The Little Middle School began as a Facebook post.

I put up a few sentences asking whether anyone would be interested in a tiny homeschool program for grades six through eight.

The timing was just right. People saw the post and spread the word. Within two weeks, we had eight or nine families ready to commit.

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I recently started a new project. I’m not ready to talk about it publicly, but message me and I’ll share.

In this new project, I’m facing all of the terrible and uncomfortable thoughts and emotions.

You know the ones. Questions like: What if this is a waste of time? What if I look stupid? What if I do it wrong?

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A few years ago, there was a bit of misguided revisionism around Shel Silverstein’s The Giving Tree. The idea was that the tree was so self-sacrificing that she enabled the boy to take and never give, and by the end she was just a stump.

I have four things to say about that: First, she was a tree. Trees don’t need to set boundaries, nor do they have that luxury.

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Back in the quiet, peaceful days before there was Internet on planes, I used to use flying time for high-level planning.

I loved the opportunity to work on my metaphorical 20,000-foot view while literally at 20,000 feet.

I always faced the same problem with this planning: The closer I got to figuring out something that I wanted to do, the more new ideas I would generate.

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A friend of mine is starting a new business.

However, he’s a little self-conscious about calling it a business. That’s because it hasn’t made any money yet. But, strictly speaking, it’s not a hobby. The intention is not to just have fun. The intention is profit, eventually.

How do we bridge that gap? How do we launch the thing if we aren’t sure whether it is going to work?

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