There's a time with every habit that we feel great... and then at some point, we hit this dip that feels like we can't do it, and so we want to give up ... It's like getting punched in the face. It's like, 'Okay, that's enough. I don't want to do this anymore.' So, we get really discouraged. And I learned that if you have a plan for when you get punched in the face and you practice with that, the dip doesn't have to be the end of the story; it's just a part of it.

School, in a lot of ways, is very much about conformity—follow the rules and you'll get along fine. It doesn't matter so much about how much you've learned but more—especially in the early days of school—how much you can actually follow the rules.

There's a quote actually by Chögyam Trungpa ... 'The bad news is that you're falling through the air with no parachute; the good news is there's no ground below.'

The reason why we have so much stuff and we have so much debt and we take on so much in our lives is really because of uncertainty and anxiety.

You've been training and doing all these things—mindfulness, meditation, breathing practices—for stressful moments. Here's your fucking stressful moment. Let's see how you handle it, hot shot. You've been doing all this supposed practice in the safe confines of your living room; let's see how you operate in the real world.

It's absolutely preparation for any kind of uncharted territory. If you're going to be an entrepreneur, if you're going to be any kind of leader in any kind of organization where you're not being told what to do but you have to figure stuff out and deal with the uncertainty of that... Unschooling is incredible preparation for that.

School, by its nature, is someone making the decisions for the kids, so it takes away all of the decision-making for them. It takes away the uncertainty of their learning path because someone else has laid it out for you.

None of the urges that I thought I needed to act on were actually commands, but they were just feelings in the body.

People really crave simplicity in their lives when they're feeling overwhelmed and chaotic and just overloaded with all the stuff—all the emails and messages and everything that we have.

It's very true that you have to throw a lot against the wall to know what works, but I would add to that: You need to throw a lot against the wall to determine what works for you, because if you're experimenting in a new medium, you really don't know what you're going to enjoy, and you don't know what you'll be good at.