What I Got Wrong about the Girlboss and Lean In Era

Everything I wished I could tell my younger self...

I was searching in my 20s to join some kind of religion, social movement, or cult. Listless and wandering, I craved a ground truth, world order, or playbook that would help me navigate life. My closest encounter with religion was when we briefly joined a Korean church in Ann Arbor, Michigan, after immigrating to the US. My parents’ church-going motivation was less religious and more pragmatic—join a vibrant community that would teach us English and help jumpstart a new life with the generosity and kindness of strangers. At home, instead of God, my parents indoctrinated me with the tenets of meritocracy, science, The American Dream, steeped in post-Cultural Revolution communist trauma.

In college, I spent years spelunking from one belief system to another, changing my major every few months. I dabbled in metaphysics and flirted with a philosophy major until I realized participating in a thousand-year-long ongoing dialogue would never give me the type of emotional closure I was seeking. Every year, I would sit down and reread my favorite Sarah Vowell Essay from Take the Cannoli, highlighting passages that spoke to my existential and lost soul. Honestly, I’m surprised I didn’t join Nexium during these ideologically philandering years.

“There comes a time halfway through any halfway decent liberal arts major's college career when she no longer has any idea what she believes. She flies violently through air polluted by conflicting ideas and theories, never stopping at one system of thought long enough to feel at home. All those books, all that talk, and, oh, the self-reflection. Am I an existentialist? A Taoist? A transcendentalist? A modernist, a postmodernist? A relativist-positivist-historicist-dadaist-deconstructionist? Was I Apollonian? Was I Dionysian (or just drunk)? Which was right and which was wrong, im pressionism or ex pressionism? And while we're at it, is there such a thing as right and wrong?”

– Sarah Vowell, Take the Cannoli

The truth is my parents had no clue how to navigate American life after immigrating to a foreign country in their thirties. Both my parents had survived the Cultural Revolution so they were skeptical of organized religion and authority except for Mao’s Little Red Book, which they were forced to recite by heart in school. At every big life infliction point in my childhood, I held my parents’ hands instead of looking to them for guidance. I was the one who educated them on the college admissions process, took them to seminars, and found a private college counselor. I guess you can call me a textbook case of a “parentified child”. Yearning for adult guidance and desperate to find a mentor who would take me under her wings, I found my answer in 2013 when Sheryl Sandberg published her book Lean In: Women, Work and the Will to Lead. Sheryl offered me a practical guidebook to work and life, filling the void where religion and clueless immigrant parents never could.

I remember sitting on a green bench in San Francisco’s South Park, reading Lean In while funemployed after leaving my first startup. I had unceremoniously left my first startup after they refused to promote me to a product manager despite doing the work of one for two years. (Perhaps it had to do with the fact I didn’t have a Stanford Computer Science degree or MBA like the other PMs but HR or leadership would never admit it.) South Park in the SOMA (South of Market) neighborhood of San Francisco was the epicenter of startups and venture capital firms in the 2010s. Instagram famously had their first office there. Earlier that week I had interviewed for a job in their old office, now taken over by a media startup called Prismatic. In the curated grassy patches of South Park’s lawn, you would find founders and VCs, vigorously making laps. The founders gesticulating and pitching while the VCs were deep in skeptical thought.

With the sun beating down on me, I diligently highlighted passages like “Take a seat on a rocketship,” “Your career is a jungle gym.” Sheryl’s words were my creed to act, assert myself, and strive to be an equal in a man’s world. By the time I got up from the bench, my leg had fallen asleep from devouring the doctrine of our patron saint, Sheryl Sandberg. Sheryl sounded a battle cry to all women to rise up, lean in, and push for equality. I was her devout disciple, believing that if I could follow her book’s advice by the letter of the law, then I too could have a fair shot at the American Dream.

My journey into Facebook coincided with the cascading rise of the Lean In movement. Lean In was published on March 11 in 2013. I joined Facebook on August 11th, 2014. When I called my dad, beaming with excitement about my Facebook offer, he reminded me with the reservation of an immigrant dad, “Don’t think you’re a success yet.” I entered Facebook with the humility, hunger, and ambition of someone grateful to be there. Never in my wildest dreams could I believe an institution like Facebook would let me in. Me, a liberal arts major, who went to a non-target school on a full-ride scholarship, who worked her way up from customer service into product…me…really?!

