May I Remember: A Journey Through Grief, Healing, and the Power of Retreat

The Fall, Then Falling Apart

Since May 19, 2023, my life has transformed. I was in the Florida Keys, ready to race my ninth Keys 100 ultramarathon, running from Key Largo to Key West, when I learned my dad had fallen and was taken away in an ambulance. I withdrew from the race—one of my dad’s favorites, where he’d worked at the 50-mile aid station for years—and drove four hours to be with him. For 31 days, I stayed by his side through hospital stays, rehab, ICU, and ultimately hospice, first willing him to heal and when it was clear that wouldn’t happen, making him comfortable as he prepared for his next adventure.

Before I had time and space to process his passing and the depth of my loss, I became the trustee of his estate, managing his possessions and executing his will. I swung between grief-stricken paralysis and hyper-efficiency, ticking off tasks in a zombie-like trance. Just as I began to reclaim my life after a rough year, I was diagnosed with my own heart issues – atrial fibrillation and supraventricular tachycardia. I wrote a poem about my dad’s decline called “Being with Truth” that begins, “There was the fall, then falling apart.” In retrospect, it applied to me, too.

For as long as I can remember, I’ve made sense of life through a blend of motion and stillness—running through the world to explore what lay beyond me, and writing to uncover what lived within. After my cardiac ablation, when I could no longer run freely, I felt trapped, as if my odometer had turned off. I sought second opinions for my erratic heart in search of the answer, “this will pass, you will be able to run and live how you used to.” When I didn’t find that answer, I kept pushing, trusting I’d reach the other side like I always did, whether I was facing life hurdles or battling my way through a challenging 100-mile race.

I was optimistic when I changed medications. Optimistic when I went off blood thinners. And then, the optimism wavered. When would I feel like my old self? When would I reach the finish line in this race I didn’t remember signing up for? When all else failed, and I couldn’t hit reset, I focused on my corporate career, because I knew there were achievable finish lines there.

As the months went on, I couldn’t kick my heavy boots feeling. For my dad. For my heart. The refrain that played in my brain was get on with it. Keep going. That’s what I had told myself whenever I faced hardship: keep going. It’s what my mom did when she battled terminal cancer, and what my dad did as he aged and faced his own health issues. They smiled, trusted, and kept going. The thing was, I wasn’t sure I could keep going the way things were. There was always so much to do, and I was unsettled and lost. I told a few friends I wished I could take a month off and cry. I had been holding in grief and loss and trying to show up daily as if everything was fine.

The Retreat that Changed Everything

I first heard Jen Pastiloff  speak in late July 2025 on Rich Roll’s podcast, just after her new book, Proof of Life, was released. Listening to her speak about loss—especially the enduring grief for her father, whom she lost at age eight, over four decades back, struck a deep chord. Her message that it’s never too late to pursue your dreams, and her practice of “beauty hunting,” the daily search for beauty in life, resonated with me. Life was pulling me forward, but parts of me were stuck in the past. I worried I had missed my chance to realize so many dreams, derailed by work demands, health issues, and grief.

I signed up for Jen’s Proof of Life Retreat spontaneously after connecting with her. She had a way of instantly making me feel I was part of her tribe with her comments: “Sign up! Come! Yay!”  Hours after committing, I feared going. What had I gotten myself into? I had already gone on a summer yoga retreat to Mallorca with a group of amazing women and had a memorable experience in the Mediterranean. And before that, I ventured to the Art of Living retreat center in North Carolina in May for a meditation retreat. I felt ridiculous signing up for another retreat. I’m not sure what I was looking for, but spending a week in Tuscany with a group of 20+ women that I’d never met and living in a villa with them meant I’d likely have to be vulnerable and share details of my life with them. The anticipation made me feel physically sick.

Finding My Place in the Puzzle

After a 10-hour delay caused by my plane at Miami International Airport being struck by lightning before takeoff, I finally arrived in Florence. When I met my first retreat friend at the hotel—her warm, lively presence filling the room adorned with 16th-century frescoes of mythological and angelic figures—I knew everything was going to be okay.

It’s hard to define what happens at a retreat with Jen. The adventure started off with the group meeting up at Santa Maria Novella train station in Florence to catch a van to Locanda Cugnanello, a villa tucked in the heart of Tuscany. It’s often challenging to meet up with friends in the middle of a foreign country, but finding women I had never met at a train station seemed daunting. And yet, it all came together with relative ease. Not only did we find one another at Santa Maria Novella, but we talked the whole van ride to the villa as if we were old friends, reuniting.

