If you master these skills, you’ll connect with people on a deeper level than you ever have before. You’ll comfortably navigate small talk and easily be able to transition to something more interesting.

Skill #1 – Fuck It! Stop Being Boring

HARD OPTION vs EASY OPTION

Skill #2 – Make Any Conversation Meaningful

FIND IT vs FAKE IT

Skill #3 – Quickly Connect Without Common Interests

COMMON EMOTIONS vs COMMON INTERESTS

Skill #4 – Never Run Out Of Things To Say

ZOOM IN & OUT

Skill #5 – Listen Like A Sponge

UNDERSTAND vs RESPOND

Skill #6 – Be Your Weird-Ass Self

GENUINE vs COOL

Skill #7 – Snap Out Of Your Social Rut

SMALL STEPS vs BIG JUMPS

Stop Being Boring

Skill #1 – Fuck It! Stop Being Boring

Habit: HARD OPTION vs EASY OPTION

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Maybe no one’s ever told you that you’re boring, but you sometimes get a sinking feeling in your stomach that hints at it. Or maybe someone has told you straight up, and it makes you feel like a worthless sack of lingonberries.

You want to be interesting and fun, but you’re trapped inside the prison of your limited social skills. The prison bars are made of your own negative beliefs and you just can’t seem to squeeze past them.

If there’s one thing you’re good at it’s tricking yourself into believing that you suck. How fun. Though the fact that you did this to yourself is actually good news, because you can turn it around. 

How You Became Boring

When you were only 4-feet tall you were all about fun. You were an explorer learning to navigate your world, and nothing was off-limits.

You burnt your hand on the stove. It didn’t stop you from playing with fire. Then you learned that there were sometimes consequences to your actions, and doubt replaced abandon.

Take Little Pete, for instance. At 4-feet Little Pete had his first crush; we’ll call her Lacey. Their class was putting on a dance performance and the boys had to choose their partners.

Lacey already had a boyfriend who she held hands with at lunchtime, but when the teacher told the girls they had to say yes to any boy who asked to be their partner, Little Pete saw his opportunity. Not one of the other boys moved, but Little Pete pounced! He didn’t give a fuck.

Lacey said no, but Miss Anderson sealed the deal. They danced together for the weeks that followed and Pete gradually won Lacey over — though he wasn’t sure what to do next with this new and unexpected state of affairs.

He avoided Lacey and repeatedly sent his best friend to ask her if she still liked him. That was the extent of their interaction together. She said yes for 3 glorious days then obviously changed her mind.

Little Pete was devastated. He had chosen to take the easiest option and ignore his true desires. He became a good little boring boy and for the next 10 years struggled with the irrational fear of talking to girls.

There was a time when you too used to act first and think later. But not anymore. Now your mind predicts everything that could possibly go wrong, and it’s usually enough to convince you to take the boring option.

Your decision process looks something like this when you’re in an uncertain situation…

The Boring Process (Codename: Bland Boris)

Trigger: “I’m not sure what to do.”

  1. Do I have to do something, or say something?
    • No: Do nothing. Play it safe.
    • Yes: Go to step 2.
  2. What’s the easiest thing I can do?
    (Least scary, least risky, lowest chance of being judged or rejected)

You’ve run this process over and over again in at least one or two areas of your life. Maybe more. You said no to your inner explorer. Congratulations, you made yourself boring.

But the good news is this. It’s not really YOU that’s boring. It’s the boring shit you choose to do. And all it takes to stop being boring is to do something different.

Why Choosing The Boring Option Makes You Feel Like Mould

There’s a problem with the Bland Boris process. We designed it to keep ourselves safe, and we feel safe when we use it, but we hate ourselves afterwards — which isn’t safe at all.

Most people don’t actually dislike us when we’re Bland Boris, because we put none of our self into our actions, so there’s nothing to dislike. They just don’t see us at all, so they have no one to connect with.

If you want people to really like you, you have to get naked, or at least show some skin.

I mean you have to give them something to like, by putting your self in your actions.

Yes, there is risk in not being boring. Some people might not like what they see when you stop hiding, but their disapproval means nothing once you find the people who do like you. Those are the connections that will fuel you. Being truly accepted for the weird monkey that you are inside is the greatest feeling in the world.

It’s a much bigger risk to be boring. You’ll never truly connect with anyone.

Imagine yourself in this situation: it’s your first day at university. You’re sitting in the lecture hall and you don’t know anyone. The speaker asks for a volunteer to stand up and tell the class about themselves, as an ice-breaker.

