1 – 5 NOVEMBER 2026 | AVENTINE HILL · ROMEDesigning Your Life Rome Retreat
An exclusive experience set in one of Rome's most beautiful private gardens, and some of her most inspiring neighborhoods. Workshops, deep conversation, and the design tools to reimagine what comes next.
The most important project you’ll ever design? Your life.
You're successful on paper. But something is pulling you toward a different chapter — and you're not quite sure what it is yet.
This retreat gives you a magical space, a proven methodology, and a community of remarkable women to collaborate with.
Built on the Designing Your Life framework developed at Stanford and codified in the New York Times bestseller, it's a structured, rigorous experience. All unfolding against the backdrop of Rome where together we draw inspiration from a city that has been reinventing itself for centuries, over delicious meals and local wine.
You'll leave with tools you can use for the rest of your life, three possible futures to inspire you, a first experiment to test the waters — and a group who will support you and hold you accountable.
Adventure, Community, Self Discovery
The shape of the week:
Welcome dinner Sunday, to meet your cohort and begin building your community
Daily life design workshops, with coaching, hands-on activities, and interactive breakout sessions
Four nights in a 4 star hotel on the Aventine Hill - one of Rome’s most peaceful and contemplative neighborhoods
Delicious, freshly prepared breakfasts and lunches each day
Closing dinner to celebrate and reflect on our time together
Roman excursions - get inspired by off-the-beaten path monuments to creativity and transformation
A one-hour post retreat call with the instructors and fellow participants for follow-up and coaching.
RETREAT DETAILS
Join Us
1–5 November 2026.
Arrive Sunday evening, depart Thursday.
Where
A private Residenza on the Aventine Hill, Rome. Accommodation details shared on registration.
Group Size
Maximum 16 women.
Designed for depth and intimacy, not scale.
⭑⭑⭑⭑⭑ "The retreat was a thoughtful and incredibly inspiring combination of looking inward, learning, and being in wonder with the strong women in the room, plus the story of Rome, a city of change and innovation, and finally...seeing possibility in your future. A combination of wonder, and getting out of your head and into those first experiments."
— Xenia Z., November 2025 participant⭑⭑⭑⭑⭑ "I am sincerely grateful for this amazing group who came together, and created a safe space for us to share honestly and provided fantastic insights throughout...if you can take the time to disconnect, it's a great opportunity to learn a process that you can use time and again in our ever changing/evolving lives."
— Laura L., November 2025 participantJoin Us
1–5 November 2026.
Arrive Sunday evening, depart Thursday.
Where
A private Residenza on the Aventine Hill, Rome. Accommodation details shared on registration.
Group Size
Maximum 16 women.
Designed for depth and intimacy, not scale.
★ ★ ★ ★ ★
"The retreat was a thoughtful and incredibly inspiring combination of looking inward, learning, and being in wonder with the strong women in the room, plus the story of Rome, a city of change and innovation, and finally...seeing possibility in your future. A combination of wonder, and getting out of your head and into those first experiments."
— Xenia Z., November 2025 participant★ ★ ★ ★ ★
"I am sincerely grateful for this amazing group who came together, and created a safe space for us to share honestly and provided fantastic insights throughout...if you can take the time to disconnect, it's a great opportunity to learn a process that you can use time and again in our ever changing/evolving lives."
— Laura L., November 2025 participant
ABOUT YOUR HOSTS
Katy Mogal
Certified Facilitator, Designing Your Life
Katy spent two decades helping people and teams navigate change and transition, at companies like Google and Fitbit, and in college and masters’ programs at California College of the Arts, and Stanford Continuing Studies. Then she designed her own next chapter, moved her family to Rome, and founded Her Bold Adventure.
She is a certified Designing Your Life facilitator, trained to guide participants through the same framework she used herself when she attended a DYL workshop in Matera, Italy, that helped set the direction of her own next act. She brings warmth, rigour, and a deep belief that the most interesting chapter of your life might be the one you haven't started yet.
She lives in Rome with her husband and two dogs, and is newly empty nested — still figuring out what to do with the quiet and extra space in the apartment.
Barbara Balletta
Community Manager
Barbara is an Italian travel designer and real estate expert who guides travellers through a more meaningful way of experiencing Italy - whether they are coming for holidays, looking for support to buy property, or planning to become future residents.
Passionate about sharing the undiscovered corners of her homeland, she launched her travel design business in 2012 while living abroad, to help friends and her international network discover a more authentic, immersive side of Italy. For our retreats, she curates cultural immersions designed to spark creativity and shape experiences that become the cornerstones of our community. For those wishing to extend their stay in Italy, she offers full curation and support.
This retreat is for you if…
You feel a pull toward something different but can't yet name what it is
You're ready to stop waiting and start designing what comes next
You'd rather prototype your way forward than plan your way to paralysis
You want to collaborate with other serious, accomplished women — not be lectured at
You believe that the right environment can change how you think
You're ready for your own bold adventure
And probably not if…
You're looking for a spa retreat or a vacation with workshops bolted on
You're not looking for a change, or thinking about a next chapter
You need everything figured out before you commit to anything
Join Us in Rome
RETREAT PROGRAMME
Sunday: Welcome Convivium
Dinner in a local trattoria beloved by Romans.
Where your cohort begins to form.
Mon-Wed: Life design workshops + Rome’s inspiration
Morning workshops in the Residenza. Afternoon excursions into Rome woven into our work.
Each morning we gather in the Residenza for workshop sessions — working through the Designing Your Life framework, doing exercises, and generating new possibilities together. Each afternoon we take Rome itself as our design partner: visits to off-the-beaten-path corners of the city that have inspired artists, thinkers and reinventors for centuries. The two halves of the day are designed to work together — the morning's ideas land differently after an afternoon in the Eternal City.
Rome as design partner
Monte dei Cocci, Testaccio market, the Aventine gardens. In Rome, transformation is everywhere.
Nestled on the enchanting Aventine Hill, our location offers a unique blend of history and modern comfort. Here, in this serene and timeless part of Rome that we will call home, we will experience a stay that invites contemplation and discovery. This tranquil sanctuary, removed from the city's bustle yet deeply connected to its soul, provides the perfect backdrop for our journey through life design, and Rome's hidden narratives and authentic treasures.
Post-retreat coaching
A one-hour group coaching session one month after the retreat, to create ongoing support and accountability. Included in registration.
Ready to Learn More?
EXPRES YOUR INTEREST
Join the Waitlist
Spaces are limited and we speak with every participant before confirming.
Fill in the form and we'll be in touch within 48 hours to set up a short conversation.
Investment: $3,300 early-bird (through September 15) / $3,600 standard.
A deposit of $1000 confirms your place, with the balance invoiced separately.