The winter break of our discontent

11 days of trying not to question everything about your life

Well, here we are everyone. The long mid-winter break where everyone who can find a way to get out of this god forsaken winter hellscape, does. It’s a quest to remember what actual grass growing from the ground looks like and a reminder that faces are meant to be felt.

The rest of us? Those left behind?

We stay back and try very, very hard to not think too deeply on all the wrong turns our lives have taken. It’s Day 2 and I gotta say, it’s not working. But if there’s one thing this annual emotional low tide has brought me, one thing that has stood out to me as this break has loomed, one thing that definitely is doing nothing to cheer me up right now it’s this—how much of my family’s life has gone by as these winters have cycled through. How little runway I have left with all of us together. And the now somewhat dumb assumption I had that we would eventually figure it all out. That time would equal expertise and good fortune.

Some days I’ll feel startled by the fact I spent so much of my life trying not to get pregnant, then desperately trying to get and stay pregnant, and then surviving such up and down years with little kids that it felt like I would be shaping and molding my family forever. That everything I thought we should be doing, we would eventually just do. That every bad habit I had on the parenting front would eventually be broken. That every financial goal I wanted us to meet would just magically be met. Just give it time.

My kids are almost thirteen and fifteen so it’s not like their bags are on the doorstep as I type this but, jeez. I find myself looking back at all the things I thought we would just naturally build up to or even just the things I counted on continuing that are gone forever.

I’ve written often about the cottage we rented in Maine every summer, one cottage in a string of cottages I grew up staying in or camping next to. Starting when my own kids were 3 and 5 we rented our little cottage for three weeks every summer. I thought, naturally, one day we’d work up to a full month. I can barely wrap my head around the financial realities of those trips now—between the luxury of not working for three weeks or the money involved in renting a cottage for that long. We had it so good then, I think now. I remember feeling like I had everything figured out, that life would always be that way. That my income would only grow, that that cottage would be available to us forever, that more than anything we deserved it all.

It’s an incredibly privileged point of view. It’s privilege that even gives you the dumb faith to assume things just always work out somehow. And it’s human nature to assume you always have time, you will always have more time.

But we lost that cottage when the owner died and it was sold off, a heartbreak I will always feel. In just the span of four years, writing (largely unpaid or poorly paid) has completely taken over my life on top of the endless hustle for advertising freelance work—the one thing that actually keeps a roof over our heads. And of course, as luck would have it, the thing that actually keeps a roof over our heads has become wildly erratic instead of an evenly ascending staircase of income like it was initially.

But back to warm weather destinations.

I’ve only left Vermont in February for somewhere warm twice in fifteen years. The first time was a trip to Turks and Caicos with one of my best friends from college. Just the two of us so, ironically, it was also the most affordable trip I’ve taken in the last fifteen years. The airfare not much more than if I had decided to fly to Oregon instead. The ramshackle hotel didn’t allow kids (hello!) and sure the sliding doors only stayed “locked” by jamming a broom handle into the track but whatever, jerks! We paid too much for almost every drink and meal but ask me how much I cared about that while I sipped a blue alcoholic slushie, relaxed in the pool, and stared out at the infinite turquoise horizon.

The second was a family trip to Sanibel Island. Due to poor planning on my part it became a multi-leg trip. Driving 5 hours from Vermont to Rhode Island to ditch our kids with family overnight to then drive to Boston to see Sleater-Kinney. Then back to Rhode Island to collect our kids and fly out to Florida. Then do the same thing in reverse (minus Sleater-Kinney) on our return. The weather in Florida was … not warm. I am the Weather Angel of Death. We spent roughly a zillion dollars to go to Legoland then had to buy overpriced sweatshirts and sweatpants for our kids on top of it all because it was just that cold. I mean, it wasn’t Vermont cold, but come on Florida. Get your shit together.

We had one half of one day that was actually hot and sunny and we stripped off our layers, sunscreening each other on a dead run to the beach. I grabbed a beer from our fridge and sat in that sun and soaked it all in. It was enough.

But for me, so often, enough is never enough. I immediately started assuming we would do that trip every February vacation. 50 degrees or really, 35 degrees, still beats minus 20 any day of the week. This would be our February vacation spot, Maine would be our summer vacation spot. It was all figured out. It was all so perfect.

Except we couldn’t afford that Florida trip, that year or any year. Four years later, we still have a deposit down on that same place and have never been able to use it. I just thought we would get back there one day, and maybe we will, but the assumptions I made about our family were based on what other families did. Families with more money, regularly-flowing-into-their-accounts money, family money, people-who-plan-and-are-good-with-money money. Those assumptions were never based on our reality.

