Missed Connections: Are Your Conversations Deep Dives Or Surface Skims?

“Good conversation is as stimulating as black coffee and just as hard to sleep after.” –Anne Morrow Lindbergh, Gift From The Sea 

“Sometimes when it looks like I’m deep in thought I’m just trying not to have a conversation with people.” –Pete Wentz

Hello friend,

At a recent holiday gathering with my immediate family, we were chatting outside on the deck when up pulled a crew of more distant relatives, many of whom I hardly know.  I am naturally reserved—probably ‘unsocial’ is more accurate—in such situations, inclined to disappear until the crowd passes through.  There was one cousin with them, however, who holds a special place in my heart, even if we don’t keep in touch beyond the photos on Facebook.  I am interested in her life and have always imagined that we could be close if the logistics of our lives matched up better.

In spite of my well-practiced social distancing precautions, I was pleased when she moved through the family and over to where I was observing the scene.  I greeted her warmly, and we proceeded to spend the next several minutes getting caught up on her family news.  Before long, my brother drifted over and started chatting with her, and our window together closed.  A few minutes later, she was gone with the rest of the visitors, probably out of my sight for a few more years.

It was a nothing conversation, but the moment seems to keep returning to my mind in these receding days.  We had a few minutes, a window.  Although it is, of course, the norm to do the standard check-in and small-talk—How long are you in town?  How is your Mom?  Do you like living in Anytown?  Blah blah blah…–we didn’t have to.  Knowing that she is an avid reader, the very first question I asked her instead could have been about the best book she has read lately, or her top five authors, or her favorite memoir (my go-to genre).  Now that would have been a good conversation!  Instead of lamenting her departure because we hadn’t really connected, as happened this time, I could have lamented being unable to finish a gripping exchange of ideas that likely would have ended with a promise to message me a list of suggestions.  Those are two very different laments.

I can tell that the reason this seemingly forgettable interaction remains unforgettable to me is that it was a wasted opportunity to feel alive.  Isn’t that what a good conversation is?  That deep connection to another human being in a moment, however brief, is the spark of Life itself.

I love Life.  I crave it in its various forms, including the ripple of the stream, the song of the bird, the breeze on my skin, and the rising of the sun.  Humans are in there, too, sharing their Life with me through their art, their compassion, their aspiration, and their acts of true love.

And yes, their conversation.  Real conversation.  Impassioned, curious, well-listened, and deeply felt conversation.  When it is fully engaged in both the give and the take, a conversation—whether it is silly or sad, with a stranger or a friend—is a priceless gem.  And like that gem, it is, unfortunately, too rare.  We just don’t take that deep, beautiful dive often enough.  Like me with my cousin, the window closes, perhaps never to be opened again with that person.

It would be easy and cliché to say that in this age of social media and texting, our faces in our screens preclude us from making those meaningful connections and having those heart-to-hearts.  But I don’t know that I believe that.  I have hung around plenty of people from older, less-techie generations and found their chatter to be nearly all of the small and space-filling variety.  And maybe these screens—provided we are willing to put them down from time to time—are so saturated with juicy information on every topic imaginable that everyone can find something that they are passionate about learning and sharing with someone else who is willing to lock eyes and listen.  Maybe these screens are the gateway to deeper conversation, not more shallow.  I hope so.

I believe in our ability to converse and to light each other up in the process.  What I am less sure of is our courage.  Let’s face it, when you attempt to go below the surface with someone, you don’t know what kind of reception you will get.  For one, these attempts are so rare, especially in traditional small-talk zones—sidelines of sporting events, walking in your neighborhood, pubs, grocery stores—so people can be taken aback by your probing and your full attention (sadly, something we also rarely seem to give).

But if you can catch someone in that perfect moment when you are both willing to be open, present, and vulnerable, Magic can happen. 

I am the first one to admit I don’t like talking with most people.  My soul sensors are fine-tuned to detect people whose energies align with mine and those who don’t.  I passionately dislike anything in life that feels like a waste of my time—errands, lines, traffic, meetings, small-talk, the list goes on—and that includes spending time with people who don’t ignite something special in my heart or mind.  Knowing that about myself, it crystallizes my challenge: to take full advantage of every moment to converse with these captivating people, to not waste any words on small-talk, but rather to plunge directly into a meaningful exchange of ideas and energies.

I have to be more opportunistic with these rare moments and more efficient about getting into the meaty portion of people’s minds.  I have to launch into my best questions from the outset rather than participate in the standard opening, anesthetic nonsense about the weather, the outfits, and the appetizers on offer.

