Learning To Cry Made Me A Better CEO
The day I realized leadership could look any way I wanted it to
I originally published this on the blog for a failed business I cofounded in 2012 with my now-husband, Jackson. It’s been feeling relevant all over again, though, so I decided to resurrect it here. Thoughts welcome!
I fell off my bike last week. Or rather, I fell on my bike, since I was still very much attached to it when I locked up my brakes and laid it down. As the waves of pain and embarrassment washed over me and I shook off a nice pedestrian’s concern, an odd thought popped into my head: “I hate always being the girl.”
“Where did that come from?” I wondered. I’ve been riding my bike in San Francisco for several years and used to commute down Market at rush hour. I’m confident about my city riding and certainly don’t think women are less proficient bikers. I do, however, ride a little slower and less aggressively than Jackson does. That’s not necessarily a guy/girl thing, but he was in front of me and stopped short for traffic when I fell.
Turning my reaction over in my mind, I realized that the feeling of trying to ride someone else’s path and then suffering the consequences felt remarkably similar to my experience of being a woman in a “man’s world.”
Being A Girl
When I was growing up, trying to figure out where I fit in the feminine/masculine spectrum, I often felt like I had only two choices:
- Be a girly girl — Do ballet and love ponies and talk about things like kissing and blusher.
- Be a tomboy — Wear overalls and hide your hair under a baseball hat. Get good at sports and learn to shit-talk. Don’t ever cry or draw attention to the fact that you’re a girl.
My mom is a smart, assured business woman; my dad is pretty much the biggest feminist I know. They both reminded me throughout childhood that I could do anything I wanted, and they taught me to ferret out the insidious, everyday sexism that most people my age believe was “fixed” by our parents’ generation. But despite all that, I frequently felt stuck somewhere between the girly girl and the tom boy.
To a casual observer, however, I clearly chose the latter. I waged water gun wars with the boys next door and watched while they set rats’ tails on fire. I rolled my eyes at romantic comedies and busted balls as the editor of my high school newspaper. I wore a lot of blazers and cut my hair short, subconsciously daring people to assume I was gay so I could catch them in their own stereotypes. Most of all, I taught myself to have a thick skin and to never let ’em see ya cry.
Then, about four years ago, I started seeing an awesome therapist and moved to San Francisco, where people actually feel their feelings (and say things like “feel your feelings” without a hint of irony). I came to understand that pretending to be tough and never asking for help was not only giving me panic attacks, it was alienating me from other people, when deep down all I wanted was to connect with them.
I kept my short hair and my blazers, but I also started to make a conscious effort to admit my vulnerabilities, including letting people see me cry. Around that same time, I saw an inspirational talk by Ana Marie Cox, the founder of Wonkette. She shared 10 tips for being a digital journalist, but one of them became a mantra for my life in general. She said: “It’s ok to have thin skin, you just have to heal quickly.”
With that in mind, let’s go back to that sidewalk, where I’m shakily holding up my bike and rubbing my wrist, and Jackson is looking at me, and I feel the tears welling up, and I know I can either snuffle a bit and laugh them off or I can… start sobbing until he wraps his arms around me, my bike between us, at which point I start truly bawling, soaking his shirt, hiccuping… you get the idea.
Five years ago I would have gone with the first option. “Don’t be such a girl,” I would have said to myself. But if there’s one thing I’ve finally figured out about “being a girl,” it’s that it works a lot better for me than trying to be a boy. I’ve spent too much of my life trying to have thick skin, when what I needed to learn was how to admit I was hurt, cry my eyes out for five minutes, and then get over it.
If I were a guy, that might not be the preferred way to deal with something like falling off my bike. I asked Jackson what he would have done in my place. He would not have been inclined to cry, he says, but he would have been embarrassed and angry. Realizing that riding off in a cloud of anger would be dangerous, he would have sat in silence until he felt calm again. (It is level-heading thinking like this, and his willingness to dissect and share it with me, that makes me love him).
I’m sure some guys would have cried. I’m sure some women would have ridden off without a second thought. My point is that his reaction would have been right for him, and mine was right for me — worrying about it making me “a girl” just gets in the way of me doing what I need to. For one thing, my body does not handle stress hormones well, so instead of letting them swim around in my bloodstream and make me sick, I’ve learned to exorcise them quickly and forcefully, often by crying (or screaming or jumping up and down like an angry toddler… seriously, I recommend you try all three some time).
Being A CEO
In my over-simplified version of the history of feminism, I see women having gone from trying to prove our value by “out-male-ing” the men, to working toward being recognized and respected for our particularly feminine traits. This is a shift I have lived out in my own life, one that I was viscerally reminded of when I fell, and one that I sense has growing importance as a woman co-founder.
When our company eventually incorporates, we’ve decided I’ll have the title of CEO. Needless to say, I’ve thought A LOT about what it would mean to be a CEO: as a woman, as a feminist, as an anxiety-prone people-pleaser, as a third-generation farmgirl, as an urban hippie…
I especially stressed myself out thinking about the roles I imagined I had to play as the CEO: the ultimate decider, the blustery visionary, the until-we-make-it faker. But then, through conversations with Jackson and other friends and mentors, I came to see that I was once again trying to define myself with someone else’s terms.
The great thing about being the CEO of a brand new company I helped create is that I can define the CEO role any way I want. If I want my role to be creating a safe space for our team to take bigger risks, listening to our users and speaking on their behalf, holding our team to our own high standards, and framing outside criticism in a healthy way — then that’s exactly what my role will be.
Starting a company, no matter the title, is already one of the hardest paths I could have chosen. Why make it even harder by trying to walk it in someone else’s shoes?
