(More) Talking to Strangers

Hi friends,As I write these words—not necessarily the ones further down, but these ones right now—I’m in an airplane over Lake Michigan on the clearest day I’ve experienced in almost five years of taking this flight. I can actually see the western shoreline, and it’s beautiful but also very distracting for someone who’s trying to work on a Tinyletter.It’s appropriate, though, because I was already planning to talk about an aspect of frequent work travel that I’ve come to cherish. And that is: conversations with the folks who make their living driving other people around.I’m perfectly content with silent cab/Lyft rides, and sometimes (albeit infrequently) I’m not in the mood to talk. But in a society where so much of our communication happen through text—especially when we’re engaging with actual strangers via the terrifying magic of the internet—it’s very comforting to me that two people who don’t know each other can have a pleasant chat during the time it takes to get from point A to B.Some of these conversations are more memorable than others, of course, but a lot of them stick in my head even years after the fact. I will always treasure the memory of the time I rode with an aspiring dancer to whom I recommended This American Life’s Live at BAM show—particularly the segment written and choreographed by “this guy Lin-Manuel Miranda,” who he’d never heard of. LMM got his MacArthur Grant maybe a week later (after which, well, you know) but for a fleeting moment I was the herald of a cultural phenomenon, even if it was to someone I’d never see again.On a grimmer note, I also think a lot about the older African American man who talked about his shock at visiting the Jim Crow South as a kid, his frustration at having to drink from a segregated water fountain. He went on to tell me about feeling hurt and betrayed when his Boy Scout troop went swimming at a ritzy country club in the north suburbs of Chicago, but he had to stay behind because it was whites-only. “The troop leader explained to me that it was just the policy,” he said, “and I understood that—but I still don’t understand why they were all okay going without me. Until then I thought they were my friends. It’s not like they had to go swimming.”I’m well aware that there are countless people in this country with stories like these, but as he was talking I realized that I’d never heard about those experiences firsthand before—not one-on-one, in a casual chat and not a Lesson on the Civil Rights Movement. There aren’t a lot of opportunities for a thirtysomething white lady to have an impromptu heart-to-heart about institutionalized racism with a sixtysomething black guy she just met—or vice/versa—but the random serendipity of a ridesharing app made it happen, and I’ll never forget it. (He also told me about the white guy he plays tennis with, who’d send him racist Obama memes “just to be funny” until he finally told him to knock it off. Because it never ends.)I have a million more little anecdotes and interactions stashed away in my brain, mostly not so momentous but all meaningful records of a point of connection between two people—temporary but nevertheless real. And I learn about myself during these car rides too. There are stories I find myself returning to—touchstones for how to quickly explain myself to a stranger—or that weirdly always seem to suggest themselves in the course of vastly different conversations.I dread the day that human-driven cars fade into obsolescence. You can have a friendly exchange with a cashier or a flight attendant or whatever, but if it extends beyond a few minutes you’re probably messing up their workflow. A longish car ride is enough time to get to know someone a little bit—someone who’s not part of your school/job/hometown social circle. You can learn from and entertain each other. And then when you part ways, you carry a piece of them with you for as long as their memory lasts.…and that, folks, is how I started getting misty-eyed about CAB RIDES of all things as my plane began its descent into Syracuse. I guess if I were indifferent to the experiences of other humans, I wouldn’t’ve taken it upon myself to become an advice columnist.Speaking of which, here’s the part where I link to the latest Dear Businesslady. I’m especially proud of this one: it’s a letter from someone who’s wondering if they can trade a potential raise for a more humane schedule, and after mentally screaming yes you can, do it and be free I wrote up some tips for putting that idea into practice.They’re making me put away my laptop soon so I should wrap this up. (It’s funny to be narrating this flight in real time, because I’ve written quite a few of these missives during airplane trip—as you may have noted from a certain persistent theme in my photos...) 

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…And now it’s nearly two weeks later. Since writing all of the above, I: got on another plane that took off late due to a massive snowstorm, missed a connecting flight and randomly spent the night in Dulles, VA, flew to San Francisco to visit some old friends and bask in the unbelievably balmy weather, saw a PHENOMENAL Run the Jewels/Lorde concert in Oakland, and came home jetlagged but happy. My good mood has diminished somewhat since—a friend’s in the hospital, another one is getting harassed online, and my beloved local craft beer bar is closing unexpectedly because of some personal conflict with the landlord—but it’s officially spring and life is full of wonders and all we can do is just enjoy the good experiences when they happen.As always, don’t forget to write in if you’re in need of work/career advice, and thanks for reading! This li’l newsletter is about to have its first birthday (the first real installment is from March 31st, 2017) and by the time I send out the next one, my book will have been in stores for a full year. Hard to believe it’s been that long since I first held Is This Working? in my delighted hands. ~court, AKA Businesslady PHOTO TIME!My musings about the beauty of Lake Michigan basically obligated me to include a picture. Here’s the view I was looking at when I started this letter, plus a bonus shot of the frozen landscape that greeted me when I stowed my computer for landing.