“We have to dare to be ourselves, however frightening or strange that self may prove to be.”
~ May Sarton
Friday greetings,
Isabella Dellolio and I first met in 2019, during the short-lived era when I had a brick-and-mortar office. She came in looking for someone to help her write a monthly newsletter for her photography business. We began working together – and haven’t stopped!
In the years since, we’ve also gotten to know each other and become friends and creative colleagues. She has done personal branding photo shoots for my business (some of you may remember the “pink chair” series…) and a super fun couples shoot for M.J. and me a few years ago. I’ve remained behind the scenes of her newsletter; we meet once a month to work on it, and no matter what else is going on in our lives or the world, we always laugh a lot.
For a while now, we have dreamed of collaborating. How could we combine writing and photography is some fun, meaningful way? We’ve bandied around ideas, but however wonderful they might have been, nothing ever quite took shape… until now!
Others see us all the time, but how often do we really pause to see ourselves in a kind and generous light?
Once we landed on this question and began brainstorming, our vision for a one-day creative retreat at Woolman Hill, a Quaker retreat center situated on 110 acres of beautiful meadows and woods right here in Western Mass, came into being quickly and easily.
The best part? You’re invited!
Learn more below, and visit Isabella’s website for further details and a link to register. We hope you’ll join us!
Shabbat Shalom and love,
Jena
ONE YOU, THREE PORTRAITS:
A Creative Retreat with Jena Schwartz & Isabella Dellolio
Imagine spending a beautiful summer day in a peaceful spot with a group of kindred spirits, creating three distinct portraits of yourself – one in writing, one through art, and one through the camera lens.
WHAT WILL WE DO?
During this relaxing day-long retreat, you will have the opportunity to connect with your stories, hear others’ voices, eat delicious food, play with art materials, have an individual portrait session, and leave feeling truly heard and seen.
Drawing on Jena’s work as a writing coach and creative facilitator and Isabella’s passion for portrait photography, this special collaboration invites you to step out of your routines and into the wide open space of your creativity.
WHO SHOULD COME?
Whether you feel comfortable in your own skin and love who you are in the world, sometimes feel invisible and wonder where you fit in, or, like most of us, some combination of the two, we designed this retreat for you. All adults are welcome; no special writing or art experience is needed.
THE FLOW
- Coffee, tea, snacks, getting settled
- Welcome and introductions
- Grounding exercise, writing prompt & a delicious stretch of time with your journal
- Sharing and witnessing facilitated by Jena
- Catered lunch and rest-and-digest time
- Playtime with collage and other art materials
- Individual portrait sessions with Isabella
- Closing circle
Join us on August 21, 2025
10am-4pm
Woolman Hill Retreat Center
South Deerfield, MA
SIZE & PRICING
There is a minimum of 8 and a maximum of 12 participants
EARLY-BIRD $375 until June 30
Get a signed copy of Jena’s new book, Fierce Encouragement: 201 Writing Prompts for Staying Grounded in Fragile Times
After June 30 - $450
ABOUT JENA & ISABELLA
Through writing and photography, we have each found a way to build a life around our respective passions. What we share is a love of storytelling, connection, fun, and authenticity. Both in our 50s, we have found that the freer we get with our own quirkiness, the more we open ourselves to joy. At a time when the world is full of heartache, we believe that it is a powerful thing to make space for self-expression, creativity, and community. We are so excited to be offering this retreat, our first collaboration, and we can’t wait to meet you!


Thank you & a book giveaway!
I’ve always been a writer who shares.
This was true in my childhood, and through my teen years, too. Then, after finishing an MFA in my mid-20s, writing took a back burner to growing other things (like babies!). I even wondered if I had lost that thread for good. Turns out, all I had to do was pick it up again, which I did in January 2007 when I signed up for a writing workshop and started my first blog. I will never forget the first time I got a comment from a non-relative!
The world of writing online has changed a thousand times since then (as have I). Social media’s obsession with followers and numbers is corrosive, in my opinion, something I often discuss with clients and folks in my writing groups. One of the most profound things a writer can remember is that every single reader counts.
This makes me wonder if it isn’t a bit contradictory to celebrate this milestone. On the other, it means celebrating 1,000 individuals – including you!
So, in the spirit of “two things can be true at the same time,” I’m celebrating with a great big THANK YOU and a BOOK GIVEAWAY.
For a chance to win an inscribed of FIERCE ENCOURAGEMENT: 201 Writing Prompts for Staying Grounded in Fragile Times, leave a comment on this FB post. I’ll pick a winner at random on Sunday, June 1 at 5pm EST. 🎉