Most people in the class will suddenly become Bland Boris. They’re not sure what to say so they say nothing. They hide.

And if they’re singled out they take the easy option. They share as close to nothing as they can: “Hi, I’m Boris and I like drinking beer and eating pizza.”

Does that sound like you? Well everybody likes pizza and beer, damn it! Stop hiding.

If you want to see yourself as an interesting person you have to take risks. You have to be okay with looking like a fool sometimes, because there’s more to gain than there is to lose.

It all starts with asking yourself better questions, which looks something like this…

The Fun Process (Codename: Fuck It Felicity)

Trigger: “I’m not sure what to do.”

  1. Do I have to do something, or say something?
    • No: What could I do anyway, for fun? Go to step 2.
    • Yes: Go to step 2.
  2. What do I truly WANT to do?
    • Example 1 — What experience do I want to create for myself?
    • Example 2 — What would make me excited or amused?
    • Example 3 — What am I afraid of doing, that at least part of me wants to do? Etc.

We stop being boring when we stop reacting to what we think other people want, and start creating what WE want.

So what does Felicity do when it’s her turn to share with the class? Her heart is racing from what she’s about to say. She’s scared but she wants to connect, so fuck it.

“I levelled up my Mage in World of Warcraft yesterday and my guild is raiding a dungeon tonight! If anyone here plays WoW come say hi.”

Now everyone in the class knows something real about Fuck It Felicity. They have something they can talk to her about. They probably feel a bit closer to her.

And they’ve already forgotten about Boris.

Stop It. Stop Being Boring

Becoming interesting can be scary at first. But you want it.

Do you know the combination of fear and desire that I’m talking about? That’s your green light. That’s your brightly-lit path away from boring.

Felicity doesn’t draw people in because she’s more interesting than the average person. She draws people in because she gets “naked”. She expresses her opinion, steps on toes, chases what she wants — and people love her for it. Because she’s real.

The next time you’re unsure what to do in a given situation, try being Fuck It Felicity instead of Bland Boris. Start small, make mistakes and learn from them.

Bland Boris’ fears come from low self-esteem or insecurity. Most of us have his fears to some degree. Applying Fuck It Felicity’s approach can help you change not just your results, but also the root of the problem over time. So go get back in touch with your inner explorer and play with fire.

Conversation Example

A real estate agent told me he wants to build trust with his clients. He tries to connect with them but the majority of the time they just give him one-word answers. The stress of trying to sell them a house gets in the way of connecting.

Bland Boris would act the way he thinks a real estate agent should act in this situation. He’d make polite small talk and tell the clients how spacious the bedroom is and how much light the living room gets because the windows face east, where the sun rises.

Fuck It Felicity might say “Listen, before I show you some houses I want you to know that I actually care about you finding a home that makes you happy. Some agents just want to offload as many houses as possible but I can’t do that… I’d feel too guilty if I forced something on you. Plus, I’m a terrible liar. So I actually want to know what you like and what you don’t like. If you promise to tell me, I’ll promise to not pretend a crappy house is great for you.”

When you share things that scare you people recognise that you’ve trusted them enough to share something scary. They admire that you’ve taken a risk for the benefit of connecting with them. You stop being boring, you become real, and they trust you back.

 

Make Any Conversation Meaningful

Skill #2 – Make Any Conversation Meaningful

Habit: FIND IT vs FAKE IT

What would happen if you were talking to someone you’d just met and they told you they were a tax accountant?

You’d say “oh cool,” follow it with some small talk and then get yourself stuck on a topic you don’t really care about, right? Like this…

“What do you do as a tax accountant?”

“Oh just a lot of looking over receipts and making spreadsheets.”

“So you must be pretty good with Excel.”

“Uhh, yeah, I guess I’m pretty good at it. I did a course on it last week actually.”

“Nice. I can use it a bit but I don’t really use it that often…”

Riveting stuff.

Want to know why this conversation is going nowhere? It’s because you’re pretending to be interested. Internally you’re thinking “how do I change the topic???” but externally you’re digging for details that you don’t even want.

You’ll never truly connect with anyone that way, because people can tell when you’re only faking interest, or just being “polite”. They don’t want to be in that conversation either, because it feels forced and empty for BOTH of you.

So what do you do?

Stop Pretending

When you run out of small talk, stop digging into details that you don’t care about. Stop asking questions that you don’t actually WANT the answer to. Stop talking shit for the sole purpose of keeping the conversation going.

