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My 10-Year Journey to Handstand

What a decade of kicking up—and falling down—taught me about my yoga practice (and myself).

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Expensive watches break when you fall on them.

My husband gave me a gorgeous timepiece for our fifth wedding anniversary. It had a silver band and the face was white with pink numbers. It made me feel much fancier than I actually am. He wanted me to wear it and think of him—which I did, 24/7, until my Handstand obsession (literally) crushed it.

I was in my favorite teacher’s yoga class. I didn’t like leaving my watch in the dressing room, so I placed it at the top right corner of my mat. When it came time to move into Handstand, I kicked up—and promptly crash landed on the watch, breaking the clasp. When I got home, I Googled the cost to repair. My Handstand fail would set me back hundreds of dollars. Embarrassed, I asked my husband to get it fixed for me (instead it sat in his dresser drawer for more than a decade).

That was 11 years ago, about a year into my Handstand journey—and just one of thousands of crashes and setbacks I experienced along the way. I’ve been doing yoga for 14 years, ever since my third (and last) baby was born, and I’ve been teaching yoga for nine years. But I’ve been obsessed with Handstands since I was a kid.

I have always thought Handstands were the epitome of cool. People who do them must be so strong and balanced and together, I believed. They look focused yet free—while upside-down! When I started practicing yoga, I remember watching the students around me float into Headstand, Crow, and Handstand. I couldn’t even touch my toes yet, but I promised myself that one day, that would be me—a yogi who could effortlessly float into challenging poses with ease. (Clearly, I had yet to grasp the yogic teaching of aparigraha, the last Yama, which means non-grasping or non-greed.)

So I set a goal: Do a Handstand within 6 months.

My long, winding, and sometimes painful path to Handstand

Because I wanted to be “good at yoga” (now I know there’s no such thing), I went to class nearly every day, rarely taking time off. My favorite sessions were hot power vinyasa practices that always included challenge poses. If I could do all of them, I thought, I would be happy. I would be accomplished. My yoga friends and teachers would respect me!

About three years into my yoga journey, I signed up for yoga teacher training at the same hot power yoga studio that had become my second home. A few of my fellow trainees were just a few years into their yoga practices as well, yet they were popping up into Handstands. I remember one close friend pressing up into Handstand for the first time when I was practicing next to her. She hopped up and down because she was so excited about her accomplishment. Sure, I was thrilled for her. But I was still kicking up and falling down. She was 17 years my junior, yet I was envious of her abilities.

As I continued to practice, I grew stronger. Within about three years, I could do Tripod Headstand, Crow, Eka Pada Koundinyasana II, and even Eight-Angle Pose. But Handstand still eluded me. I made it a priority to attend classes taught by a certain teacher because she was always Handstanding. She didn’t believe in using the wall when you kicked up. “If you use the wall, you’ll always use the wall,” she’d say. Honestly, it was terrifying. Another teacher, also an expert Handstander, was easier in his approach. But after his classes, my wrists hurt. I practiced the pose so obsessively that I developed shoulder injuries from repetitive use and poor form.

While I made small improvements over these years—I could kick up for a nanosecond, even as the hold eluded (and frustrated) me—I decided it was time to take my efforts up a notch. Inspired by a friend, I started my own Instagram challenge, #handstand365. For one year, I did a Handstand every day and posted it to my feed. I did Handstands in airports, in front of Target, at the beach, in Venice, Italy, and even in India in front of the Taj Mahal (yes, I am one of those American tourists).

My twin daughters were 13 at the time and took most of the photos. They were so used to my “Public Displays of Handstand,” they were no longer embarrassed by it. But they did tell me they were exhausted. Sometimes, it would take 20 tries before I stayed in Handstand long enough to capture a photo. In my feed, it looked like I was good at the pose. But it was an illusion. In truth, I was just kicking, not really holding. I was proud of my slow progress, but sheepish about my Handstand half-truths. At the time, I truly believed my silly self-talk: That once I achieved Handstand, my yoga practice would be fuller. So I continued.

A woman demonstrates Handstand in a dress and sneakers
The author in one of the countless Handstands she practiced over the course of her journey. (Photo: Natalie Chitwood)

And finally…

Toward the end of the year, I started to nail my Handstand. I could stay in my prized pose for a solid 3 to 5 seconds—plenty long enough for a decent snapshot. I could do Handstands at home. I could Handstand reliably in odd locations, even outdoors in front of people. While I was proud of my hard-won accomplishment—I liked when other people saw me holding Handstand (at first)—I expected to feel a big shift. I thought I would feel elated, excited, and even swan-like. But I was pretty meh about it. Once I could actually do the pose, it didn’t seem to matter much anymore.

In fact, absolutely nothing shifted or changed when I finally perfected my Handstand. My life was the same—I was still over-exercising, working too much, and pushing myself to the extreme. At this point, I was solely practicing hot power yoga, and if the class wasn’t hard enough, I left feeling disappointed.

My current relationship with Handstand: It’s complicated

I’m almost 48 years old now, and I can still Handstand—most of the time. But I no longer do it obsessively.

I realize now that the path I took to learn how to Handstand was too hard, too intense. All I focused on was the goal: the Handstand. I not only didn’t enjoy the journey leading up to it, I made myself miserable during it. I was always in a hurry, always in my head (my ego), and hardly ever in my body. My quest to Handstand sucked the joy out of my practice. If I couldn’t get into it, I would feel less than; like my practice wasn’t good enough—like I wasn’t good enough. It took years of practicing asana, studying yoga philosophy, and meditating to finally shift my perspective. I began to feel gratitude for my strong and healthy body and realized that any day I’m able to unroll my mat is a gift.

Today, I strive to strike a better balance of sthira (effort) and sukha (ease). I still teach hot power vinyasa, but I also lead slow flow, meditation, and restorative classes. I try not to work out like a fiend. I prefer far less demanding yoga classes and often practice at home. And I recently experienced an even bigger shift by starting a program to become a certified yoga therapist, in which we focus on taking care of ourselves and others. I love it.

As for my designer watch, my husband and I recently brought it back to the store for an estimate. We had to wait in line before entering the store and I had a slight urge to Handstand. (I didn’t.) Once we were admitted, they offered us sparkling water and posh snacks. After years of stressing about the high cost to fix it, we learned that the estimate wouldn’t be cheap, but it wouldn’t break the bank, either.

My Handstand experience, too, taught me that obsession comes at a price. I got injured, I was selfish around friends and family, and when I finally reached my goal, no one cared—except maybe me.

I’m still proud I can Handstand. (My ego is a work in progress.) And I learned some valuable lessons, too, such as how to be comfortable getting uncomfortable (i.e., upside down); how to fall and get back up; that if you want to do something, you just have to do it.

I enjoy other poses more now. I love Triangle, Half Moon Pose, Bound Angle Pose, and Fish. I think about how my body feels when I’m in them—open, strong, and free. While I still love challenging yoga classes, I also crave the gentle ones, too. I learned the hard way that being kind to yourself is more rewarding than standing on your hands. It took time and effort, but now I desire more ease—on and off my mat.

See also: Think You Can’t Handstand? This Sequence Will Prove Otherwise