The Value of Uncomfortable Conversations

I never tell people on airplanes that I’m a therapist.  Early in my career, a colleague advised that if he wants to have a productive or relaxing flight, he tells his seatmate that he sells life insurance.  But on a recent flight to New York, I couldn’t ignore the tears rolling down the face of the stranger sitting next to me.  After all, I chose my career because I have a mighty need to help those who are hurting.

I closed my book and turned to her.  “You look like you could use someone to talk to.”

She pointed to her computer screen.  “My boyfriend,” she told me through her tears…  “I haven’t seen him in months, and now he wants to bring someone else with him to pick me up from the airport.  What an asshole!

I glanced at her screen.  After a string of gchats about how amazing it was to have WiFi access from a plane, there was a message: “I’m hanging out with Eric right now – what do you think about him coming with me to pick you up, and we can all hang out afterwards?”

I put on my empathy/empowerment/assertiveness-is-king hat and said, “that really sucks.  I’m sure you want to see just him after such a long gap.  You know, I feel like you have the right to ask him not to bring his friend.”

A half-smile through the tears.  “Thanks.”  She turned back to her screen.  I turned back to my book.

A few minutes later, I felt her eyes on me, so I looked up.  She quickly turned back to her screen.  My eyes followed hers, and I saw her type: “Since you’re picking me up, and it’s your car, I guess I’m not really allowed to ask you not to bring Eric.”

It was very clear to me – she was being passive aggressive because the idea of direct communication, or assertiveness, was deeply uncomfortable.


Why are people afraid of uncomfortable conversations?

I can answer this question in one word: Vulnerability.

Contrary to conventional wisdom, vulnerability is not a bad thing that sets you up for pain and failure.  It’s also not inherently a rewarding thing that sets you up for feelings of relief.  What it is is a step into ambiguity, into not knowing whether you will be rewarded or punished for taking a risk.

Vulnerability is putting your squishy, open heart on the table with a tentative “plop” and saying, “here I am, fragile and wanting to be seen.  Please don’t hurt me.”  Vulnerability is knowing that someone could say, “Wow, that’s you?  What a worthless mess you are” or they could say, “Thank you for showing yourself to me.  Here’s my heart, too.”  Vulnerability is weighing the costs and benefits of those two outcomes, and deciding that the payoff of the latter is worth the risk of the former.

What vulnerability requires is courage.  And courage is something that many people, including my tearful airplane acquaintance, have trouble mustering.


We need an uncomfortable conversations revolution!

I wrote a few months ago, in an article about ghosting, that we need an uncomfortable conversations revolution.  It’s true that part of the reason we don’t get our needs met is that everyone has their own agenda, and sometimes that agenda runs contrary to our own.  But a HUGE contributor is that we’re unwilling to initiate a discussion about something that might be challenging.

What would be different if we could all push through the vulnerability and discomfort of talking about hard things?

We would get more of our needs met – yes – but we would also understand better what other people need instead of having to guess or read minds.

We would all understand each other better, and feel closer and more connected.

We would feel less shame on an individual and systemic level, and we wouldn’t feel the need to protect ourselves from it by blaming, judging, arguing, and becoming defensive.

Let’s explore each of these below.


Uncomfortable conversations help you get your needs met.

Assertiveness is an act of kindness.  When you’re assertive, you’re saying, “it’s hard to ask for this, but I know I’ll get upset with you if I don’t – and I value our relationship enough for this conversation to be worth the risk.”  You’re also eliminating the need for minefield-like conversations where the other person has to read between the lines.  (Just imagine being the woman on the plane’s boyfriend – with a response like that, what on earth is the right thing to say??)

Initiating an uncomfortable conversation doesn’t have to look like an attack – and in fact, it shouldn’t.  Instead, a successful uncomfortable conversation begins with one person kindly and respectfully asking for something they want or need.  It’s then navigated by giving your conversation partner the benefit of the doubt in order to remain calm and connected while talking about a difficult thing.

You’re not a mind reader, which you already know.  It’s much harder to remember that this is also true of the people in your life.  When you have an uncomfortable conversation, you’re relieving a loved one of the burden of trying to guess what you’re thinking – and relieving yourself of the fallout if they guess wrong.


Uncomfortable conversations lead to deeper connection.

If I’ve said it once, I’ve said it a thousand times: Connection is why we’re all here.

But what is connection?  Think about the people in your life who you feel deeply connected to.  What does that actually mean?  For most people, it means feeling seen, understood, and loved.

Uncomfortable conversations help you clarify your thoughts and feelings so that another person can see you with more depth, and understand you better.  They can also relieve qualms or doubts about whether you are loved.  Consider the following alternate response the woman on the plane might have offered:

“I’m glad you and Eric are having a good time, but I miss you a lot, and was hoping we could spend the night together, just the two of us.  Also, I know you didn’t mean to do this, but I felt sad when you suggested he come with you because the story I told myself was that you didn’t care whether we had a chance to reconnect.  I also feel a little bit afraid that you’re nervous about being alone together after all this time.”

Super vulnerable, right?  But now her boyfriend understands how she is feeling.  And maybe he responds:

“Wow, I didn’t think about it like that.  I don’t want you to feel sad or scared.  I’m really excited to see you, and we’ll have the whole week together.  Eric said he’d like to see you while you’re in town and I thought this might be a good opportunity.  It didn’t even occur to me that that would affect the dynamic when I picked you up at the airport.  That’s a really good point, and I’ll tell him we can hang out with him later in the week.  I miss you a lot, and I’m excited about seeing you in a few hours when you land!”

Now she’s likely to feel that not only is she seen on a deeper level, but also her humanness (that is, her experience of having feelings) is not a deal breaker in their relationship.  In other words, she feels loved.

Intimacy = Into Me, See.

And that’s how connection deepens.


Uncomfortable conversations mitigate shame.

Brené Brown defines shame as fear of disconnection.  It’s the sense of “I’m all alone” or “I’m not good enough” or even “I’m worthless.”  For this reason, shame thrives in conditions of secrecy.  Shame that remains unspoken grows, because all you can do is imagine what’s happening in other people’s minds.

Some people create ways to manage shame that doesn’t involve acknowledging it.  These defenses include blame, anger, defensiveness, withdrawing, and other pretty toxic emotions.  This is why shame is such a dangerous thing when it’s felt deeply by people in power.

But other people, who practice what Brown calls “shame resilience”, are really great at talking to the important people in their lives when they’re in shame.  These are people who can identify when they feel ashamed.  Rather than trying to quell it, these people reach out to supportive people who they trust.

When people untangle their shame through these uncomfortable conversations, they don’t feel the need to shame others.  When leaders are driven by courageous vulnerability rather than shame, they don’t need to abuse their power.  When shame is mitigated, we are all kinder, more loving, and more connected people.

And I genuinely believe that for all of these reasons, uncomfortable conversations can change the world.

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