The goal of a conversation is not simply to fill silence, it’s to connect with the other person. So if all you’re trying to do is fill silence, without truly being interested in what you’re talking about, you’re going to make it awkward.

If your own words bore you, they sure as hell won’t excite the other person… so don’t say them. Give your brain a chance to find something that will actually make the conversation interesting for both of you.

When Small Talk Runs Out, FIND Something YOU’RE Genuinely Curious About

You’ll reach a point in the conversation where you naturally run out of obvious “small talk” things to say. Instead of faking interest and continuing to interrogate the other person, pause to find some aspect of the current topic that you’re actually curious about. You can easily feed off of curiosity to keep a conversation going and take it to a deeper, more meaningful level.

Ask yourself: What am I genuinely excited or interested to learn here? To explore? To share?

If you don’t actually FEEL the curiosity, you haven’t found the right topic yet.

So what might spark your curiosity with the tax accountant? How about this… (if you’re interested in psychology and what motivates people to do what they do)

“You know what? I don’t think I could do numbers all daybut I’ve actually heard a few people say they love doing accounting, and I’m really curious to know what it is they love about it. What am I missing?”

“I have no idea; I don’t always love my job but I guess the one thing I do like is that you always know when you’ve done your work right, because the numbers match up, and they never lie.”

Now we’re getting into meaningful territory, because you’re not just pretending to be interested anymore. You’ll feel much more confident and comfortable taking the conversation in this direction, and the other person will open up to your genuine curiosity.

Conversation Examples

Your co-worker tells you it takes her an hour on the train to get to work every morning. After you say the obvious stuff, like “damn, it only takes me 20 minutes by car,” or “where are you coming from?”, you run out of things to say.

So what hidden aspect of her story sparks your curiosity?

For me (interested in productivity & learning) it’s this …

“What do you do with that time? Because I always try to learn something when I travel, from books or audiobooks.”


A girl on a first date tells you she has a dog named Barney. You say the stuff that comes easy, like “Aww, what kind of dog?” or “Do you teach him tricks?” — but you don’t have a dog so you don’t know to go deeper on that topic.

What are you genuinely excited or interested to explore here? To share?

For me it’s this (something I’ve wondered about) …

“I looked after my friend’s dog a few times and it was always really needy and whiney and wouldn’t leave me aloneso I’m not sure if I’d have the patience for a dog. What’s it actually like when you have your own?”


 A stranger at the gym tells you he wakes up 6am every day to go for a run. You’ve never really enjoyed running. You start with the obvious small talk: “how long do you run for?” or “where do you run?” and then you get stuck.

What are you curious to learn here?

For me it’s this (true story) …

“Man, I’ve tried building both habits  running and waking up early  but I can never keep them up for more than a few days. How the hell do you stay motivated to keep doing it every day? Like do you get to a point where you actually start to enjoy it?”

You don’t have to always dig for the meaningful stuff like this in every sentence of every conversation. But whenever you feel like you’re running out of small talk, don’t fake interest — find it.

And if you want to always know what to say in any situation, sign up for The Conversation Natural. It’s daily conversation hacks, mindset shifts and actionable advice that will teach you how to connect with people on a deeper level.

 

Quickly Connect Without Common Interests

Skill #3 – Quickly Connect Without Common Interests

Habit: COMMON EMOTIONS vs COMMON INTERESTS

People will tell you to find common interests if you want to get along with someone — and yeah, that’s fine. But what if you can’t find any?

There are literally thousands of possible “interests” we can have, but there isn’t enough time in the world to try them all, so we choose say 10. Chances are my 10 are different to your 10, because you’re probably into some weird shit, so we may not have many in common.

Something we absolutely do have in common though (unless you’re a psychopath) is that we’ve experienced the same emotions over and over and over again: joy, trust, fear, surprise, sadness, disgust, anger, anticipation, loneliness etc. So instead of looking for common “interests”, lets see if we can connect on the common emotions we experience.

You’ll often end up finding unshared interests that spark similar emotions in both of you, and that can be really interesting to explore.

What Not To Do

Say Phillip is studying to be an engineer, and Michelle is studying to be a doctor. Phillip doesn’t care about medicine and Michelle doesn’t care about engineering. They ask each other polite questions:

Phillip: Oh I hear you have to study for a long time to be a doctor. How many years do you have left?

Michelle: Yeah, I’ve got another two years. Seven total. Although you never really stop learning. What about you?

