For years, I struggled with social anxiety. I’d go to the gym, the park, even coffee shops, but I never actually talked to anyone. I always told myself: They don’t want to be bothered, It’ll be awkward, I’ll try next time. And of course, next time never came.
Two months ago, a friend suggested we try a personal challenge together — with small punishments if we failed. The rule was simple: each day we had to start at least one conversation with someone new. The punishment? Sending an embarrassing voice message to our group chat.
On the first day, I was terrified. At the gym, I noticed the guy next to me doing deadlifts, and I forced myself to say: Hey, your form looks solid, how long have you been lifting? To my surprise, he smiled, answered, and we had a short, normal conversation. It wasn’t perfect, but it was real — and I didn’t die of embarrassment. That night, logging my success felt incredible.
By day 10, something changed. I wasn’t debating in my head for 30 minutes whether I should talk to someone — I just did it. Sometimes it was small (complimenting a barista), sometimes bigger (asking someone in the park about their dog). The accountability kept me consistent, and seeing my friend’s progress made me want to keep up.
We started with just a shared google doc to track wins, but later we found an app where you can actually join challenges together and track your and others tasks, progress. Now we’re doing a “21 Days of Conversations” challenge inside the app, and it’s been one of the most motivating experiences I’ve had.
In two months, I went from avoiding eye contact to making small talk almost daily. I even reconnected with an old acquaintance because I wasn’t afraid to start a chat. It feels like for the first time, improving my social skills isn’t this huge, scary thing — it’s just part of my routine.