Bright-eyed, bushy-tailed, I entered Facebook’s Rotational Product Management Program summer of 2014 with the naiveté of a twenty-six-year-old woman, hungry to practice the principles of Lean In and learn from Sheryl in real life at Facebook Headquarters. I walked into my first day at Facebook with the earnestness that would probably make a privileged person cringe. At my old job, I had a crush on my blue blood coworker James who escaped his Upper West Side upbringing by moving out to California to spite his wealthy dad. He leaned in while drunk at a company Christmas party, whispering into my ear, “I know exactly what you’re about. You’re trying to transcend worlds.” Feeling his hot breath against my cheek, I pulled back, recoiling from his truth-telling. I couldn’t tell if he was impressed or disgusted, or both.

I followed Lean In with the religious zealousness my parents read Mao’s Little Red Book during the Cultural Revolution. Little did I know that the advice from Lean In would backfire on someone like me. Before I knew anything about intersectional feminism, Sandberg wrote her corporate guidebook with a particular audience in mind: white women. There were tell-tale signs that this book wasn’t written for someone like me in mind. I did wonder how one could land Larry Summers as their mentor early on their career without going to Harvard. Nevertheless, I wanted to believe it could work for me. I believed that if I could just internalize what Sheryl Sandberg preached and follow her advice with the precision of a technical handbook, then I, too, could ascend like her. I hoped to finally enter rooms not designed for someone like me, breathing in an increasingly rarified air excluded from my parents and ancestors.

But events in reality proved otherwise from the empowering rhetoric in Lean In. When I followed Sheryl’s advice and spoke up in meetings with male engineers, I was often met with skepticism and dismissed for being “non-technical” as a product manager with a liberal arts degree. On my first rotation, one engineering manager made up her mind about me after two weeks because I didn’t have a PhD in Computer Vision from MIT like her. She quickly took her liking with a male colleague who graduated from Dartmouth, giving him all the engineer resources, while I begged for more than one part-time engineer who only worked three days a week and was on pat leave Thursdays and Fridays.

As much as I wanted to believe that equality was within grasp if we just fought for it, I couldn’t shake an uneasy feeling. Amongst me and my close circle of women of color friends in Silicon Valley, we spoke behind closed doors and shared bizarre work situations that made us wonder if the Girlboss and Lean In movement was truly for someone like us. How can you follow a white feminist handbook if you’re someone who the system is not designed for? Where does your agency come from when you’re often deemed lesser and different by default?

When I compared my notes to the other women of color in tech, I realized I wasn’t alone in this uneasy feeling. We often found ourselves on the political chopping blocks whenever we spoke up in the workplace about unconscious bias, microaggressions, race, and gender issues. It finally dawned on me while chatting with my friend Doa about our shared corporate traumas that we both broke an implicit social norm as vocal Asian women in corporate America. Through our eerily similar stories, Doa helped me see that deviating from set social roles like obedient Asian women will unwittingly get you punished. This is not to victimize ourselves but rather call out the invisible power laws that insidiously affect minoritized individuals.

Over a decade later after Lean In was published, I serendipitously started finding old copies stooped in Brooklyn. In one week, I found five copies of Lean In on different stoops in my neighborhood. It’s almost felt like millennial women in our thirties woke up and collectively let go of the book during our spring cleanings. In retrospect, I realize how disingenuous and disenchanting being told if you just try hard enough by following the tenets of Lean In and Girlboss then everything will be fine. To presuppose an equal playing field and baseline is to be naive in oversimplifying deeply entrenched power systems.

As much as I wanted to subscribe to the Church of Sheryl Sandberg, The Wing, and Girlboss, I had to learn the hard way that white feminism—self help books, brands, spaces, and services—would never save someone like me. Like Sarah Vowell, I was so desperate to join a cult that I blindly followed the Lean In movement without first assessing if it was written for someone like me. I only slowly realized it when the girlboss era backfired on me, leaving me feeling angry, anxious-depressed, disillusioned, and burnt out.

If I could go back in time I would tell my younger self to be kinder, more compassionate, and cognizant of the invisible forces at play. I would tell her to be more strategic and observant of the power laws in an organization before brute forcing her way into a room or asking for a seat at the table—not all tables and rooms are equal. I would tell her there is nothing wrong with her earnestness, vulnerability, and authenticity. I wish her enough. I wish her an easier path than the one I have treaded.