For gay men over 50, a Palm Springs retreat creates space to rethink purpose and what comes next

For many gay men over 50, life can arrive at an unexpected crossroads — a moment shaped less by crisis than by quieter questions about connection, purpose, and what comes next. A new Palm Springs–based retreat aims to create space for men navigating that stage of life, offering time for reflection, conversation, and planning for the years ahead.

What Matters Next, a newly launched company founded in Palm Springs, is introducing a weekend retreat designed for gay men over 50. The effort comes amid research showing that LGBTQ+ adults ages 45 and older are 40% more likely than their non-LGBTQ+ peers to report feelings of loneliness.

The inaugural retreat will take place March 27 through 29 at the historic Dinah Shore Estate. Its founders say they see the gathering as the first in a series of retreats focused on helping people navigate significant life transitions.

It also arrives amid broader conversations about aging, longevity, and so-called “third acts.” For many gay men, those conversations are prompting a search for something beyond traditional social or recreational spaces — and toward opportunities that allow for deeper reflection, shared experience, and clarity about what lies ahead.

A response to a growing need

“For many gay men, this stage of life brings both freedom and unanswered questions,” said Paul Sherman, co-founder of What Matters Next. He said the retreat is intended to create space for honest conversation, reflection, and practical discussion about how participants want to move forward.

Sherman is a Harvard-educated executive and personal coach with more than 35 years of experience working with individuals and organizations navigating change. After relocating to Palm Springs eight years ago, he experienced what he describes as a pivotal period in his own life following a divorce that forced him to reconsider long-held assumptions about his future.

Approaching 60, Sherman found himself navigating a chapter he had not anticipated, one that required rethinking both personal and professional priorities.

“What I came to understand is this: life invites us to evolve, sometimes in ways we never would have scripted for ourselves,” Sherman said. “Change doesn’t always arrive gently. Sometimes it disrupts. Sometimes it redirects.”

Sherman said that shift in perspective ultimately helped him rethink what the next stage of his life could look like, and how to approach it with intention rather than resistance.

Building community through shared experience

The retreat is designed as a small-group experience, bringing participants together for guided discussions, interactive exercises, and shared reflection. Through facilitated sessions, attendees will explore questions related to purpose, well-being, and fulfillment, with conversations centered on identifying priorities and considering how to approach the years ahead.

“Many gay men reach this stage of life having achieved a great deal — professionally, personally, or both — and still find themselves asking deeper questions about meaning and connection,” said Soterios Rouman, another co-founder. “This retreat creates a structured environment where those questions can be explored alongside others facing similar transitions.”

Rouman brings his own experience of transition to the work. In 2017, at age 51, he retired after a successful career as an entrepreneur and executive and moved to Palm Springs with his longtime husband, expecting a quieter chapter ahead. Instead, his 26-year marriage ended the following year, upending plans he had long assumed were settled.

“Suddenly the retirement math had changed, along with everything else,” Rouman said.

With the support of a community of friends, Rouman said he worked through that period of uncertainty, eventually remarrying and launching a new career as an executive and personal coach. Those experiences now inform his role in shaping the retreat’s approach.

A vision shaped by lived experience

The third co-founder, Christian Winslow, adds another perspective shaped by both professional and personal change. Winslow has spent more than 25 years in corporate marketing and business development, including work launching new business initiatives and leading marketing efforts at the World Economic Forum in Davos.

A Yale graduate and San Francisco native, Winslow said his views on growth and reinvention were shaped by a series of defining experiences, including living through the AIDS crisis, navigating career shifts, caring for his parents near the end of their lives, and witnessing how relationships evolve over time.

Winslow said those experiences reinforced his belief that personal growth does not end at midlife, but often continues through periods of change and uncertainty.

Together, the three founders developed What Matters Next around shared experiences of transition and a common interest in how people navigate later stages of life. The retreat will also include guest speakers Dr. James Mellon, founding spiritual director of Global Truth Center LA, and Chad Ryan, founder of Atlas Training Co. in Palm Springs.

Palm Springs as a place of reflection

Palm Springs, long associated with reinvention and LGBTQ+ community, serves as the setting for the retreat. The Dinah Shore Estate, where the inaugural gathering will be held, offers a backdrop intended to support reflection and conversation.

Founded in Palm Springs, What Matters Next focuses on helping participants examine questions of purpose, connection, and well-being during later chapters of life. Sherman said the retreat is not framed as a solution to a problem, but rather as an opportunity for people to reflect together.

“This workshop isn’t about fixing anything,” Sherman said. “It’s about creating space to think honestly about the future, alongside others who are asking similar questions.”

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Details: The retreat is priced at $2,200 per attendee until Feb. 28. Registration includes continental breakfasts and Saturday’s lunch and gala dinner. Participation is limited due to the small-group format. Additional details, including the agenda and registration information, are available at www.whatmattersnext.com

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