Third Half Retreats
What does your Third Half hold? Join us on a retreat and let us help you find out. The topics we explore are vast and the paths forward are many.
About Our Retreats
At Third Half Advisors, we understand that transitioning out of a long and successful career is both exciting and daunting.
Our Milestone Retreats provide the structure and inspiration to help you plan your next chapter. Based on a tested curriculum that blends expert instruction, facilitated small-group work, and professional coaching, our retreats guide you through an exploration of where you are now and where you hope to go. Together with your retreat peers, you’ll use strengths-based methods and life-design techniques to map out meaningful next steps.
Some participants come to us ready to chart a detailed course forward. Others simply want to begin thinking more purposefully about what this exciting phase of life could hold. Wherever you find yourself, our retreats will meet you there.
Two Types of Retreats
Join Us at Our Next Retreat
Pathways Retreat: Nantucket
When: September 29 - October 2, 2025
Where: Nantucket, MA
Price: $3,500
Join other members of Third Half Advisors for a weekend retreat in Nantucket. Unwind in the serene beauty of Nantucket while gaining valuable insights and skills. Our retreat offers a unique blend of workshops, outdoor activities, and relaxation. Connect with like-minded individuals and enhance your personal and professional growth. Note: Attendees must have participated in a previous THA program or be schedule to do so prior to the retreat.
Reserve your spot today!
Past Retreats
Locations include: Scottsdale, Arizona; Greenwich, Connecticut; Yale University/New Haven, Connecticut; Sun Valley, Idaho; Bethesda, Maryland; Nantucket, Massachusetts; Detroit, Michigan; Duke University/Durham, North Carolina; Dallas, Texas; Ashland, Virginia
This program is the best personal day of training that I have ever participated in. Thank you all!
– Alexa Young, Third Half Retreat Attendee
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What is the Third Half Retreat all about?Our retreats are designed to help you explore your next chapter, offering a blend of personal reflection, coaching, and connection with like-minded individuals navigating similar transitions. You’ll leave with greater clarity, inspiration, and actionable steps toward your “third half” of life.
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Who typically attends a Third Half retreat?Our participants come from diverse professional backgrounds, often successful in their primary careers and now seeking purpose, balance, or new ventures. You’ll find a supportive community of people eager to explore what’s next, whether that’s lifelong learning, giving back, new hobbies, or meaningful relationships.
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Is there any preparation required before the retreat?We may ask you to complete a brief reflection exercise or assessment (such as the Clifton Strengths Assessment) ahead of time to help you get the most out of your experience. Details will be shared upon registration.
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How long is the retreat, and what’s the daily schedule like?Retreats typically last 4 days, with daily sessions running throughout the day until dinner - and we also dine together. We balance structured activities with downtime to relax, reflect, or explore the local area.
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Where is the retreat held, and what are the accommodations like?The next retreat will be held in Nantucket, MA, offering a serene oceanside retreat. Accommodations are either at a B&B, hotels, or the hosts house, and meals will be provided.
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How much does the retreat cost, and what’s included?The fee includes all sessions, materials, coaching, assesments and meals. Travel costs, accommodations, optional special activities and alcohol consumption fees are additional.
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Can I bring a guest?Our retreats are designed for individual exploration, but if you’re interested in bringing a partner or friend, let us know—we may have options depending on the retreat.
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Will there be opportunities for one-on-one coaching?Yes! Our coaches are available for individual sessions before and after the retreat. You can schedule time directly with them, or we’ll provide sign-up opportunities during the retreat.
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What should I expect during the retreat?Expect a mix of guided workshops, interactive discussions, personal reflection time, and plenty of opportunities to connect with others. Our sessions cover themes like purpose, portfolio life, and navigating life transitions with impact and intention.
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What should I pack?We recommend comfortable clothing for workshops, casual attire for downtime, resort casual for evening meals and any personal items that help you relax (journals, books, etc.). If there are specific activities like hiking, yoga, or dinners, we’ll provide a detailed packing list closer to the event.
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What if I have dietary restrictions or special needs?We’re happy to accommodate dietary preferences and other special needs. Please let us know in advance, and we’ll do our best to ensure your comfort.
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How can I stay connected with other participants after the retreat?We encourage continued connections through our Third Half community, which includes follow-up virtual sessions, networking events, and optional membership opportunities to stay engaged and supported.
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What’s the cancellation policy?We understand that plans can change. Here is our cancellation policy: Up to 90 days before the retreat: a full refund of the registration fee, minus a $400 service fee Within 90 days of the retreat start date: no refund is available We highly suggest you acquire travel insurance
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Who can I contact if I have more questions?Feel free to reach out to Leighanne@thirdhalfadvisors.com and she will be happy to assist you with any additional questions!
