The Problem With Always Choosing Optimism

Six months into a product that wasn’t working, I was still telling people the data would turn. Every week I reframed the bad numbers as “early stage noise.” Every week I chose, with great discipline, to believe the next sprint would fix it. When I finally shut it down, a friend asked how I’d missed the signals for so long. I didn’t have a good answer. I hadn’t missed them. I’d seen them clearly and kept looking away.

That distinction matters more than I realized at the time. The signals were there. What I was doing wasn’t optimism in any useful sense. It was a trained habit of not believing what I could see. And the training had come, in large part, from a culture that treats relentless positivity as a professional virtue and treats doubt as something to manage rather than something to use.

The problem with always choosing optimism is that it eventually requires you to choose against seeing clearly. No real resilience is built on that foundation.

What does positive thinking actually promise?

The modern optimism industry rests on a simple claim: expecting good outcomes makes them more likely. There is a grain of truth in this. Self-efficacy matters. Believing you can do something is correlated with actually doing it. I’m not arguing against confidence.

But the pop version of positive thinking goes further. It suggests that negative emotions are problems to be corrected, that anxiety signals weakness, that entertaining bad scenarios is self-defeating. “Manifest your goals.” “Choose joy.” “Your vibe attracts your tribe.”

This is where the philosophy breaks down under scrutiny.

Neuroscientist Tali Sharot has documented what she calls the optimism bias: our systematic tendency to overestimate the likelihood of positive events and underestimate the likelihood of negative ones. In a widely cited study, she found that about 80% of people exhibit this bias across cultures, estimating their personal futures as rosier than statistical base rates would predict. The bias has survival advantages in some contexts. But Sharot’s research also showed it leads to consistent failures in risk assessment. We underestimate project timelines, overestimate our health, underestimate how often our plans fall apart. Optimism bias, unchecked, is not a superpower. It is a systematic error. ¹

The positive thinking industry treats this bias as a feature. What the research suggests is that it needs to be corrected for, not amplified.

Why does forcing optimism feel so empty?

Forced optimism feels hollow because it requires dismissing real emotional experience in favor of a performance. This is not just a feeling. It has a clinical name.

Researchers call this toxic positivity: the insistence that people maintain a positive mindset regardless of the situation, often invalidating genuine emotional experience in the process. Clinical psychology research suggests that suppressing or dismissing negative emotions does not make them go away. It tends to amplify them. When you tell someone, or yourself, not to feel what they are feeling, you add shame to the original emotion. Now they are sad and wrong for being sad.

I have sat in too many conversations where someone is struggling, real struggle, not performative, and the response they get is some variation of “focus on the positive” or “everything happens for a reason.” I have done this myself. It feels supportive in the moment. It rarely is.

Psychologist Gabriele Oettingen spent decades studying the relationship between positive thinking and goal achievement, and her findings were counterintuitive enough to change how I think about motivation. Purely positive fantasies, visualizing the desired outcome with no acknowledgment of the obstacles, actually correlated with lower achievement in her studies. People who engaged in what she calls “mental contrasting,” imagining the goal but also concretely identifying the obstacles, performed better across domains from weight loss to academic performance to career change. The process has a name now: WOOP (Wish, Outcome, Obstacle, Plan). It works not because it is pessimistic, but because it is honest. ²

What Oettingen’s work suggests is that hope and clear-eyed assessment are not opposites. The problem is not optimism itself. It is optimism used as a substitute for thinking.

What did the Stoics actually believe about adversity?

The Stoics did not advocate for grim endurance or the suppression of emotion. Their actual practice around adversity was more subtle, and almost the inverse of what the positive thinking movement prescribes.

Growing up in Dhaka, I was surrounded by a particular strain of practical fatalism. Not despair, but a realistic acceptance that things go wrong, that circumstances are outside your control, that a good life requires learning to hold both possibility and difficulty at the same time. I did not have a name for it then. Later I found it, roughly, in Stoic philosophy.

Marcus Aurelius in particular gets conscripted into motivational content in ways that would probably confuse him. The actual Stoic practice around adversity centered on a technique called premeditatio malorum, the premeditation of evils. You deliberately imagine what could go wrong, not to spiral into anxiety, but to strip outcomes of their power to blindside you. If you have already thought carefully about how a project could fail, failure does not collapse your world. You have already been there, in your mind.

The distinction the Stoics drew, which I find genuinely useful, is between what is in your control and what is not. You can influence outcomes. You cannot guarantee them. Optimism that ignores this distinction is magical thinking. Optimism that holds this distinction, meaning I will do my best work and accept what follows, is something sturdier. It does not require suppressing your honest read of the situation. It is compatible with seeing clearly.

