The intentional roamer: Becoming a compassionate observer
I just returned from a long journey — from Canada to Maine, Massachusetts, and the Catskills — visiting family and friends along the way. Now that I’m back on Shelter Island, which feels like a wonderful home base (at least for now), I’ve been reflecting on my time with the people I love and what I’ve observed in those connections.
One theme that keeps showing up for me is how often we make assumptions about others — sometimes we’re right, but often, we’re not. We build stories about people, and those stories are a form of judgment.
I’ve noticed how easy it is to settle for difficult behavior rather than address it, perhaps because we’ve tried before and nothing changed. I’ve seen frustration and disappointment take root, and I’ve watched people choose silence because speaking up feels like too much effort — or feels pointless.
Again with the Assumptions!
But here’s the thing: true communication begins with awareness and compassion, both for ourselves and others.
If you find yourself struggling with someone’s behavior, start by looking inward.
Ask yourself: Why does this bother me? What’s really going on when this happens?
Then, instead of reacting, try sharing how you feel, not just what you dislike.
And when the moment feels right, ask the other person: Are you okay? Is there something going on you’d like to talk about?
It takes courage to ask, but it opens the door to understanding.
I’ll admit — I still catch myself judging, making assumptions, creating stories. But I’m learning that being a compassionate observer doesn’t mean ignoring what’s hard. It means noticing with awareness instead of reacting with blame. It means choosing curiosity over certainty.
I talk more about this in this week’s Intentional Roamer audio, where I share what I’ve been learning about relationships, communication, and the power of compassionate observation.
🎧 Listen here → Becoming a Compassionate Observer (Length 6:27)