How to Overcome Shyness (and Meet a Small Army of Remarkable People)

How to Overcome Shyness (and Meet a Small Army of Remarkable People)

Written by Emilie

Topics: Confidence

As announced last week, Chris Guillebeau recently rolled into town for his unconventional book tour.

I’ve been interacting with the unconventional lifestyle community for some months now, but all online. Twitter, blogging, some emails, a few Skype calls; these were my main forms of communication.

It’s easy to share your thoughts from behind a computer screen, but the real world is an entirely different beast. The unconventional meetup was going to be my very first time meeting anybody in person.

And I was nervous.

A Natural Introvert

For as long as I can remember, I’ve always been extremely shy in social settings, especially when it comes to big groups of strangers.

But I wanted more than anything to meet some of these strangers. I mean, (unless you happen to live somewhere like Portland), how often do you get the chance to meet up with the lifestyle design community in your daily life? I also felt somewhat accountable to YOU after blabbing about this so resolutely on the blog last week.

All to say, that if I had shown up, sat quietly and then left, I would have felt profoundly disappointed in myself.

So yes, I was nervous.

The Meetup

I arrived with one of my best friends. Beyond reading Puttylike, he’s not really into the whole dream-pursuit/lifestyle thing but I think he’s mildly curious and has an open mind, so I invited him along. We grabbed a couple chairs near the front and spoke amongst ourselves.

Before the talk, Chris came over to chat. He asked us to fill out our name tags and to mark down one unconventional thing about ourselves. That’s right… ONE. “That’s going to be hard for you,” he added. Hah… Someone’s been reading my blog. ;)

Lucky for me, I’ve gotten good at answering questions like this in roundabout ways.

What was my one unconventional thing? ‘I’m a Multipotentialite,’ I wrote.

Easy. Done.

After Chris’ presentation and a short Q&A, people began lining up to get their books signed. As the crowd cleared out, I thought, now what?

Throw Yourself into the Leadership Role (or have it Thrust Upon You)

And that’s when a friendly girl approached me and introduced herself. “Don’t you think it would be cool if we organized a local group for the art of non-conformity?” “Yes!” (Finally!) I replied.

I pulled out my Moleskine and she jotted down her email address. And that was it. Suddenly, I (as the one with the Moleskine notebook), had been nominated. I had to go collect email addresses!

And that’s exactly what I did.

I worked my way down the line and chatted with everybody. I met some incredible travelers, artists, students. It was such a diverse group and such a pleasure. Better yet, as I collected email addresses, my goal of forming a local network of awesome people was coming together.

And what of the shyness? Well to be honest, I was still nervous. But did it stop me? No. I had no choice but to proceed. I was on a mission and someone else was counting on me.

Don’t Give Yourself an Out

As I began my networking mission, the friend I had arrived with decided to leave.

And as much as I love you, friend (because I know you’re reading this), being completely alone made an enormous difference when it came to meeting new people. Suddenly I had no one to turn to when I was feeling uncomfortable. This meant that I had better step up.

It’s always easier to meet new people when you don’t have anyone else to rely on. Don’t give yourself an out. Make it so that you have to talk to new people.

We Crave Community

As I mingled, I noticed that people seemed apprehensive for the first five seconds of us talking. People aren’t used to being approached by strangers. It breaks the unspoken rules about behaviour in public spaces. However, very quickly, they seemed to relax and become quite chatty. They began talking to each other too. In fact, everyone started opening up.

Whether it’s in the online community or in real life, we all crave community. We want to connect with like-minded people and share our ideas.

The problem is, we’re all shy.

When you find yourself in a situation like this, don’t deny that you feel uncomfortable. Just be the one who proceeds anyway. If you take the lead, others will follow.

Seth Godin puts it nicely in his book Tribes:

Leadership is scarce because few people are willing to go through the discomfort required to lead. This scarcity makes leadership valuable. If everyone tries to lead all the time, not much happens. It’s discomfort that creates the leverage that makes leadership worthwhile.

