(This post is a reply to Kaj's "My attempt to explain Looking" and Valentine's Kenshō. The target audience is people who feel like they have a good grasp on the underlying concepts but of course the post might also be interesting for other people)
I have the feeling that both you and Valentine mix the concept of Looking together with no-self even through they are independent for each other. In the Zen Buddhist theoretical landscape they are linked together but linking them together is a specific position of that tradition.
My main approach and the concept I have to think about this space comes from Danis Bois. He is an interesting Frenchman, who discovered mediation while learning to be an osteopath. The next ten years he spent 8 hours per day meditating, traveled to guru's in India and taught what he called at the time Fascia therapy. At a time where he was successful with his life in the spiritual community he thought they were too dogmatic and decided to go to university. He studied education as his major and become a professor in Portugal and recently retired from being a professor.
There's no renunciation of the self in Bois work. He grants that it often makes sense to think about having multiple 'I' but neither of them is false. On the other hand having a strong feeling of existence is a key in his way.
David Chapman wrote a lot about the conflict between Consensus Buddhism and Tantra Buddhism. Zen Buddhism is part of what Chapman calls consensus Buddhism. One of the key differences is that consensus Buddhism seeks the renunciation of the self while Tantra doesn't.
While the path of renunciation exists, I consider it to be in conflict with the standard rational goals of having an impact on the world. Given the predominance of Zen in popular culture it might seem like it's the only valid path, but it's not the only spiritual path that enables the ability to Look.
Both Danis Bois paradigm and Tantra care a lot about relationships and consider relating to be important. Going deeply into what that means is a subject for another post but fortunately we have the shared concept of Circling. Circling is about exploring how we relate to each other.
Just like mindfulness meditation is a condensed version of Zen, Circling feels to me like a condensed version of a spiritual path of being in relation.
In my model of the world I can imagine a person who spends a lot of time Circling developing the ability to look in the process. At the same time I wouldn't expect them to renunciation their self.