Best Chapter Yet! ~
Brave & Boundless
TTWK FALL Retreat 2025
You’ve felt it—that undeniable spark, that knowing there’s more waiting for you. You’ve maybe already taken bold steps on your own—stretching yourself, daring to dream bigger, and leaning into your own growth. Now it’s time to go even deeper, to ground yourself in a confidence that doesn’t waver and a love for yourself that’s fierce and unshakable.
Welcome to Brave and Boundless—the next evolution of your journey.
Why "Brave and Boundless?"
Maybe you've tasted the freedom that comes from shedding old patterns and saying yes to yourself, maybe you haven't but you're MORE than ready for that. But life keeps shifting, and it’s easy to get caught up in the chaos of what’s going on around you. This retreat is about being the sky, not the weather—finding that unshakable place within you that holds steady no matter the storm. It’s about knowing who you are at your core and standing rooted in your truth and power, no matter what comes your way.
This is the next chapter of your journey. If you're ready to explore what it means to step out of old roles and into new possibilities—now is the time to see what unfolds as you continue that story. Brave and Boundless is where you’ll build on the courage you’ve already shown, diving deeper into your own transformation and letting your inner strength guide the way.
Why Join Us?
This isn’t just another retreat—it’s a space to fully embody the bold, unwavering spirit you know you’re capable of. You’ll be surrounded by women who are also ready to take the next step on their journey, moving from insight to action and letting the story continue to unfold. Together, we’ll deepen our confidence, celebrate our growth, and support one another as we navigate what’s next.
Imagine stepping into a space where you are fully seen and deeply supported—surrounded by women who get it and who hold you up as you rise even higher. Picture leaving with an undeniable and strong sense of clarity—rooted in who you are and confident in how you stand in the world. This is more than a getaway—it’s a declaration that your story is still unfolding, and your best is yet to come.
What to Expect:
- Grounded Confidence: Root yourself in your own truth, no matter what’s happening around you. Be the sky, not the weather.
- Dynamic Self-Love: Embrace your own power and presence with boldness and grace.
- Continuing the "Hero(ine)’s Journey": Explore the next chapter of your story, building on the insights and courage you’re uncovering.
- Authentic Connection: Create and deepen bonds with women who know how to show up for themselves and each other.
Celebration + Joy: Honor how far you’ve come and revel in where you’re headed next.

Join us on October 3rd in Chicago, Illinois
Lisa and Kari would LOVE for you to join them at their Fall 2025 retreat to celebrate YOU! This retreat is for you if you are ready to launch or celebrate YOUR BEST CHAPTER YET because IT GETS BETTER each year...
when
Friday, October 3rd to Sunday, October 5th
(gorgeous time of year in Chi-town)
where
voco Chicago Downtown
(right along the river!)
350 W Wolf Point Plaza Building 1, Chicago, IL 60654
who
You! Along with a group of dynamic women who are stepping into making this chapter the juiciest and most vibrant years yet, and ready to embrace and celebrate their Unique, amazing, fabulous selves!
what
Besides some fun and laughter (given!), we look forward to welcoming you and pampering you with yummy food and libations, to co-creating a sacred space for letting go of anything holding you back from living your life fully, and to help you create your own unique roadmap for more joy, more success, and less of whatever is holding you back.
Pre and Post virtual gatherings to be scheduled in late September and in late October to enhance your connection as a group as well as ensure you continue to feel supported in your wildest dreams for the year ahead.
setting
Retreat takes place at the stylish and centrally located voco Downtown Chicago! Enjoy stunning views of the Windy City, sleek guest rooms at an affordable group rate, and convenient access to the Chicago Riverwalk.
costs
Attendance:
$875 deposit plus one more payment of $750 by September 20, 2025
~OR~
$1,750* PAY IN FULL by September 20, 2025 and receive a bonus 60 minute coaching call with Kari or Lisa (your choice)
Meals
Included with Attendance:
Friday October 3:
Welcome Reception, hors d;oeuvres and Dinner
Saturday October 4:
Breakfast, snacks, lunch, HH apps
(Saturday dinner out: self-pay)
Sunday, October 5:
Brunch before departing
Accommodations:
$189 (King bed) or $199 (2 queen beds), nightly
A block of discounted rooms have been reserved for your selection on retreat property at voco Downtown Chicago Hotel. Link to book rooms will be provided after you register or "SAVE YOUR SPOT" with your $250 registration deposit.
retreat content
Friday Evening:
Opening Circle & Intention setting
Saturday:
Morning and afternoon sessions, with breaks for
stretch and lunch
Sunday:
Morning Activity, Closing Circle and Celebration
travel
Chicago has two airports:
O'Hare and Midway
The Closing Circle will complete by 12pm Central time
For flight planning purposes, FYI: 30 min drive to O'Hare and about 55min by train; 20 min drive to Midway and 40 min by train.
Meet your hosts!
Lisa Callahan
Lisa is a total badass who will make you fall over laughing while simultaneously lifting you up. Besides being the best co-host a podcaster could ask for, she is also a business life coach who coaches successful women with big ideas and goals who need help stepping into the confidence required to enhance and actually enjoy that success. Lisa brings wit and wisdom to all her endeavors, so you’re in for a treat!
- Kari Morin
Kari Morin
Kari Morin is the kindest person you will ever meet. She is a Master Coach who has the ability to see all the possibilities you hold. If you want to feel seen, heard and held as you break through your limiting beliefs, Kari is the woman you want by your side. She is married and has three amazing boys that she is raising to be really good men. Iam so proud to have her as my partner and bestie. I expect we will grow old together drinking wine and laughing our asses off.
- Lisa Callahan