That first night at the villa, sitting around in a circle in the chandeliered and airy yoga room, daylight piercing through the sky lights, Jen placed pouches into the center of the room, and we were each to claim one. There was a stone in each pouch with a word inscribed on it, and our first sharing exercise was to go around the room showing our stone and expressing what the word meant to us. My word was dream. While Jen’s hearing is typically strained, with an ear infection and cold in play, she had lost her hearing, and was relying fully on lip reading. She sat on each of our mats and watched us intently as we spoke.

I didn’t say that one of my life mantras was dream big. I didn’t say that over past year, between grief, responsibilities, and navigating a life-altering heart diagnosis, I had forgotten about dreaming. That I was often working nonstop as work was about getting things done and I was finding solace in efficiency. In fact, I don’t remember what I said, because the stone in my hand had a message that overpowered all my thoughts that night. It was what I needed to hear: dream.

The Courage to Be Seen

The first few days, each time I sat in that yoga room with the group, knowing I may be called on to speak and read my writing, my heart pounded. Not a small ba-bump, but a thump so intense that I felt like I was vibrating. I had never experienced my heart so active in stillness. Being there with Jen and that group of women, my heart letting me know it was present, I had two choices: to let my optimistic inclination take over and keep smiling, pretending all was happy and well, or I could share how rattled and lost I felt over the last few months, and be seen. Listening to the other women, their honesty, their searching, my choice became easy.

Jen said that every woman at her retreat is a piece of the puzzle that shapes our collective experience. She was right. Each woman brought something essential to our dynamic. Their stories revealed truths about ourselves and opened doors to possibility. Their art, their lives, and their companionship enriched us all. The retreat became an exercise in listening, creating, learning, and showing up. We formed the pieces of a puzzle that came together as a vibrant proof-of-life mural.

Daily Flow and Beauty Hunting

Mornings commenced with sunrise meditation. We would make our coffees and cappuccinos, and walk outside into the twilight and sit amongst one another in silence, the air chilled and crisp. It was nice to experience comfortable silences with my proof of life teammates. As the sun illuminated the sky, bathing it in orange and golden hues, I went on hikes and jogs up the rocky and winding driveway of Villa Locanda Cugnanello, passing by apple and olive trees and lavender fields, and out the front gate, where a mile or two down the narrow and scenic road lined with cypress and English oak trees, I’d about face and head back. The view as I approached the villa always took my breath away: rolling hills and lush landscape sprinkled with rows of lavender, and a yurt, standing guard. Seeing the cars by the villa’s gate and people scattered about the porch, it felt like coming home.

Some mornings we practiced yoga, others we did a foundations class which was a blend of movements. We spent our days writing and painting – one day the directions were to “make bad art!” – and listening and learning about one another. We learned about beauty hunting and the goal of finding five beautiful things each day to admire and reflect on and throughout the week, I marveled at how much beauty I was absorbing.

The story I tell myself, the story I live by, is that I must always keep doing. I never feel like it’s enough, whether I’m at work or writing or up until this year, running races. I don’t feel like I deserve time outs. During my time in Tuscany, I took time outs, even if the time outs meant that I had to deal with my grief and ask myself questions about my life I’ve been avoiding: What do I want? What matters to me?

One morning we wrote poems about things we suck at. I wrote “How to Rest,” which began, “Stop setting an alarm clock that blares you awake at 4:45 am; Stop living by your overbooked calendar and start loving blank slates.” We were inducted us into the School of Whatever Works, where there are no rules. Where you figure it out as you go, and do what you need to survive and make it work for your life.

Every day, we completed the phrase: May I remember _____. For me, it was remembering to make space for myself in my life. Remembering to feel my feelings instead of pushing past them. It was remembering to honor the joy, accept the pain, and love it all, even the moments that suck and make me want to cry for a month. It was remembering to dream big dreams.

We were asked to think about our maps, and where our X would be. With the loss of my parents and the subsequent feelings of being uprooted and floating, I don’t know where my X is. All week, I thought about that. If I didn’t know where my X was, how did I know where I was heading? How would I know if I arrived?

Jen read us questions from a children’s book to stimulate our creativity: How can you help to keep your body well? How are living things alike? How is a snowman different than a real man? What is the moon like? The last question brought me back to something Jen wrote in her On Being Human memoir that was so profound to me: “the moon is never missing any of itself. We just can’t see it. People are like that, too.” While many of us may have started off as crescents early in the week, as the days went on and we began to live more in our own skin and share ourselves, we waxed fuller.

