Up in the Air

I'm Esalen-bound. But first, let's Write It Anyway!

Y’all caught me in an unseasonably good mood this morning because in three days I’m off to Big Sur, California, to lead Writing for Shame Resilience: Turning Shame Into Your Superpower, a generative workshop based on my book Shame On You, We’ll be working with shame the way I know best—by naming it, understanding it, and transforming it into something like resilience, authenticity, even connection. The workshop, which runs March 30–April 3, was technically full, but I couldn’t help myself—I opened a couple more spots.

If California feels too far, I’ll be teaching a similar workshop at Omega in July. But for those impulse types, it’s not too late to book a last minute flight from NY to San Francisco. Ask me how I know!

I know because it took me until yesterday to realize that the nonrefundable ticket I bought back in February for this Saturday was taking me to Monterrey, Mexico—not Monterey, California—and so this morning I got to enjoy the deeply humbling experience of rebooking a new flight.

I am generally pretty forgiving of myself when I make mistakes, but a waste $700+ hits particularly hard right now, as my husband and I are scrambling to come up with an earnest money deposit and get pre-qualified for a mortgage on a new house. For the past three weeks, I’ve been talking about money with anyone and everyone who asks how I’m doing—which is to say, more honestly than most people are prepared for and I sometimes I walk away from those conversations with a raging vulnerability hangover, but I can’t help myself.

In a culture that treats success as proof of virtue, money becomes moralized: too much and you’re suspect, too little and you’re to blame. Freelancers in particular often project stability, momentum, success—because the alternative is to admit how contingent it all is, how much depends on luck, timing, and invisible support. We also think that being successful relies on looking successful, even when your income is uneven or precarious. We end up measuring ourselves against other people’s projections, not their actual conditions, never mind those conditions are wildly different.

The result is a quiet, collective distortion: everyone curating and comparing, no one telling the truth.

So here’s the part I’m not supposed to say out loud. Early in our marriage, my husband had a stable career making six figures, with benefits and health insurance. His income gave me the freedom to build a life as a freelance writer and writing coach, while a generous gift from his father helped us buy our first home.

Then, almost at the same time I sold a book, he was let go from his job, and our roles reversed overnight. He picked up consulting projects when they came along, but for the most part, we lived on my income. About a year ago, we relocated to Nyack to be closer to my son’s private school, and instead of selling our family home, we turned it into an Airbnb.

We made just enough to cover our bills and keep things moving. But living in temporary housing took a toll, and when the town began cracking down on short-term rentals, we made the difficult decision to sell.

That’s my beautiful home! (But not for much longer)

A month later, we are swimming in offers. But even with that equity, the best we can afford in our current community is at the bottom of the market, and our sublet is up June 1. We’re searching for the cheapest house in a competitive town, on a tight timeline, and there have been moments these past months where I’ve felt completely groundless.

Financial insecurity chips away at the image I have of myself and my husband: educated adults who know how to pay bills, file taxes, make responsible choices. When the math stops mathing, I’m thrust back into childhood—years of food scarcity and housing instability, living in my grandmother’s basement, dreaming of a real home that never quite materialized.

I want to tell you that we figured it out—and maybe thanks to some combination of privilege, creativity, and luck, we have—but the solution I landed on is still up in the air. And in a couple of days, I will be too: away from my desk, with limited WiFi, suspended in that uncomfortable in-between where nothing is fully resolved.

Going through something like this reminds me that everyone is going through something. We’re all walking around carrying our own private uncertainties, trying to hold it together in public. For a lot of people, that “something” is money.

Which means that even when someone looks successful—living in a beautiful home, teaching at prestigious institutions, moving through the world seemingly with ease—you’re still only seeing a sliver of the truth. The rest of it stays hidden unless they’re willing to tell you.

This is part of why I keep coming back to writing as a way through—one of the only places I know where you can tell the truth without having it all figured out first.

Tonight, we Write It Anyway!, 6-8pm EST. Write It Anyway is my free generative writing workshop, held the last Wednesday of every month. Only two people showed up for the January workshop, so I’m kind of nervous no one will come tonight. I know I probably should promote it better, but—well, I just told you all the shit on my plate. And of course, we all have a list of shit that keeps us from our creative life—hence the reason this monthly workshop exists. Let me know if you want in and I’ll send you the link.