185,000 Conversations and Counting: A Harvard Barber Reveals the Secrets to Mastering the Art of Conversation

Anthony at the Central Barber Shop

A few months ago I moved to Cambridge, Massachusetts in America for grad school. And as people do, as soon as they begin to call a place home is to find things of both convenience and comfort, in and around the space they live. A small departmental store around the corner for a daily stock of groceries, a quiet place with hopefully some green solace to walk through on sunny days, a place of faith (if one needs it), a reference that marks a closeness to home, a house that that makes you feel beautiful (as you walk past it), a clinic for an unforeseen emergency, a restaurant that is affordable and can be hinged to for small celebrations and a salon that’ll keep you from looking haggard. 

If I may admit, of all the things on that list, finding a barber who will understand your style, keep you looking good, and give you a timely appointment is as critical as locating a good doctor for a medical predicament. I say that with assurance because a similar quest engulfed my first few weeks at Harvard. I juggled between overpriced salons and the ones that offered such diverse options that it felt more of a life-decision less of a haircut. 

Finally, on a warm Wednesday afternoon, along the usual route to college, I discovered (a funny expression for something that has always been there) the ‘Central Barber Shop’; a compact hair cutting parlor tucked next to the Harvard Law School, subdued by the aromatic pizza joint next to it called ‘Stoked.’ And ‘stoked’ I was indeed but about a haircut not so much the pizza place.  

It is here, I first met Anthony. Tall, talkative and highly self-aware. He comes tracing the legacy of parents who, too, ran a barber shop back in his hometown. Influenced, in the initial years, he made an effort to join his father’s business to get a headstart. Although, within two weeks of luggaging the family expectations, it was concluded that he would have to chart a path of his own. It’s been 31 years since; and Anthony has assisted and served, on an average, 20 people a day, five days a week, for 31 long years now. 

While he unpacks his long career, as he chops off my long unkempt hair into a neat vogue, I cannot help but notice the astute articulation skills Anthony exhibits. He engages with you not only with a superficial, customer-server, transactional approach but rather in an intimate, personalized manner. His conversations have depth, they are informed, almost guided like a dialogue in a themed-highbrow-conference; yet warm enough to drift free-flow, just as one would with a friend, on a saturday night house party by the bonfire, away from the crowd.

As much as I would like to feel privileged and special by Anthony’s captivating conversational prowess, I am aware by the sheer Math of his career that he has spoken to roughly over 185,000 people (20 people X 5 days x 50 weeks x 31 years). He is not a hobbyist talker but a masterful conversationalist. One who develops a certain lustrous ease with all and every kind of person he finds in his company. On that reflective note, I turn my gaze towards Anthony again, less as a customer this time instead more from that of a Wisdom Historian. Given the landscape of his job, his own willingness to be immersed in it, and somewhat an occupational hazard to speak with every person who sits in front of him, I am curious to understand what constitutes a good conversation for him? And if, at all, people in the world can learn the nuances of something as simple, yet as complex, as having a dialogue with another human being, whether they know them or not. 

At first, he shies away from acknowledging he knows anything, at all. Slowly, over the course of the next few visits, without much push, he starts to unfurl observations he has made and as a result, epiphanies he has had. His gifts of drawing in an introvert and cajoling an extrovert are impeccable. Here are four gems that surface from churning the introspective motor, greased in his layered insights:

1. People don’t think too much about ‘what they say’ rather ‘what they sound like’ 

Most people, Anthony recounts, want to measure their words, in every instance. They are more concerned (read worried) about sounding thoughtful, intellectual, informed and articulate than they are about the thought they hope to convey. Paying attention to what you wish to sound like, interrupts what you desire to say. He admits, “Well, in some situations this kind of overthinking is needed of course, but regular conversations don't have to have you on your best foot forward. They can be more organic, natural.” In the minutiae of everyday life, not every issue is sensitive or taboo and hence, must not be probed with such suffocating scrutiny. 

