"How long will that actually take?"

We underestimate how long tasks will take because we picture them as one thing instead of a series of steps. In a 2004 study, psychologists Justin Kruger and Matt Evans found that when people broke a task into its parts before estimating, their time estimates got longer and more accurate. Listing the steps first is the fastest fix for a schedule that never works.

There's one question I ask so often my clients can predict it.

"How long do you think that'll take?"

I ask it because the answer tells me whether their week is real or a wish. And the first answer is almost always wrong. A client recently told me sorting the photos and video from a work trip would take "an afternoon." She got through the first few days of the trip and realized the afternoon was already gone. Her real estimate, once she looked at it honestly? About six more hours.

She's not bad at planning. She's human.

Why we're so bad at this

When you picture a task, you picture it as one thing. "Write the newsletter." One box. Feels like an hour.

But "write the newsletter" is really: pick a topic, find the example, write the draft, cut it down, find an image, set it up in MailerLite, test it, fix the link that broke, and schedule it. That's not an hour. That's an afternoon.

Psychologists call the general problem the planning fallacy. I covered it in my post on quarterly planning, where honors students thought their thesis would take about 34 days and it took about 56.

The fix: unpack it

In 2004, Justin Kruger and Matt Evans tested something simple. Before people estimated how long a task would take, like holiday shopping or formatting a document, some were asked to list out all the steps first.

The people who "unpacked" the task gave longer estimates. And those longer estimates were closer to how long the task actually took.

That's it. No app. No system. Just listing the steps before you guess.

It works because your brain can't skip what's written in front of you. The little steps you'd normally forget, like logging in, tracking down the file, waiting on someone's reply, are suddenly right there.

How to use this every week

  1. Take your top three tasks for the week. Not all of them. Three.

  2. List the steps for each one. Quick and messy is fine.

  3. Estimate each step, then add them up. Whatever number you get will feel too big. It probably isn't.

  4. Add a buffer. Something always comes up. I tell clients to add at least 25%.

  5. Check yourself afterward. At the end of the week, write down how long it really took. After a month, you'll know your own "fudge factor." For a lot of my clients, it's about 1.5. If they think something takes two hours, it takes three.

If your time comes in small pieces, this matters even more. Once you know the real steps, you can match them to the time you actually have. That's how you build a business in 20-minute scraps.

The real payoff

When your estimates are honest, your week stops lying to you. You stop ending every Friday feeling behind on a plan that was never possible. And you can say yes or no to new things based on the time you actually have.

So next time you write something on your list, ask yourself the question I'd ask you. How long will that actually take?

If you want someone asking you that every week, and helping you build a week that fits, here's how I coach.

Frequently asked questions

Why do I always underestimate how long tasks take?

Most people picture a task as one step instead of many, so they leave out the small parts that add up. Psychologists call this the planning fallacy.

What is the unpacking effect?

It's the finding that breaking a task into its steps before estimating leads to longer, more accurate estimates. Kruger and Evans demonstrated it in a 2004 study.

How much buffer should I add to my time estimates?

Start with at least 25%, then track how long tasks really take for a few weeks. Your own numbers will tell you your personal buffer.

Sources: Kruger, J., & Evans, M. (2004). If you don't want to be late, enumerate: Unpacking reduces the planning fallacy. Journal of Experimental Social Psychology, 40(5), 586–598. · Buehler, R., Griffin, D., & Ross, M. (1994). Exploring the "planning fallacy." Journal of Personality and Social Psychology, 67(3), 366–381."How long will that actually take?"

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