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Why I Left My Big Fancy Tech Job and Wrote a Book

Several years ago, I was sitting in the audience at a big tech conference, learning about a startup that made it easy for people to rent rooms in other people’s houses for short stays. In a world where people can now travel to any part of the world and share someone else’s home, could we hope, the CEO asked, for greater cross-cultural understanding? “Would nations have less war if the residents lived together?”

I closed my eyes, breathed deeply, and felt an immense sense of peace and hope for humanity wash over me.

Then I opened my eyes and thought, “Isn’t this basically a hotel in someone’s house — a cool, convenient, unregulated hotel?”

When it was my turn to take the stage, I too had a grandiose proclamation: Our startup, I declared, was helping people make meaningful connections in the real world.

What I really should have said was: We help people hook up.

On the plane ride home, I began to write what would eventually become The Big Disruption, a satirical novel based on my experience working at both a startup and one of the biggest tech companies in the world. I had no goal at the time other than to provide a bit of cathartic escape from the tech industry, where, on the surface, things seemed really important and exciting.

We were doing big things!

Bringing the internet to the developing world!

Singing songs to orphans!

But also, on some level, it all felt a bit off.

So, where to begin?

Should I start with the early stage companies? Like the time I was at a startupand the founder I was working for — a guy who owned a hundred shirts in the same color and quoted Steve Jobs on a daily basis — asked me whether we should hand out dildos as company swag or consider converting our social media platform into an anonymous sex club. (We even whiteboarded it.)

Or maybe I could start with the money — all the absurd valuations with seemingly little basis in reality. Or the time a partner at a VC “jokingly” offered up my female friend, his employee, as an enticement for a founder to work with his firm.

You can’t really claim that you’re building for everyone in the world when your own workforce doesn’t remotely resemble the outside world.

Or maybe I should start with the tech workers. The employees at my most recent job — running PR at a huge tech company — were some of the smartest, most passionate people I’ve ever worked with. They worked through the night to help people in a natural disaster. They gave money and vacation time to help the sick family members of other employees. They ran marathons on the weekend to raise money for clean water in Africa.

They also spent the weekday complaining on company message boards about the brand of water stocked in the micro-kitchens.

Then there are the amazing products. The progressive politics. The mighty ethical stands against evil. These are the things that, in my twenties, pulled me to tech in the first place and made me think I was embarking on something truly different.

To be sure, Silicon Valley has built some great products that have truly changed our lives for the better. And I do think that in many, many ways, it has taken noble stands during difficult times and helped redefine what people expect from companies, well beyond just the tech industry. It has also led me to some of my best friends and greatest opportunities, for which I am very grateful. There is so much I really do love about this world.

But there is also what drove me to leave the big tech company last fall and take a break. The issues that I got tired of defending at parties. The endless use of “scale” as an excuse for being unable to solve problems in a human way. The faux earnestness, the self-righteousness. All those cheery product ads set to ukulele music.