Over the years, I’ve encountered my fair share of trolling, and what I’ve learned is that it’s an art. What the finest trolls know is that in order to really get under someone’s skin, the attack must fulfill two conditions: 1) some tiny part of the person believes the message is true; and 2) they’re ashamed of it.

Suppose you tell me you’d rather eat dirt than my cooking. That’s rude, but I’m not going to get defensive. This is because I’m not ashamed of my cooking: I know the insides of my pots are scorched from many a kitchen mishap. …

This was first published on my mailing list The Year of the Looking Glass. Sign up to get essays like these in your inbox 1–2 times a month.

I have a confession to make.

As a designer, for years my primary goal was striving to improve my product intuition.

You see, I believed:

• The most wonderful products are that way because of a leader’s keen insights borne of their intuition.
• People in suits and ties looking at sheets and sheets of numbers are missing the critical point — what it feels like. What’s the story that’s going around. …

After nearly 14 years at Facebook, the time has come for me to embark on a new adventure.

It’s hard to say goodbye to a place that has been so much a part of my life. The closest metaphor I have for it is “leaving home.” (In fact, I have spent more years at Facebook than I did living with my own parents before heading off for college!)

Facebook is the first and only place I’ve ever had a full-time job. It’s where I was introduced me to the profession of design, to the practice of management, to the exhilarating and chaotic swirl of Silicon Valley’s start-up culture. From the first day I walked into the scrappy offices of a college site created by recent college grads, Facebook has been an enormous part of my identity and and my community. I grew up here. Its values will always run through my bones and color the lens from which I see the world. Some of my best friends today are people I’ve hacked with. I am so, so grateful to Mark and to the brilliant, good-hearted people that I’ve had the privilege of working with and learning from. …

It’s been more than two months since the world as we know it was upended, and life has found a way to continue its relentless march forward. New routines have been discovered, but old habits have resurfaced. At home, it’s easy to let the days blend together into a blur of screens.

With summer approaching, I find myself thinking about the book Chasing Daylight, which has been lingering in my mind. Written by the late Eugene O’Kelly, a prominent finance CEO who found out he had terminal brain cancer and only three months to live, the book chronicles his final mission: to die well. …

“How do you achieve work-life balance?”

Whenever I do a fireside chat or a Q&A, this question will pop up like a predictable, well-crisped piece of toast. The question almost always comes from a woman. Most recently, a high school student asked it during a Q&A in Chicago. I suppose the stroller next to me that held my sleeping newborn was the equivalent of a neon sign blaring “ASK ME ABOUT MOTHERHOOD!”

But as often as I get this question about work-life balance, it still stumps me. Putting aside the fact that men almost never seem to get asked how they “do it all” (a topic for another day), I end up giving different answers every time, which probably makes me look extremely inconsistent. …

In the house that I grew up in, there was a formula for the American Dream.

My parents believed this so deeply that they left China with a one-way plane ticket and hundreds of dollars in folded bills, their mouths full of broken English.

Here is how the formula went: learn English. Get the top marks in your class. Stay at least a grade level or two ahead on math and science. Enter and win academic competitions (science fair, math tournaments, etc). Ace the SATs. Become the valedictorian of your high school. Attend an Ivy League school. Study medicine or law. …

Coffee Chat Series?

One of my favorite things to do as a design leader is to meet one-on-one with someone in my organization for what I call a “coffee chat.” It may or may not include coffee (sometimes, ice cream is involved; occasionally there is lunch; frequently, there are no beverages at all), but the concept is the same: let’s spend time informally getting to know each other. I want to know what you care about, how you got here, and where you want to go. And I want to support you however I can.

This Coffee Chat Series summarizes the most common topics, questions, and conclusions from the amazing conversations I’ve had over the years with designers at every stage in their careers. Hopefully, it’s a useful guide both for other designers out there and those who work with them. …

Have you ever struggled to make a certain conversation productive?

Maybe you’d like to give your coworker critical feedback that he definitely needs to hear, but you can’t bear to do it because you know he’ll immediately ball up like a porcupine and shoot quills at you while defending himself to the death.

Maybe it’s discussing your upcoming wedding plans with your mom because you can’t agree on whether your second cousin twice removed (and other family in that relationship sphere) should be invited, so the conversation always ends the same way, with you threatening to elope and your mom calling you the ungrateful black sheep of the family. …