And rather than just waiting around hoping that I happen upon one of my favorite people and that they happen to have time for me at that moment, I also need to be better about seeking them out.  This directive struck me hard this week as I was strolling through the Twitterverse.  Amidst all of the politics and pop culture, I stumbled upon this humble gem by the octogenarian news man Dan Rather (who happens to be a fountain of simple wisdom): That person you keep thinking, “I should call them.”  You should.  Do it.  Pass it on.

That seemingly innocuous little note had the effect of simultaneously slapping me in the face and kicking me in the butt, giving me a wake-up call about all the people I so often think about talking to but never make the effort to reach them.  Dan is right.  I need to do it.  My life would be infinitely richer for it.

I want that richer life.  I want those richer conversations.  I guess it all circles back to that issue of Courage.  If you want something—in this case, a richer life full of deep, meaningful exchanges with fascinating people who stir my soul—and you know what it takes to get it, you have to be willing to stick your neck out.  I have to be willing to feel awkward in order to feel energized and enlightened.  I have to be brave enough to follow my “Hello” with a question I really want to know the answer to, one that can stimulate a lively exchange.  I must set aside my anxiety about picking up the phone and calling someone who hasn’t heard from me in a long time.  I must display the same courage that I implore you to summon.  That seems only fair.  I can do that.

Hello, World, I am ready to converse!

How about you?  How open and assertive are you in your pursuit of good conversation?  Open up your journal and wade through your interactions with the people in your life.  How deeply are you reaching below the surface in your usual conversations with the people you are interested in?  Not the people whom you cannot avoid in the regular course of your day—at your job or in your neighborhood or your hangouts—but the people whom you would choose to interact with; nobody wants to take a deep dive with someone they can barely tolerate.  So, for those intriguing characters in your world, how aggressively do you pursue their true nature and interests?  In your encounters with them, do you make it a point to raise topics that will lead to a lively exchange and perhaps some personal growth for each of you?  Do you try to draw out their life story?  Do you probe for their opinions on important matters, whether the politics of the day or a life situation you are struggling with?  Do you ask them to educate you on something you don’t understand?  If they are natural storytellers, do you try to coax them into a fascinating or funny tale?  Do you request specific favorites or lists, such as favorite books, movies, music, vacations, games, foods, etc. that you know will spark a spirited discussion?  Which of these types of inquiries seems to work best for you to get the kind of feedback and deep connection that satisfies you?  How aware are you of the quality of the conversation as you are having it?  How much time typically passes after you have had a wonderful give-and-take before you realize its rewards and think to yourself, “I want to do that again!”?  How often do you find yourself in one of these discussions?  Do you usually arrive there intentionally or accidentally?  How often does an interaction end leaving you with some regret—like me with my cousin—that you didn’t make the effort to go deeper?  Do you think it is because you lacked the courage in the moment to probe them, or were you just not mindful enough of how shallow the conversation was until after it was over, stuck in the habits of our usual superficiality?  Why are we so superficial in general?  Is it just a matter of practicality, us being unable to take a deep dive very often due to things like time constraints and other people overhearing what we would like kept private?  Or are we afraid of being vulnerable, of exposing things about ourselves that will be open to judgment from others?  Or are we shallow?  On a scale of 1 to 10, with 1 being shallow and 10 being deep, how deep are your conversations with the people you want to connect with?  How do you think that number compare to the average person?  How does it compare to the people you admire the most?  Who are those people?  Who in your life—whether it’s been 10 minutes or 10 years since you have spoken to them–would you love to get a phone call or a visit from so you can share stories, ideas, and passions?  How often do you think about calling or visiting them?  How much would it enrich your life?  What keeps you from doing it?  Does that fear or justification feel more important than the joy, the growth, and the inspiration that the connection would bring to you (and to them)?  If you could pick just one person to reach out to today for whatever reason, who would it be?  What would you ask them?  What would you share?  I dare you!  How much deeper do you want your connections to be?  How much richer do you want your life to be?  Are the two answers the same?  What is your next step to go further below the surface?  Leave me a reply and let me know: Are your conversations satisfying to your soul?

Take the plunge,

William

P.S. If this letter resonated with you, please share it.  Let it be another way to deepen your relationships.

P.P.S. If this way of probing yourself feels helpful to you, consider buying my book Journal of YOU: Uncovering The Beauty That Is Your Truth at your favorite online retailers.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.