One of the downsides of working in a field where so much is beholden to the almighty billable hour is that my brain has started to re-wire itself to engage the day in terms of one-hour chunks. This model is reinforced by other phenomena in life - calendaring software like iCal and Google Calendar make it easy to parcel out the day in discrete bits of time, beeps, alarms and bells go off on the hour mark in many workplace and educational settings, and then there's the cultural convention that "all meetings take about an hour" unless otherwise noted. We're increasingly a people whose quality of life and measure of productivity has everything to do with the 24-hour clock.
I generally don't mind this standard when I'm in "work mode," but I've noticed a very undesirable side effect on the rest of my life: I've been slowly losing the ability to spend open-ended social time with people, without my brain trying to fit it in to some predetermined scheduling blocks. The end result is that I think I'm less open to the wonderful, serendipitous experiences and discoveries that one can make in the comfortable and unregulated presence of friends and loved ones.
I've written before about the cues we give and get for when a conversation is going to go deeper, and when it's probably not. To answer my own question about what kinds of states of being allows you to go deeper in conversation, I've been actively working on spending more open-ended time with people I care about and want to get to know better. I have a few thoughts about how it's going, and what approaches are working: