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How to Become Less Shy

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Lots of people ask me about getting over shyness, so I’ll tell you what I know. I’ll never be a center-of-attention type, but over the past decade I’ve gone from being too timid to even order food over the phone, to feeling like I’m the more assured one most of the time when I meet someone new. I believe this kind of transformation is possible for just about anyone.

Being shy and being an introvert are often conflated, so we should clarify the difference. An introvert is someone who is stimulated by the inner world of thoughts and feelings more than they are by external events. I am an introvert, and you probably are too—this blog has always been focused on that inner side of life.

Shyness is a self-reinforcing nervousness around people, especially people you don’t know. I don’t believe anybody actually likes being shy. Being reserved is one thing—I’ll always be a happily reserved person—but shyness is not a pleasant quality to bear. It’s a form of chronic pain.

Most people experience it to some extent, maybe only in certain situations. But for some people it is a pervasive, self-defining feeling. These examples from an older post may sound familiar: 

  • People you’ve already met introduce themselves to you multiple times. They don’t remember you because you didn’t say anything.
  • Somebody speaking to your party always looks to someone else for a response, never you.
  • You often hope someone else in the group will say something, to kill the silence.
  • You get nervous, or even resentful, when your friend departs for the restroom, leaving you with someone you don’t know well.
  • When someone in your group has to take the lead, like addressing the host at a restaurant, and you slow your pace a bit so that someone else gets there first.

It is a life of deference and small acts of cowardice. It sucks and you shouldn’t settle for it.

As with every area of growth, progress for me happened in little breakthroughs. Here are four.

Quit denying the importance of small talk.

A traditional safety-shield for the shy person is to dismiss small talk as insufferable or disingenuous. Why “make conversation” when it’s not happening naturally? Clearly if there was something interesting to talk about, we’d talk about that. Why do we pretend that we care about some twice-removed acquaintance’s work, or their plans for the summer, or the obvious fact that it is raining?

The old standards—What do you do? How do you know the host? Do you have plans for the weekend?—are standards for a reason. They’re low-risk and they get words moving. They warm the air between two people, and make deeper lines of conversation possible. They get you into the foyer of a possible human connection. From there, you can see into the drawing room, where stories, hobbies and aspirations are being shared.

Demonizing small talk is like avoiding the front door just because everything that happens there is so predictable. Being civilized means helping people to be comfortable by offering a bit of formality and predictability: knock on the door, enter graciously, shake hands and let them take your coat. Small talk earns you the right to make deeper connections. It’s like letting a dog sniff you before trying to pet it—maybe the little ritual does nothing for you directly, but that’s not the point.

Change the way you relate to your cringe-inducing memories.

It’s not only shy people who are plagued by visions of dumb things they said or did in the past. All of us have mortifying video clips in our heads that could play at any time: greeting several people at a wedding before discovering the booger on the side of your nose, or using the word vagina instead of Virginia during a class presentation, or worse.

I’m convinced, however, that shy people tend to find their cringe-inducing memories much more unbearable than self-assured people do. They think of them like scars, permanent features of their personality, direct evidence of their social ineptitude. The threat of another wound makes interaction seem a lot more dangerous, reinforcing habits of avoidance.

The typical way to respond to an embarrassing memory is to try and rewrite it in your mind whenever it comes up. You imagine a corrected version of the story, in which you escape humiliation with a slick move or a witty comeback. This fantasy buys maybe a second of relief, and then you remember what really happened and you cringe a second time.

The key to taking them less seriously is to recognize that it is the only the experience of remembering that is painful—the event itself is long over—and this experience doesn’t have to last long. You’re not dealing with an embarrassing event in the past, you’re dealing with an annoying thought, right now.

This has to happen now and then. Your mind is mostly just a connect-the-dots machine. Something reminded it of an image in your memory bank, and the brain went and retrieved it the way a well-meaning cat brings you a dead bird. Think of it as your mind simply stubbing its toe. These cringey memories are a short, painful collision with something in the present, not the long-term pain of a disfigured soul.

