Since Sunday’s newsletter was a mega-dose of Five Big Questions, I wanted to make today’s a bit more personal. So, I’m sharing the answers to some of your wonderful questions. (Thank you!)
I’ve been loving the synergy in this community lately, so if there’s anything you’d like to add on any of these topics—or anything else you’d like to ask—please feel free to leave it in the comments.
What do you love most about NYC? I’ve never visited so I’m always curious about this. I feel New Yorkers can’t really pinpoint specific things but rather describe a more intangible attachment. Would love to know your thoughts!
My first instinct is to offer that most clichéd line: “It’s the energy.” Words as true as they are intangible. But in an attempt at specificity, here is what I love, in no particular order:
It’s eminently walkable. It packs a punch. On any given day, you’re liable to witness every human emotion (and much of the time, to feel them, too). The forced intimacy of observing strangers in small spaces. The dizzying array of cuisine. Central Park in October. How every neighborhood is its own microcosm. The people watching. The fashion—from high to low and everything in between. The curious way you are always and never alone. Bagels.
There is a pervasive myth that the city is a place where dreams come true, and though reality may say otherwise, a vague sense of possibility lingers in the air. NYC isn’t an easy place—it’s crowded and dirty and competitive and loud and egregiously, unrelentingly expensive. The entire month of July smells like being trapped inside a trash bin. It’s not for everyone, but I like that, too. Rick Rubin said, “the best art divides the audience,” and that certainly rings true. New York is very good art.
I’d love to hear more about your relationship to writing, as both a creative outlet and a career, and how it’s shifted over the years.
I never set out to be a Writer because I didn’t think it was a viable career choice. But no matter what I did—and I did a lot of things—I found that I’d rather be writing.
As anyone who chased their passion can likely attest, it’s a big shift to ask a thing you love—a thing that has only ever served as an escape—to become the thing that supports you. It’s no longer a pure relationship; it takes on a certain amount of pressure. When it comes to writing, this can be a good thing, because I have to produce. Waiting indefinitely for inspiration to strike will not pay the bills. On the flip side, what I write “for work” is often different than what I create “for me”—less playful, and typically crafted with the audience or client or outcome in mind.
Like all things, my relationship to my creative writing is cyclical. There are seasons that feel inspired and energized and seasons that are decidedly…less so. I try to actively engage in practices that make it feel fun—separate from writing-as-work. Writing longhand is a big one for me.
A successful journalist once cautioned against pursuing writing as a career, likening it to “having homework for the rest of your life.” This line frequently haunts me. It’s not untrue. But I can’t imagine it any other way.

What are your favorite restaurants in NYC?
This is where I reveal how deeply uncool I am. I’ve been known to frequent the same places and only venture somewhere “happening” when I am a) expressly invited, or b) dining with out-of-town visitors. But I love my spots for a reason.
While NY boasts no shortage of incredible Italian restaurants (you can’t go wrong with Frankie’s, and I could not be more excited about just-opened Roscioli) I am partial to one in my immediate vicinity: Bevacco, in Brooklyn Heights. If you go, you must try the Parmesan Crème Brûlée.
For a rustic, romantic vibe, River Deli (not a deli!) is as charming as they come, and the brown butter sage ravioli is a delight. On the upscale end of the spectrum, Rezdôra always delivers.
I’m not vegan (see aforementioned crème brûlée), but I eat plant-based much of the time, and these are my beloved plant-forward standbys:
For a truly memorable dining experience: Dirt Candy (one of only two vegetarian restaurants in NYC with a Michelin star).
For an intimate dinner or romantic date: Avant Garden, which just re-opened in a spot that’s like dining at the White Rabbit’s sexy hidden loft.
For a fun time: Jajaja Mexicana. Do not skip the nachos.
For a casual meal: Peacefood in Union Square. I recommend the chickpea fries to start. I’m also a big fan of the carrot cake.
For takeout or a quick meal: Le Botaniste.
I’ve begrudgingly dragged many whiny, carnivorous friends to all of these places, and in every case, they were surprised and delighted by their meals. And often went back without me.

What’s a time when something didn’t live up to your expectations?