 “I asked a guy the other day, ‘How was your weekend?’ and he took an indefinite pause to throw back an answer. He wanted to be coherent and precise, in his answer, which is more effort in an easy conversation than the conversation itself.  The other extreme is an automated response, ‘Good. And yours?’” This boomerang exchange, Anthony advises, hurts the sacredness of engaging with ideas and intention we hold. If every give and take with someone appears to be a grind, people will soon restrain themselves from going with the flow. Consider that in the light of what Mark Nepo said, ‘Be a verb, not a noun.’

2. Be confident; not cocky

The train to arrogance passes through the sub-station of confidence and can choose to stop there, if one is aware and mindful. “My mother used to say when I was growing up that you are a cocky boy Anthony. I feel, I channelised that critique into being more confident”, he shares. You don’t have to be intimidated by people and their knowledge or their understanding of the world. The defense mechanism to belittle another person or to outshine their perspective comes as a response to the threat they appear to be. Being anchored in what you know and remembering it often to enlighten the other can come handy, without having your guard rails up constantly. Your timid voice can be trained into sounding strong and bold as much as an egotistical one can be tamed to hear what others have to offer. Use that as a guiding light to build further, not to shut down or to retaliate with pomposity. 

Sometimes, listening is also an effective contribution. Unloading big words, constructing large sentences, projecting complex words and confusing someone, isn't evidence of intellect and grandiose. Simplicity in communication can also display your credence. 

3. Don’t pretend; stick to your truth

If you begin from a place of pleasing someone, you will have to act. For a long time. Every interaction will be punctuated with a heightened effort to impress upon someone your amazement. Dance the dance that you know little choreography of. Sooner or later, you will miss a beat, fall out of rhythm or else, you’ll have to constantly alter the script to fit the expectation they have of you. 

Anthony recollects, “My boss was like that. He would say one thing to one person and another to the next customer and then people would say but last time you said something else. He was a Republican for one and a democrat for another. A football enthusiast for one and a non-sports fan for another.” 

Building consistency and inviting authenticity to your conversations will liberate you from putting a false front. You are always a refugee in a ‘make believe world’; it never morphs into a permanent home. 

4. Don’t be afraid to use your ‘I don’t know’ superpower

“Those people who think they know everything are a great annoyance to those of us who do,” remarked Isaac Asimov. Echoing the sentiment of Asimov’s statement, Anthony comments: “Most people, especially the well-read, literate minds feel this solid pressure to speak about almost anything under the Sun.” The moment you press on to clarify the specifics, they crumble.” You have to relentlessly reroute the conversation to reality. Exasperated from this artifice, he notes: “Even when they are clueless, they will bullshit and beat around the bush about the topic without actually contributing anything to it. I ask someone about football or a hurricane in a country or anything that is in the news off late, and I can see, almost immediately, if the person really is aware or cares about the situation or if they are faffing. Saying ‘Oh! I have no clue” gives you an opportunity to learn, to soak in, not show off.” 

‘Tell me more’, ‘I am unsure if I can say anything about that’, ‘Could you inform me’, ‘Let me learn a bit about that’, are equally appropriate responses. As the proverb goes: There is no shame in not knowing, the shame lies in not finding out. 


As I leave Anthony’s shop with a sharp haircut and an enriched mind, I think to myself that ‘The Art of Conversation’ isn't about flamboyance, etiquette, thick vocabulary, or flashing a degree from an overpriced college. It's about something simple and profound: building a connection. It is about understanding yourself through someone and someone through your own curiosity. Conversations are guided tours to your innermost thoughts, your evolving opinions, your small mindedness at times and your awe-inspiring beliefs. A conversation is priceless because it transcends from confusion to clarity. It thrusts us into being understood and allows for others to be empathized with in return. The ability to talk to anyone cultivates a garden of adventure and awakening. It births our identity, crafts it with intricate love in every possible effort made to express oneself, sincerely. It creates and dissolves disputes, sways and serves discourses. A conversation is the foundation of everything that has ever happened. 

From bars to boardrooms, from classes to conferences, from fine-dining tables where decisions of the world are made to cushioned barber-shop chairs that are carefree, a conversation is our biggest tool of feeling included. As Alexander Pope thoughtfully wrote, "True ease in talking comes from art, not chance, as those who move easiest have learned to dance." 

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