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Sunday, Oct 13, 2024 – Monday, Oct 14, 2024 

Rediscover, Reignite
& Realize Your Purpose

One or two-day retreat for women entrepreneurs and professionals.

Litchfield, CT

Women Entrepreneurs,
Aspiring Business Owners,
& Mid-Career Professionals!

Did you have a vision and want to bring it back?

Did you have a passion and purpose once upon a time and lost it?

Did you once have a clear purpose that you cannot find anymore?

Have you lost the drive or ambition you once possessed?

Looking Out of Window

Reconnect with Your "Why"


Revisit the reasons you started your entrepreneurial or career journey. Reignite your sense of purpose and motivation.


Seek Inspiration and Mentorship as it allows you to learn from the experiences of others, gain valuable insights, and stay motivated, helping you navigate challenges and achieve your goals.


Surround yourself with other inspiring women entrepreneurs and professionals. Hearing their stories and gaining new perspectives will provide fresh motivation and innovative ideas.


Invest in your self-care and balance. Burnout will significantly reduce passion. Make time for self-care and activities that rejuvenate you.


Set New Goals and Challenges: Losing passion often stems from feeling stagnant. In this retreat, you’ll set new, exciting goals or challenges for yourself and your business.


Acknowledge and celebrate the small victories, and progress you make. Recognizing your achievements, no matter how minor, will boost your morale and remind you of your capabilities, fueling your passion to continue pushing forward.

Who Should Attend the Retreat?

Are you open to exploring new learning opportunities and investing in your skills and knowledge?

Do you believe in the value of investing in yourself to achieve greater success and fulfillment?

Are you committed to prioritizing your own development and well-being?

Do you see yourself setting aside time and effort for self-improvement and self-care?

If so, you are ready to embark on a transformative journey towards leveraging your purpose and elevating your business or career. Join Coach Jackie for a one or two-day experience like no other, nestled in the serene beauty of Litchfield, CT during the height of autumn foliage.

In a world filled with uncertainty, finding and following your passion is not just a luxury—it is your greatest security. Women Entrepreneurs, aspiring entrepreneurs, and professionals: move beyond fear and hesitation as you explore the power of self-discovery to gain clarity and reconnect to your purpose during this retreat.


Facilitated by Coach Jackie, a seasoned Leadership Development and Mental Fitness Coach, this immersive event is designed to be a catalyst for connection, renewal, and action.

About Your Retreat Leader

Coach Jackie Ross is a Professional Certified Coach, credentialed by the International Coaching Federation. She’s a Certified Positive Intelligence Coach with training in Leadership Development and Mental Fitness. Jackie is the author of the book Manage UP! The Ultimate Guide to Managing Your Manager and a professional speaker and presenter.

Since 2013, she’s been helping ambitious entrepreneurs and professionals transform from uncertainty to powerful levels of confidence and career clarity.

Portrait of cheerful mixed age range multi ethnic women celebrating International Women's

About the Retreat

The core of the retreat is a life-changing full-day workshop on Monday, October 14, 2024.  In addition, for a limited number of attendees, you’re invited to join us for a special add-on day with an optional overnight on Sunday, October 13, so you can fully take in the depth and breadth of this journey.



Workshop Only

Monday, October 14, 2024

Includes a continental breakfast and a full nutritious lunch.

Early Bird: $277 
After August 1: $327


Workshop + Add On

Sunday, October 13 - Monday, October 14, 2024

Includes workshop with a continental breakfast, full nutritious lunch on Monday, and on Sunday guided hike, wine tasting, and dinner add-on.

Early Bird: $377 
After August 1: $447


VIP Package

Sunday, October 13 - Monday, October 14, 2024

Includes workshop with a full nutritious breakfast & lunch on Monday, and on Sunday guided hike, wine tasting, dinner and overnight stay at Wisdom House.

