Retreats & Events
Step away from the day-to-day. Make space for what’s next.
Sometimes a change of scenery creates the space people need to think more clearly, connect more deeply, and come back with a renewed sense of direction.
Systems Success helps plan thoughtfully curated retreats and group experiences for entrepreneurs, leaders, writers, creatives, and other small groups who want meaningful time away together.
From venue selection and activities to travel logistics, payment coordination, and the details in between, Jolene can help turn an idea into an experience that feels intentional without feeling over-planned.
Have a destination in mind? Great. Only have the beginning of an idea? That works too.
Sometimes the best way forward is to step away.
A retreat can create room for conversations, ideas, and connections that are difficult to make space for in everyday life.
You may be planning a retreat for:
Women entrepreneurs
Create space to reflect on the business, reconnect with what matters, and spend meaningful time with other women who understand the demands of entrepreneurship.
Writers and creatives
Make room for inspiration, focused creative work, new experiences, and time away from the distractions of normal routines.
Leadership teams and business owners
Step outside the usual environment to think strategically, strengthen relationships, and have the conversations that get pushed aside during the workweek.
Small groups and communities
Bring people together around a shared purpose, interest, or experience in a setting that encourages real connection.
Every retreat is different. The starting point is understanding who is coming, why you are gathering, and what you want people to take away from the experience.
Thoughtfully planned. Loosely held.
The best retreats have enough structure to make everything work and enough breathing room to let the experience unfold.
Some groups need facilitated conversations and focused time together. Others need creativity, exploration, good food, quiet mornings, cultural experiences, or time to simply wander.
Your retreat can be shaped around the experience you want to create rather than a packed itinerary everyone has to follow.
Depending on the retreat, your experience may include:
- Group conversations or facilitated sessions
- Independent reflection or creative time
- Local food and cultural experiences
- Excursions and activities
- Shared meals
- Time to explore independently
- Leadership, business, writing, or creative sessions
- Informal time to connect and recharge
The goal is not to fill every hour. It is to create the right environment for the people and purpose behind the retreat.
Plan Your Own Retreat
You bring the idea. We’ll help make the pieces work together.
Maybe you already know where you want to go.
Maybe you know who you want to bring but have no idea where to start.
Or maybe you have been saying, “We should plan a retreat,” for years and need someone to help turn that idea into something real.
Systems Success can help coordinate the practical pieces that support the experience you want to create.
01
Venue selection
Identify a setting that fits your group, goals, budget, and desired experience.
02
Activities and experiences
Build in opportunities for connection, creativity, exploration, culture, or simply having a little fun together.
03
Travel logistics
Think through the practical details involved in getting people where they need to be.
04
Payment processing
Help manage the administrative side of collecting and coordinating participant payments when needed.
05
Retreat flow and scheduling
Create enough structure to keep the experience organized without making every minute feel scheduled.
06
Additional coordination
Work through the other details needed to help the retreat come together smoothly.
You do not need to arrive with a finished plan. The first conversation is about your group, your goals, and the kind of experience you want to create.
A little proof that stepping away can lead somewhere meaningful.
Past Retreats
Jolene has previously hosted retreat experiences in Sorrento, Italy for women entrepreneurs and women writers.
Those retreats combined shared experiences, local culture, time to explore, meaningful conversation, and space for participants to reflect, create, and enjoy being somewhere completely different from home.
The goal was never to keep everyone moving from one scheduled activity to the next. Instead, the retreats were designed to give participants a flexible framework for experiencing Sorrento together while still having room to make the trip their own.
Sorrento, Italy
Past retreat experiences included a mix of:
- Local dining and shared meals
- Cultural experiences and excursions
- Independent exploration
- Creative or facilitated time
- Small-group connection
- Space to slow down and enjoy the destination
“Jolene knows Sorrento like the back of her hand. There were so many hidden gems that I would’ve never found on my own.”
You can use this past experience as inspiration for your own retreat, or create something completely different.
Retreat Planning FAQs
What kind of retreat could you create with the right support?
Maybe it is a leadership getaway with your team.
Maybe it is a writing retreat with people who understand the creative process.
Maybe it is a few unforgettable days with a group of women who need space to reconnect with themselves, their work, and one another.
Wherever you are starting, you do not need to have all the details figured out.
Bring the destination if you have one. Bring the idea if you don’t.
Tell Jolene what you are imagining and start exploring what your retreat could look like.