The Power of Writing Prompts and Our Weekend Share Thread

A Q&A with Jena Schwartz and our weekly chance to share your writing

Jessica Smock

May 10, 2025

What did you write this week? Share your latest Post or Note in the comments.

Today I also want to bring you a Q&A with

Jena Schwartz

who writes on Substack at

Dispatches from Daily Life

. Jena is a writing coach, poet, author of four books, most recently Fierce Encouragement: 201 Writing Prompts for Staying Grounded in Fragile Times.

We are also some of her biggest fans, and so we are thrilled to collaborate with her on a prompt-based writing group, starting this Monday, May 12th.

The three-week group is called “Blossom” and uses a mini-collection of prompts from Fierce Encouragement. Learn more HERE.

We’ve hosted our own prompt-based groups and workshops over the years, and I was curious to ask Jena about her thoughts on what makes prompts — and these groups based on them — so special.

Tell us the story of your book of prompts, Fierce Encouragement.

Jena: "Little by little, then all of a sudden." This is a saying I love that describes how so many things have unfolded in my life and work – including this book. In late 2014, wrote 10 prompts for what would be my very first 2-week online writing group. Twelve people signed up, and it was absolutely magical.

The next month, I wrote 10 more prompts and offered a new 2-week group, then another, then another, then I was offering two groups a month because more and more people wanted to participate. This all happened in the context of a scary and lonely moment in my life, as I was newly remarried and my spouse had developed a frightening, rare chronic illness. I had a full-time job and two school-age kids.

Writing these prompts and facilitating the groups became a lifeline for me as much as they were creative offerings to a really beautiful, growing community of kindred spirits. That's all the "little by little" part. In other words, I did not know I was writing a book. I was living a life, trying to tend to my own spirit, and creating a livelihood. When Covid hit, I had an urge to take all of this creative material that was sitting unused and dormant on my desktop and make it somehow evergreen. That's when I assembled the manuscript. But it still took another few years before I published it. I had to wade through all kinds of self-doubt to reach that "all of a sudden" moment, which came in late 2024. Marking the 10-year anniversary of doing this work in the world felt really significant and meaningful.

Why do you love writing prompts?

Jena: The funny thing is that my first thought upon reading this question was, "I don't always love writing prompts!" Sometimes I've had people tell me they hated a prompt, and it drew writing out of them that they didn't know was lying in wait. So what I love about writing prompts is just that: I do not have to love them to engage with them.

They give me something to push off against, like the end of a pool when you're swimming laps (which I don't, but the metaphor works!). So often, starting is the hardest part.

A prompt can relieve some of the pressure around getting those first words on the page. There is literally no way to do a writing prompt "wrong" or get a writing prompt "right," so for people who want to write who get stuck or paralyzed by perfectionism or overthinking (ask me how I know), a prompt offers a hand and says, "Hey, here. I've got you."

Which is your favorite prompt from the "Blossom" mini-collection that we'll be using in our writing group?

Jena: Ah, that's a hard one since each prompt brings up specific moments and memories for me! From the "Blossom" chapter/collection, I feel a lot of tenderness for the "Gifts" prompt. At the time I wrote it, my parents still lived in their home of 40 years. Even though they have since moved to a retirement community, I still can't walk into their apartment without one of them giving me something. It could be a book or a pair of socks. Just yesterday, my mom tried to get me to choose something, anything, to bring home with me! So there is a real sweetness for me around that prompt. It's also an example of something so universal – gifts – that becomes extraordinarily personal with each individual response to the prompt. I like things like this, that start out sounding rather unremarkable but open the door to so many stories.

What does your writing practice look like?

Jena: I get asked this question a lot!

I have found that people often imagine that I am very disciplined or that I write every day. Neither of those things is true. My writing practice is often intuitive, sometimes erratic, and pops up anywhere and everywhere.

Honestly, it can feel a bit helter-skelter. It kind of has a life of its own, like a bird I'm always in relationship with that comes and goes freely through the windows of my mind and heart. Sometimes I find myself writing when I'm walking or running, and I've used voice notes to record myself, then come home to transcribe that raw material to flesh out and then shape. Sometimes I'll start writing a Facebook post and realize after a few sentences that it's something more, and I'll take it offline to work on. Sometimes I'll unconsciously be gathering things up – thoughts, reactions to things, stories or songs or images – over the course of several days, and then I'll sit down to see if I can somehow weave them all together. In terms of accountability, I have always been a participant-facilitator, meaning I practice alongside the people in my groups. And my newsletter also offers me a weekly structure; I always publish something on Substack on Friday mornings, even though many weeks I don't know what I will write in advance.

One thing I would add is that I do not believe there is a "right way" to have a writing practice. There have always been stretches in my life when I was barely writing, or not writing at all. I used to worry during those times that it was over. I would feel convinced that I might never write another word. But so far that has never happened.

What are you working on now?

Jena: Just this month, I completed a two-year training and became a Certified Facilitator of the Jewish Studio Process (www.jewishstudioproject.org). I also made a huge life decision not to go to rabbinical school, which is what I thought was next for me. I intend to continue leading groups and coaching individual clients, and I'm also sitting in a place of having opened up some space for the unknown that feels full of possibility. I'm curious and unhurried about what new ideas, offerings, and collaborations will emerge!