5 Steps for Overcoming Shyness

So to sum up, overcoming shyness and meeting new people can be accomplished in the following ways:

1. When you’re at your shyest and want to cower in the corner, do the opposite

The body follows the mind and the mind follows the body. Behave like a confident person would and you’ll soon start to feel confident too.

2. Show up to events alone (or have your friend ditch you mid-event)

Don’t give yourself an out. Create the circumstances whereby you have no safety net to fall back on and no choice but to talk to new people.

3. Make yourself accountable to someone else

Volunteer to be in charge or tell someone (your blog visitors, for example) about your plan to meet new people. If you know you’ll have to report back to someone, you’ll feel more pressure to step up.

4. Embrace the unknown and make use of the adrenaline

There’s something fulfilling about thrusting yourself into the unknown and having to fend for yourself. It requires that you trust yourself. Once you do it, you feel almost invincible.

I’ve grown to love putting myself on the spot like this. I’ve noticed that I tend to perform at a much higher level when, for example, I don’t over-prepare for a presentation. Being on the spot and having to ‘wing it’ a little usually results in a far more inspired speech. It’s like saying: “Emilie, I trust you. I know you can do this!” You end up rising to your own expectations. Whereas if you’ve written out your entire speech, it’s like telling yourself that you don’t trust yourself. The over-preparation becomes a crutch.

5. Act like Talking to Strangers is Completely Normal

Peoples reactions are often determined by the way information is presented. If you behave uncomfortably, they will respond uncomfortably. But project (or feign) confidence, and very quickly people will follow your lead.

The main thing is to SMILE. A smile and some solid eye contact goes a long way. All it takes is a few seconds. After that, they will relax and you can as well.


To all the lovely people I met the other day, thank you for giving me some practice stepping out of my comfort zone. It was a pleasure meeting you all and lets stay in touch. Also, a big thanks to Chris for swinging by our cold city!

How have you overcome shyness? Do you have any tips for meeting new people in unconventional settings?


  1. Thanks so much for coming out! (And for writing this great post.)

  2. Rebecca says:

    It’s true… we are all shy.

    I think I am kind of unconventionally outgoing and that has caused me to have similar insecurities and has created some shyness in me over the years. I became afraid that I was being perceived as creepy or coming on too strong by being so enthusiastic and energetic – maybe people were just making fun of me as soon as walked away? Maybe they were calling me a loser? Paranoia rules!

    But I stopped giving a shit and figured that if anyone was making fun of me for being kind and outgoing and friendly, that was really their own personal problem. Not mine. Confidence and smiles go thousands of kilometres too.

    • Emilie says:

      Definitely. If people respond in a rude or distrustful way, it’s really because of their own insecurities. Let them be unhappy and judgmental and go make your friends. It’s much happier on this side of the pond.

      Thanks for the comment Rebecca. Hope you’re having fun over there in Reykjavik!

  3. Sinoun says:

    Wonderful article! I can certainly relate (I think we all can). It’s always much easier to do the less risky things and stick to what we’re used to, than it is to push ourselves forward to do the things that scare us. I’ve learned that even if things don’t go our way, at least we can be happy knowing we didn’t take the cowardly road and that we can always learn from our mistakes.

    Needless to say, I met some really cool people there (including you Emilie) and I am happy you took the initiative to get all our emails. As you were going through the line, I remember thinking to myself “Wow, this girl is pretty awesome, I wish I had the guts to do that!”

    Kudos to you and your wonderful blog!


    • Emilie says:

      Aw thanks Sinoun. It was so nice meeting you as well. I especially love meeting fellow multipotentialites. :)

      “I’ve learned that even if things don’t go our way, at least we can be happy knowing we didn’t take the cowardly road and that we can always learn from our mistakes”

      I COMPLETELY agree. I try to base my accomplishments not on the outcome of a given situation, but on my own action and how many ‘risks’ I take. Pretty much once you say hi, you’ve already won.

      Ultimately we can’t control anybody but ourselves and people have all kinds of motivations for reacting the way they do, most of which have nothing to do with us.

