The Other Side of Shyness: How I Stopped Being Shy

As far back as I can remember I was shy. I was scared to speak with strangers, even for something as trivial as ordering food at a restaurant. My heart would race, my throat would clench, my mind would spin on how I’d be perceived… how I’d be judged. Now, I don’t care.

I remember one afternoon circa 1993, when my mom stopped the hunter green minivan with the faux-wood paneling, handed me money, and told me to run into the convenience store to get milk. I curled into myself and shook my head. I was NOT going. Give me a tetanus shot, make me do dishes, heck have me scoop dog poo… anything but have to talk to the cashier. No. Way. My sister — two years my junior with not one ounce of social anxiety and lax impulse restraint — leapt from her seat reaching for the $5 bill. “I’ll do it! I’ll do it!” She clamored. “No,” my mom said, yanking the money away from my sister’s reach, “your sister needs the practice.” My sister balked. I crumbled. I survived the 2-minute errand, but it was far from a cure. Bless my mother

Decades went by and I was still shy. Cashiers and waitstaff no longer made me shrivel, but I would never dream of entering an unfamiliar room and striking up a conversation. Making friends was hard. Really hard.

More often than I’d like to admit, there were incidents in my early life when a close friend sought to expand the social circle, not wanting to end our friendship, but simply wanting to add to the group. Anxiety and ego inevitably overwhelmed me, and I would foolishly take the request as a traitorous dagger (which it was not — at all — but just try telling me that back then!) Because I couldn’t fathom reaching out to gather more friendships, I was jealous of others’ ability to do so. I felt vulnerable and defensive. Lesser. So I would get angry and end the friendship. Stupid, right? Yep.

Come young adulthood, the first years of corporate life were challenging. Most of my coworkers were at least a decade my senior and in different life stages than recent-college-grad me. I made myself even more guarded with a “work” me and a “home” me, hoping to off-set my obvious youth with professionalism. Needless to say, that level of detachment paired with shyness was not conducive to numerous work friendships.

Then I got engaged. People I barely knew would approach me with wedding-related questions throughout a workday. My shyness was waning with the increased socializing. One wedding and a few years later, I was pregnant. My world changed.


Being pregnant granted me access to a secret club that was constantly seeking members: parents! That baby belly was like a beacon to any parent — young, old, first-time, or seasoned — and even grandparents to immediately strike up conversation. And once I was really showing, the world had a talking point in full view. As long as I kept a sense of humor and viewed awkward questions and others’ verbal diarrhea as fodder for my mental “shit people say” list, it was all good.

Then, I had my first child. I was set on giving her a variety of experiences, getting her socialized, getting her out. I took her to mom meet-ups and baby-and-me tumbling classes, story times and swim classes. We did something every day.

One day, as I entered a mom meet-up, I felt the anxiety and internal concerns over others’ perceptions bubble up within me. Then, I looked down at my chubtastic baby and thought: “but I have a built-in buddy!” And I was at ease. Being alone in a busy room without someone to talk to wasn’t so scary anymore because I had my daughter beside me. I was OK.

Not too long after, I had my middle son. I was so busy nursing my newborn while chasing my toddler, I didn’t have the time to worry what others thought. Instead, I sought out friends who resonated with me, who shared perspectives and viewpoints with me, who could relate to my present life stage. I still hesitated before reaching out, but I was getting better.

Two years later, I had my third child and by then I was comfortable with myself. I was so focused on my own standard daily chaos that I could hardly care less if you gave me the side-eye for having a tantruming toddler (that says more about you than me, afterall) or balked at my snot-smeared yoga pants and breastmilk-spotted nursing cami. I had way too much stuff to wrangle to worry about that. Even more, I realized most other people were like me and had too much going on in their own heads and lives to give me much thought! So why assume they’re judging me harshly when I may not even be on their radar or, if I am, maybe it’s positively so. If they are actually being mentally critical of me, why should I care anyway?

Less shy, I began conversing freely with fellow moms at playgrounds, classes, story times, and in the grocery store. After two incidents when I let my fear stand in the way of asking, “Want to do a playdate sometime?” (The mom version of “Wanna grab a drink?”) and subsequently suffered missed-friendship regret, I decided to do better.

I began listening to my gut, honoring my intuition. If I was drawn to connect, smile at, or chat up someone — even if I didn’t immediately understand why — I did it. And that is how I began making some of my dearest, strongest friendships: listening to my inner self, not my fears.

I was now on the other side of shyness. I could easily enter a room with confidence, seek out a person with whom I could relate, and start a conversation. I became the human shepherd, constantly aware of those on the periphery, gauging shyness verses disinterest. If I sensed shyness, I tried to bring them into the fold. If I felt a group with whom I was talking appeared unwelcoming or closed-off to others, I changed my positioning and body language to open the circle. I never wanted to make others feel the way I had so long felt: judged, alone.

I had not realized how far I’d come until recently at the playground. A mom I’d only met last year was floored to hear I was ever shy. I was floored she was floored! Little did she know, I spent more of my existence shy than not. I surely have changed. And for that I am grateful.

The world is a brighter, friendlier place when you’re on the other side of shyness. I like it here.


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