Published on
Posted under
Introvert Tips

I Grew Up Painfully Shy — These 5 Habits Slowly Built My Confidence


In old family photos, I’m easy to spot: I’m either hiding behind a soccer ball or latched tightly onto my mom or dad.

I was terrified of meeting new people as a kid. Throw in the fact I stuttered, had coke-bottle glasses (think Ralphy from The Christmas Story except with paralyzing acne), moved every year or two for my dad’s job, and I can’t remember a day when I didn’t have to wipe the sweat off my hands before shaking someone else’s.

If you’d told me I’d later end up moving to new countries on my own and helping people improve their confidence, communication skills, and relationships for a living, I probably wouldn’t have liked you very much. But that’s exactly what happened.

Like most positive change that takes place, this didn’t happen overnight and it definitely wasn’t always fun. By slowly pushing myself, however, I eventually got comfortable in my own skin. Out of all the hacks, tips, and tricks I’ve tried, the five habits below have paid the biggest dividends.

1. Give confidence to others

“Stand like an alpha!” “Project your voice!” “Just take the jump, Johnny!” In certain situations, this typical advice can be beneficial. But there’s an easier way to begin to grow your self-esteem in social situations that deserves more play — do what you can to grow the confidence of others.

  • Tell the people who get you what they mean to you.
  • Keep an eye out for how people are improving.
  • Send supportive messages to people.

In short, see others in the way you wish they’d see you.

I used to see my shyness and stutter as a weakness. As I got older, I realized it’s my biggest strength. While other people were talking, I was listening. And when it came time to help, I was tuned in to what people needed.

Think about how you feel when someone notices you. Especially when the lift comes from someone you don’t know very well. Confidence may be rewarded heavily in our society.

But so are thoughtfulness and kindness.

This is especially true as we get older as most people begin to define friends as those who make them feel comfortable and good about themselves.

2. Master the least-painful uncomfortable situation

You don’t have to crush your fear of heights by jumping out of a plane. When it comes to your fear of social situations, the same rule applies. Start smart by starting small. Grab a rung on the social ladder that’s a bit of a stretch and after finding your legs, climb up slowly from there.

Put yourself into situations where people aren’t likely to shut you down.

  • Going to bars or cafés during off-hours to make small talk with the staff is one way to do this as their job is to pay attention to you.
  • Make a rule to always smile and say hello to cashiers and ask how their day’s going.

These quick interactions will not only build a positive reputation around town, but they’ll also help you when the stakes begin to rise.

When I was 23, I took a sales job to get over my fear of human beings once and for all. I was still a nervous wreck, but I wasn’t starting from zero because of the social confidence I’d gained working odd jobs in college that demanded me being out in front of people but for limited amounts of time.

The beauty of gaining social confidence is opportunities are all around you. Instead of being reactive, choose just one situation where you can go first.

Whatever you chose, make sure you make a commitment to do it consistently. More times than not, success looks a lot like taking the small right steps on a regular basis.

3. Reach out to talk to people you connect with online (who are also shy)

Despite a ton of negative aspects, if you use social media to be social, it can be an incredible tool for building your conversation skills and in turn, your confidence.

Every week for the past three years, I’ve reached out to someone who’s doing something cool requesting a chance to speak with them. This may sound like the last thing you want to do. But again, I began by connecting with people who talked online about growing up lacking confidence or being introverted which turned out to be a really smart thing to do.

  • “I loved your article about X! How did you get into writing?”
  • “What you said about Y really got me thinking. How’d you come up with that?”
  • “I never would have guessed you grew up shy also as you come off as extremely confident. What’s your trick?”

A big part of making connections with people is learning how to be spontaneous in conversation. But write down a few easy questions to kick things off in topics both you and the person you’re reaching out to are interested in and take note of their answers and think about how you can make a strong second impression.

Maybe you can recommend them a book you came across in an area they’re interested in. Or maybe you can connect them with someone who can help them solve a problem they’re facing.

If I’ve learned anything in this journey it’s that most people won’t bash you for being interested in them.

4. Use these 2 smartphone functions to your advantage

The late-great Larry King — arguably the best conversationalist of our time alongside Oprah — used to talk out loud to himself every chance he got when he was growing up. He imagined how conversations would go and which questions he could ask as a follow-up.

Steal Larry’s habit, but instead of talking to an invisible friend, break out your smartphone and record yourself so you can go back to see what you got right and where you went wrong.

If you struggle with things to talk about, write out 20 common interview questions and record yourself answering one a day until you’re happy with your answer. You can also practice telling your favorite stories and work to get them as engaging as possible. This may feel uncomfortable at first, but the difference between the first take and the tenth will blow you away and you’ll see that you absolutely have the ability to improve.

Recording yourself is one option, taking advantage of the voice message you probably have available on your phone is another. If you aren’t happy with what you said when leaving a message to a friend, delete it until you get the message tight.

Rarely are the voice messages people receive from me the first take. Like a lot of people, I have a tendency to express myself better once I’ve left the room.

The beauty of this option is you can walk in and out of the room as many times as you need while listening to the replay to build off what you got right while working on the moments you got tripped up.

5. Teach what you know

When I moved to Spain a decade ago, in order to survive, I taught English as it was one of the few jobs that didn’t demand legal EU working papers. I thought the experience would be a massive waste of time. But like a lot of things I didn’t want to do in the past, I learned a ton.

At that point in my life, I’d already worked in sales but the majority of my job was spent with people one-on-one or in small groups and I still had a serious fear of speaking to large groups. I was by no means an expert in grammar, but I was pretty good at speaking English which is what most of my students wanted. Not only that, but it opened my eyes to the power of conversation design where I guided the class, but they did most of the talking.

  • If you’re into tech, offer to teach beginners.
  • If you’re into cooking, offer to give some classes to friends.
  • If you’re into a sport, get involved with coaching kids.

A lot of people break out in cold sweats when thinking about taking the stage. But if you think about it, it’s just teaching.

And the fastest way to grow your confidence in this area is to put yourself in low-stakes situations where you talk about what you already know.

Pulling it all together

When thinking about how I grew my confidence, one theme becomes very apparent. Rather than jumping into situations that scared the life out of me, I took small but deliberate steps, and over time, the momentum I gained began to carry me through more difficult situations.

But the important thing is I kept walking.

If you’re someone who learns by having your back pushed up against a wall, by all means, dive into what scares you the most. If you aren’t, don’t sweat it as there’s nothing wrong with slowly chipping away at your fears.

And when in doubt, if you can’t seem to raise your own confidence, lift others.

People who are persistently thoughtful will always stand out.

I write about this topic often. If you enjoyed it, feel free to follow along for weekly articles here.