Fool Yourself with Style

I’m not into productivity hacks, I don’t read self-help books, and I’ve never been a fan of motivational mantras. But I do like getting things done, and not because I’m a high performer, but because I’m kind of lazy. My ideal state, though I know it never really exists, is to have nothing left hanging, no unsolved problems weighing on my mind. That’s what drives me to act: the quiet satisfaction of being done. And oddly enough, some of the mental quirks we’re told to avoid, like wishful thinking or underestimating the effort, can actually help make that happen.

It sounds counterintuitive, of course. We’re taught to be realistic. Grounded. Rational. We praise strategic thinking and long-term planning. But beneath every great ambition lies something more fragile and strangely powerful: self-deception.

After all, decades of behavioral science warn us about the dangers of faulty thinking. The planning fallacy, for instance, coined by Daniel Kahneman and Amos Tversky, describes our chronic tendency to underestimate how long projects will take. We assume things will go smoothly, even when past experience suggests otherwise. Whether it’s building a product, launching a startup, or writing a book, our estimates are almost always wrong: too short, too neat, too optimistic.

Then there’s wishful thinking, which leads us to overestimate our chances of success and downplay risks. It’s closely linked to the optimism bias: the belief that good things are more likely to happen to us than to others. These are cognitive distortions. On paper, they look like mental bugs.

But here’s the paradox: they might also be features. Because if we were truly rational, accurately predicting the time, cost, and pain involved in every goal, many of us would never start.

In Thinking, Fast and Slow, Kahneman reflects on the double-edged nature of optimism:

“The bias is very costly in the planning of projects, but it may also be beneficial… Optimists are normally cheerful and happy, and therefore popular; they are resilient in adapting to failures and setbacks, and their chances of clinical depression are reduced.”

Optimism, even when slightly detached from reality, helps us persist. It fuels motivation. It keeps us moving through uncertainty.

Behavioral economist Rory Sutherland pushes this even further. He argues that progress often comes not from logic, but from belief, especially belief not yet tested by harsh reality:

“If people knew how hard it was to do something before they did it, they’d never do it at all.”

That’s why so many ventures begin with the illusion that they’ll be easier than they are. You tell yourself, I’ll launch this in three months. It takes nine. But if you’d known that from the start, you might never have started at all.

And this isn’t just true for entrepreneurs. If you’ve ever tried to train for a marathon, pick up a new language, or switch careers, you know how it goes: you think it’ll be easier, faster, or smoother than it is. You underestimate the effort, overestimate your stamina, and dive in anyway. Funny enough, that’s usually what sparks the first step.

So the trick isn’t to shut down optimism, but to let a bit of discipline quietly shape it, so your excitement becomes something you can actually build on. Psychologist Gabriele Oettingen provides a compelling model in her book Rethinking Positive Thinking. Her research shows that indulging in positive fantasies alone can reduce effort, because your brain feels like you’ve already succeeded. But when you follow those fantasies with an honest assessment of what stands in your way (a process called mental contrasting), motivation rebounds.

“Positive thinking fools our minds into perceiving that we’ve already attained our goal, slackening our readiness to pursue it,” Oettingen writes. “But if we imagine the obstacles clearly, and contrast them with our desired future, we prepare ourselves mentally for the journey.”

In other words, hope works best when it’s grounded.

Still, we shouldn’t underestimate the emotional function of hopeful illusions. In a world of volatility and noise, a slight cognitive bias can act like psychological armor. As Stanford psychologist Carol Dweck showed in her work on mindset, belief in change, even when unproven, can alter outcomes. Believing you can grow makes you more likely to act in ways that produce growth. It’s a self-fulfilling loop.

The same goes for timelines. Think of the planning fallacy not as a failure of logic, but as a bootstrapping tool. It makes large challenges seem manageable. It gets the project on the calendar. And then, yes, adjustments come. But you’ve already committed. You’re in motion.

So yes, you’ll probably underestimate how long your next big project will take. And you might overestimate your odds of success. But that’s not always a flaw. ground it in consistent action, focus on the process, stay open to feedback, and keep showing up with grit.

Sources & Further Reading

• Daniel Kahneman – Thinking, Fast and Slow [1]
• Gabriele Oettingen – Rethinking Positive Thinking: Inside the New Science of Motivation [2]
• Rory Sutherland – Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life [3]
• Carol S. Dweck – Mindset: The New Psychology of Success [4]