Early Bird: $597 - $647
After August 1: $647 - $697

Rediscover, Reignite, & Realize Your Purpose: A Workshop for Women Entrepreneurs and Professionals

Monday, October 14, 2024

Registration 9 am | Event begins 9:30 am – 5 pm EST

Wisdom House Retreat and Conference Center, Litchfield, CT

International Women's Day portrait of united multi ethnic mixed age range women in busines

The "Rediscover, Reignite, and Realize Your Purpose" workshop is designed to empower women entrepreneurs and professionals by guiding you through a transformative journey of self-discovery and actionable goal-setting.

The serene and picturesque Wisdom House Retreat and Conference Center offers a tranquil setting perfect for reflection and growth. Participants are greeted with a continental breakfast, allowing for casual networking and a relaxed start to the day. The welcoming ceremony sets a positive and inclusive tone, fostering a sense of community among attendees.

The morning session introduces the concept of Ikigai, a Japanese philosophy that combines passion, mission, vocation, and profession to help individuals find their true purpose. This is followed by an engaging exploration of personal values, encouraging participants to align their professional endeavors with their core beliefs. 

After a healthy and nutritious lunch, the Goshen Playhouse Players, our local improv troupe, will delight us with a surprise attraction. Known for their quick wit and interactive performances, they'll engage you in spontaneous scenes and games, ensuring laughter and unexpected twists. Their unique brand of humor and improvisation promises to make this an unforgettable afternoon kick-off filled with joy and entertainment.

The remainder of the afternoon focuses on practical application, with sessions dedicated to designing and planning achievable goals. Attendees will learn strategies to bridge the gap between their ideas and execution, ensuring they leave with a clear roadmap to success.

The day concludes with closing ceremonies, celebrating the insights gained and the connections made, leaving everyone inspired and equipped to realize their fullest potential.

Pre-Workshop Add On: Guided Hike & Wine Tasting

Sunday, October 13, 2024

1 pm – 6 pm EST | 1 – 3:30 pm: Guided Hike in Washington, CT | 4 – 6 pm: It's the Little Things, Wine and Food, Fun or Play Wine Tasting

Locations TBD

Woman with Hiking Poles

Join Coach Jackie for an unforgettable prelude to the retreat amidst the picturesque beauty of Litchfield Connecticut.  The Fall foliage will be at its peak on Sunday, October 13 when we will embark on a rejuvenating 3-mile guided hike through the idyllic landscapes, enveloped in a tapestry of vibrant autumn colors in beautiful Washington CT.

Coach Jackie developed and hosts the Litchfield CT LGBTQ+ Hiking and Social Meetup Group and has been leading group hikes for over two years throughout the State of Connecticut and Massachusetts.  Since Feb 2022, Coach Jackie has led over 100 hikes and her group has 270+ members. 

As the golden sun begins to descend, we will head over to a local restaurant in Litchfield and indulge in a wine tasting led by Sommelier, Alison Miller, and cuisine crafted from locally sourced ingredients, perfectly complemented by a cozy ambiance. 

Alison Miller is a lifestyle and wine entrepreneur and Founder of Artisan Wine Group, creating innovative wine events, and curating exceptional wine selections. She is a WSET Advanced/ Level 3 certified in wine and spirits. She has traveled to over 30 wine regions around the world, gaining insights and appreciation for different cultures and styles of wine. She enjoys combining her love for wine, education, and storytelling to make wine more accessible and fun for everyone.


Coach Jackie is thrilled to be partnering with Alison who will enhance the theme’s overall experience of renewing our purpose.

This pre-workshop add-on promises a day of relaxation, connection, wine education, and culinary delight, setting the stage for a transformative experience awaiting you the following day.

Overnight Stay at Wisdom House (Part of VIP Package)

Sunday, October 13, 2024

Wisdom House Retreat and Conference Center, Litchfield, CT


Wisdom House, located in Litchfield CT, hosts meetings, conferences, and retreats for a variety of organizations. They welcome over 500 groups annually, many returning year after year. 

Accommodations & Amenities:

You will be staying in a private room either with an attached ensuite bathroom or a shared hall bathroom. 

