The Millennial Dream Dash
Listen to the clues of your life
This Weekend Edition of Ecstatic features Bailey Gillespie
“It is, I think, that we are all so alone in what lies deepest in our souls, so unable to find the words and perhaps the courage to speak with unlocked hearts, that we do not know at all that it is the same with others.”
— Sheldon Vanauken, A Severe Mercy.
I’M A VORACIOUS DREAMER, and I’ve come to realize that this means the object of my longings will never come to full fruition.
In my early 30s, most of my dreams still burned bright. They layered like pearls on a string, each one distinct yet bound together by a shared vision: the dream to write, move to Nashville, meet a good guy, develop a retreat center or some other community third space, and host people in a home of my own—one filled with music and conversation, good meals, an herb garden in the backyard, bookshelves everywhere, and friends gathered from all walks of life. I called it my “George Bailey lassos the moon” dream. Exhilarating, yet always just out of reach.
THIS IDEA OF WARMTH and home was a refuge against the deep unrest that permeated my body daily. Most months, my time and money went toward things like functional medicine and bodywork, capsules of things I couldn’t pronounce, therapy, lab tests, and memory foam pillows to support the vertebrae in my neck while I slept.
Along with chronic pain from a family car accident when I was 17 (and two since), I also had PMDD, which is a severe mood disorder caused by brain sensitivity to hormone fluctuations. It wreaked havoc on my emotional health, along with every close relationship, to the point where I only felt sane and secure maybe one or two weeks out of the month. I also had a host of undiagnosed symptoms including digestive pain, brain fog, food allergies, nausea, and fatigue. I overturned every stone in sight and didn’t know where else to go or what to do. I was desperate to be well.
After years of prayer and oil fingerprints pressed onto my forehead in the shape of a cross, my heart broke when I realized the healing must not be coming. Psalm 34:10 promises that “those who trust in the Lord will lack no good thing,” yet day after day, I circled back to the same question: Is God withholding good from me? Just as my favorite book heroines had left the places they knew, I suspected that I too would have to leave the comfort of home one day to confront my longings.
AS A MILLENNIAL, I belong to a generation well-acquainted with disillusionment. The Pew Research Center describes how most of us came of age and entered the workforce at the peak of an economic recession, uniquely shaping our conception of the future. I know many friends who feel a bit forgotten—like they blinked and missed the boat. “The long-term effects of this ‘slow start’ for Millennials will be a factor in American society for decades,” says Pew. Of course, we’re not the only ones to feel the ache of unmet longing. It is universal.
Today, our homes, degree programs, doctors’ offices, and counseling rooms are filled with people yearning for the delayed fulfillment of childhood dreams. Many are still unmarried in their 30s and 40s, do not own a home, have moved back in with family or other single adults, are approaching the age when having kids is unlikely, and are dealing with a mental or chronic health condition. This is a lot to carry, especially when disillusionment also runs deep within the Church—a place where we long for hope and rest but often find false promises. We live in an era hungry for something as big as a miracle or as simple as an understanding friend who will listen.
Unmet longings can feel more like withheld love when they persist for longer than we think we can bear. Although disillusionment is not a bad thing, it’s fed in unhelpful ways by a culture that values the pursuit of passion more than perseverance.
Dr. Alicia Britt Chole is a leadership mentor who believes disillusionment is necessary for healthy spiritual formation. It’s a well-traveled path by believers, not the evidence of failure or abandonment. In her book, The Night Is Normal (a fabulous read!), Chole says, “In disillusionment, God invites us to reframe questions as companions, to see that our senses neither create nor negate his presence and to experience the fellowship of Jesus’s suffering. In disillusionment, shiny (yet sometimes shallow) ideals are lost, as deeper (yet initially duller) reality is gained.” As painful as it can be, disillusionment offers us the gift of deepening our trust in God and walking by faith. “Answers do not carry us through the night,” she writes. “Love does.”
IN THE SPRING of 2019, a new friend hosted a songwriting retreat at his home in Nashville, Tennessee. Gluten-free brownies bubbled away in the oven while incense trailed up to the ceiling, giving the room a musky aroma mingled with chocolatey sweetness. Our group gathered on the living room floor. I was the only non-songwriter in the house but was excited to make friends with people who shared both my faith and creative wiring. By now, this dream had taken time to settle into me the way rain settles into the earth after a good storm. Four years in the making, the move from California to Tennessee was a huge step of trust. Beneath all the questions was a quiet, faith-filled knowing. I just had to go. And God would be with me.
Our host rolled up the sleeves of his button-down shirt and invited us to close our eyes while he read a blessing by the Irish poet, John O’Donohue. It was an apt invocation called “For a Friend on the Arrival of Illness”:
May you find in yourself a courageous hospitality
toward what is difficult, painful, and unknown.
May you learn to use this illness as a lantern
to illuminate the new qualities that will emerge in you.
May you find the wisdom to listen to your illness.
Ask it why it came. Why it chose your friendship.
Where it wants to take you.
What it wants you to know.
The words gripped me.
Despite my longing for a space to practice hospitality, it had never crossed my mind to show this same welcoming spirit to the unwanted parts of my life. The parts, like illness, that God in his divine mystery allowed to persist. Wasn’t this a sign of resignation? A white flag?
