Guest commentator: Jack Wittenstein, Junior Business Analyst at Children’s Hospital of Philadelphia

We’ve all been there. That first day of classes, that first networking event, that first day of work when we’re filled with anxiety, anticipating who we’ll meet and if we’ll fit in. It’s the same feeling many of us get when we know we should introduce ourselves to someone new but freeze on the spot. Or is that just me? Social anxiety around new conversations is endemic and a significant reason why many of us feel disconnected from the world. Through the art of conversation and becoming fearless in our interactions, we can rebuild these lost connections. 

To the 99% of us who aren’t Don Draper, this anxiety around talking to strangers can be paralyzing. The butterflies we feel when talking to strangers are an evolutionary response meant to assess the risk of misjudging intentions or facing disapproval. In the Stone Age, this could exclude one from the tribe; today, physical threats of stranger interactions are less prevalent, but the underlying psychology persists. Humans are wired to seek predictability and controlled environments. Interactions with strangers disrupt this notion of control, leading to heightened alertness and, often, anxiety.  

New conversations are difficult because they introduce uncertainty around how much we believe others like us. Rather than embracing uncertainty and considering the relationships and experiences we could build, we catastrophize the outcomes of meeting new people by assuming we will be ruthlessly judged and rejected by failing to make good first impressions.  

The Liking Gap was coined by psychologists to describe the discrepancy between how we think others perceive us and how they actually perceive us. In practice, it’s common for people to assume they like someone much more than they are liked by their partner in conversation. Coupled with humans’ inherent contempt for the unpredictable, the Liking Gap is largely attributed to why many people never step out of their comfort zone, never make an introduction, and never take a risk. Our conceptions of what others think of us are more often misconceptions, rooted in no semblance of reality. 

In his book, The Laws of Connection, David Robson encourages his readers to give themselves a reality check when confronted with these self-deprecating thoughts in conversation. “…consider the very worst scenario that you fear, then ask the following questions: 

  • How bad would that really be if it happened? 
  • What are the odds of that happening? 
  • How would I cope if the worst came to pass?” 

Considering these questions as we confront intrusive thoughts helps us rationalize our fears and insecurities around conversation in a very pragmatic way. Robson helps us realize that the downside to conversation is negligible if it exists at all.  

In other words, it’s all internal. 

Every negative thought you’ve had, every time you panicked that something you said came out wrong, every time you convinced yourself that initiating conversation with someone new would mean you could never show your face in public ever again—it was all internal. This entire time, we have misinterpreted the butterflies as a sign of fear, but simply reframing the context of our interactions can have profound benefits for how we build and maintain long-term relationships. Rather than considering the downsides—for which there are relatively few, consider the idea that the person you are about to meet might be the next most important person in your life.  

Life is a lot more gratifying when we retrain our brains to lean into discomfort by interpreting the anxious feeling as a sign that something great could happen. Conversations are the conduit to form new experiences. They teach us to be curious, to empathize, to be vulnerable, and to adapt to unpredictability. In other words, conversations enable us to be comfortable being uncomfortable, which is the basis of grit and resilience: characteristics that are integral for personal and professional advancement. They can turn strangers into friends, coffee dates into marriages, and interviews into jobs1. The art of conversation challenges us to think critically, engage with novel perspectives, and foster deep connections with others, enriching our understanding of the world and strengthening the bonds between us.

Conversation is becoming a lost art in the age of screens. As social media and remote work become more prevalent, the idea of initiating conversation with strangers in the real world can feel more unnerving than ever. It’s easy to take the path of least resistance—to justify our fears and let life happen to us without challenging ourselves to form new connections. But in doing so, we close the door to countless opportunities to grow, discover, and experience the richness of life that comes from meaningful relationships and personal transformation.  

In a 2018 interview, Jeff Bezos reflected on the risk of leaving a comfortable job to build Amazon. “When you think about the things you will regret when you’re 80, they’re almost always the things that you did not do. They’re acts of omission. Very rarely are you going to regret something that you did that failed and didn’t work.” This is equally true in business as it is in personal life. The last thing you want is to reflect on the past only to ask yourself why you didn’t go for it, why you didn’t go to the event, why you didn’t introduce yourself, why you didn’t tell that special someone how you feel. 

Take the leap. What do you really have to lose? 

1Boothby, E. J., Cooney, G., Sandstrom, G. M., & Clark, M. S. (2018). The liking gap in conversations: Do people like us more than we think? Psychological Science, 29(11), 1742–1756. https://doi.org/10.1177/0956797618783714