About My Novel, Where I'm Moving, and How I Get Stuff Done
honest answers to your personal questions.
My birthday is this week.
I considered writing a “40 things I’ve learned in 40 years” post, but I did that last year and frankly don’t think I could top it. So instead, I thought it might be fun to answer some of your questions.
But first, a disclaimer — I love reading AMAs because they indulge my nosiness and allow for a sense of connection, and I’ve done my best to provide that. While everything that follows is my honest experience, it is by no means advice.
How do you keep going? I often start something, doubt it, pause, question, and realize nothing is being made. How do you consistently create material without overthinking it?
Oh, do I know this feeling. I am historically terrible with follow-through, yet amazing at perpetuating self-doubt. My resume and my desktop, not to mention multiple corners of the internet, are littered with the detritus of abandoned projects, partially executed proposals, half-written novels, unfinished screenplays, and business ideas that never saw the light of day.
But I’ve found there are a few things that urge me onward. We’ll start with two that are not particularly positive. The first is pressure (peer, financial, societal, and otherwise). Pressure is a strong motivator, though not always the healthiest. I don’t want to let people down. I don’t want to let myself down. In many cases, if I don’t produce, I don’t get paid. So, I power through.
The second is dopamine. (Like I said, honesty, not advice.) After the quiet incubation stage of a project, unleashing it can feel terrifying, exhilarating, satisfying... and then I want to do it again.
Another helpful factor is accountability. Whether it’s a class or group where you share material, a virtual meetup, a challenge like 1000 Words, a friend who checks in on you, a sticker chart where you track your progress… Everything feels more manageable if you aren’t doing it (entirely) on your own.
Yet, for any undertaking, the biggest motivator I’ve found is connecting to that deeper why. (And reminding myself of it, as often as necessary.) Why do you want to make the thing in the first place? Out of love? Escape? To fulfill a dream? To honor a promise? To help or connect with others?
If I’m having a hard time showing up, I’ll remember the times someone else’s work — a blog or book or essay — made a difference in my life. And I’ll think that if what I make can help just one person feel seen or entertained or understood or inspired or less alone, it will be worth it.
For what it’s worth, that one’s a lot more motivating than pressure or dopamine, and I do recommend it.
To your final question, about consistently creating material without overthinking it, well, I create material and I overthink it. By this point, I’ve accepted that overthinking is part of my process, which I suspect may be the case for a lot of people. Overthinking can be a sign of discernment, thoughtfulness, and care. Sometimes, I’ll trick myself by saying, “We’ll just try it.” That quiets my overthinking mind enough to take some action. Eventually, momentum carries me just far enough to glimpse the other side.
I’d love to hear whatever you’re willing to share about your novel: how it came to be a goal of yours to write one, whether the plot and characters have developed easily or not, how you think about balancing nonfiction and fiction writing, etc.!
Thank you for asking this question!
Writing a novel has been a goal since I first stacked multiple sheets of paper, folded them in half, stapled them together, and tried to sell them to my parents. In my early twenties, I wrote a novel that I deemed too green to see the light of day. It promptly went into a drawer, never to be seen again.
In the ensuing years, I worked around books in various capacities, at a literary agency, as an acquiring editor, and eventually as a ghostwriter. I wrote a series of novels for children, which I am very proud of, and to date, have cowritten 13 books.
But I still haven’t written The Novel.
By this point, it feels less like a goal and more like a necessity — something I need to just do already so I can live with myself.
I started a draft a few years back and got pretty far along but grew disillusioned with the plot. In a nutshell, there was an Elon Musk-esque character who convinced the world of its imminent demise by gaining control of the media… and when actual Elon bought actual Twitter, this became way less interesting to me.
Now I’ve landed on an entirely different direction. It’s about timelines — how we expect them to unfold vs. how they actually do — and friendship, two topics near and dear to my heart.
In terms of writing fiction, I love character development and world building. I LOVE writing dialogue. I do not relish plotting. (I find it’s much easier to see and develop structure and pacing on someone else’s book, where you have some distance from it.)
