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365 days of overcoming social anxiety

by Kim Kaletsky

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I’ve struggled with social anxiety off and on since middle school. It’s interfered with many of my relationships, and it’s stopped me from performing an endless list of seemingly simple social tasks like calling the dentist and asking store employees for help.

The most common advice I’ve received is that I should “just say hi” to more strangers and “just push myself a little bit”—both nice sentiments, but the more professors, friends, and bosses insisted getting over my anxiety was merely a matter of pushing myself a little harder, the stronger my anxiety felt. Growing into early adulthood, I became more and more bogged down by everyone’s expectation that I essentially go to bed, wrap myself in a meditative cocoon of blankets, and emerge the next morning a triumphant social butterfly free of all anxiety. It was an expectation that I’d internalized, and it’d paralyzed any growth or change.

I tried “do one scary thing a day” strategies several times during college, but often gave up after failing to do some hugely terrifying thing like talking to someone in line at Starbucks on Day 2. The repeated failures forced me to accept that the “just say hi” strategy wasn’t working. I needed to re-strategize. So I gave up trying to become a social butterfly overnight and became a mental mountain climber instead.

That’s when I decided to start a year-long journey modeled after 365-day photo challenges I’d seen on social media. I called it my 365-Day Overcoming Social Anxiety Challenge. The objective: I’d perform at least one anxiety-provoking task, no matter how small or large, every single day for the next year.

Free of self-imposed expectations to be perfect, I began seeing anxiety-provoking opportunities everywhere.

I started small, texting friends who usually texted me first and asking interns at work how they were doing. I repeated the same process every day until I was often doing it automatically: see an opportunity to act, give the voice of anxiety in my head a minute at the mic, then grab the mic, challenge its opinion, and get done what I planned to get done. I interspersed large tasks with small tasks, careful not to overextend myself by doing something too difficult every day, and supplemented the work with meditation and journaling. By the end of the first two months, I’d already moved up to more difficult tasks, like raising concerns with bosses and attending large events by myself.

It took three months before I missed my first day. I’d had a rough afternoon—I’d been too anxious to join a staff lunch at work and was disappointed in myself for not even taking a cup of coffee into the conference room and joining for five minutes. The moment left me with a lingering lack of confidence. I attended the first of a six-week writing workshop that night and failed to do what I’d planned to do all day: speak up unprompted at least once during the workshop.

I did the only logical thing I could do when I got home—I cried, lamenting my failure. I was convinced three months of hard work had been for nothing.

But I didn’t let the misstep stop me. The next day I pushed my way through a series of anxiety-provoking phone calls at work, making the missed day’s lesson clear: one slip wasn’t necessarily the end of the entire mountain climb.

So I let the day go. I decided there was room in the 365-day challenge for “pass” days. If I got sick or had a rough day, I wanted to make sure I had space to be imperfect, to rest after a mistake, not push myself to work harder.

Free of self-imposed expectations to be perfect, I began seeing anxiety-provoking opportunities everywhere. When I started grad school and found myself at a “mix and mingle” reception for incoming students, for example, I immediately located someone not talking to anyone and started a conversation. As an undergrad, I’d spent an entire orientation week trying to do the same thing without any success, yet here I was approaching a stranger within the first ten minutes. Sure, the conversation was a bit forced—there’s always room for improvement—but I’d done it. It felt huge, like eight months of hard work paying off.

Much of the challenge’s effectiveness, I think, stems from its reliance on what I’ve learned in counseling and therapy about cognitive behavioral therapy and exposure therapy, both of which have proven to be extremely effective methods for overcoming social anxiety. But I’d also mixed that with other concepts like self-care and self-love, which I’d cultivated during guided meditations and talk therapy.

It’s that combination of self-discipline and self-forgiveness that’s made the effort successful so far. It’s helped me pull my anxious self-kicking and screaming through my largest social anxiety mountain climb yet. But it’s also helped me approach that climb with a willingness to let go of mistakes, so they don’t slow me down.

Recently, a journalist contacted me over Twitter inviting me to do a video interview. I instinctively wanted to pretend I was too busy to see the tweet and continue my quiet, interview-free business as usual. But I also saw opportunity in the message—an opportunity to challenge myself to do something terrifying. Two days later, I was at the publication’s office. And despite feeling so anxious the night before that it took me nearly three hours to fall asleep, I was nothing but calm during the interview. It felt like real, definitive proof: even three hundred days in, the challenge was working.

The author of this post is an editorial contributor to Headspace. These are their views, experiences and results and theirs alone. This contributor was paid for their writing.

Kim Kaletsky

Kim Kaletsky is an essayist and lit mag blogger whose work has appeared in the New York Times, Huffington Post, Susan Cain's Quiet Revolution blog, and more. Kim lives in New York and works at a non-profit by day.