      Thanks for the comment and for the kind words! Keep in touch Sinoun.

  4. Angela says:

    I am way too shy for my own good. Hearing about how you overcame your shyness gives me hope that I can do the same. I’ll definitely try out some of your tips. I’ve never thought about using adrenaline to my advantage when I’m shy. Great tip!

    • Emilie says:

      Cool, thanks Angela. Yeah the adrenaline can totally work in your favour if you don’t try to fight it. I’ve found this very useful on many occasions.

  5. Nick Laborde says:

    I can really relate to your situation because I have a hard time in those events my self. I’ve found that volunteering for something, much like you did is a great way to break the ice.

    As a proud introvert I’ve learned that it’s also much easier if you’re around like minded people (Small Army of Remarkable People). I missed the book tour when it rolled through Atlanta, but I’m going to #WDS, that should make up for it real nice.

    It’s also important to remember that being an introvert and being shy are two separate things. Shyness is generally confidence related (something you can change).

    The universe seems to be trying to tell me something, I think I’m gonna write about the misconceptions of being an introvert. I think we’re mis understood.

    Thanks for the solid advice and congrates for jumping out of the comfort zone.

    • Emilie says:

      Hi Nick,

      Please send me a link to that article once you publish it. I’m pretty sure I’m guilty of confusing ‘shy’ with ‘introvert’, being both at various points in my life. I’d love to get a bit more clarification on the differences.

      Thanks for the comment Nick. And I’ll see you at the #WDS!!

      • tizzielish says:

        I am not sure what ‘shy’ means but I am pretty clear about what introvert means. A person is ‘introverted’ when they tend to get their energy from within their own selves. An extrovert, for comparison, tends to get their energy from others. So an extrovert seeks connection with others to charge their own batteries, whereas an introvert turns inward.

        I thought I was an extrovert until my mid-forties when I took a class about personality types. I have always talked a lot so I assumed I was an extrovert. The class instructor overheard me say that and he asked if anyone else in the class thought that the distinction between introvert and extrovert had anything to do with noise volume. Everyone raised their hands.

        Then he said we were all wrong. That the difference between being introverted and extroverted had nothing to do with how much a person talked, esp. how much they might talk in situations where they didn’t know people. Intro- extro- has to do with where a person gets their energy.

        I am most definitely an introvert but I talk a lot.

        I also think I am shy. But I am not completely decided about the shy label. I know that I talk a lot when I am feeling shy to hide my shyness and this is a good trick. I know that many people think I am not shy, coming to the conclusion because I am talking but they don’t actually know me very well. The more I am talking, the more I am hiding. I guess I am shy. I hide my shyness with chatter. It is a tricky thing.

  6. FearfulGirl says:

    My mother is a singer. She gets up in front of big crowds on a loud PA system and blasts out June Carter songs. She oozes confidence. Once I asked her for advice on how I could be as confident as she is. She said, “I’m not confident. I’m terrified. I just pretend to be confident.”

    So I think point 5 is key. Remember that everyone else is probably just as scared as you are.

    • Emilie says:

      Good story! It’s so true too. I don’t believe people who claim to never be afraid. Everyone gets scared, it’s human nature. Some people just proceed anyway.

      Your website is pretty cool there FearfulGirl. I like your spin on the whole adventure blog idea. Good stuff.

      • FearfulGirl says:

        Why thank you! I wrote a memoir and a major theme is fear. I was terrified of water, but I was given the opportunity to sail a boat (with a man I met in a bar) across the Pacific. I decided to face my fear, I didn’t want to regret saying ‘No.’

        I think it’s okay to be scared of something (the ocean, crowds, socialising) but fear isn’t a good enough reason to avoid living life and having incredible experiences. Otherwise, you’re just left with regrets.

        Nice website, excellent content!

  7. Sending this to all my shy people! Good stuff as always.

  8. Over coming shyness starts with taking consistent action towards your dreams. as long as we continue to work towards our goals..then you win. Just make sure you pat yourself on the back when you make progress. Great post Emilie.