To get through it faster, never engage with the story itself. Instead, notice what that little thump of memory has done to your body in the present moment: the tight stomach, the shrinking shoulders, whatever the symptoms are for you. Don’t fight these feelings, let them radiate through you for a bit. Notice them start to dissipate, then move on to the next part of your day.

Resist the urge to imagine how it could have gone, what you could have said. That’s a fool’s bet. Let it be like it was. It’s gone, and forgotten by everyone but you.

Make a sport out of talking to people.

We ought to devote a subject in grade school to certain social micro-skills: how to finish a sentence without tapering off; how to make non-threatening eye-contact; how to ask questions people actually enjoy answering; how to move a conversation along when it starts to stall; how to ask for something; how to say something dumb and not make a big deal of it.

Building these skills reverses the direction of the shyness feedback loop. It is not an overstatement to say this: these skills make nearly every aspect of life easier, every day, forever. 

In every single interaction, you can make something easier that was once hard. The idea isn’t to constantly be evaluating how you’re doing, it’s to push one little aspect forward each time. Maybe you can be a little bit less mumbly with this next sentence. Maybe you can be the first one to introduce yourself this time. Maybe you can move this stalled conversation along to its end, instead of waiting for the other person to do it.

Usually you can make some small improvement just by trying. Sometimes you can’t, but it doesn’t matter because you have a hundred chances a day. These little victories pile up like money in the bank.

It’s hard to overstate the value of these micro-skills, and they improve quickly when you make a sport of using them. It is exhilarating to come away from a conversation knowing you broke new ground. Good social micro-skills make people assured and capable. They make people rich. They create friendships and support networks. A single good conversation can change your life, so imagine what can happen when you’re making them all the time. It doesn’t matter where you’re starting; something can be improved every time, and every time you do it feels awesome.

(If you aren’t sure quite what to practice, it’s hard to find a better starting point than Dale Carnegie’s beloved How to Win Friends and Influence People. Even if you’ve read it, read it again.)

Notice when you’re feeling nervous, and don’t leave.

Shy people are good at disappearing from parties and get-togethers.  To the timid, these events can feel fundamentally dangerous, and to leave feels like a huge relief.

But fleeing from social situations makes future get-togethers more difficult. Shyness begins to reinforce itself when you believe that the pain of embarrassment or self-consciousness can never be allowed to happen, that it’s damaging to you.

The truth is the opposite, however: what’s damaging is the refusal to ever experience those feelings. This is the crux of the shyness problem. By avoiding social discomfort like it’s poison, you end up making something unpleasant into something unbearable. Those feelings become a really big deal, a danger you have to plan your life around. You create your own kryptonite.

What shy people need, more than anything, is some experience allowing nervousness and self-consciousness happen to them, without fleeing the scene. They need to bear some of these feelings, to see that they dissipate when you resist the impulse to run from them.

Stay at the party. Let those feelings linger inside you, but don’t leave. Have some low-risk conversations, and let yourself feel however you feel during them. That’s the feeling of shyness going away. You need to demonstrate to your brain that nervousness is just a passing feeling. It’s not an emergency, and it’s not an identity.

You’re outsmarting the shyness here with an expert move, actually allowing it instead of running from it. This is yet another application for the practicing of mindfulness. You sit right in the nervousness and let it be there, and nothing comes crashing down.

When you do this, the shyness loses its ability to reinforce itself. If it can’t make you run, it can’t do anything.

Camp Calm is happening next month

campcalm-165So far more than 700 people have signed up to hear more about my virtual meditation workshop, Camp Calm. I’m sending out the first update in the next couple of days. Learn more here.




Photo by Joe del Tufo
Thehappyphilosopher December 7, 2015 at 1:09 am

I like the application of mindfulness here. When we realize it is just our thoughts and fears causing physical responses in our body then it makes it easier to just observe what happens and let it be as it is. The more we can live in the moment of talking or interacting with someone the easier it is to get away from those feelings.

Many people get totally confused by the introvert vs. shyness thing, but they often do go together.