That is a different thing from the “manifest your goals” version. It does not ask you to believe harder. It asks you to prepare better.

What changed when I started sitting with difficulty?

Sitting with difficulty, rather than optimism-washing it away, made my thinking sharper and my judgment more reliable. That surprised me.

For a while I tried to be the kind of person who projected confidence and forward momentum at all times. In tech especially, there is enormous social pressure to be bullish on your product, your team, your ability to figure things out. Admitting uncertainty can feel like a vulnerability to be exploited. Investors, colleagues, users, everyone seems to want the version of you that is certain.

I am not sure when I started losing patience with that posture. Partly it was watching founders I respected go down with ships they should have abandoned earlier, unable to let themselves believe the signals their own data was sending. Partly it was noticing that the people I actually trusted, the ones whose judgment I relied on, were the ones who could say “I don’t know” or “this is harder than I expected” without it reading as defeat.

There is research from organizational psychology to back this up. Amy Edmondson’s foundational work on psychological safety, the ability to surface bad news, voice concerns, and admit mistakes, identified it as one of the strongest predictors of team performance. ³ Enforced optimism is psychologically unsafe by design. It creates cultures where people learn to perform positivity rather than report reality. That is dangerous in any system where decisions depend on accurate information.

My own shift was quieter and less dramatic than any of that research suggests. I started noticing that when I let myself actually sit with a bad outcome, not catastrophize, not spiral, just acknowledge it clearly, something changed. The thinking got sharper. I stopped spending energy on the performance of confidence and could use it on the actual problem. Clarity about what was wrong turned out to be more useful than hope that it wasn’t.

I did not become a pessimist. I still make things. I still start projects with more conviction than the numbers justify. But I try not to confuse that optimism with a prohibition on seeing straight.

Is there a better way to hold hope?

A more sustainable version of optimism is a disposition toward action rather than a filter on perception. It means staying willing to try, to iterate, to believe the next attempt might work. It does not require editing out your honest read of the situation.

The philosopher William James, writing about what he called the “will to believe,” made a version of this argument. In genuinely uncertain situations, where no amount of evidence can settle the question in advance, choosing to act as if something is possible is itself a reasonable bet. That is not the same as pretending obstacles do not exist. It is choosing to act anyway, with open eyes.

That framing I can work with. Hope as a commitment to keep showing up, not as a requirement to feel good about the odds. It leaves room for the clear assessment you need in order to make good decisions, and it does not ask you to perform a feeling you do not have.

The cult of positive thinking collapses this distinction. It treats the feeling of confidence as the thing you need to generate, then implies the outcomes will follow. What it actually produces, at scale, is a lot of people who have learned to look confident while quietly ignoring the data in front of them.

I spent six months doing that. I do not think I was weak for it. I think I was well-trained.

What does this mean practically?

The alternative to forced optimism is not pessimism. It is calibration combined with commitment.

Calibration means letting yourself actually assess the situation. If a project is three months from running out of money, that is information. If a relationship has the same argument every week without resolution, that is information. If a product has been flat for a year, that is information. Positive thinking that requires you to explain away that information is not making you more resilient. It is making you less accurate, and less accurate people make worse decisions.

Commitment means staying in the game anyway. Not because you have convinced yourself the odds are better than they are, but because you have decided that acting on the possibility is worth it to you. This is closer to what James actually meant by the will to believe. Not wishful thinking. Deliberate engagement with uncertainty.

Oettingen’s WOOP process is a good practical tool for this. State the wish. Imagine the best outcome. Identify the specific obstacle most likely to get in the way. Make an implementation plan for when you hit that obstacle. The process does not ask you to feel optimistic. It asks you to prepare honestly and then act.

The Stoic premeditatio malorum works similarly. You are not dwelling on the worst case. You are removing its power to blindside you. When you have already thought about how things could go wrong, you stop spending mental energy protecting yourself from the possibility. That energy is available for the actual problem.

None of this is complicated. It is just the opposite of what the positive thinking industry has been selling for thirty years.

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The cheerful face in the mirror is not the same thing as wisdom. Sometimes the bravest thing is to look clearly at what is actually there, acknowledge it without flinching, and then decide what you are going to do about it. That decision, made with open eyes, is the only kind of optimism I have found worth trusting.

Footnotes

1. Sharot, T. (2011). The optimism bias. Current Biology, 21(23), R941-R945. https://doi.org/10.1016/j.cub.2011.10.030 ↩

2. Oettingen, G. (2012). Future thought and behaviour change. European Review of Social Psychology, 23(1), 1-63. https://doi.org/10.1080/10463283.2011.643207 ↩

3. Edmondson, A. C. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44(2), 350-383. https://doi.org/10.2307/2666999 ↩