Phillip: I still have three years.

Michelle: And what do you want to do as an engineer when you graduate?

Phillip: I haven’t really thought about it, but it’ll be good to start making money.

Michelle: Yeah I know what you mean, I still haven’t paid off my car.

This is pretty boring, right? Neither of them are offering up any emotional information. This chit­chat isn’t going to cut it.

At this shallow level of conversation, they have to keep thinking of new topics every few seconds. The ideas will dry up pretty soon and it’ll get awkward. It’s much easier to explore emotional experience than to explore unshared interests.

How To Explore Emotions In Conversation

These types of questions are your friends:

  • WHAT do you like about that?
  • WHAT made you want that?
  • WHAT scares you about that?
  • WHAT are you hoping to get out of that?
  • HOW did you make that decision?

Essentially any question that uncovers “what makes you feel that way?” or “what makes you think that way?”

WHAT tends to work better than WHY because WHAT feels like you’re curious and WHY can sometimes feel like an attack, making them close up and get defensive.

“WHY do you like that?” 

“Because I do. F### you!” 

Seeing It In Action

So back to Phillip and Michelle. Now that they know how to explore common emotions, how does their conversation go?

Phillip: I haven’t really thought about what I want to do as an engineer but I guess I like the idea of having my own company one day.

Michelle: What makes you want to have your own company?

Phillip: Hmm, I usually perform best under pressure, so I like the idea of being responsible for everything.

Michelle: Oh I know what you mean! That’s how I feel when I think of saving someone’s life at the last minute in the emergency room. I want to be the one making the decisions.

Phillip: Jesus, that’s intense. Is that what made you decide to become a Doctor? The pressure?

Michelle: Yeah, I guess that’s a big part of it.

Phillip: Wow. I guess that’s similar to how I feel about engineering. A lot of people can die if you design your bridge wrong, and I’d rather be the one who checks everything than trust someone else to do it.

Michelle:  So does that mean you hate it when other people boss you around too?

Phillip: OMG that’s the worst! I can’t stand it when other people tell me what to do.

Fun! Turns out they’re both leaders (or control freaks). Now they can geek out on that common emotional experience instead of blabbing about interests that they don’t connect on.

Other Conversation Examples

Say you love Brazilian Jiu-Jitsu (BJJ), but whenever you talk about it you bore people to death. The trick is to connect the topic of BJJ to the emotional experience you get from it.

If someone is stressed, for instance: “Hey, you know what I do to relieve stress? BJJ. Because it gets me out of my head and into my body…”

So you’re not really talking about BJJ. You’re talking about relieving stress and getting out of your head. Because that’s something anyone can connect with.

If someone is sad: “Yeah I get sad sometimes. But I have one place I go where it’s impossible to be sad. It always makes me happy again, because I’m free to express myself and be creative, etc.”

Now you’re talking about relieving sadness, expressing yourself and being creative, and BJJ is just a vehicle for that stuff.

Note that you’re not trying to necessarily convince them to try BJJ, because it’s not really BJJ that relieves your stress and makes you happy. It’s certain elements of BJJ: the depth, the options, the creativity, the technicality, the competition, the culture etc. And someone else might get those same benefits from some other hobby.

So hearing you talk about BJJ in those terms might make them think, “Fuck, I get those same feelings from drawing.

So they can talk about drawing while you talk about BJJ, and you’ll both be interested in the conversation because you’ve created similarities between the two interests, based on emotional experience.


Say you’re talking to someone who doesn’t love playing guitar. They won’t want to talk about specific guitar stuff like famous guitarists, or types of equipment, because they won’t have a clue what you’re talking about.

A much more interesting conversation for them would be, for example, if you tell them about how you’re always striving to improve your skills, and how the payoff of being able to play a new song makes all the hours of practise worthwhile.

They’ll be able to connect that emotional experience to something else in their lives and talk to you about that. Maybe they get the same experience from mastering new yoga positions, for instance.

 

Never Run Out Of Things To Say In Conversation

Skill #4 – Never Run Out Of Things To Say

Habit: ZOOM IN & OUT

Say you’re in a conversation about your friend’s car, and you don’t know anything about cars. You run out of things to say. What are your options?

Some people zoom out on topics — they want to talk about a more general concept. Other people zoom in — they want to talk about specific details. Both can be useful for changing the subject and giving you something to say.