  •  All guest rooms include desks, chairs, and beautiful New England views

  • Super dining and meal options for breakfast & lunch on Monday, October 14th

  • Coffee, tea, and artesian well water available in their 24-hour hospitality rooms

  •  An outdoor Labyrinth

  •  Gardens and outdoor spaces for contemplation

  • Chapel

  • Art Gallery

  • Wi-Fi available throughout the facility

  • Two kitchenettes with refrigerators and microwaves

  • Bookstore

  • Walking distance to Topsmead State Forest

  •  1 mile from Litchfield Center

Why Attend a Live In-Person Retreat?

Since we live in a virtual world you may be asking why you should attend an in-person live event.

Here is why:

Attending a live event for women entrepreneurs and professionals offers several distinct advantages over participating in an online event. Here are some powerful reasons to choose to attend this live event:

🧘‍♀️ Distraction-Free Environment

Being physically present at this live event will help you to minimize distractions.  Without the interruptions of daily life or the temptation to multitask, you can fully immerse yourself in the event, maximizing your focus and engagement.  The Wisdom House Retreat and Conference Center offers a peaceful and beautiful location that has an outdoor Labyrinth, gardens, and outdoor spaces for contemplation, an art gallery and walking distance to Topsmead State Forest.

🌈 Supportive Community for Women

Attending a women-only or women-identified-only event fosters a supportive and empowering environment. It provides conditions to create a safe space to share experiences, challenges, and successes unique to women, promoting solidarity, mutual encouragement, and a sense of belonging. This exclusive focus can enhance personal and professional growth in ways that are particularly meaningful and impactful for women.

🗨️ Instant Feedback & Interaction

 At this live event, you will ask questions and get immediate feedback from the facilitators.  The real-time interaction can clarify doubts, provide deeper insights, and foster a more dynamic and engaging discussion.

👏 Hands-On Learning

This live event offers an engaging and interactive experience that allows for hands-on learning. This practical approach will enhance understanding and retention of information, providing you with a deeper learning experience.

🤝 Networking Opportunities

This live event will provide unparalleled opportunities for face-to-face networking. You can meet other entrepreneurs, leaders, potential collaborators, and like-minded individuals, and you can start to foster relationships that can lead to future collaborations, partnerships, and professional growth.

🍃 Immersive Experience

The atmosphere of this live event, set in beautiful Litchfield CT, will be inspiring. The energy of the attendees, the direct interaction with the speaker(s), and the tangible environment will create a memorable and impactful experience that is difficult to replicate online.

“Coach Jackie was an amazing part of our Career Portal Lounge at the ASHA Convention. She presented mini-workshops that left our members with practical tips that they could use immediately. Even with the short timeframe of each workshop (20 minutes), she was able to excite, inform, and engage with each of the participants and leave them with a "nugget" of information that empowered and energized them. Members came back to attend more than one session and members requested her by name to get more one-on-one time with her during our resume review program. Coach Jackie has an approachable and calming presence making people gravitate to her. Her kind and warm nature make her a pleasure to work with and we hope to work with her again.”

Alexis Redmond

Systems-Focused Association Member Leader,

ASAE Diversity Executive Leadership Program (DELP) Scholar


Why spend the weekend in Litchfield CT?


White Memorial Boardwalk | Photo: Discovering CT

Visiting Litchfield, CT, during the height of the fall foliage is a perfect weekend getaway for those seeking a blend of history, scenic beauty, and delightful experiences. Nestled in the picturesque Litchfield Hills, this charming town comes alive with vibrant autumn colors, offering stunning views at every turn.

Visit Litchfield CT, it notes “scenic, historic, and lifestyle amenity-rich Litchfield, Connecticut, named a top small town destination by Smithsonian Magazine and a Top 20-weekend getaway in New England by Travel + Leisure for our rich history, scenic beauty and nature preserves, outdoor activities, shopping, dining, signature community events, and great people!

You can enjoy a leisurely tour of local wineries such as Hawk Ridge Vineyard and Sunset Meadow Vineyards, where you can savor exquisite wines amidst the breathtaking backdrop of fall leaves. Indulge in exceptional dining experiences at quaint restaurants like West Street Grill, known for its farm-to-table cuisine. For outdoor enthusiasts, the area boasts numerous hiking trails, including those at White Memorial Conservation Center, providing an immersive nature experience. Whether exploring historic landmarks, like the Litchfield Historical Society, or simply taking in scenic vistas, Litchfield promises a memorable and enriching autumn escape.

