I almost sent a text I would have regretted.

Someone had misinterpreted something I’d said, and I wanted to fix it — without making things worse. So I started composing a carefully worded message before I caught myself. Instead of hiding behind my iPhone screen, I picked it up and called her.

Within five minutes, what could have spiraled into a drawn-out misunderstanding was resolved. My voice did what twenty text messages never could — conveying my genuine concern, clearing the air, and ending with a laugh.

It reminded me how powerful (and increasingly rare) a real, unscripted (and yes, sometimes messy and awkward) conversation has become.

Chances are, you’ve seen it too: a group of young people sitting together, all on their phones — more likely to text a meme than share a real fear. I call this the connection paradox — surrounded by communication tools, yet starved of genuine connection.

At the heart of it lies something subtle but powerful: a growing reluctance to brave the awkward moments that real connection demands.

We’ve become masters of impression management — curating, editing, scripting — but amateurs at vulnerability.

We draft and redraft our replies. Some even put them into ChatGPT to polish (and yes, I see the irony of writing that here). But beneath all that polish often lies fear — fear of judgment, rejection, fumbling our words, or losing face.

“The leaders I work with rarely struggle to set strategy. What they struggle with most? The awkward conversations that bring that strategy to life.”

And it’s not just Gen Z I’m talking about. We all do it. Even seasoned leaders I work with often find themselves avoiding discomfort. Just last week, I asked a group of executives where they most regret not being braver in their careers. The majority said it was in addressing people issues. One shared:

“I should have let someone go sooner. I kept hoping things would turn around, even though I knew that was unlikely. It just felt easier to delay.”

It’s rarely a lack of intellect or information that holds leaders back — or perpetuates their biggest (avoidable) problems. It’s fear. Fear of the fallout. Fear of confrontation. Fear of defensiveness. Fear of holding people accountable — and the tension that may follow.

In an AI-fueled world of polished communication, genuine connection has never been rarer — or more valuable.

Because it’s not in grand declarations of strategy that trust and culture are built. It’s in the small, courageous, messy moments of human honesty that bring those strategies to life. Yet these are precisely the moments where courage counts most — not in setting bold strategies, but in having the honest, human conversations that bring them to life.

Long before GenAI came along, we were already defaulting to digital distance — sending emails instead of talking, texting instead of calling, posting instead of showing up. (I even wrote a Forbes column on “talking over texting” back in 2012.)

Now, with AI permeating every corner of our lives, communication requires even less of us. It doesn’t just make it easier to avoid awkward conversations — it spares us the effort of even crafting them. But here’s the thing: when something feels too easy, it often is.

“Every time we dodge an awkward moment, we weaken the interpersonal muscle that builds authentic connection and trust — and widen the gap between the influence we have and the influence we want.”

Because it’s not our perfect delivery that earns trust — it’s our willingness to be real. To show up unscripted. To be uncertain and sometimes clumsy. To be fully, awkwardly, imperfectly human. No wonder people today are more connected than ever — yet feel more alone.

📉 In 1990, 75% of Americans said they had a best friend. Today, only 59% do.

📉 The share of people with no close friends at all has quadrupled.

📉 Only 23% of employees say they feel truly connected at work.

📉 Gen Z reports the highest levels of anxiety and loneliness in the workplace.

This isn’t coincidence. It’s the predictable result of a culture fluent in emojis and memes but less practiced in emotional nuance, conversation, and good old-fashioned eye contact. Another irony: we end up experiencing more stress over time than the discomfort we sought to avoid.

We often suffer more from the compounded stress of avoiding an awkward moment that requires us to lay our vulnerability on the line than from braving the moment itself.

It’s why one of the most underrated superpowers today is our willingness to brave the awkward. To make the ask. To give the feedback. To extend the invite. To say how we really feel. Because the things we most want — trust, influence, belonging, confidence, connection — are often waiting just past the awkward moment we least want to face.

If we want to raise braver kids, build stronger teams, and nurture more connected communities, we must re-normalize the awkwardness that comes with being human.

We have to be the ones who go first — who pick up the phone, who start the honest conversation, who say:

“I’m sorry.” “I need help.” “I’m feeling upset.” “I don’t quite know how to say this, but…”

Because in today’s curated world of polished perfection, people are hungry for what’s real. I know I’m not alone when I say I’d much rather build a relationship or work with someone who fumbles over their words but speaks from the heart than someone who hides behind a screen.

So next time you’re tempted to send a perfectly edited message — or say nothing at all — pause.

Ask yourself:

“What might open up if I were willing to brave the awkward moment?”

Connection isn’t built through perfect performance. It’s built through genuine presence.