If you zoom in on your friend’s car, you might come up with…

  • Make/Model
  • Performance
  • Price
  • How it keeps breaking down
  • The mysterious stain on the back seat

And if you zoom out, you might come up with…

  • Other modes of transport
  • Fuel consumption
  • Racing
  • Global warming
  • Rich men who buy expensive cars to get girls

If you zoom in on visiting your grandma, you might come up with…

  • Her cooking
  • Her health
  • Her stories
  • How she wants you to get married as soon as possible
  • How she thinks vodka is medicine

If you zoom out, you might come up with…

  • The importance of family
  • The process of getting old
  • Death
  • Wisdom
  • What the future will be like when you’re old

You’ve probably had conversations with people where you just can’t seem to click with them. It could be because they want to zoom out while you want to zoom in, or vice-versa.

Conversation Example

Amy: How was your day?

Vince: Good. Productive. I got a lot done. How was yours?

Amy: Well! When I woke up I made toast, with butter and vegemite. I left it in the toaster a little too long and it got a bit burnt, but I scraped it off with a knife and it was fine. Then I cycled to work. I went down Oxford Street this time instead of my usual route down Henry Cotton Drive because I wanted a change.

Amy (continued): My boss didn’t have much for me to do today so I made an appointment to see the Doctor next Wednesday at 5pm and spent the rest of the day on Facebook chatting to Sofia about her baby, Ivan, who has a cold, and to Frank about the new Porsche he bought. Then I came home down Oxford Street again because it was so lovely in the morning. It wasn’t as nice in the evening. And now I’m talking to you.

Vince: So was your day good or not?

Amy: I want to hear what you did all day.

Vince is zooming out, thinking about the bigger picture. He wants to understand the point of what Amy is telling him. What does it mean? Did she have a good day or a bad day?

Amy is zooming in, thinking about specifics. She wants to know what made Vince’s day good or bad. What does he mean by productive? What did he get done?

If you find yourself in a conversation that feels like the other person comes from a different planet —  or maybe they just look bored listening to you talk — they might want to zoom the other way.

Maybe they’re not interested in the details of your car, so they want to zoom out, or maybe they want to tell you all the details of their visit with grandma, so they keep zooming back in.

All you have to do to connect with them is zoom in the same direction. If they’re zooming in, give them details and examples. If they’re zooming out, give them the meaning behind your details and examples. The bigger picture.

Either that or explain to them why you’re more interested in zooming the opposite way: “Hey all these details don’t really mean much to me, but I want to know __.”

They may not share your zoom preference, but at least there won’t be any miscommunication.

And if you want to always know what to say in any situation, sign up for The Conversation Natural. It’s daily conversation hacks, mindset shifts and actionable advice that will teach you how to connect with people on a deeper level.

 

Listen Like A Sponge

Skill #5 – Listen Like A Sponge

Habit: UNDERSTAND vs RESPOND

What makes a good listener?

A good listener doesn’t just listen to find something that he can respond to. Listening is not the same as hearing – it’s not about just giving the other person a chance to speak. In fact, a good listener might often interrupt the person who’s talking. Here’s why…

A good listener listens to understand. To absorb. That means they ASK inquisitive questions that help them make sense of what the other person is telling them. But it doesn’t end there.

By asking well-structured, challenging questions, you’re actually helping the other person understand themselves. They have to pause, process their feelings, and figure out what they think. That’s why it feels meaningful for them.

And while they’re processing, they feel like YOU care enough to actually want to understand them, and that creates a connection between you.

So ask less fact-based questions, because they’re easy to answer. They already have a ready-made response for those.

Ask MORE questions that make them think and reflect.

If you’re worried that you’re asking too many questions – like it’s an interview –  they’ll only really get that feeling if you’re collecting facts, e.g. “How long are you going to be overseas for?” and “What countries are you visiting?” and “What are you going to do?”

It doesn’t happen if you’re making them reflect – as long as they feel comfortable with you and with the environment you’re in – e.g. “What are you going to miss most while you’re overseas?” or “What are you hoping to get out of the trip?” or “Is there anything you’re worried about?”

Because those deeper questions, which they have to process, naturally lead to longer and more open responses, which then lead to even deeper questions.

Conversation Examples

A girlfriend told me, “I don’t like it when you tell me how to do things. I feel like you’re judging me.”

“I’m not judging you.” I said. “It was just a suggestion.”

I was not listening.

