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Radical Listening, and why it’s so hard

Updated: Jul 21, 2023

Listening is a skill that is strangely difficult to do well. I mean, all we’re doing is hearing words, making sense of them, and not talking, right? But we all know that real listening takes a high level of steadiness and openness, in both our hearts and in our minds. And it takes rock-solid restraint to refrain from doling out advice or related stories rather than hearing our friends, family members and co-workers out to the fullest extent.


Kate Johnson’s book Radical Friendship is organized around the 7 qualities of a noble friend that are described in a passage from the Buddha’s teachings called the Mitta Sutta. One of these seven qualities is the ability to keep your secrets. These friends can be entrusted with your intimate truths, through compassionate listening.

Apparently, listening well has been a struggle for a long time, because Zen Buddhist teachings address several obstacles that get in the way of compassionate listening. As Johnson describes in her chapter about listening, these obstacles are framed in ancient texts as an analogy, The Four Cups.



Musicians Aoife O'Donovan, Sara Watkins and Sarah Jarosz - members of the band I'm with Her.

1. Our Cup is already full. We think we know what the listener will say before we even hear it. We make assumptions, either because we know this person very well, or because we’re letting our biases obscure the complexity of the individual we’re listening to.

2. Our Cup is dirty. Our listening can be contaminated in three major ways: greed, hatred, and delusion. Greed can be expanded to include ego selfishness and our own need to be liked and validated. Hatred in its more subtle forms includes judgment and comparison. Delusion is mental confusion that can be as innocuous as mental fogginess or as stubborn as willful ignorance.

3. Our Cup is upside down. We refuse to listen to someone with whom we will surely disagree. There is no opening for dialogue.

4. Our Cup has a hole in it. It’s in one ear and out the other. Whether it’s forgetful listening, distracted listening, or lazy listening that won’t stretch to integrate something new and potentially complex, this behavior communicates a lack of care for the person speaking as well as the content of what they are sharing.


These 4 obstacles pretty much sum up all the ways my listening falls short, and I'm finding those cups surprisingly handy. The concrete image of a cup that is either full, dirty, upside-down or leaking wakes me up to how I can listen with more care, throughout the day. And this doesn't only apply to how I listen to people. As a music lover, I realize that these obstacles get in the way of my true appreciation of it as well. For instance, when I hear a song by an artist who has been recording for many years, I assume I know their work and usually don’t bother checking out their new material. I also listen in a critical, competitive way to musicians who are making music similar to mine. I'm reluctant to listen to music whose themes will challenge my views, rather than considering them and trying to at least understand their perspective. And all the streaming services at my fingertips, I’m especially guilty of treating music casually, as background noise, and not giving it the full attention it deserves.

I am still digesting all the wisdom from Kate Johnson’s clear, inviting book. I aspire to be a noble friend, but it’s a tall order! Paying attention to how I listen is an essential first step. And careful listening will enable me to befriend music more fully, too.


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