Oh so many things, but the first that comes to mind is a little experience called adulthood. Adulthood has not lived up to my expectations. I thought adults knew who they were. I thought they knew what they were doing. I thought they understood, for the most part, how stuff worked. Typing this, I have to laugh.
Even (long) after I became an adult, I kept expecting some door to open, some event to usher me into the real thing. I expected more certainty. I expected to feel more settled, more official, more “together.” But there are positives to this, too. I still get curious and carried away with random interests, topics, tangents. And I’m constantly discovering new facets of my identity, sometimes to my great surprise.
How did you become such an expert with tarot?
Firstly, thank you for calling me an expert! My past self (who nervously consulted a booklet during readings) would be thrilled to hear this. I could tell you that I’ve read books on the topic, took classes, and practiced pulling cards for myself and others—and all of that is true. But there is a simpler answer.
At its core, tarot is the story of universal human experience. We can make our studies as deep as we want—there’s no shortage of signs and symbolism and history to delve into. But right off the bat, every card corresponds to a feeling or experience—something we already understand. So, in a way, we’re all experts. When I realized this, everything clicked into place.
This last question wasn’t submitted as an AMA, but was left as a comment on a recent newsletter. I wanted to re-post it here, because I’ve seen this come up a lot recently—on Notes, social media, in conversations—and it’s something so many of us grapple with (me included). Sometimes, even if there are no magical solutions, it’s nice to know you’re not alone.
I stumbled upon your newsletter a few months ago when I promised myself that I would write here more frequently. I’ve struggled with being a writer, or even showing up for my craft and sometimes I think I spend too long just moping about my lack of success. How do you keep showing up for your work here, week after week? Don’t you feel demotivated and indifferent towards it sometimes?
This is an excellent question. I don't have a simple answer, but I'll do my best.
Yes, I feel unmotivated and apathetic about my writing at least fifty percent of the time. Some months I'm into it, others, not so much. If I get right down to it, though, these feelings are usually not about the writing itself. Often it's because I doubt my own worthiness, or because I see someone who seems to have an easier/better/more successful time and wonder what I’m doing wrong.
I've been dedicated to showing up here, week after week, because writing is now my job and therefore non-negotiable. I was also fortunate to have some readers from the beginning, which helped me feel accountable to the cadence I'd promised. But long before this newsletter, there were various blogs and other projects I launched and abandoned, for years (nearly 20, if we’re counting). The internet is littered with the detritus of my inconsistency. But I've gotten better with time.
With writing or any daunting-but-meaningful undertaking, I’ve found it’s helpful to have a why—some deeper reason to keep showing up, even when it’s hard. I took a peek at your newsletter and noticed you say one aim of your writing is to help people feel less alone. That's a wonderful why. And that's a big part of what keeps me motivated, too. Whenever I don't feel like showing up, I think of all the writers whose words made a difference to me over the years—in advice columns and interviews and personal essays and memoirs and novels. And I think that if something I share has the power to make just one person's week better, it'll be worth it. (Often, after I've actually written, it makes my week better, too.)
I hope this helps. I'm happy you're reading and even happier that you're writing. Keep going.
Thank you again for you wonderful questions, and as always, for reading. I’ll see you on Sunday. x
My best friend from high school and I took AP writing classes together at a small, Midwestern, all girls, catholic school. We would spend hours on the phone typing (on a typewriter!) reading paragraphs out loud, listening to each other, changing things. Over and over. It was pure happiness. 41 years later, she’s still my best friend, the person I send book recommendations to, little things I write and things I’ve read that I know she will love. When I am reading something really good, I sometimes rush to the end so I can share it as soon as possible. I almost always send you to her. I just did that again, first thing, after finishing this. We have lived across the country from each other almost all those years since high school. Thank you for being one of the things that keeps us connected. Truly. And also…I too am constantly comparing how my adult life has failed to measure up, in many different ways. But in between all my failures, I know I am a good friend. I have a feeling you are too. That’s worth a lot I think. I hope you never stop writing. Xoxox
Though I’m hardly one to comment, or even like a post, I want you to know Caroline, your words touch me. Thank you for showing up for making me stop and think, and making my day all the better for it ❤️