Regardless of how I experienced it, her experience was that I was judging her. A bad listener focuses on responding to explain his own experience. A good listener focuses on understanding the other person’s experience:

  • “Which part makes you feel like I’m judging you?”
  • “Was it what I said, or how I said it?”
  • “How would you like me to make suggestions in future? Or would you prefer it if I didn’t make suggestions?”

A good listener improves the way he relates to people by understanding how they think. Understanding what’s important to them.

A bad listener learns nothing and pushes people away.


At an interview for a sales job I was asked, “How will you bring us new clients?”

I didn’t have an answer prepared. I panicked and charged forward blindly with an empty, generic answer. Any blog post on sales would’ve listed off the same uninspired strategies.

I was not listening.

A good listener would’ve unpacked the interviewer’s question to understand what he was looking for first, then used that ammunition to craft a tailored, though-out response:

“Good question. I’d love to ask a few things about your current strategy first if that’s alright?”

  • “What’s your biggest bottleneck right now in getting new clients on board?”
  • “What strategies have worked best so far?”
  • “Is there anything you definitely wouldn’t try?”

A good listener makes sure he understands all of the information before responding.

A bad listener jumps the gun.

 

Be Your Weird-Ass Self

Skill #6 – Be Your Weird-Ass Self

Habit: GENUINE vs COOL

 

Joe Is A Cool Motherf-cker

Whenever Joe talks to you, you get the distinct feeling that he’s better than you. Not because of anything he says. Just because he’s cool, you know?

You want Joe to like you, so you act cool around him. Instead of saying what you genuinely feel, you always try to think of the cool thing to say. You often decide that your first thought isn’t good enough, so you keep it to yourself and say what a cool person would say instead.

Instead of bringing up topics that genuinely interest you, you talk about whatever Joe wants to talk about… because he’d probably find your own interests a bit weird. Or just not that cool.

Whenever Joe asks you a personal question, you make a joke and refocus the conversation onto Joe as quickly as you can. Because people like talking about themselves, right?

You feel like you know Joe pretty well, so you consider him a friend.

Now say YOU’RE Joe, and the person described above is Steve.

Steve Is A Quiet Guy

You don’t mind having a chat with Steve now and then, but you always stick to small talk, because anything deeper seems to make him uncomfortable.

He’s not the easiest person to talk to because you have to do all of the work. He’s always polite and acts interested in whatever topic you bring up, sure… but he doesn’t really bring up any topics of his own, so you don’t know what he’s truly interested in.

Steve’s a good listener, in the sense that he hears what you’re saying. He smiles, nods and says, “that’s cool”, but he doesn’t really add his own opinion to the conversation. He always seems to agree with you, so you doubt whether he’s being genuine.

Sometimes he’ll make a funny comment, but it’s like he’s just trying to get a laugh, and you haven’t seen much depth to him beyond that. He seems like a smart guy but he’s never really said or asked anything that made you stop and think.

You feel like you don’t really know Steve that well, so you consider him an acquaintance.

How To Be Cool

Joe is your boss, your popular co-worker and that hot girl in your business class. He’s anyone you find intimidating. Joe pulls off “cool” by being genuine, while you pull off “wet blanket” by trying to act cool.

If you want any chance of connecting with the Joes of the world, you have to embrace your uniqueness instead of hiding it. That means you have to…

  • Bring up conversation topics that interest you, even if you think they’re weird
  • Contribute your honest opinions, even if you disagree with someone
  • Consider whether a deeper, more genuine response would serve you better than empty banter in a given situation
  • Show people that you’re comfortable sharing personal things about yourself

Those weird and uncool hobbies that you don’t like to talk about are part of what makes you interesting. The trick is being able to communicate your passion in a way that the other person can connect with.

The quirky thoughts that pop into your head, that you decide aren’t good enough to share… those are the things that make a conversation with you REAL. If you constantly censor your genuine reactions, then talking to you is like talking to a lifeless robot.

True, if you say whatever comes to mind you might say some weird shit. But that weird shit is unique to you, and that’s what people connect with. It’s authentic. Give it a go and see what happens, because trying to sound cool all the time is empty and unfulfilling.

The key to connecting with cool mother-ckers like Joe, and having them value you as a friend, is not about acting or pretending or figuring out what a cool person would say.

It’s about learning the right way to communicate the true you to the world. It’s about gradually peeling away the layers of falseness you’ve buried yourself under to try to fit in. It’s about being genuine.

Conversation Examples

Say a girl you’re interested in tells you she’s into rap music and sends you a link to a track she likes. You hate rap but you want to seem cool, because you want her to like you, so you tell her it’s a cool track.