  9. Over-preperation as a crutch. Oof. It also makes a mighty fine delay tactic. As in, I-can’t-start-now-I’m-not-prepared-even-though-I’ve-been-researching-this-one-idea-for-two-weeks-now.

    And so, I take up your challenge, whether you meant it that way or not. I arrive in Rio on Tuesday week and I’ll be living there for six weeks. Within the first week I am going to sign up for caipoera and before the first class ends I will find a practice partner. Maybe even a small group.

    I’m @KathrynTHunter on twitter and you’re all welcome to hold me to this declaration there.

  10. Brian Gerald says:

    Congrats on your successes. Look at you, the new leader of the Canadian non-conformity movement!

  11. Anh Han says:

    Emillie! Great post (yet again)!

    As a massive introvert myself (and multipotenialist) I can definitely relate to what you are saying. I still get nervous when I talk to strangers but with a little practice I’ve managed to become a little better.

    I now like to call myself a “social introvert”.

    The biggest thing by far for my progress was to stop over thinking things. As introverts our world is internalised. We worry that people will think we are weird, or that our sense of style is awkward, or we won’t have anything interesting to say.

    We are very good at analysing what could go wrong, or realising that the situation isn’t ideal that we never step out of comfort zone.

    The thing is, no one really cares. Everyone is waiting to be approached. Just decide to be the one doing the approaching.

    • Emilie says:

      Hey Anh,

      That’s a good term: “social introvert”. And I think you’re right about the over-thinking. I mean introverts/multipotentialites like you and I create blogs to dissect life and philosophize! It works in the blogosphere though- gives us a better understanding of human behaviour and how to get the most out of life.

      I think you’re right though that when you’re in the moment, the same skills that lead to insightful comments on a blog, can result in social paralysis. And then yeah, it’s like you said. We’ve got to pull through it and break free of our comfort zones.

      I too have made a big effort not to over-think things when I’m in the moment. I’m a whole lot better than I used to be, that’s for sure.

      Thanks Anh. Always enjoy hearing from you!

  12. Peter J says:

    If your feeling un-comfortable when your about to speak to someone else your new to, chances are they are going to be feeling un-comfortable too. I wish i could say, “just get on and speak” but the world doesn’t work like that, so we all seem to shy back a bit even though everyone else around is also shy :P

    I think a fair bit of our motivation can come from, as you said, having it thrust upon you. That girl came up to you and said “Don’t you think it would be cool if we organized a local group for the art of non-conformity?” similar as someone inspirational to us might say something that will get us started.

    Great post Emilie :)

    • Emilie says:

      Yup, having an opportunity thrust upon you is a great way to get started. You need to take advantage of it when it comes your way though. I could just as easily have easily handed her my email address and gone back to being shy. But I used her approach as a catalyst to take on the responsibility for collecting email addresses.

      Still, the principle’s the same. Sign up for something that will naturally put you in a leadership position and you’ll feel far more motivated to take charge.

  13. ayngelina says:

    So true that we’re all shy. Most people would say that I’m an extrovert but honestly being in new situations gives me such anxiety. But I do find that if I get over the first hurdle and just put myself out there it always pays off.

    • Emilie says:


      My mom (who’s a psych professor) was telling me about this term for a truism that everybody believes about themselves. I forget the word for it, but the classic example is something like “deep down, I’m actually a shy person.” Apparently that’s a statement everyone believes to be true about themselves. Interesting, eh?

      And yeah, the first step is totally the hardest! It’s the anticipation and the over-thinking BEFORE the first step that drives you crazy. Once you take the plunge, it’s no sweat.

      Thanks for swinging by! Enjoy your last day in Ecuador! Where are you headed next?

  14. Abe says:

    Steps 4 and 5 are such good tips. I have a hard time silencing that inner rational dude in my head (I’m pretty sure he wears a monocle) when it comes to meeting new people. The mantra, “Aww, screw it” helps too. Whatever happens after that statement is usually not that bad. If anything, it’s a story to laugh at and learn from.

