How do you practice conversations with social anxiety?

young people talking to each other to illustrate an article on How to practice conversations with social anxiety
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Having had conversations with 10,000+ strangers over the last decade, here’s one question I get asked a lot:

“So, how do I get better at conversations?”

And if you have social anxiety like Barbara and I do, things are just a tad bit more challenging… OK, much more challenging. (Let’s be honest for a sec, shall we?)

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On some days, talking to people can feel like this:

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What do I even say!?

Or this:

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Uhh. What was I going to say again?

Now, here’s the good news: You can have great conversations even if you feel anxious.

And here’s even better news…

The key is NOT improving social skills.

It’s improving your ability to accept anxiety and connect despite that.

You don’t have to believe me or even the research (which, by the way, says that most socially anxious people don’t have a social skills deficit — it’s the anxiety that gets in the way.)

Just recall a conversation you had with a family or friend (anyone you love and trust, really). How did you talk and listen? What kind of questions did you ask? Chances are, you were a conversation rockstar because you weren’t overwhelmed by your anxiety.

Based on my experience — as well as what I’ve learned from multiple therapists — here are five ways to practice conversations with social anxiety:

1. Practice being neighbors with your anxiety

A big reason why conversations feel so hard is your struggle with anxiety. It’s not OK to have anxiety, after all… right? Isn’t it a negative emotion that you should reduce or eliminate?

The thing is, the more you fight against your anxiety — the more you try to push it away — the stronger it gets. And, even if your anxiety doesn’t get worse in the process, your attention is already yanked away from the conversation.

On the other hand, when you acknowledge your anxiety, you make it easier to focus on the conversation. But how? Here’s a metaphor for you…

Think about your anxiety as that neurotic neighbor who gets alarmed at almost everyone who walks by his house.

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You might not like your neighbor, nor do you have to be friends with him, but you can at least acknowledge his presence. Just say hi and go about your day 🙂

2. Practice swimming in your thoughts (vs. drowning in them)

This took me years to learn, honestly. And I can see why it’s so hard: most of us take our thoughts as the entire reality. We aren’t taught to question our thoughts. But they are only the partial reality — they might not even be accurate at all!

Let’s do a little experiment to prove what I just said. Write down the first five thoughts that come to your mind. For each thought, ask yourself these questions:

  • Is this thought 100% true?
  • Is this thought true all the time?
  • How do I know anyway? What evidence do I have to prove that it’s true?

Chances are, what might seem like reality at first will seem less certain. This is a crucial insight, as it helps you take your thoughts less seriously. You will get hooked by your anxiety-driven thoughts still, but their pull will become weaker over time.

(Here are other ways to be more aware of your thoughts.)

3.  Practice noticing the positives too

Social anxiety often distorts your attention, which makes you overfocus on the negative things in social situations. This triggers a vicious cycle where you become more and more fixated on anything that’s remotely anxiety-provoking. I call this the Social Anxiety Spiral:

One powerful way to break the Social Anxiety Spiral is shifting your attention to the positives. In fact, possible positives will do — you’ll want to interpret even ambiguous social signals as signs of interest.
Here are a few examples:

  • Did they listen to what you said without interrupting? That’s a positive.
  • Did they continue chatting with you even when you “looked shaky”? That’s a positive too.
  • Did they smile at your joke? Hell yeah, that’s a positive!

This doesn’t mean that signs of disinterest — like frowning or awkward silence — will go away. But you’re choosing to amplify the positives while noticing the negatives.

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4. Practice disagreement (just because you can)

A major trigger of social anxiety is rejection. And it’s because of the fear of rejection that many people avoid disagreeing with others. But when you play it safe, you also end up washing out the color of your personality. 

While you might not want to go through 100 Days Of Rejection, consider disagreeing more often. This helps you test your belief that disagreement is bad, for example, “If I disagree, they won’t like me”. 

More likely than not, you will realize that it’s not a big deal to have different opinions! 

Here are a few ways to start being more disagreeable — more of who you actually are:

  • Make it playful: You don’t need a reason, even! Just disagree for the heck of it.
  • Make it simple: You can simply say “no” or “I disagree”.
  • Make it frequent: The more you disagree, the more capacity you will build for social discomfort. 

(And btw, disagreeing doesn’t mean that you’re rude… it just means that you’re assertive. Learn more about being assertive here.)

5. Practice conversations while feeling “not good enough” 

The thought that you don’t match up to your or someone else’s social standards is scary. But here’s what’s even scarier: when it successfully persuades you to avoid social situations, which then maintains and increases your social anxiety.

There have been many times when I think, “I need to improve my social skills, feel more ready, etc. before I talk with…”

While there might be a grain of truth, what I realized is that I don’t have to wait to have the conversation. I can connect while feeling the stinging rawness of my inadequacies.

And you know what? I never feel completely ready. Even after 10,000+ conversations with people from all walks of life, I still feel anxiety when I approach a stranger!

So, here’s one last insight I’ll leave you with…

The ultimate conversation practice for people with social anxiety is the practice of leaning into insecurities.

It’s when you lean into your fears — again and again — that you find the courage you’ve been looking for.

This article was written by Ian Chew. Ian is the founder of Deeper Conversations. Despite his social anxiety, he’s had conversations with over 10,000 people, and he’s been featured by top media outlets like CBC, Inc. Magazine, and TEDx.

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