This is a dick move on your part because now she’s going to keep sending you rap music, thinking you’re enjoying it. Thinking she’s your music discovery guru, because you like everything she sends you.

And how do you think she’s going to feel when she finds out you never liked any of it? That you didn’t have the backbone to tell her?

You don’t have to be a party pooper when expressing your opinion, like “this music is trash and I can’t believe you like it.”

You can do it like this, with a positive spin about something else, that comes from somewhere genuine.

“I’m not the biggest fan of rap. But I’m pretty sure I’d like this track more if it came with a video of you dancing to it.”


Say a work colleague gives you a compliment: “Hey man, that was a really good presentation you gave yesterday.”

You don’t really agree because you think you could’ve done a better job. And you want to act cool so you shrug off the compliment with an attempt at a joke: “Nah I sounded like Donald Trump up there.”

You’re kind of ripping people off by not accepting their compliments graciously. They’re choosing to open up a little to give you that compliment (which is a risk they don’t have to take) and they want to feel good about making you feel good. But you rob them of that afterglow when you brush off their opinion.

So even if you do disagree with your colleague’s opinion, you can still accept his compliment genuinely, like this:

“Thanks man, I really appreciate you saying that.”

You’re not saying you agree with him. But you ARE genuinely grateful for the fact that he made the effort to come and tell you, right? So tell him that and let him feel good about it.


Say you’re an aspiring musician in a band, and someone asks you a personal question, like “what you want to do with your life?”

Do you tell them you want to get famous and party all the time, to seem cool, and to deter them from digging deeper? Or do you open up about your dream of making people dance, of being your own boss, of having an outlet for your creativity… and then express your doubts as to whether it’s all possible?

You’re not risking anything with the first “cool” response, because it’s bullshit.

But the second response opens you up to their judgement, because it’s genuine. They know this. And when they see you take that risk, they feel like they can share something similar from their life, because you’ve already proved that you’ll understand.

So they’ll drop their mask too.

 

Snap Out Of Your Social Rut

Skill #7 – Snap Out Of Your Social Rut

Habit: SMALL STEPS vs BIG JUMPS

I don’t know about you, but sometimes I feel antisocial.

If I’m working on a big project, I go into “work mode” and tend to avoid interactions so I can get more work done. Then after a period of reinforcing that habit I find it harder to connect with people. I don’t feel as witty, I’m slower to come up with responses, and I run out of things to say.

If you choose to avoid conversation regularly, your brain learns that you don’t need that particular muscle. Over time you’ll struggle to remember how to use it well.

If you avoid people consistently your brain spends less time focused on others and more time focused on your internal thoughts — you know, gems like these:

  • “I can’t think of anything to say.”
  • “She doesn’t like me.”
  • “These people are better than me.”

Those are the muscles you’re building, and they’ll trip you up when you’re trying to make friends.

The good news is that this happens to everyone. You’re not going to be on your game all the time, and you’ll go through phases where you can’t seem to connect with anyone. But what can you do to pull yourself out of it? How do you become more social when you’re just not feeling it?

Saying Anything Is Better Than Saying Nothing

Each time you make the choice to stay silent instead of saying something (anything!), you make it slightly more difficult to be social. Because the next time you’re faced with that same choice you’ll be more likely to make the same decision.

On the other hand, each time you make the choice to say something instead of staying silent, you make it easier for yourself to be social next time.

Now you might be thinking, “But I can’t say anything because I don’t know what to say!” — and to you I say, “Bullshit.”

It’s simple. Do you recognise the following thoughts?

Should I say “Thanks, have a great day” to the café staff as I’m walking out? Or should I just say nothing?

Should I say “Hi, how are you?” to the person who sits next to me on the bus? Or should I stare at my feet?

Should I ask the taxi driver how his day has been? Or should I scroll through my Facebook feed?

How often do you choose to say nothing?

Even if these interactions last just 10 seconds before going back to silence, deciding to initiate them is psychologically better for you than staying in your head. Your brain will go, “Oh, maybe I should focus externally a bit more,” and your negative thoughts will decrease.

So stop saying nothing, and start saying something.

How To Pull Yourself Out Of A Social Rut

If you’re feeling antisocial, expect to fail at this a bunch. It’s totally fine, you’ll get better. Start with Step 1 below and fuck it up until you consistently get it right, then tackle the next step.