    • Emilie says:

      Hey Abe,

      “Aww, screw it” is a great mantra. Sort of a reminder that even if you come off as a total weirdo, it really doesn’t matter. These are people you will likely never see again and you really have nothing to lose.

  15. Hi Emelie,
    I know that uncomfortable feeling all too well. But like you, I force myself to overcome it. Even while I’m shaking on the inside, I resolve to project confidence and a smile. I’m glad smiling works because if it didn’t I’d be in a lot of trouble. :) In addition to that, I give myself a quota – I must talk to x amount of people before I can stop. I’ve also been in situations where I had to make it a point to talk to every single person.
    I just roll up my sleeves and take a deep breathe, because like you, I’ve got some leading to do. Thanks for a wonderfully refreshing post.

    • Emilie says:

      That’s great Kiesha! It’s so important to push yourself. Good for you.

      And yeah, smiling goes a LONG way. It sounds so simple, but most people forget to smile when they’re nervous. It’s the same as forcing yourself to talk to strangers- the mind follows the body. Smile like you’re comfortable and you’ll soon start feeling more comfortable.

      Thanks for swinging by and for the insightful comment Kiesha!

      p.s. also thanks for being comment #30… That’s a record for me. :)

  16. fjordz says:

    I can relate to this. Nice reading this post. I guess, overcoming shyness rely on your willingness to overcome it. If you really wanted to get rid of your shyness, face it. I know its hard but that’s the only way you can initiate something to improve yourself.

    • Emilie says:

      Hi Fjordz,

      You’re so right, it’s all up to you. Nobody can get you over shyness, you need to take the initiative yourself. People also think of it as something inherent that can’t be changed, but it’s really not. You can learn to overcome your fear of strangers and in the process you might end up with some really great new friends! All it takes is a bit of practice and bravery.

  17. Mark Powers says:

    Great post, Emilie! Very true that we all feel that way, at least once in a while. But stepping up and forcing yourself to do the opposite is the only way to grow past it. Love your site- thanks!

  18. Emilie says:

    Hey thanks Mark! By the way, I love what you’re doing over on your site. Music + personal development = awesome!!

  19. Katie says:

    When I was 5, I was at my grandmother’s playing Go Fish! in her living room, when her boyfriend (my soon to be step-grandfather) came over. I hid under the lazy boy in her bedroom for about five hours until he left. How’s that for ‘naturally shy?’

    Thanks for the post Emilie, you’re right, it’s good to go somewhere alone and not give yourself an out by not speaking to anyone. You’ve got balls!

    • Emilie says:

      Hey Katie,

      That’s intense. It’s interesting how some of us are programmed at such a young age to be weary of strangers. There are probably good evolutionary reasons for that.

      But so much of adulthood seems to be about overriding those natural fears and insecurities and getting our instincts back in check with present day realities, like the fact that most people are perfectly friendly and aren’t out to hurt us.

      Thanks for the comment Katie! :)

      p.s. Go Fish with the grandmother! aww

  20. Abby says:

    Great post. I’m shy too :)

    When I moved away for university, I imagined the worst that could happen (people wouldn’t like me and I wouldn’t make any friends) and started to daydream about suffering through 4 years then going somewhere else (Europe?) and trying again to make friends.

    I was wrong twice (I made friends, and I won’t graduate in 4 years It’s going to be 5.)

    • Emilie says:

      That’s awesome Abby.

      It’s interesting how a shared experience, be it university or a book tour meetup, can provide a good backdrop for meeting other people. You all have a common reason for being there and a natural urge to connect over that shared commonality.

      Thanks for the comment. :)

  21. Susan says:

    I stumbled upon your blog after seeing a tweet on a more recent post – the ‘screw employment’ one and found this one after. I can relate to being shy. I’ve been to a couple group meetups and I always tend to be quiet. As a new business owner, I know I have to go out there and network which requires me to actually talk to strangers. This post has some great advice, and I’ll definitely apply it to the next meetup I go to!

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