I tried to win a writing retreat in Italy
and became a writer instead
My sister and I were walking around the block, catching up on life and talking about our kids. Feeling silly, I throw this out in the air: "So...I'm trying to win a writing retreat in Tuscany, Italy."
"Italy??" She's looking at me like I'm crazy.
"I joined a writing challenge, where I have to write at least 100 words a day. I have to check-in every day through a link in an email, and at the end of the year there's a drawing. The grand prize is a week-long writing retreat in Italy."
"Would you actually go?"
"Yeah! I've looked at the dates, and the baby would be a year old so ...it could work." I shrug, like a trip overseas would be no big deal for a mom of seven small children.
When I tell her that only a couple hundred people are doing the challenge, she becomes even more concerned.
"Cat, what if you win??"
"I'd go! I'd have to buy a plane ticket and maybe Sterling would come with. We'd have to find someone to be with the kids of course." I try to say this like it's totally normal, like I do this kind of thing all the time. I tell her that the point of it is getting into the daily habit of writing, because getting started everyday can be the hardest part. The conversation drifts elsewhere and we finish our walk, circling back to the house. There are babies to get back to inside.
The months go by and I continue to participate in the writing challenge. Writing at my kitchen table night after night, sometimes writing until my head finds the notebook, like I'm in high school again, falling asleep on my school work. It's not always fun, and many days it feels a lot like a school assignment. Most of what I write are the ramblings of a tired mom, but some of it has been worth revisiting, mulling over and editing.
Earlier this year I was laying in a hospital bed, after giving birth to my seventh child. With my sleeping newborn on my chest, I started typing up the birth story. Honestly, I just wanted to sleep. But more than that, I wanted to win a trip to Italy! So I pulled out my phone and wrote, making sure afterwards to "check-in" to the writing challenge.
Sometimes on gray winter days I daydream and picture myself in a quiet villa at an Italian vineyard. But mostly, I think about what I'm going to write next. Also, I pray that I'll have the energy to write something slightly more thoughtful than tired ramblings.
On New Year’s they announced the winners. I had only missed 15 days all year, which still put me in the drawing because I was allowed to miss up to 45.
We were at a friend's house a couple hours away, one of those beautiful places that lacks reliable cell phone service. Because of this, I wasn't able to refresh my email every 10 minutes like I wanted to, waiting for the results. Finally, on the way home, I'm able to check.
I take a deep breath. I tell myself, Ok, you probably didn't win the 8-day writing retreat in Italy. There are other prizes...maybe you won a smaller prize?
I open up the email. I have to scroll past something inspirational first in the email newsletter. I finally get to the list of winners. I scan the page for my name.
I scan it again... more slowly this time.
I wait a few minutes before breaking the news to my husband.
"So... I didn't win anything."
He graciously shares in my disappointment. He's been my biggest supporter all year, often reminding me to "check-in" my writing when I might have forgotten.
"Really? Nothing?"
"Nothing. Not even the free writing prompts for a year! And 12 people won that!"
"Bummer."
"Yup. Well maybe next year!" I say, trying to lighten the mood.
We listen to the sounds of the road and the radio static. I look out into the dark. I'm a little disappointed but more than that...I'm feeling relieved.
I'm relieved because I hate flying, and the thought of having to wean a one-year-old to go to a writing retreat, Italy or not, sounds awful the more that I think about it.
Spring will come around and I won't be writing in some romantic vineyard in Italy. I'll likely be spending my evenings next to a bowl of fermenting sourdough at my kitchen table, fly-strips overhead and supper crumbs at my feet.
I'll likely be typing up some tired ramblings with a sleeping baby in my arms, writing at least 100 words a day— in Iowa.
Catherine Pfenning
Here’s a link to the writing challenge. It’s not too late to join for 2025! https://alanwatt.com/writing-resources/writing-challenge/
It sounds like it was a win to me!