A mentor once asked me, if you aren’t disappointing other people, who are you disappointing? It was one of those ah-ha moments when I came face to face (not for the first time) with my lifelong habit of “being good.” I’m so wired for it that it takes an effort to be honest with myself. Which is why writing in my journal brings such relief – it’s a no B.S. zone.

Recently I was asked what advice I would share with my 21-year-old self. She needed plenty of advice! One bit is: don’t be afraid to disappoint others. You’re going to anyway, so you might as well get used to it, rather than trying to avoid it. The freedom I felt from this advice tells me I’ve rarely followed it myself. The upside of having a son moving into his teens is that I’m getting a lot of practice, because I seem to disappoint him several times a day.

Lately, I’m trying on a different perspective, taken from the idea that our outer reality reflects our inner alignment. If I’ve proposed a course of action and half of my close friends and family are for it, but half are against, that indicates that I myself am only 50% on board. My other half is resisting, which shows up in my life as people counseling me not to do it.

I learned from Stephen Pressfield’s “The War of Art” that resistance is a compass reliably pointing me to an area of greatest potential growth. It’s tempting to push against someone who is standing in the way of my plans or challenging me to be practical or realistic for a change. But that person is really doing me a great service by showing me my own internal resistance. We’re back to who gets disappointed, aren’t we?

Resistance also shows me my “habits of Separation,” as described by Charles Eisenstein in this book. These habits are ingrained behaviors that reinforce the story that I am a separate, isolated individual, unconnected from the natural world or from other people. My avoidance of disappointing others is one of those habits, related to the belief that I can control people and outcomes. Seeking approval and being good are similar habits that help me to maintain a safe – but lonely – distance from others.

When I seek a loved one’s blessing for a proposed course of action and he refuses to give it, that feels like a betrayal. My reactive story goes like this: if he really understood me or cared about my future, he would happily jump on board this latest train. There’s an opening when I can see it as a valuable reflection of my own inner resistance. It’s at least a more truthful point from which to make a decision about whose turn it is to be disappointed.