I spent the past few weeks in a hell at least partly of my own making, a horrible psychic space I return to annually.

No one likes tax season, but I seem to have raised dreading it to an art form, or potential new DSM diagnosis. Willful ignorance, fear, and shame drive me to repeat the same bad decisions, leaving me so paralyzed with anxiety that I can barely function when March rolls around. Then I sweat and dry-heave through the gathering and deciphering of forms for my accountant, vacillating wildly between urgency and avoidance.

Part of the problem is I’ve long been a freelancer with inconsistent work across a variety of fields (journalism, digital media, publishing, academia), resulting in an unpredictable income. It’s not uncommon for me to make $65K one year, $30K the next, $75K the year after that, then $22K, then, on rare occasions, as much as $90K or more. This makes preparing my return and estimating my quarterly taxes difficult not only for me, but for my CPA, too.

It also makes me feel ashamed for being all over the place, professionally and financially, even though it’s not entirely my fault; I work in precarious fields, and I’ve never enjoyed certain advantages. I suppose those are both reasons I might have chosen differently. Maybe in my early 30s I should have stayed in the boring but steady trade magazine lane, and never aspired to write consumer journalism, personal essays, and books—risky gambits with dodgy returns, better suited for people who are better set up.

Acquaintances who don’t work in my fields naturally ask, “What about a real job?” meaning regular W2 employment. But there are virtually no jobs to be had these days. For a variety of reasons—advanced age, limited access, location—I can’t compete for the few remaining ones. And even when I landed a steady, decent-paying gig for five years, that’s all it was—a gig, 1099 contract work.

In the past, my accountant has asked the real-job question, too. It makes me nostalgic for the days when I used a different accountant, one who specialized in freelance writers and artists, who was much less fazed by my income being all over the map. A few years ago Brian’s CPA urged us to file jointly, and employ only him. I went along with it and fired mine, even though this guy specializes in small businesses, like Brian’s old company (newly defunct, making this year’s taxes a little more complicated, oy). Somehow it made sense to me at the time, and I made the switch.

***

Regardless of who’s preparing my taxes, though, the biggest problem here is me. I have always been freaked out by money and the accounting of it. I have some (perhaps gendered?) idea that I don’t know how to tabulate it correctly, even though for a flaky creative weirdo, I’ve always been surprisingly good at math.

I worry that I don’t understand the (confusingly arbitrary!) rules of what you’re allowed to write off and what you’re not, and that I’m somehow incapable of learning them. Or, if I do learn them, what if I find out I’ve been doing this wrong all along? Then will I have to go back and correct all my past returns? What if I don’t write off enough, as my accountant keeps telling me? What if I write off too much? What if I write off the wrong things?

What if I get in trouble? (I’m not even sure what “in trouble” means. It’s just some childish concept that haunts me.)

Regardless of who’s preparing my taxes, though, the biggest problem here is me. I have always been freaked out by money and the accounting of it. I have some (perhaps gendered?) idea that I don’t know how to tabulate correctly, even though for a flaky creative weirdo, I’ve always been surprisingly good at math.

There are tools available to me, but I’m terrified of employing them. I possess but don’t use Quicken. For three years now I have paid the annual fee, and updated the software, but not once opened it. I have this notion that it’ll be really hard for me to figure out how to implement it—how to attach my accounts in a way that makes sense, and how to make sure all my transactions get recorded properly. Of course, that would require me to tell it how to record my transactions properly, which would first necessitate that I learn what to tell it. (I’m visibly shaking just thinking about this.)

Money matters and taxes feel like this big, inscrutable cloud of doom hanging over my head, which I’m afraid to look at closely enough to decipher. My fear makes me feel ashamed. That shame makes me feel additionally ashamed, and is mixed in with two other conflicting flavors of it: I’m ashamed of not having ever had much money; I’m even more ashamed on the occasions when I’ve earned decently. There’s this feeling that money is dirty and bad, and it will suck all the virtue right out of you.

***

Where did I get these crazy ideas? Like all of us, I’m sure I absorbed my parents’ financial attitudes and anxieties. Money was always very tight—my parents were school teachers—but their divorce made it all much worse.

I flash back often to the years after my parents split, when my mom worked three jobs yet still could barely afford to fix her broken-down Dodge Dart. The leader of her teacher’s union at the time, she expressed a deep disdain for the rich. When much better-off members of our synagogue rode by in shiny new Cadillacs, she’d narrow her eyes and hiss, Ostentatious! Or, Nouveau riche! I took on this point of view, and then it seems to have warped into a whole other insane perspective in my mind.

There’s also some weird shame-by-association that comes from being related (by marriage, but still) to Sidney Schwartz, one of the oldest felons to go to prison in this country. Sidney’s wife, Bebe, was the sister of my maternal Grandfather’s second wife, Frankie. Put more simply: Sidney and Bebe were my grandfather’s brother- and sister-in-law, and we saw a lot of them.

Sidney was running a Ponzi scheme, and I definitely am not! But something about witnessing the corruption and downfall of a guy in whose home I attended Passover seders—who had served as president of our temple—made me deeply suspicious of those who had money, and afraid to become one of them.