You’ll notice your confidence increase with every step. You’ll genuinely feel more comfortable around people, more motivated to talk, and more willing to take bigger risks if you just open your mouth and do this, step by step.

Step 1: Make eye contact and smile.

Keep doing this with new people, and try new ways of doing it until you consistently get smiles back. Their smiles will make you feel more confident and will prepare you for the next step.

Step 2: Go out of your way to greet service staff.

Things like “Hi, how’s your day so far?” or “Thanks, that coffee was delicious,” etc.

Keep trying this in different ways until you consistently get positive comments back. Their positive comments will make you feel more comfortable.

Step 3: Say “Hi” when walking past strangers in public.

Keep trying this until you’re comfortable doing it. Without worrying about whether or not you get a response.

Step 4: Make quick observations and verbalise them.

Like “Oh what a cute dog,” or “Cool shirt.”

You can end the conversation there. Keep trying this in different ways until the fear tapers off.

Step 5: Make a real effort to continue the initial conversation.

Just say anything at all after the initial introduction. Like “Where are you from?” or “What’s your dog’s name?” or “You look like you’re on your way to something important.”

You can end the conversation there. Keep trying this until you can consistently continue conversations beyond the initial introduction and get positive reactions.

If this sounds difficult to you, it means you probably haven’t worked your way to step 5 yet. Getting through steps 1-4 makes step 5 easier, and so on.

Step 6: Add something personal about yourself.

Like, “I want to get a dog one day. It’d be nice to have something to take care of.” Or “You know I usually avoid taking risks but I’m starting to wonder if I should change that.” Or “I love __. I could talk about it for hours.”

Rather than trying to impress people with what you say, just aim to keep yourself entertained.

Step 7: Ask something that makes the other person think. 

For example, “What made you decide to get into that?” or “Are you usually lucky or unlucky?”, or “What’s something your friends would say you’re great at?” Anything that they have to reflect on before answering.

Now you’re having a legitimate conversation.

Often the only thing you need to do is get the conversation started with a genuinely curious question, like lighting a fire, and they’ll keep it going for you. Keep trying this until people consistently open up to you.

Step 8: Shut up and listen.

Now that you’re more comfortable and skilled in conversation, you might want to talk more.

Just make sure you also give the other person space to talk. Focus on them and really try to understand who they are and what they’re talking about.

Step 9: Start a group conversation.

For example, “Where are you guys from?” on a walking tour, or “Did anyone see that thing in the news today?” with your co-workers, or “Does anyone know if Wonder Woman is a good movie?” on a plane.

Keep trying this until you can comfortably start a conversation with multiple people.

And of course do it without being the loud and obnoxious guy who doesn’t know when to stop talking. Be aware of other people’s reactions and drop the conversation if no one seems interested. They’ll appreciate your social awareness.

Also make a habit of involving the quieter members of the group. Ask them for their thoughts and give them some attention, because they might just be waiting for an opening to share.

Step 10: Organise events and invite people.

Get friends to bring other friends that you haven’t met yet.

Now you’re leading the social circle. Keep trying this in different ways until you get over your irrational fear of rejection.

At this point the world is your oyster. You’re taking much bigger risks than you were when you started this whole thing because you’ve built a consistent habit of getting out of your head and saying SOMETHING.

Your comments became more playful as you iterated on each step. You started asking better questions over time. You learned what gets a shitty response and how to get a good one instead.

This isn’t the end of the road. It’s just a solid foundation that lets you take control of your social life. From here you’ll decide what risks you want to take, and which direction you want to grow in.

And if you’re struggling with any of the steps, add your own smaller steps. For example, you can ask the time or directions before verbalising observations if that’s easier.

You Won’t Become More Social Just By Thinking About It

The only way to become a social person is by DOING.

You sit there hesitating to talk, trying to think of the right thing to say. Trying to find that magic line that will get the reaction you’re looking for, but you won’t find it that way. You’ll fall on your ass, because it takes actually TALKING to learn how to do this.

Saying ANYTHING is better than saying nothing. If you’re always watching how the other person reacts (and you should be), you’ll gradually stop saying things that get negative reactions. You’ll naturally adjust over time. If you’re not saying the wrong things sometimes, you’ll never find the right things.

So get up and say something (anything!) to the next person you see. Take that small first step. It’s a skill you develop by doing it, and not somesthing you’re born with.

And if you want to always know what to say in any situation, sign up for The Conversation Natural. It’s daily conversation hacks, mindset shifts and actionable advice that will teach you how to connect with people on a deeper level.