Wise Gatherings: Building Meaningful Connections in Retirement

December, 2024

Over the years, I’ve come to realize the immense power of small, intentional groups. These “wise gatherings” have been a cornerstone of my personal and professional life, and now, as a semi-retiree, they remain a source of connection, growth, and joy. Today, I want to share what I’ve learned about creating and sustaining these groups, drawing from my own experiences, and invite you to consider how wise gatherings could enrich your life, too.

The Birth of a Wise Gathering

My journey with small groups began in 2003 when I attended a career coaching conference. Daniel Pink, a thought leader and author of Free Agent Nation, delivered the keynote. His talk was fascinating, but one part stuck with me: his discussion about the challenges of free agency, including social and intellectual isolation, limited resources, and self-absorption. These downsides mirror what many solo entrepreneurs and retirees face, and his proposed solution F.A.N. (Free Agent Nation clubs) piqued my interest.

Inspired by Pink’s idea, I gathered four of my former career transition clients who were each pursuing entrepreneurship. We formed a quarterly F.A.N. club, meeting every three months, to share resources and ideas about navigating self-employment. It was energizing to connect with others facing similar challenges, and this initial experiment planted the seed for what I now call wise gatherings.

A Lifelong Experiment in Connection

After two years, I decided to take things further. I invited seven peers, all career coaches with an interest in independent practice, to join a monthly mastermind group. For 18 years this group has been, and remains, a consistent source of inspiration, problem-solving, and camaraderie.

We meet monthly, often over “happy hour,” rotating between restaurants and each other’s homes. Occasionally, we’ve ventured further, organizing summer retreats or holiday gatherings. What makes this group special is our shared commitment to mutual support. We talk about business strategies, offer feedback, and celebrate each other’s milestones. It’s like having a personal board of directors, a group of people who have your back and want to see you succeed.

Stories from the Front Lines

Let me share two stories that highlight the value of these groups.

The Pink Party F.A.N. Club

One of my favorite early experiences was with our quarterly F.A.N. club. I started this group with four people who had all received pink slips. One of the members decided to throw a “pink party” and invite several of her friends and former colleagues who had received their own pink slips. We all arrived in pink outfits that night and shared stories and laughter.

I remember how we once invited Daniel Pink himself to join one of our meetings. To our surprise, he accepted! For an hour, we discussed the ups and downs of self-employment while he shared and gathered insights for his next book. It was surreal but also deeply affirming. That moment crystallized for me how small groups could be transformative, not just for solving problems but also for building confidence and fostering creativity.

The True North Experiment

Years later, I started another kind of group, inspired by the True North Groups book, by Bill George and Doug Baker Sr. This time, I wanted a mix of personal and professional development. I invited 13 people, friends, colleagues, and clients, to join me in a nine-month experimental group.

The structure was simple but powerful. Every monthly meeting began with three-minute check-ins, when each person (timed with my trusty phone timer) shared how they were doing since the last session. Following this, we would move to a deeper topic, often facilitated by one of the members.

At the end of the nine-month experiment, eight of us decided to commit long-term. Today, this same group has been meeting for nearly a decade, tackling more than 100 topics and becoming a trusted circle of friends. The trust and vulnerability we’ve cultivated are rare and precious qualities that make this group a true north for me.

The Secret to Wise Gatherings

Looking back, I can distill my years of experience into ten lessons for creating successful gatherings:

1. Choose the Right People:
Find members who are both interested and interesting. These are people who listen actively, engage deeply, and contribute thoughtfully.

2. Define the Group’s Purpose:
Agree on your mission and membership criteria. Whether it’s professional development, personal growth, or intellectual curiosity, clarity is key.

3. Have a Champion:
Every group needs someone to lead and organize—someone to keep the train on the tracks.

4. Experiment First:
Start with a trial phase. This allows everyone to test the fit before committing. My nine-month experiment with the True North Group was essential for its long-term success.

5. Set Ground Rules and Structure:
Behavioral guidelines help maintain focus and respect. Tools like a timer can ensure everyone gets their turn to speak.

6. Be Consistent:
Regular meetings at a set location and time build reliability. Over time, this routine becomes a comforting rhythm.

7. Adapt as Needed:
Flexibility is vital. During the pandemic, for example, many group meetings shifted to Zoom, ensuring we stayed connected.

8. Share Leadership:
Rotate facilitation to avoid burnout and bring fresh perspectives to the group.

9. Balance Seriousness and Fun:
Wise gatherings should nourish both the mind and the heart. Laughter and light-hearted moments are just as important as deep discussions.

10. Foster Trust and Vulnerability:
Create a safe space where members feel comfortable sharing their true selves. This is the foundation of any successful group.

Beyond the Meetings: The Portfolio Life

As I transitioned into semi-retirement in 2019, I embraced what I call a “portfolio life.” This means balancing part-time work, learning, giving, health, and leisure. Wise gatherings fit seamlessly into this model. They provide opportunities to learn from others, giving back through mentoring and group facilitation, and enjoying healthy and meaningful social interactions.

Whether I’m a student or instructor in an OLLI (Osher Lifelong Learning Institute) class, participating in a mastermind entrepreneurial group, a special interest group, or catching up with friends and digging into an important topic over a True North session, these gatherings enrich my life in countless ways.

My Invitation to You

If you’re a retired, semi-retired, or soon to be retired lifelong learner, I encourage you to explore the idea of wise gatherings. Whether it’s starting or joining a book club, a peer mentoring group, a discussion circle, or taking an adult education class, the possibilities are endless. Start small, experiment, and see where it takes you. The rewards—a sense of belonging, personal growth, and shared wisdom—are well worth the effort.

Let’s create spaces where we not only learn from each other but also grow together. Wise gatherings have transformed my life, and I believe they can do the same for you. So, what will your gathering look like?