The perfect plan trap
Nothing will go as planned
🏷️ Categories: Mental models, Decision making and biases, Mathematics.
Some people mistake being realistic for being pessimistic.
In reality, they’re almost opposites.
Thinking with your feet on the ground is the most powerful antidote against disappointment and chaos—and it secures any decision or project you have in your hands. But no, we live in a world that pays disproportionate attention to the extraordinary.
The entrepreneur who made millions and started in a garage.
The athlete with no resources who was discovered and signed by a major team.
The writer who self-published and went on to sell millions of copies.
They all have one thing in common: they’re extraordinary cases. The exception.
The worst thing we can do is use them as a reference. But we do it. We love epic stories because they motivate us. Then we try the same… and crash into reality. The best-case scenario is a statistical outlier.
If you want to reach your goals, plan better, and avoid derailment—keep reading.
Being realistic isn’t about killing dreams.
It’s about bringing the unreal into the real world.
The Problem of Expectations
We love extraordinary cases and want to be one of them.
That motivation can blind us, leading to unnecessary risks and reliance on unrealistic plans. This is called the planning fallacy—a classic form of self-deception. In fact, only 30% of people meet their own deadlines, and just 11% do when they plan with high expectations (Buehler et al., 1994).
I know. It stings. But that’s how reality works.
What’s wild is that this happens even after people have failed many times. Each new goal brings its own dose of optimism. We plan for the best possible outcome, convinced this time it’ll work...
And then it fails again.
Sydney Opera House: Planned for 1963. Opened in 1973. Cost 14 times the initial budget.
Berlin Brandenburg Airport: Planned for 2011. Opened in 2020. Cost 3 to 4 times more than expected.
Guggenheim Museum Bilbao: Planned for 1994. Opened in 1997. Cost nearly 3 times more than estimated.
Panama Canal: Planned for the late 19th century. Opened in 1914. Cost at least 3 times more than expected.
We’re not talking about amateurs. We’re talking governments, renowned architects, engineers, multi-million-dollar investments... So what made them fail so spectacularly? The same thing that gets to all of us: assuming the best-case scenario and ignoring conjunctive bias.
Conjunctive Bias
Every change you make in a plan is a change to a complex system.
That means you’ll almost never get the ideal result. No matter how well you plan each step, the more steps depend on each other, the higher the odds that if one thing fails, the whole plan collapses. Each extra step doesn’t add risk—it multiplies it.
That’s why large projects almost never meet their deadlines or budgets.
Because they rely on many different things happening in perfect sync. And in real life, perfect sync almost never happens. Due to the butterfly effect, even the smallest change can completely derail a plan.
An extreme case: Shakespeare’s starlings.
Eugene Schieffelin, an ornithologist obsessed with Shakespeare, released 100 starlings in Central Park to “bring the wildlife of Shakespeare’s plays to New York.” Today, there are over 200 million in the U.S. They’re invasive, cause plane crashes, and destroy crops.
His love of Shakespeare caused an ecological disaster.
Let’s flip the scenario.
If you’re planning a beach day this Saturday, and the best-case scenario is: no flat tire, everyone agrees on the time, and no one forgets their swimsuit—you’ll probably make it. There are fewer variables, so more chances of success.
But many of us plan as if life were a day at the beach.
That’s why extraordinary outcomes in big plans are statistical anomalies. The truth is, they’re just one of millions of possibilities. They might happen, but it’s much wiser to prepare for the probability that they won’t—which is far more likely.
For that, you have the following tools:
Inversion: Instead of thinking “How can I succeed?”, ask “How could I fail?” Think about the potential obstacles that could derail your plan. We tend to overfocus on how to make things happen, and ignore what to avoid.
Break down your plan: Don’t say “I’ll finish my book in a month.” Break it down: research, outline, chapters, editing. Estimate each part of your big projects. According to Forsyth & Burt (2008), this method produces more realistic timelines.
Precautionary reserve: If you’re setting a deadline to publish a book with a publisher and you normally write 1,000 words per day, plan with 800 words per day. If success depends on everything going right, you’ll likely fail.
Study average cases: Planning to launch an online course? Don’t base your timeline on your excitement. Look at how long it took people with cases similar to yours. If most took 6 months, you probably will too.
Your expectations matter.
Anticipating multiple outcomes protects you emotionally.
If the best happens—amazing!
If something worse happens—it’s not the end of the world. Knowing life won’t be a smooth ride prepares you for the bumps and failures. Because they will come.
Live with the excitement of someone building castles in the sky—
But place each brick like someone building on solid ground.
Nothing more to say.
✍️ Your turn: Do your plans and goals need everything to go right in order to work... or could they still work even if things go wrong?
💭 Quote of the day: "It's never the changes we want that change everything."
—Junot Diaz, The Brief Wondrous Life of Oscar Wao
See you in the next letter! 👋
References 📚
Buehler, R., Griffin, D., & Ross, M. (1994). Exploring the «planning fallacy»: Why people underestimate their task completion times. Journal Of Personality And Social Psychology, 67(3), 366-381. URL