Lisbon, Portugal
Design Your Good Life Retreat
Inspire. Explore. Execute.
The Good Life Abroad is partnering with Third Half Advisors™ to bring you the Design Your Good Life retreat in Lisbon, Portugal, as part of a two week short stay program, February 2-16, 2027.
The Third Half Advisors program takes place over four days mid-way through The Good Life Abroad experience. This retreat is carefully integrated in, so you’ll have time to enjoy The Good Life Abroad’s community and activities, along with the rich culture of Lisbon, while planning your next life chapter.
Third Half Advisors Program
Third Half Advisors are specialists in helping people realize their best post-career lives. For seven years, Third Half Advisors has defined the standard in “next steps” planning, enabling over-55-ers to redirect their creativity and energy to build authentic and fulfilling futures.
Are you driven to learn, connect with others, and contribute to your community in new ways?
Are you looking for greater purpose in your days?
Do you finally have the freedom to design the next chapter of your life, but aren’t sure where to begin?
If you answered “yes” to any of these questions, consider joining this Third Half Advisors Design Your Good Life retreat.
You’ll gather with a small group of like-minded travelers exploring what’s driving you right now and what’s possible for your future. Then you’ll use proven methods to design your path forward.
Start living your best life – by design!
Core Pillars of the Design Your Good Life Retreat
Intimate Group Setting
The small group fosters deep connections, creative inspiration, and thought-partnering as you each design your paths forward - together. Attendance is capped at 15.
Proven Methodology
Guided by a values-based approach and Life Design practices, you’ll gain insights into your goals, expand your options, and commit to meaningful actions.
Immersive Retreat Environment
You’ll step away from life’s daily distractions to reflect and grow in the beautiful Lisbon setting. Half-day programming means your afternoons and evenings are free to relax, reflect, explore, and commune with fellow Third Halfers.
Expert Facilitation
Our experienced coach will guide you through a curriculum tailored to deliver transformative outcomes. Additional one-on-one coaching is also available. You’ll leave the retreat with concrete steps toward your own best next chapter!
Meet Your Coach
Dr. Rachel Bishop, Executive Coach & Facilitator | Third Half Advisors
Rachel brings a background in medicine, military leadership, and life design to her coaching work with Third Half Advisors. She holds an executive coaching certificate from Georgetown University and has extensive experience coaching leaders in industry, government, and medicine. As a certified Design Your Life® coach, Rachel helps individuals navigate their journeys from full working lives to purposeful next chapters through intentional reinvention.
Raised in a Foreign Service family, Rachel has lived and worked across five continents. After graduating from MIT, she served in the U.S. Army before attending medical school at the University of Pennsylvania. In her 25-year career, Rachel led teams in healthcare and global humanitarian missions while working for the National Institutes of Health and Johns Hopkins Medicine, where she founded a leadership coaching program.
Rachel currently divides her time between clinical care and coaching. She loves trail runs with her dogs, mixing drinks for friends, and reading. She lives outside Washington, D.C., with her husband and the youngest of four children who make up their blended family.
Program Schedule
Approximately 9:00am – 1:00pm daily
Day 1: Foundations: Life design overview, understanding your Clifton Strengths, values exercise
Day 2: Discovery: Portfolio Life assessment - past, present, future
Day 3: Exploration: Odyssey Planning - exploring what’s possible using the power of design teams
Day 4: Design: Making change, prototyping, next steps, and accountability
Your TGLA Experience
A furnished apartment with a fully stocked kitchen or kitchenette, Wi-Fi, weekly cleanings, utilities and more included.
Local living — apartments in residential areas near transit and local life.
2–3 curated community events per week: walking tours, local meals, happy hours, etc.
Weekly optional excursions or day trips.
Local support via your Community Manager (English speaking).
Personalized recommendations (restaurants, markets, hidden gems).
Travel medical insurance for the duration of your program through our trusted insurance partners.
Your Experience Always Includes
Curated Community Events
Meet other travelers in structured yet optional meetups - perfect whether you want to socialize or have space.
Local Community Manager
A local point person appointed to help you feel grounded, supported, and safely connected.
Cultural Immersion & Independent Time
Scheduled experiences like walking tours and local workshops, balanced with days to explore on your own.
Your Apartment
Chiado Program Site
Upscale Living in the Heart of Historical Chiado
The Design Your Good Life retreat will be taking place out of our Chiado program site. These elevated apartments are located in a cluster of beautifully restored buildings within the same small area, offering a stylish, more boutique stay while keeping you steps from cafés, theaters, viewpoints and shopping.
Expect upgraded interiors, refined furnishings, air-conditioning, sound-insulated windows and fully equipped modern kitchens. Every property is vetted for safety, convenience, and quality, so you can focus on what really matters: exploring the city, building confidence abroad, and enjoying your adventure without worry.
All apartments include:
Premium linens
Elevator
Weekly cleaning
Utilities
Washing machine
Coffee maker
Smart TV
High speed wi-fi
Fully equipped kitchen
1 or 2 Bathrooms
Community Manager
Vera S.
