School of the Possible

School of the Possible

Monday memo #91

Estimate.

Dave Gray's avatar
Dave Gray
Sep 08, 2025
∙ Paid

The Monday memo is food for thought to fuel your week.

Hi everyone,

Next time you go out for a walk, try this: Pick a landmark in the distance and guess how long it will take you to reach that point. Make a note of the time you made the guess. When you get to the landmark, check and see how accurate your guess was.

If you make this a habit, you will soon find that your estimates get better and better.

The goal of estimating is not to be accurate right away. That would only be a temptation to cheat, by speeding up or slowing down your pace to arrive on the dot.

The goal is to get better at estimating, to gain a better understanding of your natural pace. How long does it take you to get somewhere, when you’re not dawdling or rushing, just walking?

When you estimate, you give yourself permission to be wrong.

A need for perfect information can easily become a reason not to start at all. It might be nice to know exactly how long a project will take, exactly how much it will cost, exactly what the outcome will be. But life doesn’t work that way. Life rewards those who can make reasonable guesses and adjust as they go. A rough estimate that gets you moving beats a perfect calculation that keeps you stuck.

Estimation is also a skill that improves with practice. The more you estimate, the better your guesses become. You develop a feel for things.

Since I have a practice of estimating distance as I walk, I know that my walking pace is about 3 miles per hour. I know that it takes me about 20 minutes to walk a mile. That’s my natural pace, which includes stopping to take pictures, which I often do.

Exercise.

Here’s your exercise for the week: Practice estimating everything you do. Don’t look things up; just guess first. How many words do you write in an hour? How long does it take you to read a chapter in the book you’re reading? How much will your groceries cost? How many steps to the coffee shop? How far will you get on your project today?

Make your estimate, then check the actual number. Keep a simple log. Not to judge yourself, but to calibrate your instincts. You’re not trying to be right. You’re trying to develop a feel for things.

At the end of the week, look back at your estimates. Where were you consistently over or under? What patterns do you notice? More importantly, notice how making quick estimates freed you from the paralysis of needing perfect information.

The goal isn’t precision. It’s gaining a better sense of how you make progress on things that matter to you.

This week, practice estimating. See what happens.


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