And I am terrible with balancing writing fiction with rolling newsletter deadlines and other freelance work. (I’ll be sharing more about this, and what I’ve learned about prioritizing the things we love, in the coming weeks.)
Have you encountered people in your personal life signing up for your newsletter that you'd rather not read it?
In a word, yes.
I appreciate every person who reads this newsletter — the subscribers on all tiers, the commenters and the lurkers, those who open every issue and those who read only when the mood strikes. This newsletter is part creative practice, part service (especially the weekly reading), and my wish is for it to find its way to anyone who may benefit from it, in any way.
In terms of my writing, I have nothing to hide. Anecdotes involving others are typically anonymized or posted with their permission. I strive to make this a place where all feel welcome, including anyone in my life who might see it. Some friends read it, some friends don’t, and that’s okay with me.
My mom was not a fan of this publication. She didn’t subscribe but she did read (and comment on) it, and that — all of that — bothered me. It was always in the back of my mind, and I held back and censored myself for a long time.
In the same vein, there are a few subscribers from various parts of my life where I get the sense they read to keep tabs on what I’m up to vs. to enjoy or support it. They never like, comment or otherwise engage, yet when I see them, they seem to have read everything (and have a disparaging remark at the ready). The rational part of me wants to dismiss this with a wave and an eye roll. But some deeper part of me — the same part that spent most of my life seeking acknowledgment, support, or validation of my work — doesn’t appreciate it.
That being said, none of them are paid subscribers (whom I treasure!), who receive the more personal, vulnerable posts. So in a sense, I’m always comfortable with whoever’s reading.
How did you have the courage to train for a full marathon? I'm working on my 4th half and am intimidated by a full.
First off, thank you for suggesting I had courage. I might describe my motivation as closer to delusion, but sometimes these play out the same way.
Though I’d long dabbled in running, I never considered a marathon until two years ago, during a particularly challenging shitty time in my life. My mom was sick, my dog’s health started to falter, my career was mid-pivot. I felt sad and powerless, desperate for a place to funnel my intensity.
A marathon seemed long and arduous and out-of-my-reach enough to provide ample escape. I was also attracted to the metaphor of people going the distance, each with their own goals, fears, and motivations.
I took it one step at a time. While a training plan rarely goes off without a hitch (due to injuries or weather or life), I relish the gradual build they offer. There are few things more satisfying than plugging my training into a spreadsheet (perhaps the only time I love a spreadsheet) and ticking off each box when a workout is complete.
While I didn’t set off with the courage to actually go through with it, I hoped I’d find it along the way. I also hoped that by attempting something I hadn’t tried before, I’d discover parts of myself I hadn’t yet met. (I did.)
I would be remiss not to say, it’s okay that you’re intimidated by a full marathon; it’s intimidating by design. I’d imagine anyone gearing up to run the Boston Marathon tomorrow would say the same thing, regardless of how many times they’ve done it before. If it’s something you want, know that you can take it step by step — both in terms of the training and the actual race.
Any time we’re staring down a formidable challenge — whether we chose it or not — it asks: Who might we be on the other side? There’s only one way to find out.
You’ve written recently about becoming disillusioned with NYC life. What would you look for in a new home if you were to leave? Are there plans you have that are incompatible with city living, or are you just craving change?
This answer is deeply unsexy, in that the decision isn’t due to any craving, but rather the realities of NYC’s high cost of living. Everything is at a premium, square footage is at a minimum, rents are at an all-time high, and after twenty-two (!) years of making it work, I am feeling the squeeze.
That being said, if and when I do leave, I’d love to take full advantage of the not-NYC things another place has to offer, be it more space, access to nature, a different climate, and/or lower cost of living.
I am an urban creature and still very much under this city’s spell, so the next move isn’t clear. We’ve considered various towns outside the city. We’ve considered other cities. There are a couple frontrunners and no concrete plans at the moment, though I’ll certainly keep you posted!
(I received a couple questions about what it’s like to live here, a topic I love so much I wrote about it in our first AMA. I’ve also shared more about the good and not-so-good parts of NYC living.)
Can you share any recommendations for clothes, books, home goods, personal care products, anything you’ve been loving lately?
