rhythms, play to your best self. That is, only make important decisions and tackle the hardest tasks when your mind is at its best during the day (usually, early on in your day before decision fatigue (discussed below) has set in).

Practice Strengths

Find ways to exercise your strengths. For example, a study by Peterson et al. found that the more often a person uses their top strengths in daily life, the less likely they are to suffer from depression, and the more likely they are to report life satisfaction. Similarly, Peterson et al.’s research has shown that people who use one of their top five strengths in a new and different way every day for one week experienced significant increases in happiness and less depression, and those effects continued to be present when measured three and six months later.

In sum, to cultivate your optimism:

  1. Apply Seligman’s ABCDs when bad events happen,

Cultivating Pessimism

Pessimism, taken to its extremes, can have abysmal psychological consequences. But, as noted above, there are plenty of situations where a healthy dose of pessimism can save your hide.

What’s the “right” way to cultivate and utilize pessimism, then?

The answer is what psych research calls “defensive pessimism.” Generally, this involves anticipating possible problems and how you will cope with them.

You can divide defensive pessimism into three buckets of questions: (1) the considered (i.e., what you know or are considering), (2) the unconsidered (i.e., what you don’t know or aren’t considering), and (3) how human psychology distorts your thinking.

Here are some questions to tap into defensive pessimism:

What You Know or Are Considering

  • Vet Evidence — If you’re relying on evidence to make decisions, vet it. What would make it non-representative? Will past behavior continue? Are there alternative explanations for what happened?

What You Do Not Know or Are Not Considering

  • Pre-Mortem — One of the most effective ways to tap into defensive pessimism is the “pre-mortem.” Before starting an endeavor, ask: “Assuming this fails, why does it fail?” As Kahneman explains in Thinking Fast and Slow, this tool “encourages even supporters of the decision to search for possible threats that they had not considered earlier.”

Behavioral Psych Errors

Your brain has evolved many short cuts (aka, “heuristics”) that are typically adaptive. However, they can also lead you astray. Any good form of defensive pessimism should consider these heuristic errors, such as:

  • Incentive Bias — What incentives do you have that may misguide your judgment?

To use defensive pessimism, you should ask questions like those above without letting them paralyze you. Which leads to the crux of this post: how do optimism and pessimism fit together best?

Global Optimism, Local Pessimism

Take a look at the tools for cultivating optimism and pessimism above. See any themes?

You can describe the optimism tools as cultivating your general perception of how you respond to what the world presents to you. For example, gratitude journaling re-wires your brain to more easily see the positives in life.

In contrast, you can describe the defensive pessimism tools as cultivating your response to and analysis of specific decisions beforehand. For example, the pre-mortem is an anticipatory strategy for a specific scenario.

Optimism and pessimism, when cultivated separately and properly, seem to fit together best with the principle: apply global optimism with local pessimism.

Or, as the saying goes, “hope for the best, prepare for the worst.”

This view of optimism and pessimism also shifts the paradigm; instead of viewing the two as permanent and binary character traits, you can, and should, view them as decision-making skills.

Quick Note on Depression

As mentioned, pessimism can, in excess, lead to depression. If you feel you’re depressed or at risk of depression, please, please, please seek help. Don’t tell yourself you can “think your problems away” alone. Remember the rumination point discussed above? Don’t overanalyze: take action, seek help, reach out to others.

Taking care of your mental health is not something to be ashamed of, or to be put off. It’s something to be proud of; after all, the human condition matters and, if you don’t take care of it, there will be consequences.

A Mental Model for When to Use Local Pessimism

If optimism should be your default, global strategy, and pessimism should be a local strategy for specific scenarios, when, exactly, should you call on defensive pessimism? You can’t go around doing a full-blown pessimistic analysis of whether to buy a medium or large coffee every morning.

Ultimately, you should develop your own rules of thumb based on your own risk tolerance. But some ideas to get you started are:

  • Risk of Ruin — One of Martin Seligman’s signposts for using pessimism is: “If the cost of failure is high, optimism is the wrong strategy.” This aligns with the common investing and finance advice: “protect your downside and the upside takes care of itself.”


To recap, a starting point of a mental model for using optimism and pessimism wisely is as follows:

Both Are Optimal

Optimism and pessimism each offer adaptive benefits. It’s not entirely clear whether they’re completely binary traits on a spectrum, but recent studies suggest they are, to some extent, independent attributes. In light of this, you can and should cultivate both as somewhat distinct skills.

Cultivating Optimism

  • ABCDs — Practice your ABCDs (i.e., dispute your responding beliefs to adverse events).

Cultivating Pessimism

  • What You Know and Consider — Ask questions like: can I really rely on what I know? What would disprove it?

The Balancing Act

The best approach to balancing the two seems to be: cultivate global optimism with local pessimism. Seek to be a general optimist that applies critical, pessimistic thinking to specific scenarios that warrant it. As Sean Achor explains in The Happiness Advantage, “[t]he ideal mindset isn’t heedless of risk, but it does give priority to the good. Not just because that makes us happier but because that is precisely what creates more good.”

Establish your own rules for when to trigger pessimism based on your own appetite for risk. However, at a minimum, you should apply defensive pessimism when there is the risk of ruin (financial, emotional, or otherwise), or when analytic reasoning is required.

The human condition is beautifully messy, and the above model is just that: a model to help you think about how you perceive the world. In the words of Charlie Munger, “all models are wrong, but some are useful.” So consider this mental model a starting point to be updated with your own experience. In that vein, any and all comments are welcome.


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Benjamin, Andrew G. H. et al., The Role of Legal Education in Producing Psychological Distress Among Law Students and Lawyers, American Bar Foundation Research Journal (1986)

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Cho, Jeena, Attorney Suicide: What Every Lawyer Needs to Know, ABA Journal (Jan. 1, 2019)

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Emmons, Robert A. and McCullough, Michael E., Counting Blessings Versus Burdens, J. of Personality and Social Psychology (2003)

Kahneman, Daniel, Thinking Fast and Slow, Farrar, Straus and Giroux (2013)

Kim, Eric et al., Optimism and Cause-Specific Mortality, Am. J. Epidemiol. (2017)

Peterson, Todd and Peterson, Elizabeth, Stemming the Tide of Law Student Depression, Yale Journal of Health Policy, Law, and Ethics (Volume 9, 2009)

Puri, Manju and Robinson, David T., Optimism and Economic Choice, J. Fin. Econ. 71, 79–82 (2007)

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Segerstrom, Susan, Optimism and Resources: Effects on Each Other and on Health over 10 Years, J. Res. Pers. (2013)

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Lawyer in SF @ fintech startup. Enthusiast of antifragilism, mental models and psychology. Connect @

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