Great post. Thx!

David Cain December 7, 2015 at 8:21 am

That’s really where the tires meet the pavement. Like anything else, it’s just an experience in the present moment. If you can notice the present-moment symptoms, that’s all you have to deal with. The past can’t be dealt with.

Tanuj Kalia December 7, 2015 at 2:16 am

David, have you done the Landmark Forum? It says very similar things.

Just one example. You said “Your mind is mostly just a connect-the-dots machine.” Landmark says “Your mind is a meaning making machine.”

David Cain December 7, 2015 at 8:23 am

Never done the landmark forum, no.

Stanislav December 7, 2015 at 2:26 am

I love this. I usually avoid small talk with people I’m shy around because I feel like that’s not enough to be seen as an intellectual, or even a somewhat-interesting person. But not talking when you want to is sometimes the equivalent of being dishonest. I will try to be more assertive and open. Thanks always for sharing, Dave.:)

David Cain December 7, 2015 at 8:26 am

I didn’t really expand on this, but much of shyness has to do with how we evaluate ourselves and how we hope to be evaluated by others. A big step is opening yourself up to bad or unfair evaluations. Ironically, we tend to show our worst sides when we’re trying to hide our faults.

Sarah Noelle December 7, 2015 at 5:46 am

“These little victories pile up like money in the bank,” love it. As someone who grew up very shy and is on a continuing journey to become more comfortable opening up in social situations, I really appreciate this post.

I’ve been noticing recently that even though I’ve made a lot of progress in terms of being able to introduce myself to people, and start and actively participate in conversations, the one less-than-desirable behavior that continues to linger around for me is a serious lack of eye contact when speaking to people. I’m more aware of it these days because I’ve been teaching a class this semester, and I find that it’s very difficult for me to make much eye contact with students while lecturing. (When I sent around an anonymous survey asking for feedback after the first couple of classes, one student actually wrote, “try to make more eye contact” — ha! Very insightful.)

I really like your focus on “noticing and not leaving” — I think it can be easy, as a shy person, to say, “Well, this is just who I am, it’s just my personality” and use that as an excuse to not participate in social situations. It can be like a sort of identity-reinforcing act. But I totally agree with you that there’s a lot of potential value in staying and confronting the nervousness.

David Cain December 7, 2015 at 8:30 am

I think eye contact is just a matter of practice. I was fifteen when someone mentioned that I never make eye contact, and so I started trying to do it. I remember how intense it was at first — I would forget what I was saying. But it’s like anything else. It gets harder when you avoid it and easier when you do it anyway.

The “this is who I am” argument is really limiting, and it doesn’t even make any sense. It really means “I can’t expect myself to act in any way I’ve never acted before” which can only keep you stuck in one place.

Carley December 7, 2015 at 6:12 am

How would you differentiate shyness from social anxiety?

David Cain December 7, 2015 at 8:33 am

Depends who you talk to I guess. The way I think of it, we call it social anxiety when it involves overwhelming anxiety reactions. Or maybe we call it social anxiety when we seek treatment for it. Nobody is overwhelmed in every circumstance though, so the place to push our social skills is when we feel inhibited or nervous but not yet overwhelmed.

Natalia Filson December 7, 2015 at 7:32 am

What helped me was was understanding that I am an introvert and recognizing and respecting introversion in others. If you encounter an extrovert, the communication is easy. Just throw out a topic and let them talk. With other introverts, I always felt awkward silence. Once I understood my own difficulty socializing, I can project it on others. Compassionate silence can be very comforting. Small talk topics are not very good with fellow introverts, you have to bring out heavy guns – meaningful topics to discuss. Also, understand that other person’s silence is not a sign of disinterest, but their own social anxiety. Compassionate listening is the key.

David Cain December 7, 2015 at 8:38 am

You know you’ve reached a good point with someone when you can be silent together with no awkwardness.