Vera has two main passions: traveling and telling stories. From an early age, she left her hometown in the Algarve to explore the world. Since then, she has lived and worked in several countries, including Portugal, Spain, the UK, the USA, and Morocco. In 2010, she moved to Lisbon — the city of her heart. Over the years, she has worked as a tour leader, sharing her love of discovery with others. Vera treasures uncovering hidden gems and crafting unforgettable experiences, simply for the pleasure of seeing a smile of genuine happiness on someone’s face.
Watch the Webinar
Join Good Life Abroad founder Andrew Motiwalla and Dr. Rachel Bishop of Third Half Advisors as they introduce the Design Your Good Life Retreat in Lisbon, Portugal—a unique two-week program that blends authentic European living with expert life design coaching for adults 55+. Whether you're ready for a big change or simply want to be more intentional about what comes next, this is for you.
Ready to Design Your Best Life?
We can’t wait to share this adventure with you. If you’re ready to create your best life plan in a stunning destination, here’s how to get started:
Click here to register.
Reserve your spot with a $495 deposit.
Complete our intake form and join a Welcome Call with your Program Coordinator to review the neighborhood, apartment options, and what to expect.
Get excited — your Community Manager will reach out with details and resources before you arrive.
Frequently Asked Questions
The retreat is designed to help you explore your next chapter, offering a blend of personal reflection and collaboration with a team of like-minded individuals navigating similar transitions. You’ll leave with greater clarity, inspiration, and actionable steps toward your “third half” of life.
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.
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.
Spend some time thinking carefully about what is motivating you to participate. Where are you on your Third Half journey? What aspects of your life are most important to you right now? What is going well? What are you hoping to change? These questions can serve as your launching point when we begin our time together.
Third Half retreats are immersive, growth-oriented experiences! Come prepared to be internally curious, to think deeply and creatively, and to be part of a warm community of people on a growth journey together. You can expect to leave with greater awareness of your current drivers, and a plan for building an authentic and fulfilling next chapter.
Our coaches are available for individual coaching sessions before, during, and after the retreat at an additional cost. You can schedule time directly with them, and we’ll also provide sign-up opportunities during the retreat.
Dress comfortably! Nature settings can help clear the mind and inspire fresh ideas. When possible and weather permitting, we may conduct portions of the retreat outdoors. Please bring appropriate clothing and carry layers that will allow you to move from indoors to outdoors with ease.
Third Half transitions touch all aspects of life, affecting life partners and other significant relationships. Couples have found that exploring this together can be enriching and powerful, in addition to a lot of fun!
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.
We understand that plans can change. Here is our Cancellation & Refund Policy.
For questions about Third Half Advisors, please reach out to Leighanne@thirdhalfadvisors.com. Leighanne will be happy to answer additional questions or arrange a virtual meeting with one of our coaches to help you explore your goals and see if this retreat will serve your needs. We’re excited to meet you!
For questions about The Good Life Abroad, click Get in Touch.
Yes — absolutely. While we schedule 2–3 community events per week (walking tours, local meals, happy hours, optional excursions, etc.), we build in plenty of “free time” so you can explore, relax, or immerse yourself at your own pace.
Yes. All participants have their own private, furnished apartment complete with a kitchen or kitchenette, WiFi, and included utilities.
All apartments are within the same building as other participants, so you have your own home base with the community just steps away — the perfect balance of personal space and nearby connection.
Your stay always includes:
A furnished apartment (with kitchen/kitchenette, utilities, WiFi).
Local living in a residential area with easy transit, close to cafés, shops, and local landmarks.
2–3 curated community events per week (walking tours, meals, social gatherings, etc.), plus optional weekly excursions or day trips.
Local support through a dedicated English-speaking Community Manager, personalized local recommendations, and assistance with travel health/insurance guidance.
Third Half Advisors Client Testimonials
See what past and current clients have to say about their experience with Third Half Advisors.
Based on 11 reviews
“The coaches and fellow participants were incredible! I walked away from the retreat with a clear set of ways I can make meaningful changes happen.”
Amelia
“This program is a critical exercise for anyone who is heading into their 60s. It invigorates your mind, body, and soul.”
Bob
“Third Half Advisors helped me begin the discovery process about what the next phase of my life could be.”
Jessica
“I left the retreat eager and motivated to take the next steps. I now have clarity and a concrete plan moving forward.”
Lilia
"Rachel is a coaching super-star! She turned us into collaborative team thinkers so that each of us experienced personal “aha” moments, new realizations and possibilities."
Lisa
“The retreat showed me how I can bring purpose and enjoyment to the Third Half of my life and made me excited to begin.”
Mac
“The program gave me great insights into myself, validated some decisions I was unsure of, and gave me confidence to execute on those decisions.”
Phil
“The coaches helped me develop a path for creative projects — with simple, actionable strategies to balance them with everyday retired life, and real hope for personal change.”
Richard
“With a structured process, the retreat gave me fresh ideas, new perspectives, and renewed energy to move forward.”
Sau
“This was invaluable in my transition to retirement, or rather, to my Third Half.”
Susan
“This retreat helped me create a plan to navigate important upcoming decisions — in a relaxed setting that fostered intense collaboration and brought real clarity.”
Frank