If you don’t live in Vermont (and even if you do), maybe this all sounds like so many tiny violins. If you don’t even go on one vacation a year, who the hell thinks they deserve two?! The truth is, we’re all continuously measuring ourselves against everyone around us, whether we like it or not. Looking back on my own childhood, I can’t name even one family in our entire school who ever went on a vacation outside of the United States. Now I can easily tick off the names of two dozen families who do this every year. But yes, still, the tiniest of all violins.

Sometimes I wonder what I am struggling with more—my inability to consistently provide my family with that sort of life and level of security, my jealousy over the parents who can, my combined sadness (my kids are growing up!) and anticipation over my impending freedom (my kids are growing up!) as time passes faster and faster, or my stubborn (selfish?) refusal to step off the treadmill and just appreciate what is right in front of me right now. Perhaps it’s a combination of just all of it.

This break is a long one. A long ass one. I will be spending it working, I will be spending it writing as I try to simultaneously push two books toward an early March deadline. I will be missing out on the quick 4-day trip my family is taking to Rhode Island—a trip I planned and now have to bail on. I will be spending it wondering how I ever thought it was going to be possible to live a life where I could do something meaningful and creatively fulfilling for me; be supportive, present, and focused on my kids; be financially responsible for everyone and everything; and somehow be able to occasionally relax in the middle of all of it.

Sometimes I wonder, what stories are we all telling ourselves about ourselves? What stories are we telling ourselves about other people? Who do we think has it all figured out and do they, really? Please tell me how to figure it all out.

McSweeney’s: “Animated Features Forthcoming From John Lasseter’s New Studio”
The Belladonna: “MasterClass: I Teach Pettiness”
• Satire & Humor Festival (NYC): I will be doing a workshop, a book panel, and taking part in the Evening of Humorous Readings! Check out all the amazing events and get tickets here.
• Philosophy Week (Burlington, VT): Check back here for updates on the talk Amanda Gustafson and I will be doing on 3/29 at Maglianero!

• META LULZ: “It’s Time For My Weekly Writing Newsletter and I Have Nearly Given Up” by Adrienne Teeley on Submittable
• AUTISM: “As a writer, I say go ahead and write what you want. As a parent, I find this terrifying, given the way neurotypical people project false motives and feelings onto the actions of others every day.” Read the full essay “The Trouble With Autism in Novels” by Marie Myung-Ok Lee in The New York Times
• MUSIC: I had the occasion to go back down the rabbit hole of this video after Emily Nussbaum of The New Yorker tweeted about this song a little bit ago. Made me cry when I first saw it, made me cry watching it again two years later. Worth your time and attention. “Black Boys on Mopeds” (Sinéad O’Connor cover) by Swale. And the story behind the video: “Birthday thoughts about the deaths of black men and women at the hands of police.”
• 😭😭😭: “When a Newton family welcomed a baby who is deaf, 20 neighbors learned sign language” from The Boston Globe and on CBS Sunday Morning 😭😭😭
CARTOON LYFE: Although this is an old interview (from 2017) with Emma Allen, it’s a great peek behind the scenes of The New Yorker and her role as Cartoon Editor. “New Yorker Cartoon Editor Emma Allen on How to Be Funny in the Age of Instagram, VR, and Donald Trump” from ArtNet
COMEDY: Staying with the behind the scenes vibe, this video of the whole cue card operation at Saturday Night Live. TURNS OUT THIS IS A STRESSFUL THING TO WATCH/THINK ABOUT.
• DESIGN: Holy hell, look at these things: “The Art of Book Covers (1820–1914)” from The Public Domain Review.
• NOSTALGIA: “Stinson Carter, who is working on a memoir about his time at the hotel, recalled watching the era of analog celebrity dying before his eyes, night after night: ‘You went from having a private hotel to a hotel that was assailed by paparazzi to a hotel where the celebrities themselves’—armed with phone cameras— ‘were their own paparazzi.’ The amiable twentysomething bartender from Louisiana had grown accustomed to having Joan Baez invite him in to chat about the 60s, or sitting with Radiohead’s Jonny Greenwood as he strummed a guitar, or talking about books and politics and life with Hunter S. Thompson or Swedish actor Stellan Skarsgård. ‘All of these experiences, they happened because these people knew that I didn’t have a device in my pocket that was spying on them.’” from “Secrets of the Chateau Marmont” in Vanity Fair.

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