Square has a no-policy vacation policy. That’s an explicit policy that there is no policy for when or how you vacation. As long as the work gets done somehow and you don’t leave your colleagues stranded in the middle of unfamiliar code you can do what you need.
So this October I enrolled in a language school in Florence, Italy, I removed the Square email account from my phone, and I went to live abroad without a computer for a month.
I’ve long been a believer in the embarrassment model for explaining adult language acquisition: That the only reason kids learn languages faster is that they are more comfortable making mistakes then their taller counterparts. Kids are actually really stupid if you think about it. It’s no wonder they take 11 years to learn a language that an adult could learn in 3 or 4. If an adult has as much exposure as a kid and is willing to be as embarrassed and can use all their advanced grownup mental faculties then they can learn quickly.
This was my chance to prove it. I had a month away from work in which to get as good at Italian as I could. I was prepared to be embarrassed. I was eager for it, actually, knowing that it was the thing that would enable my education and help me show up any 5-year-olds who might also be learning Italian. What I was not prepared for was the sustained and complete nature of the embarrassment.
When I arrived in Florence I needed help finding the apartment where I would live with a family. The first store I saw was a leather goods shop with fancy designer bags on the walls and a friendly-looking middle aged signora behind a podium-like desk. I confidently walked up to her and asked something that was a mix of one Italian word (mispronounced), a word that I now realize I made up and only thought was Italian, and the word for “here” as I pointed to the paper on which an address was written. The best English translation of what I said would be “helrp graaaa here.” She drew me a little map of where to go but the look on her face told me a 5-year-old would have done better.
I was mortified but I left the store, headed off to my new home, and never saw her again. That first interaction played itself out dozens of times every day over the next couple weeks as I would go into a store, embarrass myself thoroughly, and continue on. I discovered a secret about pride while doing this that helped me immeasurably and I that I hope to hold on to forever: there’s a lower limit to how embarrassed you can be.
Embarrassment is like getting wet. It’s highly uncomfortable to get wet when you’re dry. Getting even wetter causes further discomfort but then you reach a point where you’re completely saturated. Once there someone could dump a bucket of water over your head or throw you in a lake and you’re not going to feel any more discomfort (from the feeling of the water, anyway). Once I had been humiliated a dozen or so times in a day I almost didn’t notice when the guy selling roasted nuts paused for a full second in between each word as he talked at me or when the guy at the bookstore looked like he wanted to pat me on the head like a puppy.
But the real benefit isn’t that I stopped feeling embarrassed, it’s that I was able to learn at full speed. There was no longer any fear of failure or sense of pride distracting my brain from the hard task of forming new neural paths. It was exhilarating and is something I’ve brought home with me to the U.S.. My company is filled with amazing engineers with skills that dwarf my own. If I attempt to look smart at Square I’ll never be able to learn as fast as if I accept my limitations, let people see my weaknesses and strengths clearly, and let them teach me as fast as my brain can go.