Coach Jackie will provide a comprehensive list of recommended places to stay and enjoy during your weekend venture to Litchfield Hills.

Litchfield CT is just:

  • 2 hours 30 minutes from Boston

  • 2 hours 15 minutes from NYC

  • 2 hours 20 minutes from Providence, RI

  • 1 hour 30 minutes from Stamford CT

  • 55 minutes from Western MA

  • 50 minutes from Hartford CT

Contemplating at Work

Women Entrepreneurs, Aspiring Entrepreneurs, and Mid-Career Professionals!

Do you have entrepreneurial aspirations or are already running your own business but feel disconnected from your original purpose and are seeking realignment?

Was there a time when you had a burning passion that has since disappeared?

Did you ever have a calling that you no longer feel connected to?

Have you let go of any goals or dreams you once cherished?

Did you ever lose enthusiasm for something you were once passionate about?

Have you ever felt a strong sense of purpose that you have lost over time?

Have you been working for several years but feel stuck or unfulfilled in your current role and are looking to make a significant change or pivot in your career?

Was there something you once pursued with great energy that you have abandoned?

Did you ever lose interest in a purpose that once drove you?

Have you had a passion that faded away with time?

Did you once have a purpose that you no longer follow?

Have you lost sight of a dream you once had?

You should attend this retreat if you… 

Have ever had a passion or purpose that you lost along the way

Had a dream or goal that faded over time

Ever felt strongly about something that you've since let go of

Ever lost a sense of purpose you once had

Ever felt passionate about something that you no longer care about

You Will Go From...

Confusion and Aimlessness to Clarity and Direction

Gain a clear understanding of your true passions and purpose, helping you design a business and career path aligned with your true self.

Discouragement to Inspiration

Be inspired by Coach Jackie’s dynamic presence and grounded compassion, igniting your sense of possibility and potential.

Isolation to Community Support

Connect with like-minded leaders in a supportive environment, fostering collaboration and mutual encouragement.

Paralyzed and Lost to Actionable Strategies

Leave with practical action steps and a solid plan to continue your journey towards a life and career you love.

Disempowerment to Empowerment

Learn practical strategies to overcome your fears and challenges, unlocking your inner strength and resilience to create professional success.

Lack of Skill-to-Skill Development

Acquire hands-on exercises and time-tested techniques to turn your talents into tangible opportunities and income streams.

Stress, Distress and Overwhelm to Peace Amidst Change

Develop tools to find inner peace and resilience amidst life's inevitable fluctuations and challenges.

Lack of a Professional Tribe to Ongoing Support

Optionally join a support group and build your professional tribe to sustain and deepen your newfound strength and strategies beyond the workshop, ensuring long-term growth and success.

Do not miss this opportunity to Rediscover, Reignite, & Realize Your Purpose.

Reserve your spot today and take the first step towards a future filled with passion, purpose, and possibility.

Revitalize those feelings you had that you no longer do.

Rekindle your passion.

Reclaim your ambition that you lost along the way.

Rediscover your purpose that was once important to you.

Reignite the motivation for something you once loved.

If these goals resonate with you, Coach Jackie invites you to register for this memorable workshop today. Designed specifically for women entrepreneurs and professionals, this workshop will guide you through the essential steps to renew your purpose and reignite your passion. Join us to embark on a journey of empowerment, rediscovery, and professional growth. Do not miss this opportunity to elevate your impact and find renewed direction in your career and life. Register now and take the first step towards a more purposeful and fulfilling future.

Multi-ethnic group of happy mature women embracing and dancing against grey background.jpg

So that you receive the most value from this experience, Coach Jackie lovingly asks that you honor her agreement of participation:

  • End-to-End Attendance: Please be prepared to be present from beginning to end.

  • Full Engagement & Presence: We ask that you show up fully present and ready to engage, so you AND others receive the most value from this experience.


Thank you for your understanding!

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