EverBound: How do we stay human among careless people?
Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism
Dear Readers,
One of the realities I learned to accept in my 30s —I am someone’s villain. It used to eat at me that someone could be telling my story.
But we’re all unreliable narrators—at least to a degree. We each tell our stories, in hopes of being seen as the protagonist, hero, victim. I love it as a literary device in fiction, but in personal storytelling, I don’t know who’s the villain or the victim; who's telling the truth and who's not. In reality, it’s completely gray.
Yet, society needs a narrative, and Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism by Sarah Wynn-Williams gives us one.
Confession: I slogged through this book. It’s an insider exposé of Facebook with a larger critique of culture and Silicon Valley power. Within every anecdote, there’s a failure of morality by so many people who either did something bad or stayed silent when it mattered, including her.
She kicks her opus off with a quote from The Great Gatsby by F. Scott Fitzgerald:
They were careless people, Tom and Daisy – they smashed up things and creatures and then retreated back into their money or their vast carelessness or whatever it was that kept them together, and let other people clean up the mess they had made.
An interesting part of The Great Gatsby is its unreliable narrator, Nick Carraway. The characters share a collective carelessness, which he places himself on the outside of as a kind of witness. The book is his testimony. He makes judgments without interrogating his own complicity or moral ambiguity. Wynn-Williams is so similar in this regard that I hope the tie-in to The Great Gatsby is a clever wink at us, not just a way to slap careless people into the fold.
Wynn-Williams is one of the careless people. Yet, she doesn’t grapple with her culpability. She points out the recklessness of many, including Facebook executives, but her own recklessness is left to the reader to discern. She travels solo with no plans to Myanmar while pregnant, all in the name of Facebook’s mission to connect the world. It made me mad at Facebook and her. Still, it was one of the few times I understood her—and what I perceive as a compulsion to do a good job in the proximity of power.
I don’t know her motives for writing this book—atonement, shedding guilt, placing blame, money grab. The book doesn’t have much new information; it just confirms the unscrupulousness at Facebook. She rightly takes jabs at Mark Zuckerberg and Sheryl Sandberg. However, her critiques of the latter feel recycled—it’s no secret “lean in” is a sham. It’s clearly a dehumanizing culture.
The stories do their part to villainize. She’s supporting high net worth individuals with shrinking empathy bubbles because there are so few people they relate to or who speak truth to them. Wealth, money, status, and appearances are very much a part of this tale alongside a worthy critique of capitalism.
I want so badly for her to walk away. Even when she infuriates me, I feel tenderness and kinship to her. She keeps telling herself she’ll leave after whatever perceived hurdle is next. Depressingly so, she’s fired after reporting an executive for harassment. It’s awful; I get why she doesn’t want to be lumped in with this crowd.
By portraying herself as an observer, she excludes herself from the systemic moral failures and structural carelessness. Even the phrase careless people is an outward judgment. But I wanted inward reflection from her. Accountability can’t exist without reflection. So does she not see herself as accountable or responsible for any of the negative impacts of Facebook? Or did she just not reveal them to us?
My bigger question is—If you’re part of a system that causes harm even if you’re not in charge, what accountability do you have to others?
It can’t be indifference. Unlike Tom and Daisy, we have to leave it better than we found it, not as a mess for others to clean up.
And my biggest question is—How do we stay human among careless people?
This part is personal for me. I quit an executive role because after years of almost, I concluded it would never meet my bar for an ethical organization. However, while I begged, pleaded, waited for it to get better—I was a leader in a harmful system. That’s something I’m still understanding and untangling. I outstayed my soul because I thought it would be worth the money or experience. It wasn’t. I thought I could change it from the inside. I couldn’t.
I’m still in the painstaking process of interrogating my decision-making and sense of self during my time with that employer. I inventory my intentions, judgments, and what I want to do differently next time. It’s a lot of introspection, and gosh, I would have loved to hear from someone who was also complicit in a careless company.
My main takeaway is—leave a company once it’s clear the mission isn’t real. It takes courage and defiance of what’s expected of you to quit. But you get to keep your soul. That I know.
In the end, Wynn-Williams is at times a villain, victim, both, none. Our culture eschews this moral grayness. We like a clear villain. We like someone to root for or hate, for judgment to be easy. But unexamined, it’s dehumanizing. If we’re going to build something better—at work, in our politics, in ourselves—we’ll need to get comfortable with and reflect upon our moral grayness.
XoXo,
Courtney
Hi, I’m Courtney. I’ve spent over a decade in tech companies as a Head of People and startup fixer, working directly with founders. My founders have been featured in Fast Company, Fortune, Inc., People, and more. I’m currently cooking up something new.
✍️This was originally published on Medium.