During the week, we visited the ancient towns of San Gimignano and Siena and savored rich and creamy (vegan) gelato and stunning panoramic city views. We walked through the Siena Cathedral, a 13th century Gothic masterpiece, with its intricate black and white marble design and its exquisite collections of statues and medieval books and visited the shop of contemporary artist Serena Bifolchi, who creates vivid and vibrant floral designs with paint she derives from flowers, fruits, and vegetables.

Legacy and Letting Go

Early in the week, Jen hosted a reading under the stars in which we were encouraged to share our writings, and later in the week she hosted an impromptu award ceremony in which we each received medals and had to share an acceptance speech. I used to say to a friend who ran two miles daily, “why would you even put on running clothes to run two miles?” Now I understand why. It all matters. “I, Jodi Weiss, give myself a medal for continuing to show up each morning in my running attire and trying to run a few feet further than I did the day before to resemble something that is like my former training and racing self. Slow, steady, and showing up. For me, the journey is always going to be worth it.”

Then there was the final night, when we had our collective 100-year-old birthday party and each one of us gave a speech about reaching 100. When we imagine our legacy, it’s amazing how our mind works – where will we be? What have we accomplished? How do we feel? Is our life everything we wanted it to be, or are we falling short, and if so, what can we change now so that the journey to our years ahead matters.

Thinking about the future helped me to understand the present. I have been in a fog for the past year. Here and not here. When my mom passed, I ran my way through the fog and found my way back to her and to myself over a span of 12 years of running long and far, my dad accompanying me to dozens of big, scary races. Losing my mom forged a new relationship with my dad. In the days leading up to his death, my dad and I made promises. I assured him I would keep running and he assured me he would be with me for all the runs. I took that to be literal. But maybe there were other adventures in my life I couldn’t get to while I was running so many hours a week – maybe that’s what I’m working through now.

One night one of the women shared with me that my dad may be in limbo until I let him go. I had forgotten about that phase of clinging to the dead and how I had held on to my mom for so long until I let her go, realizing she was in me all along. So that’s what I will try to do moving forward for my dad – not ask him to wait for me until I run again, but let him move on and trust we will find one another when it’s time.

Proof of Life

From our first circle gathering, Jen was clear that we would go home changed. I’ve been on many retreats—writing, yoga, ultrarunning races that were spiritual journeys—but this was different. The shift wasn’t visible from the outside, but inside, everything had changed. It was the first time in so long that I let go of the mask I’d been wearing and really thought about where I’ve been, what I want, and where I’m going with my life. It was the first time in ages I didn’t second-guess or judge myself for every word and action. I was living in my skin and I stayed with it, as painful as it was at times.

There were so many wonderful snapshots in my beauty hunting, from playing with Timo the dog, and Brenda, the rambunctious puppy full of love and curiosity, to talking to the two warm and engaging young daughters that one of the women brought with her. Then there was our house mom, who was known to show up at early morning activities in leopard pajamas with her hair in rollers. There was witnessing our group painting under the vibrant blue Tuscan sky for hours as if there was nothing else in the world that mattered. Reckless abandon at its finest. Eating delicious meals daily alongside women I enjoyed spending time with. Going back to my room each night and catching up with my roommate as the moon glowed outside our open window, a slight breeze drifting in. And then there was the writing. Jen shared so many prompts that stirred up our creative spirits: the age you felt most like you. What you would take with you if you had a few moments to leave your home. Something you had forgotten about yourself.

So much. I had forgotten so much.

The days in my 20’s when I fell in love with yoga, and how after morning yoga practice on weekends, I’d hide away in book stores and spend my afternoons writing and how creating short stories opened so many doors inside of me. I had forgotten the love and devotion that had gone into writing my novel, and how for so many years that creative pursuit filled my life. I had forgotten about the laughter with my mom when we’d shop at Macy’s and little boutiques in mid-town Manhattan, and the Saturday night dinner celebrations in New York City with my parents before sickness and death came. I remembered that I had traveled so far, literally covering 1,000’s of miles on foot, but I wasn’t done yet. There were so many more chapters ahead. And for the first time in a long time, that excited me. I wasn’t exactly where I wanted to be, but I wasn’t done yet. The retreat and all the people I met reminded me of that.

May I remember the cries, the laughs, the safe space, and how meeting women who were brave and courageous inspired me to feel and think and play. May I remember to keep taking chances, living life in the now – the only time there ever is – and accepting the highs and lows as part of the map of myself, and trusting that when I’m being authentic, I’m living at X. May I remember my gratitude for Jen, and making us all feel loved, seen, insisting that we stay grounded and real, and for bringing us all together. May I remember that sometimes all it takes to change our lives is getting on a plane and trusting that the journey will be worth it, and that I just may find magic under a magnificent Tuscan sky.