For Women Who Know Life is Richer When We Cross Paths:
On Leave Circles
Want to be more than your job title, your roles or your current life stage?
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Beyond our daily roles and responsibilities, we crave deeper connection. A space where we can be ourselves, share what’s on our minds and find wisdom in each other’s stories -- especially when life gets (as Annmarie from our Winter 2025 Circle perfectly put it) “too lifey.”
"Women of all ages, experiences, and abilities manage complex layers of challenges every day, everywhere. We all need help remembering that." -- Jori, Winter 2025 Circle
Right now, you might be:
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Surrounded by people but still feeling oddly alone at times
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Feeling overwhelmed and suspect there's a better way
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Navigating a transition (or feeling one approaching)
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Craving conversations that go deeper than logistics and small talk
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Wondering if other women are navigating the same questions you are
The On Leave Circles Experience:
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Real conversations that go beyond small talk, from setting boundaries to dreaming bigger
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Protected space for the self-discovery you’ve been putting at the bottom of your to-do list​​
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Connection with women outside your usual circles (because sometimes the best insights come from unexpected places)
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Fresh perspectives on life’s challenges and celebrations​
Here's what makes Circles special:
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Intentionally intimate (7 participants plus Liz)
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Thoughtfully mixed groups that cross usual social circles, ages and life phases
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Real conversations about real life, with no other expertise required!
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Virtual connection that fits your life – meaning you can join from home after bedtime routines, during work trips or in your coziest loungewear
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Spring 2025 Cohort Details:
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6 1-hour sessions in April and May
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Tuesday evenings @ 8:30 p.m. EST / 5:30 p.m. PST
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April 1, 8, 15, 22 and May 6, 13 (skipping April 29)
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Virtual small group conversations on Google Meet, with no commute needed
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Investment: $297 for the full spring series
“You will gain incredible insight on how you move through the world, while being inspired by women with different perspectives.” – Lauren, Winter 2025 Circle
HEAR MORE FROM OUR WINTER 2025 CIRCLE:​
100%
Gained new perspectives
86%
Said they would do something differently as a result
100%
Would recommend Circles to others
Our Winter Circle brought together new moms and empty nesters, career-focused professionals and recent retirees, and the magic happened precisely because of these different perspectives.​​​​​​​​
“I honestly went in blind. At most, I figured I was getting to set aside 60 mins to learn from others and get to meet women outside of the bubble I’ve built around me. This experience ended up being part group therapy, part guidance, part challenging and 100% fun. I looked forward to my Tuesday evenings.” -- Annmarie, Winter 2025 Circle​
PICTURE THIS:
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You’re in your favorite cozy spot, cup of tea or glass of wine in hand, joining a small group of thoughtful women for conversations that matter. Expect authentic dialogue about the things we’re all navigating, from different perspectives that will expand your own.
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​What exactly do we talk about?
Each week, we explore themes that touch all our lives -- from the various roles we play, to what gives and takes our energy, to creating meaningful boundaries.
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A typical Circle flows naturally:
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A warm welcome and quick check-in
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A thought-provoking theme and questions
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Space for everyone’s voice and experience
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The conversation flows where it needs to go
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A nudge on what to notice ahead of the next week
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“I loved the way you came with a focus for each week but truly let the conversation go where it went naturally while also steering us back on track when needed. The organic conversations was awesome but I appreciated the "topics" for each night as well.” – Ellen, Winter 2025 Circle
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“The Circle Cohorts can provide a simple message or a deep lesson - sometimes both. It was a solid weekly reminder of the importance of hearing multiple perspectives.” – Jori, Winter 2025 Circle
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​​About Your Guide:
As your facilitator, Liz aims to create a space for everyone with the mix of structure and flexibility On Leave has come to be known for across all of our experiences. She has been trained as a coach.
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​​​​​​​​“Great job facilitating. No easy task, but you helped each person have a chance to share and feel heard. Women don’t get a lot of that, so, thank you.” – Jori, Winter 2025 Circle
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“You made us all feel so comfortable and prompted amazing discussions each week. I am so glad I signed up for Circles and cannot wait to keep the work going in my life.” – Lauren, Winter 2025 Circle​​​​
WHY CIRCLES? WHY NOW?
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Liz created On Leave Circles after witnessing something magical during On Leave's February 2024 virtual pre-launch event: women from different walks of life, connecting over shared experiences they rarely get to voice aloud. From guilt about self-care to validating for each other that filling our own cups isn’t selfish but necessary. ​
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While a full weekend away can be transformative, there's also power in smaller, consistent moments of connection. Right now, as we all navigate an increasingly complex world, these conversations feel more vital than ever.
"Do it! If you’re seeking an uplifting, supportive environment with an energy of connection and conviviality, invest in carving out an hour of tea time with others who love to reflect and uplift others. You’ll feel inspired, motivated, at home–and make friends.” – Chess, Winter 2025 Circle
WHAT YOU'LL TAKE AWAY:
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​New Perspectives
“I loved the varied perspectives and life experiences of the group. While totally supported and heard, we weren’t in an echo chamber which was both helpful and inspiring!” – Julie, Winter 2025 Circle​
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Genuine Connection
“The opportunity to connect with other women seeking value and connection is too important to miss - grasp it with both hands!” – Mary Kate, Winter 2025 Circle
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Self-Discovery
"Go in with no expectations and you will come out surprised at how much you've learned about yourself." -- AnnMarie, Winter 2025 Circle
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Real Change
"My cohort was an excellent reminder of how important it is to create values-led boundaries that help us preserve and restore energy, make space for serendipity (even mid-chaos), and notice and appreciate the moments that make life magical.” – Jori, Winter 2025 Circle​​
HAVE QUESTIONS?​​​​
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What if I need to miss a session?
We’ll help you stay connected if you need to miss a session. Most of the participants in our Winter cohort had to miss one session for expected or unexpected reasons. To maintain group dynamics, we ask that you seek to commit to at least 5 of the 6 sessions.
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Why meet weekly for six (nearly) consecutive weeks?
Based on feedback from our first cohort, we’ve learned that maintaining momentum creates the best experience. While there won’t be homework per se, On Leave will follow up with headlines from each conversation and a thing or two to consider ahead of our next conversation.
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What happens after the six weeks?
We’re developing an optional “alumni” program to help you maintain connection with both your cohort and women from previous cohorts. This will provide ongoing opportunities for connection and introspection with a growing community of thoughtful women.
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“The time you’re taking to invest in yourself by connecting with women of various backgrounds is 110% worth it. You won’t regret it.” – Ellen, Winter 2025 Circle