Oh, and then there’s having witnessed that grandfather’s financial ruin. He ran a successful Seventh Avenue women’s sportswear business for years, then died too deeply in debt to even cover the cost of his funeral. After growing up poor, he became very flashy with his money once he had some, buying Frankie a 7.5-carat diamond ring, driving fancy cars, eating at expensive restaurants.

With me he was intermittently generous and stingy. For example, he refused to make good on his offer to help me pay for college, but one semester sent me up to SUNY Albany—the state school I was putting myself through—in a chauffeured limousine. Imagine the looks on the faces of my suite mates, to whom I’d insisted I couldn’t afford to chip in for common-room decorations.

While we were sitting shiva for that grandfather, a woman named Sylvia Weiss slipped a note under the door for his grieving widow, Frankie. “I loved him, too,” Sylvia wrote, “and he owed me $2,000.” In the envelope she included a copy of the canceled check.

On my dad’s side, my grandmother died of a brain tumor in 1963, the story goes, because my grandfather insisted she wait a year before seeking treatment, after which time he’d qualify for better health insurance. After she passed away, when my parents were helping him move, they discovered my grandfather had over $100,000 in cash stuffed in his mattress. My father didn’t talk to him for five years after that discovery—the first five years of my life; I didn’t meet my paternal grandfather and his second wife until I was in Kindergarten. I remember being confused about who those people were.

Clearly I’ve internalized my family’s money drama and shame. I’m sure there are other contributing factors of which I’m not fully aware, but the bottom line is this: I’m ashamed about my financial picture no matter how it looks. And I’m afraid to approach money and doing my taxes like a normal adult.

I know, I know—I sound like a walking women’s-magazine-article cliche from the ‘90s. Back then, someone sent me to one of those free seminars for women that have in the title something about not wasting money on lattes. But that’s pretty much all I took away from it: No lattes. Which is fine, because I don’t even like lattes.

So, here I am, just aimlessly going about my latte-less freelance existence in a semi-constant state of panic and paralysis that worsens every tax season. I think I need some sort of financial therapist, or a support group. Debtors Anonymous is the only one I know of, and it doesn’t feel like the right place for me, because I’m not in debt, and as a rule, I don’t get myself into it. I don’t use credit cards at all. I never spend more than I have. My only debt is the (very affordable) mortgage on my house, which we were fortunate to get as a foreclosure.

An acquaintance who attends DA once diagnosed me with “pauperism,” a discomfort with earning and keeping money. He suggested I was unconsciously keeping myself poor—which maybe rings true?—and that was a reason I should attend meetings, too. But it still doesn’t seem like a fit to me.

***

I think about that “pauperism” diagnosis a lot. I sure am uncomfortable when I earn decently! Like I sort of am right now. I’m almost afraid to admit that I’m doing really well with Oldster Magazine and Memoir Land. It’s so jarring for me. I feel guilty about it, go figure.

(Ironically—given the state of journalism, digital media, and publishing—taking a “real job” now, if even there were any, would be riskier than continuing to put out my own publications for as long as that remains viable. I mean, look what happened to people who left stable jobs to go to Tudum, Netflix’s publication, and more recently The Messenger. Not to mention so many other outlets that have left writers and editors high and dry after recruiting them, then canning them after a few months.)

Damnit, I’m supposed to be the virtuous underdog, not a success story. But here I am, somehow, with over 70,000 subscribers to my three newsletters. Only a fraction of those subscriptions are paid, but it’s enough for me to live on, while also paying contributors—to the tune of $20,000 to writers, guest editors, and illustrators in 2023. No one’s getting rich contributing to my publications, but I’m paying $50, $100, and $200 for various kinds of contributions, and that’s more than a lot of literary magazines are offering. I feel good about this.

People are enjoying what I’m doing with both publications. Both keep growing, and I’m really proud of what I’ve created. Recently one essay from Oldster and another from Memoir Land were nominated for Pushcart Prizes by members of the Pushcart editorial board. Last year an essay from Oldster received notable mention in The Best American Essays, edited by Vivian Gornick. I seem to be doing something right, and I only hope I get to keep doing it. (🤞🏼 🙏 ) But it’s also totally freaking me out.

***

I included some of this (feelings and all) in a two-page narrative I sent to my accountant last week. I do this every year. One time when I was in his office, he picked up the Word document I’d printed out for him, and handed it to an assistant, adding, “She writes me these stories.” They both laughed.

But writing out the story of my annual income is so much more intuitive (and calming) for me than accounting for it in…an accounting program…which fucking terrifies me.

Each year after my tax return is prepared and sent in, I promise myself I’ll finally conquer my fear, act like a grownup, and learn to use Quicken. And then I don’t.

Maybe this is the year I finally do. Maybe it’s also the year I look for a new accountant, one who understands (neurotic) freelancers.

In other news…

• If you’re in the mid-Hudson Valley, this Sunday at 11am I’ll be moderating a panel at the Woodstock Bookfest called “The New Old,” featuring

  Lyn Slater
  , author of How to Be Old,
  Melissa Giberson
  , author of Late Bloomer: Finding My Authentic Self at Midlife, and
  Abigail Thomas
  , author most recently of Still Life at 80.

  

  Get Tickets