In his classic book The Four Hour Work Week, Tim Ferriss points out that it unrealistic and unreasonable goals are easier to achieve than realistic and reasonable ones.

As he memorably put it, “I’ll run through walls to get a catamaran trip through the Greek Islands, but I might not change my brand of cereal for a weekend trip through Columbus, Ohio.”

There are a few reasons for this. Tim points out the adrenaline and passion involved that can drive you toward an especially enticing result, along with the lack of competition one might find in going for something particularly difficult.

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A colleague is struggling with what to call his new business.

Really, he doesn’t have a business yet. All he has is an idea.

I used to get stuck there, too. I used to fret about names and logos and office space. I worried about finding the perfect photo and headline for a website, the right software to manage the project. I didn’t want to mess up my thing by doing it wrong.

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The Atlanta Public Schools have decided to shorten their school year by two weeks.

Due to teacher contracts, the district may not have been able to do the pre-planning necessary to launch a virtual school year effectively. The administrators have a lot of professional development planned in order to do so, and they’ve pushed back their start date in order to accommodate it.

My team and I can certainly relate. Time is short. We have dozens of students starting school this week, and we could definitely use another few weeks to put the finishing touches on our programming.

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In teaching or coaching, there are moments in which you sense that it would be counterproductive to push further.

Maybe the student has just had a breakthrough after a period of intense effort. Or maybe you get the feeling that she’s already pushing as hard as she can.

Or perhaps, it just feels fragile. A question or suggestion, no matter how gentle or well-intentioned, could cause the whole thing to disappear, like breath upon a snowflake.

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I wrote yesterday about my reluctance to push a student through developmentally inappropriate material on a too-fast timeline. There is a flip side, however. Learning is not linear, and it’s important to recognize when a student is actually ready to take a leap.

Here’s the uncomfortable part: It may be before you’re ready, and they may leap right over you.

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