When Being Cautiously Optimistic Is Enough
I have a guest post up at hannahrowenfry.com, and I want to tell you a little about it and why it felt important to write.
The post is called "Me, My Invisible Popemobile, and Wild Goose Festival," and it's about the time I showed up alone to a festival with thousands of Christian strangers, carrying what I can only describe as my own invisible version of the bulletproof cart the Pope used to ride around in.
Here's a bit from the piece:
"Along with my fear and doubt and the invisible protective shield I'd begun forming around me like my own version of the bulletproof cart the Pope used to drive around in, I was also looking forward to being there. I like to travel. I like to learn new things. I like to have meaningful encounters. As I mentioned earlier, I even like Christians. So, I was cautiously optimistic. That's a great descriptor, but let's put 'cautiously' in all caps. I was CAUTIOUSLY optimistic."
I wrote that piece for Hannah's site, but I keep thinking about it in the context of what we're doing here at Flourish Anyway®.
And here’s something I’ve realized: being cautiously optimistic is flourishing anyway.
It doesn't mean your guard is fully down. It doesn't mean the past hurt didn't happen or that your wariness isn't warranted. It doesn't mean you've resolved all of your complicated feelings about the thing or the people in front of you.
It just means you showed up anyway. You said yes anyway. You walked into the tent carrying your invisible Popemobile and your very practiced poker face and you let something good happen to you anyway.
I left that festival with my cautiously a little smaller and my optimistic a little larger than when I'd arrived. I hadn't asked for that shift. I hadn't seen it coming. But that's often how flourishing anyway works. It’s usually not a grand transformation. It’s more of a gentle loosening of something stubborn inside you.
I'll be returning to Wild Goose Festival this year to lead a session inspired by my forthcoming book, Spiritual Direction for Writers: Everyday Rituals for Your Writing Life, and to co-lead another session with Hannah Rowen Fry on our forthcoming anthology, Take More Retreats: A Guidebook for Writers, Journalers, and Creative Souls.
I'll still probably bring my invisible Popemobile. But I'm cautiously OPTIMISTIC about what's ahead.
Read the full post at hannahrowenfry.com
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Thanks so much for being here. Thanks for thinking a bit about what it means for you to flourish anyway. Feel free to email me if you're up for sharing your thoughts.
And much love to the creative souls. May we flourish anyway today and all days.
💚Charlotte
Charlotte Donlon is a writer, spiritual director, and gatherer whose work centers on helping people explore themes of belonging, artful encoutners, spiritual growth, and how to Flourish Anyway®, even when life is full, busy, or chaotic. Her work has woven together themes of belonging, art, and soul exploration for more than 25 years. With a Master of Fine Arts in creative writing (2015-2018) and a certificate in spiritual direction (2018-2020), Charlotte guides writers and other creative souls in developing sanctuaries of acceptance and connection.
A Christian in the Episcopal church who believes the tenets of the Nicene Creed, Charlotte employs a universal framework of belonging and connection in her spiritual direction work. She fosters meaningful, soulful conversations and gatherings that are welcoming to all—regardless of faith tradition or spiritual inclinations.
In 2020, Broadleaf Books published Charlotte's first book, The Great Belonging: How Loneliness Leads Us to Each Other.Spiritual Direction for Writers: Everyday Rituals for Your Writing Life is slated for release by Here Below Books in September 2026. Three volumes of Charlotte's "Guidebooks for the Soul"—Take More Retreats, The Great Belonging Project, and Belonging Through Art—will also be published in 2026.
As the founder of several initiatives, Charlotte has established herself as a thought leader and an authentic presence at the intersection of creativity and spirituality. Her essays have been featured in publications such as The Washington Post, The Christian Century, Christianity Today, Catapult, and The Millions, among others. A new essay about art conservation, Joan Mitchell, and mystery is forthcoming with Image journal.
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Flourish Anyway® is Charlotte’s online hub for all of her writing, spiritual direction, small press, gatherings, and other offerings.