Planning Fallacy
Why we underestimate how long tasks will take and how to use the planning fallacy to position your product as the time-saving solution.
In this issue
Hey 👋 The Crew here.
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Ever started a “quick” 5-minute task that ended up taking an hour?
Or promised a campaign in two weeks…and a month later, you’re “almost done”?
That’s the Planning Fallacy. It’s the cognitive bias where we chronically underestimate the time, cost, and risk of future tasks—even when our past experience proves we’re bad at it.
It’s not only you. This bias is universal. Psychologists Daniel Kahneman and Amos Tversky first identified this in 1979 when they noted we take an optimistic, best-case scenario “inside view”.
We ignore the “outside view,” which is the hard data from all our similar, delayed projects.
The MIT study from Buehler, Griffin, and Ross is even more revealing. They had students estimate thesis completion times:
- Their average prediction: 34 days.
- The reality: 55.5 days.
Why does this happen? We anchor on ideal conditions. Traffic will be light. The design team will do their creative tasks on time. Every meeting will be efficient. It rarely ever does.
But this disconnect between our optimistic plans and messy reality creates the perfect marketing opportunity.
Three ways you can leverage The Planning Fallacy
Sell the shortcut
Most people underestimate task complexity.
What you can do is position your product as the time-saver that bridges the gap between expectation and reality.
Who does this well? Instacart. Its messaging focuses on “time saved” rather than convenience.
“Get groceries in as little as an hour” speaks directly to people who think they need to “quickly run to the store.”
The message? You thought it’d be quick, but we’re actually quick.
Instacart’s campaigns promise saved hours, turning the planning fallacy into a competitive advantage.
Create the “progress inflation”
Do you know what your customers absolutely adore? Feeling like they’re further along than they expected.
What you can do: Align their optimistic timelines by celebrating early wins. You can probably guess who’s an absolute master at this:
The obnoxious owl, of course. Complete one lesson, and Duolingo showers you with achievements. “5-day streak!” “You’re in the top 10% today!”
These notifications make progress feel faster than anticipated.
But this gamified approach isn’t exclusive to Duolingo. Reddit also has an “upvoting streak” for example, providing rewards if you engage with their platform every day. And many others.
Why this is important: Users may underestimate how long language learning takes, but Duolingo’s gamification creates frequent dopamine hits that make them feel like they’re progressing… which of course keeps them in the app.
The planning fallacy makes the journey feel longer than expected. So Duolingo and others artificially accelerate perceived progress with badges and streaks. And it works.
Emphasize the “hidden” tasks, then bundle them
Talking about planning often feels like going from A to B.
But most of the time, the planning itself has extra unseen steps… er letters.
People forget all the micro-steps involved in completing something. But you can remind them and bundle these overlooked tasks into your offer.
Chewy’s Autoship program does this brilliantly. Pet owners consistently underestimate the time and hassle of keeping supplies stocked. They think, “I’ll just order when I’m running low.”
… But that requires remembering to check inventory, placing the order, and timing delivery correctly. Chewy bundles all these invisible tasks into automated recurring deliveries.
Their marketing emphasizes “never miss a dose” messaging because customers routinely misjudge when they’ll need more food.
In a way, you’re also bundling the cognitive labor of remembering all those micro steps.
The result? In 2021, Autoship drove 70% of Chewy’s revenue. This year, it amounted to 80% of all sales. By solving a planning problem customers didn’t fully realize they had.
Time to plan something similar for your brand, too. Oh, did we say “plan?” It wasn’t intentional.
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ADVERTISING:Google’s Liz Reid confirmed that “richer and deeper” content gets clicks in AI Overviews. So naturally, Google is actively promoting work that shows real expertise and a human perspective, all while expanding its definition of spam. Unique takes are an asset.
YOUTUBE: Heads up, YouTube’s new Culture and Trends report is out. The big takeaway? Niche communities are the real trendsetters. They build cinematic universes around products, and their recommendations hold massive weight. Time to go look for micro influencers?
VIDEO MARKETING: Platforms might be pushing longer videos, but shoppers have spoken. Short-form content is king, and it’s preferred by 63% of users across surveyed countries. In the US, it’s 57%. So keep your content snackable and you’ll keep your audience happy. Nom nom.
ICYMI, last time we looked at the Curse of Knowledge.
The “Running late” Crew
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