6 Daily Challenges To Overcome Shyness

As a recovering shy person who occasionally relapses by hanging out in the corners of rooms at parties, I know firsthand how being shy can get in the way of a life well-lived.

On particularly adventurous days (or particularly caffeinated ones) the shyness melts away and I’m out there meeting people, exploring new places, and saying hello to strangers.

On other days… not so much. It’s easy to let others do the talking at dinner, let coworkers have ideas at pitch meetings, and just overall let the world pass me by.

Given that introverts make up an estimated 25-40% of the population (and who knows how many people identify as extroverted introverts… or introverted extroverts), I’m guessing I’m not alone. 

To that end, today I’m sharing six daily challenges you can try to overcome shyness in both your personal and professional lives (and no, none of them involve liquid courage!).

While I’m all for the power of being an introvert (I see you, Susan Cain!), society tends to reward extroverted behavior. To give my shy people a bit more power in their day-to-day lives, below are six areas where we can struggle, along with a daily challenge designed to help us overcome shyness.

Shy people may find it hard to start conversations, especially with people they don't know well. 

This can make it challenging for them to build new relationships or make new connections in a professional setting.

Challenge: Spark up a conversation with one person you don't know each day. This could be as simple as asking a stranger for the time or complimenting someone on their outfit. Do it, and you could even unlock one of the impressive awards from our Get Out There IRLA Pack for pushing past your comfort zone!

Despite it being a word that makes most people groan, networking is an essential part of many professional fields. Doing it well requires a certain level of comfort with meeting new people and making small talk. 

Shy folks may struggle with networking events or other social situations that require them to repeatedly meet people in a forced environment.

Challenge: Set a goal to attend at least one networking event this week. This doesn’t have to just be limited to professional meetings. Find an informal gathering of people in your industry. Challenge yourself to meet and talk with at least three new people at each event.

In group settings, it’s easy to let the loudest people keep talking. Let it go on for too long, and it becomes difficult to chime back in. Even though shy individuals may have valuable insights and opinions, it can be harder to vocalize them, leading to difficulties in social settings.

Challenge: Practice expressing your opinions in low-pressure situations, such as with friends at your next Millennials Only Brunch. Set a goal to speak up at least once during each group conversation or meeting.

Speaking from experience, being shy can hold you back from asserting yourself in professional situations, such as negotiating a raise. After all, we figure we’ve done the work, so surely it will be rewarded… right? The unsurprising answer is that not speaking up can make it challenging for shy folks to advance in their careers or achieve personal goals.

Challenge: Ask for what you want or need at least once each day. This could be as simple as requesting a specific task at work or asking for help with something you're struggling with.

As the old joke goes, public speaking is the number one fear. In second place? Death. Public speaking is a common fear for many people, but it can be particularly challenging for those who are shy. Speaking in front of a group can cause anxiety and nervousness, making it hard for shy individuals to present themselves confidently.

Challenge: Give a short speech or presentation to a friend or family member each week. Start with a topic that you're comfortable with and gradually challenge yourself to speak on more challenging or unfamiliar topics. The main challenge here is to stand up and be the center of attention. 

Making and maintaining friendships can be challenging for any adult, especially as they get older. If you’re trying to overcome shyness, that struggle to initiate social interactions can feel even more pronounced. Still, we believe you’re never too old to find new friends!

Challenge: Set a goal to attend at least one social event or gathering each week. This could be a meetup group, a class, or a club. Challenge yourself to initiate a conversation with at least one new person at each event. If you make that event an acting, improv, or dance class, you can even unlock another of these Get Out There IRLA medals!