Issue #7: Reflections after 60 days at Stripe + photos from my trip to Chicago
A newsletter to distract you from all the election stress (but don't forget to vote!)
Hey dumpling fam,
On a scale from 1 to 10, what’s your anxiety level right now? In addition to the national outcomes, I’m worried about local San Francisco elections. We’re voting on a new mayor, six new supervisors, four new school board commissioners and City College commissioners, 15 local ballot measures, and 10 state ballot measures. It feels like there’s so much at stake, especially for our children and the next generation of SF residents.
My childhood friend Linxiao was in town Saturday, and he and his wife have been feverishly organizing for the last two months in Pennsylvania where they live. To take his mind off the stress, we went to play old school arcade games at Free Gold Watch followed by hot bowls of pho on Haight Street. I was reminded that in moments like these, nothing is better than a bit of human connection–preferably involving good food–AND a bit of distraction.
So here’s hoping that my newsletter today provides both those things. As always, you can drop me a DM here or on Instagram. I love hearing from you!
Xo Cathay
TRIP REPORT FROM CHICAGO
A couple weeks ago, I was assigned to produce a series of videos about Stripe users that reflect the best of Chicago. I don’t think my manager knew when he gave me the assignment, how much it would mean to me. Northwestern University is my alma mater (I’m, ahem, between my 15- and 20-year reunion) and while I adored Evanston, I spent every minute I could in Chicago proper.
When I think of the city, my memories are full of visual and auditory texture: Riding the El at all hours of the day and night, the rumbling tracks drowning out my headphones even at max volume; dropping a dollar into the donation box at the Art Institute (back when it was free entry) and spending a sleepy afternoon watching art students sketch in the gallery with all the marble statues; standing until my feet hurt in the back of the crowd at the Green Mill, listening to a gypsy jazz combo; savoring a crispy bit of fried ravioli at Kingston Mines before jumping back on the dance floor; and joining the press of bodies trying to touch the stage at the Aragon Ballroom. In much the way that food dominates my memories of SF, art and music are core to my experiences in Chicago.
Once I landed and checked into my hotel, I walked across the street to the Bean. And I was struck by how everything looked the same. Not in a stodgy, traditional, stuck-in-the-past kind of way, but in a solid, stable, I’ll-always-be-there-for-you kind of way. And that’s probably the best single word I can use to describe Chicago, the reason why its institutions have such incredible legacies–Second City! Alinea! Frank Lloyd Wright!–because it’s a city with endurance. That was incredibly comforting to me during this otherwise volatile time.
Have you ever been to Chicago? What did you think? What was memorable for you?
60-DAY REFLECTIONS
I’ve been at Stripe now for about two months, and there’s a tradition at the company to write 60-day reflections, so I thought I’d share a few observations.
A lot of people have been asking me, “How does it feel going back to a 9-5 job? Has it been a big adjustment?” To which I cheekily respond, “As opposed to working 24 hours a day? It feels great!” The answer is meant to be funny… unless you’re a small business owner or an entrepreneur. In which case, I’m speaking the plain old truth 🙂
Stripe is exceeding my expectations. I think back to a year ago, when I was clawing my way out of severe depression, when there were days I was too crushed by the weight of my choices to even get out of bed, and now, I’m happy. It’s a huge relief.
Here are some good things:
I feel free. That probably sounds backwards, because entrepreneurship is supposed to be all about freedom. But when I started the business, I couldn’t have imagined how shackled I would become–worrying about Dumpling Club day and night, never able to completely disconnect. Being able to stop working at the end of the day seems like such a simple thing, but after 60 days, I still feel a little zing of pleasure every time I close my laptop for the night.
I like having a manager. Never thought I’d say those words, ha! In theory, nothing beats being your own boss and at Dumpling Club, I had total control (no co-founders or even investors!). That independence was short-lived though: Once I hired a team, I felt a deep sense of responsibility to not only listen to my employees and take into account their input, but also to make sure I was doing right by them. Caring for my team was the hardest thing I’ve ever done in my life (and I’m still not convinced I did it particularly well). So for now, I’m happy to have a manager. Yes, it means that someone gives me directions and I have to follow them; but it also means someone covers for me when I’m sick, gives me constructive feedback so I can improve, and looks after my wellbeing. It feels really good to have someone watching out for me, for a change.
Everything I learned at Dumpling Club is helping me now. For a while, I was really worried that I’d invested years of my life into Dumpling Club with nothing to show for it. I’d risked my family’s savings and the golden years of my tech career, only to close up shop?! But in my initial days at Stripe, I’ve been surprised at how often I’ve pulled from my experience running a small business–and I’m conscious that without that perspective, I’m not sure I would have even landed this job. It’s gratifying to think that maybe this was part of life’s grand plan for me.
Of course, there are some challenging things too:
Writing about another company’s mission, in another voice, is really hard. Most of my writing is in my own voice, writing about the things I care about: Entrepreneurship, parenting, food, art and music, my identity as an Asian American. Writing about Stripe in Stripe’s voice is daunting. For example, when I write about myself, I tend to start from a point of vulnerability, which helps me connect with my audience emotionally. But vulnerability isn’t a great look for most corporations, least of all a company that manages money for a loooot of people. So I have to find different ways of connecting with people in my writing and that’s proving to be a big adjustment.
I miss having a direct community outlet. There’s a lot of horrible things happening out in the world right now, and when Dumpling Club was open, I had this very direct way in which I could comfort people. People would come to me for all sorts of reasons–when they were homesick, when their pet died, when their family member was ill, when they lost their jobs, or when they just needed a moment to decompress. It was grounding to be able to help with such immediacy, and I feel a little unmoored now that I don’t have that outlet.
But there’s one thing we can all do to help each other… and that is to VOTE! If you live in San Francisco, you might feel like the national election is out of your control, but the local election is very much up to YOU. Please mail-in your ballots or get to your neighborhood poll on Tuesday.
I spent my Sunday morning getting out the vote for Jaime Huling and John Jersin who are running for school board and Heather McCarty who’s running for City College board. Contributing even the tiniest to their hard months of campaigning is helping me feel more in control of the outcomes for our school communities. Cheers to a better future for all our kids!