Ken Lyons December 7, 2015 at 8:16 am

Good Morning and good post. Breaking the ice of communication on Monday morning is seldom easy. I relate it to swimming. The hardest part is is getting in the water. Once you are in, take a few easy, deliberate strokes and you become acclimated. Anticipatory restlessness trails off in your wake.

Thanks for the forum.

David Cain December 7, 2015 at 8:39 am

Better to dive in than to lower yourself — less time to second-guess things :)

Dan December 7, 2015 at 11:32 am

Love the idea of seeing it as “a sport.” Namely, as a sort of play, or intricate dance, that need not really “go” anywhere, but be done well and engaged fully for its own sake – complete with graceful movements and missteps! I often find myself reflecting on something Alan Watts said:

“Interesting people are interested.”

Taking that approach, sincerely and genuinely, has enriched any conversation I’ve been in. It “takes the pressure off” me, in a way, and leaves me hanging on every word of the other person. There is no way to ‘be interested’ wrong! I even find myself listening to each word I’m saying in response, and wondering where one will carry to the next (and being surprised and delighted by where it goes). Also helps to keep in mind something I’ve felt but recently heard put succinctly:

“Everybody knows something, nobody knows everything.”

Along those lines, everybody has experienced something, and nobody has experienced everything. You’re bound to hear something new in any conversation. And, even if it doesn’t seem “new,” hearing that people share certain experiences/feelings is its own form of fascinating (and can be a great relief) all the same.

Dan December 7, 2015 at 11:43 am

An addendum in that same vein: think of your conversations in the same way Bob “Happy Little Trees!” Ross would paint. When he would “screw up” with a seemingly errant brush stroke, he’d just turn it into a field of flowers, or stream, or use it to enrich the painting otherwise. He would just brush it off (sorry, couldn’t help it) and cheerfully insist:

“We don’t make mistakes, we have happy accidents.”

David Cain December 8, 2015 at 5:53 pm

I love Bob Ross!

David Cain December 7, 2015 at 6:02 pm

Making things into sports or games has been a hugely successful strategy for me in pretty much every area of self improvement I’ve tried. It adds an element of instant gratification, in areas where often we’re mostly concerned with long term rewards.

Love this: “There’s no way to ‘be interested’ wrong”. So much social anxiety hinges on the worry that you’ll be a boring or inadequate speaker, but being interested will almost give the other person a good experience, which they will associate with you.

Michael December 7, 2015 at 1:38 pm

Really good stuff. Thanks for this one. I especially liked this line:

“The key to taking them less seriously is to recognize that it is the only the experience of remembering that is painful—the event itself is long over—and this experience doesn’t have to last long. You’re not dealing with an embarrassing event in the past, you’re dealing with an annoying thought, right now.”

The idea that all of our thoughts, whether about the future or the past, are still taking place _now_, has really changed the way I look at life. It’s a reminder of how the thoughts that I think are taking me away are really just thoughts, and I’m still here, with those thoughts poking around. But the thoughts aren’t me. It’s always nice to be reminded of that, and it’s enabled me to get much better at not dwelling on embarrassing memories, or better at not holding onto anger, or negative thoughts in general. And once you know you have the ability to let go of those thoughts, it’s less scary to open oneself up to social situations that might prove awkward or difficult.

“Stay at the party.”
When at a party or event full of acquaintances, but not friends, it’s just as easy to stay but bury myself in my smartphone, waiting for someone else to begin a conversation. Which, like you say, just reinforces the shyness.

David Cain December 7, 2015 at 6:09 pm

Learning to see thoughts as thoughts makes life much much simpler, in so many areas in life, but we have such trouble differentiating our memories from the experience that created it. Dealing with a thought is actually possible — dealing with a past experience isn’t. No action can be taken on it. This is where the meditation becomes so handy, because you learn to recognize thoughts as thoughts in real time, and they are easy to manage. They’re just a little mirage in the mind. It’s the reaction to the thought that’s real, and that’s so painful.

Ian December 7, 2015 at 1:56 pm

Interesting point about making small talk. When entering conversations as a shy person I quite often feel I have to say something smart or witty to hold the attention of the other party. Quite often this small talk does lead to deeper conversations as I find commonalities in our discussion.

