How to Become Less Shy

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.

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Camp Calm is happening next month

So 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.

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Photo by Joe del Tufo

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