Yes! I’m working on a future issue dedicated to this very topic.
Thank you so much to everyone who submitted these wonderful questions. (I wish I had space to answer more, but I’ve saved some for the next round.) And thanks to you, for reading!
If you’ve been thinking about upgrading (and you’d like to make my birthday that much sweeter) now is a great time! 💛 Thank you for reading, and for your support.
Card of the Week
Here is this week’s card for the collective, as well as some thoughts to carry into the days ahead. As most modern readers will tell you, the tarot is not about fortunetelling, nor is it about neat, definitive answers. The cards are simply one path to reflection, a way of better knowing ourselves and others through universal themes. If this reading resonates with you, great! And if not, no worries. Take whatever may be helpful and leave the rest.
With the sword of truth in one hand and the scales of justice in the other, Justice cuts a striking figure. Powerful. Imposing. Dignified. Certain.
Traditionally, the image on this card pays homage to the goddess Justitia, the figure often glimpsed outside courthouses. Justitia wears a blindfold, to signify that the law does not discriminate. In tarot, Justice speaks to our ability to see Truth, and thus is depicted without it.
Despite all this — the name, the scales, the robe, the columns — this card does not automatically relate to some legal matter. Nor does it dwell in the realm of fairness, rectitude, or righteousness. At its core, Justice aims to uncover the truth. Not in a “burden of proof” sense, but by asking, “What resonates in my core?”
As we learn from the time we are children, fairness is a myth. “That’s not fair!” we might cry, when something doesn’t go in our favor, or when a peer gets away with something we can’t. “That’s not fair!” we think, throughout our days, confronted with vast differences in fate and luck and privilege. There are infinite ways to view the world, endless mysteries to uncover. Many of them are wondrous. None of them are fair.
This week’s card urges us to let go of fairness once and for all, and instead focus on honesty.
What matters to us? Where can we take responsibility? Responsibility, in this case, is not something moral. It simply means embracing that whatever you do (or don’t do) contributes to your story, adds to your character, deepens your experience of life.
The scales speak to the balance between the past and the future — what we cannot change, and what we cannot (yet) see. This card reminds us that we create our selves, with every thought and action. We are not beholden to the past. By examining it, understanding it, and accepting it, we set ourselves free.
Justice sits between two columns — solid, sturdy, immovable — dwelling in the space between extremes. We often picture outcomes in terms of best or worse-case scenarios. We see decisions as either/or. We label situations as good or bad. But reality often happens in shades of grey.
We may be concerned with making the “right” choices. Not from a moral angle (though this is certainly worth considering), but from a place that assumes a “correct” path exists. If only it were so simple.
If we observe scales, we will notice that they are never perfectly still — even when empty or balanced. There is always a bit of sway, a sense of movement.
As in life.
In the days ahead, this card urges us to be flexible. To seek grey areas, to embrace knowledge and information, challenge and change. The more we live, the more we learn, the closer we come to understanding.
There is no such thing as right nor wrong. There is only Truth.
Happy birthday Caroline!!! 🪅💕 I hope you have the most wonderful week. As always, baby Caroline melts me into oblivion. The little baby book! The kewpie doll! 😍 I loved this AMA. For anyone on the fence on becoming a paid subscriber, JUST DO IT ALREADY! I started reading Caroline's newsletter months ago and I've had such a wonderful time experiencing the world through Caroline's words.
Happy Birthday, Caroline! Regarding leaving NYC: I’m a native New Yorker who left NYC after living there for 40 years (1976-2016) and moved to Chicago and love it. I still love New York City, it’s my home, but despite its many problems, Chicago has offered space and affordability on the rental front and Lake Michigan is always near and I love the people here. Like you, I’m a city mouse, so this move offered city life and outside of it other places to explore nearby. Plus, my brother owns a restaurant here, so there’s always food! Don’t know if Chicago is on your radar, but I have found it a happy transition — I’m at a later and different stage of life from you, but I’ve found friends here of many different generations who love it. Wishing you all good things in the year ahead! Ps - I love the Tarot pull! ✨