David Cain December 7, 2015 at 6:10 pm

Wit is almost never necessary. When it happens it happens. Much better to be boring now and then than suffer over not being witty enough. Ironically, wit develops as you speak more, so that boring small talk creates wit in the long run.

Samuel Mandell December 7, 2015 at 6:00 pm

1. Some really lovely writing in this piece:

“They warm the air between two people, and make deeper lines of conversation possible. They get you into the foyer of a possible human connection. From there, you can see into the drawing room, where stories, hobbies and aspirations are being shared.”

2. When talking about those embarrassing memories that sometime threaten to overwhelm you:
“Don’t fight these feelings, let them radiate through you for a bit. Notice them start to dissipate, then move on to the next part of your day.”

I find that being KIND to myself as those memories come up, and acknowledging the thing I’m embarrassed about helps a lot. So if an painful memory of something I perceive as silly or dumb that I’ve done comes up, I’ll try to think to myself “Haha, boy you goofed that one up! Next time let’s see if someone is going in for a hug before extending a handshake into their stomach!”

Then I can look at those memories as more funny (as if someone was telling me a funny story about something embarrassing that happened to them) and don’t keep stamping my identity with that embarrassing moment.

Brene Brown has some great stuff on shame that speaks to this as well.

David Cain December 8, 2015 at 5:48 pm

I find that being KIND to myself as those memories come up, and acknowledging the thing I’m embarrassed about helps a lot.

This is so true. And whenever we fight with the thing that happened, by fantasizing or getting angry, we’re trying to deny our fallibility, like we’re unable to say: I did X and felt embarrassed. We are much harder on ourselves than we would be on anyone else.

Makeda December 8, 2015 at 2:24 am

This article really resonated with me. Describing shyness as a “chronic pain” perfectly describes the inner angst I felt but couldn’t describe. I hope to take on the challenges posed here. But I wanted to get your thoughts on something. How does alcohol and other stimulants which reduce your inhibitions play a role in overcoming shyness? Is it a crutch which produces no long term improvement? Or is it a leg up in an already arduous task? How did you use (or not use) it for this specific purpose?

David Cain December 8, 2015 at 5:53 pm

That’s a great question and I’m glad you asked it… I guess it’s kind of a mixed bag. I know that for me, it was essential in my late teens and early twenties. I was able to open up with people in ways I probably couldn’t have without alcohol. That’s not a good thing, but I know that for me it let me be myself a little more than I felt able to, most of the time.

It can certainly become a crutch, but it did introduce me to the feeling that it’s okay to talk to people, even people you don’t know. I don’t know how else I would have become accustomed to that feeling.

Of course, alcohol has all kinds of downsides and today it’s almost entirely a liability for socializing for me. But I can’t deny it helped me for quite a while.

Javier G December 9, 2015 at 5:55 am

I have found that what you wrote may be applicable to other situations just as well.
I’m struggling quite badly with procrastination at work, just as I did with shyness when I was younger. And I’m finding that the answer might be the same, if I stay with the anxiety and do not leave (to twitter, the web, whatever…) it looses a little bit of its grip on me, and I can build my confidence little by little…
Aaaah, mindfulness, so liberating, yet so hard.

Thanks again for your work

howhumansconnect December 11, 2015 at 2:33 pm

Interesting point about small talk being the “gateway” towards more meaningful conversation. We generally don’t just launch into a conversation about a shared hobby or whatnot without learning more of who you’re talking to.

Like many others, I’ve always disliked small talk for all the reasons you’ve stated. I’d rather be by myself than have a conversation we’ve all had a hundred times before. However, some of the best conversations I’ve had turned from conversations I was initially trying to leave from. I guess we need to realize small talk sometimes leads nowhere and other times leads towards a great conversation.

Mercury December 12, 2015 at 4:12 pm

I honestly think they should make a Shy People Anonymous group, where shy people can get together and work on being shy together.

I’m not even joking. Why can’t this exist? It would be awesome.

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