Are We Listening? On Meaningful Conversation

Coffee is one of my favourite beverages. Not only because I enjoy having a cup (and many times two) of the dark elixir but because it’s often accompanied by good, if not great and memorable, conversation.

These memorable conversations usually take place with one or more of my friends and/or family, sometimes in a private home, sometimes at a coffee shop. Sometimes it follows a meal, sometimes not. 

What each conversation has in common, other than a beverage of some kind, is that there is no agenda, there is no timeframe or time limit. Once we've experienced it one, I find that almost everyone knows something good or great is about to happen but this last point we never bring up because it might kill the magic of it all.

These conversations can be exceptional because they're free flowing in nature, respectful and uninhibited in both subject and depth.

The progression of these conversations is relatively predictable. It usually goes as follows:

  1. First, we exchange pleasantries, a necessary lubricant to any interaction.
  2. Next, we catch up on what everyone’s been up to, to get a better understanding of what's been going on. You know, life.
  3. Then comes the good stuff. We hit upon a topic we want to delve into because it feels like the right time and the right place (and this could be anything).
  4. Sometimes, we even reach eureka moments, flashes of insight that invites us to dive into subjects, problems or ideas on our own time some time after the conversation.

If the conversation is particularly good, #3 and #4 repeat themselves once or more, with each topic developing at its own pace and with its own unique crescendo. I live for these moments. I cherish them. They represent opportunities for personal growth that is difficult to achieve individually. (If you're great having conversations with yourself, I'm jealous.)

I’m grateful for these exchanges. At the same time, the though of them saddens me because I believe they’re growing exceedingly rare for a number of reasons: time, attention span, diversity of personal experience & interests and payoff.


These conversations take time. They can last anywhere from two to four or more hours. Many would argue that we don’t have this luxury of time anymore, that we’re too busy, have too many obligations to devote that kind of time to just talking.

To add to the above, these conversations are impeded by a hard stop. If we want to get lost in conversation, we can’t have a hard stop to it. Who can get lost in thought if they’re looking at their watch?

 Attention Span

Taking a deep dive into one or more unexpected subjects takes both time and sustained focus. One topic can monopolize the entire discussion, sometimes for hours.

In this age of immediacy few of us can resist the reflex of looking at our [not so] smartphones, an action that rips us from the depth of the conversation, making it difficult to dive back in to the same extent. Smartphones have another effect as well: they reduce our ability to concentrate and, given these exchanges require undivided attention and focus, we are finding it increasingly difficult to dive into them. And no, a back and forth on Facebook, Twitter, etc. doesn't even come close to making up for this loss. (For more on this topic, I highly recommend Cal Newport's book "Deep Work".)

Diversity of Personal Experience & Interests

In this age of social media, specialization and of tighter social circles, it's becoming exceedingly rare to be surrounded by people who are materially different than we are (background, age, ethnicity, profession, orientation, style, attitudes, beliefs, temperaments). The depth and breadth of these conversations is strongly correlated with what we will take away from it and the more alike we are, the less likely it is that we will take away something of interest or importance that we wouldn’t have come across on our own.

And it makes sense that we've gravitated in this direction. If we have less time and reduced attention spans, we don’t want to take the time to bring others up to speed on a concept, and idea or a lifestyle we know well, unless there’s a good reason for it. The investment just doesn't seem worth it. And an impromptu conversation might just be dismissed as not good enough of a reason to justify the required effort.


In order to want to participate in these conversations, we need to care about these lightbulb or eureka moments. For some of us, they represent the stuff the good life is made of. They’re moments of insight and connection to others that add that secret sauce that make day-to-day living so much better. For others, the question is “So what?” Why bother investing all this time talking?

To this question, I would answer that it’s what we do with these moments of insight, that secret sauce, that matters. Rarely does one of these deep exploratory conversations not lead me to do something with what I’ve discovered. This might be reading a book someone referenced, looking up an organization or program someone mentioned, following up on something someone said that I need to better understand or even writing an article like this one.

It also helps me appreciate that we all have deep knowledge in one or more subjects and that we can learn a lot from each other, when we take the time to. Learning doesn’t just happen in school, by reading text books and by taking continuing ed classes. We can learn from just about anyone, anytime and anywhere. These conversations serve as a good reminder of this fact.

This last reason for partaking in deep conversation was well understood in England in the 17th & 18th century. Coffee houses were considered places of learning where men—yes, at that time, only men—of all walks of life would congregate and discuss all matters, including politics and news of the day, as well as taking deeper dives into a number of subjects. The reason they were so popular was the diversity of ideas and opinions patrons could find there. They never knew exactly what they were going to get, but it was likely to be good and that kept them coming back. Contrast that with today's coffee shop where over half the patrons are staring at a screen or simply rush in and out for their morning pick-me-up.

Life is Not a To Do List

When I compare the long term benefit of these conversations to what our modern day selves think we need from every interaction, the differences could not be more stark. I cringe to think that the only appointments we want to keep these days tend to be those those that have “a set agenda and/or clear deliverables”. That includes the now-popular mastermind groups, many of which appear to have turned into accountability and problem-solving groups to tackle the issues of the day. They remind me of forced workplace and school mentorship programs. Not only could they could be so much more but most of them fail because they lack connection and depth, the stuff that makes them worthwhile in the first place.

Life is not a to do list of necessary tasks and achievements. It’s a somewhat-organized type of wandering and that wandering helps us live better lives, both in the moment and over the long term by exposing us to thoughts, ideas and subjects we wouldn’t likely discover on our own. I’ve learned to trust this wandering and to appreciate how linear it can appear in retrospect.

Coffee anyone?

Image credit/copyright: Nauzan /

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