Design Your Good Life Retreat in Lisbon, Portugal

Design Your Good Life Retreat in Lisbon: Webinar Recap

What happens when expert life design coaching meets two weeks of authentic living in one of Europe's most beautiful cities? We explored exactly that.

Recently, The Good Life Abroad founder Andrew Motiwalla hosted a special webinar alongside Dr. Rachel Bishop, a certified coach and facilitator at Third Half Advisors, to introduce a first-of-its-kind specialty program: the Design Your Good Life Retreat in Lisbon, Portugal.

If you missed it—or want to revisit the highlights—here's everything covered.

What Is the Design Your Good Life Retreat?

This unique two-week program is a partnership between The Good Life Abroad and Third Half Advisors, blending two powerful experiences into one:

1. The Good Life Abroad's signature community living model — 14 nights in a modern, vetted apartment in Lisbon's culturally rich Chiado neighborhood, surrounded by a built-in community of like-minded travelers aged 55+.

2. A four-day life design retreat facilitated in person by Dr. Rachel Bishop, woven into the middle of your two weeks abroad.

The result is an immersive experience that's equal parts cultural adventure and intentional self-discovery.

Why Lisbon?

Andrew shared why Lisbon is the ideal backdrop for this kind of program. The Chiado neighborhood places you within walking distance of historic plazas, local restaurants, grocery stores, and the city's iconic streetcars and metro lines. The city is compact and walkable—though famously hilly, so pack those good walking shoes.

The apartments are fully furnished, modern, and specifically vetted for the comfort of adults 55+: think walk-in showers, full kitchens, spacious living areas, and elevator access. Everyone stays in one of two buildings right around the corner from each other, so your community is literally next door.

And Lisbon's temperate climate, riverside breezes, and world-class pastéis de nata? Those are just a bonus.

What Does a Typical Two Weeks Look Like?

The program kicks off with an orientation morning, a historical walking tour of Lisbon's neighborhoods, and a welcome party that evening. From there, your days are a beautiful blend of independent exploration and community events—all optional, none mandatory.

Included activities throughout the two weeks:

• Neighborhood walking tours

• Happy hours and rooftop gatherings

• A hands-on cooking class exploring Portuguese cuisine and culture

• Community lunches in local neighborhoods

• The four-day life design retreat (mornings, leaving afternoons and evenings free)

• A farewell dinner and party to close out the experience

And connecting it all is the WhatsApp community group, where participants organize book clubs, morning runs, affinity outings, and everything in between.

Who Is Third Half Advisors?

Dr. Rachel Bishop introduced Third Half Advisors as a company specializing in helping people plan their next chapter—everything beyond the financial planning side of retirement that often gets overlooked. Their approach is high-touch, personalized, strengths-based, and purpose-driven.

The name "Third Half"? It's not bad math—it's a philosophy. Life has more than two halves, and the third is yours to design.

Their community is nearly 1,500 people strong, and their programming includes life design retreats, virtual milestone programs, corporate succession coaching, and an expert panel of advisors covering topics from where to live in retirement to legacy planning and publishing books.

The Four-Day Life Design Retreat

Rachel walked attendees through the arc of the retreat, which takes place over four half-days (leaving afternoons and evenings completely free for exploration):

Day 1 – Taking Stock You'll reflect on where you are right now. What motivates you? How are you spending your time? Using tools like the Clifton StrengthsFinder assessment and Third Half's own values-to-time decision matrix, you'll start identifying gaps between how you're living and how you want to be living.

Day 2 – Ideation This is the creative, playful part. Participants brainstorm possible futures—dream big, filter nothing. Rachel shared that this often surfaces long-dormant passions and interests that got sidelined during working and family-raising years.

Day 3 – Prototyping Using concepts from the Designing Your Life framework developed at Stanford's Design School, participants move from big dreams to small, low-risk experiments. The goal isn't to make sweeping life changes overnight—it's to try things on, talk to people, and test ideas before committing to them.

Day 4 – Action & Accountability You leave with concrete next steps: the people you want to talk to, the experiments you want to run, and an accountability plan to keep the momentum going.

Rachel was clear: no goal is too small, and no goal is too big. Whether you're trying to carve out time for a creative passion at home, consider a move abroad, launch a new project, or simply feel more purposeful in your days—this retreat is designed to help you get there.

Why Combine These Two Programs?

Andrew put it well: "The informal moments—over a meal or a drink, bouncing ideas off Rachel directly—that access alone is pretty extraordinary."

The retreat benefit of being somewhere unfamiliar is intentional, not incidental. When you step out of your familiar environment, you step out of familiar thinking patterns. New places invite new possibilities. And doing this surrounded by a small cohort of like-minded travelers—people who came because they love to explore and because they want to be intentional about what comes next—creates a uniquely powerful dynamic.

Past retreat cohorts have stayed connected for years. Three participants from one retreat, Rachel shared, recently went on a biking trip together—from different states, years later.

Who Is This For?

This program is designed for adults 55+ who:

• Finally have the freedom to intentionally design their next chapter

• Want to travel meaningfully, not just check destinations off a list

• Are looking for greater purpose, connection, or creative expression in their days

• Would benefit from slowing down, reflecting, and envisioning what a fulfilling future actually looks like for them

Solo travelers are enthusiastically welcome, as are couples. The cohort is intentionally small—capped at 15 people—to preserve the intimacy and personalization that makes the retreat so effective.

What's Included in the Program Fee?

• 14 nights in a modern, fully furnished apartment in Lisbon's Chiado neighborhood (1- or 2-bedroom options available)

• High-speed Wi-Fi and smart TVs in all apartments

• All community activities and events (walking tours, cooking class, happy hours, lunches, welcome and farewell parties)

• Support of your local Community Manager, Vera, a Lisbon expert available Monday–Friday

• The four-day life design retreat with Dr. Rachel Bishop

• Travel medical insurance

Not included: airfare, airport transfers (Uber is plentiful and affordable in Lisbon), groceries, phone service, and any personal weekend travel.

Ready to Learn More?

This program is listed under Specialty Programs on the Good Life Abroad website, and spots are limited to 15 participants. If you're curious but not quite sure if it's the right fit, you can request a one-on-one discovery call with Dr. Rachel Bishop directly through the website—no pressure, just a conversation.

You can also reach the Good Life Abroad team at info@thegoodlifeabroad.com or by phone at (866) 668-9579.

Explore the Design Your Good Life Retreat →

Want to talk directly with Dr. Rachel Bishop about whether this retreat is the right fit for you? Email Leighanne@thirdhalfadvisors.com to schedule a one-on-one discovery conversation.