Sunlight warmed my skin as it glowed through the dual-paned window. I laid my journal aside, listening while the rest of the house came alive for the next few hours with the sounds of guitar strums and pencil scratches, confessional moments and laughter, along with the aroma of vegetable soup. In many ways, it was the “George Bailey lassos the moon” dream now sprung to life. But did I belong in it? So much lay outside my control, but the words to that blessing gave me something solid to hold onto. Maybe this alone was why I was here. God knew that on a Saturday in springtime, a writer from California would need to know that she was seen and not forgotten.
I LIVED IN Nashville for two and a half years. The first year was a string of delights, a season of fulfillment. The next one brought shattered hopes as I watched nearly every dream I carried out with me unravel like a ball of yarn. Perhaps craziest of all was a deadly tornado that hit the city in the middle of the night just before the lockdowns—a natural disaster that, devastating as it was, got buried almost overnight by national headlines.
By the spring of 2021, I sensed a need to return home and recommit to my physical health. I packed my belongings with that pesky question still rumbling around in my heart: Is God withholding good from me? Moving into my little brother’s childhood bedroom was humbling at my age, but there was peace in being near family again. Mom made up the guest bed and prayed with me nightly. We baked and watched Gilmore Girls. I found a full-time copywriting job that allowed me to work from home. Two months later, I was hospitalized after a thyroid episode and diagnosed with Graves’ disease.
ULTIMATELY, OUR DESIRES point to Christ. They stir in us a deep yearning for the wholeness of eternity—a wholeness we catch glimpses, tastes, and whispers of in this life. Come, they say. There is something true and beautiful that lies beyond. Paying attention to the desires that drive us, and being willing to name them, invites God into those tender places where he longs to meet us with his love.
By following my dream of moving to Nashville, I experienced God's goodness in ways I never would have if I had stayed home. He spoke to me through bluegrass, summer thunderstorms, the fragrance of honeysuckle, opportunities to sharpen my writing craft, grilled catfish, landscapes so beautiful they take your breath away, and long walks filled with conversations I will carry with me for the rest of my life.
Instead of constantly forever trying to make meaning from the chaos of life, we can rest in the unknowing. We can rest in the arms of Love. “Now we see things imperfectly, like puzzling reflections in a mirror, but then we will see everything with perfect clarity,” says 1 Corinthians 13:12 in the New Living Translation. “All that I know now is partial and incomplete, but then I will know everything completely, just as God now knows me completely.”
THE GOLDEN HOUR backlit our table with the glow of an orangey-pink California sunset. I clasped the hand of the man next to me. It was the evening of our wedding, and he wore a burnt orange suit that matched his personality. Pink Lady apples lay strewn across the tables, and a wine barrel supported a cake infused with honey, rosemary, buttercream, and fresh blackberries. I sighed with gratitude.
After moving back home, I met the man who became my husband. He was a young, blue-eyed veteran named Noah who had served four years as an Army medic before also returning home from out of state. Most surprising was our age gap. He was ten years younger, a detail I had to warm up to. But the man also had premature graying hair (thank God!) and patience in spades. While preparing for his honorable discharge, he got the call from home that his mom was dying of pneumonia, instigating an early return before she passed. We met shortly after, both navigating our unique griefs as we worked to rebuild our lives.
My illness did not go away once I was in a committed relationship, but Noah’s love became a resting place. Knowing that his name means rest in Hebrew is not lost on me. Instead of healing my body as I prayed, God brought a skilled endocrinologist who put me on high-dose thyroid medication and the Autoimmune Protocol (AIP) diet. This led to remission, yet I still have daily symptoms that vary from mild to debilitating. Instead of removing my PMDD, God brought a partner who honored that part of my story and who willingly chooses my particular set of problems every single day. I don’t fully know how to receive this kind of love yet, but I am learning.
“LISTEN TO YOUR LIFE,” wrote Frederick Buechner, an American writer and minister. “See it for the fathomless mystery it is.” This quote has been an anchoring thought and a healthy challenge amidst life’s highs and lows. Just because a dream ends doesn’t mean it fails. Maybe we’ll outgrow our early dreams. Or maybe, in their endings, they’ll become a bridge to what’s next. Similarly, just because our desire remains, it doesn’t mean God withholds good from us. I believe this now, though the ache remains. Instead, as pain points have become constellations illuminated against the night sky, I’ve learned to trace God’s faithful presence in the midst of my suffering from point to point, illuminating the cosmos of care that we live in as those who live and walk in his marvelous light.
Bailey Gillespie
Writer & Podcast Host
Bailey is a writer from Northern California. After a career in higher education and publishing, she now hosts a podcast called Listen to Your Life and cares deeply about helping millennials walk in hope and well-being. Besides writing, she enjoys road trips to the coast, good stories, farmers markets, and cooking. Bailey regularly contributes to other publications and has written on art, women’s health, and spiritual formation for IAPMD Global, She Reads Truth, The Rabbit Room, and Jessup University. You can follow her on Instagram @baileylgillespie and find her on Substack at baileygillespie.substack.com.
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I felt the goodness of God in everything I see, inside me and outside. The lines between me and the other softened just enough to glimpse our unity. And in our unity, there can only be peace.
So beautiful written. I can see and feel every word you write. It moved me deeply, and helped me adjust my own perspective on living with chronic illness. Looking forward to hearing more from you.