My Reunion Tour
The Program was Lived before it was Led
In 2020, at 59 years old, something broke.
I had spent my adult life as an achiever — a builder, a launcher, a person who could always find a way forward. That identity had served me well. It had also quietly become my entire sense of self.
Then I relaunched a business with confidence. And it produced nothing. Months of silence. Not one client. The coping mechanism I had always relied on — the one that had never truly failed me — stopped working.
That was the beginning of My Reunion Tour.
What followed was five years I could not have engineered: a season of honest reckoning, Ignatian formation, spiritual direction, lament, and the slow, daily writing of nearly 1,000 poems chronicling a transformation I didn't choose but came to receive. It ended with a ceremony — a speech I wrote for no audience, then eventually delivered to the people I love — naming who I had been, honoring what that person had built, and committing to become someone different.
I am not the same person who started that journey. And most people who know me now have never met the person I was.
"My Reunion Tour is not a program I developed. It is a journey I survived — and came to love. I am still on it. I just have five years of unfolding to share."
Every element of this program — every season, every tool, every invitation — has been walked before it was offered. That is the only credential that matters here.

How this Journey Began
Loyal Soldier
By honoring an identity that once served an earlier version of life, Winston finds new freedom in retiring his Loyal Soldier through a powerful process.
oneLife Maps™
Mapping out significant peaks and valleys of life helps Winston notice how God was using all of his experiences for a greater purpose.
Spiritual Direction
Winston discovers how Spiritual Direction helps him navigate a challenging season by walking with his spiritual companion, Sibyl.
The Journey: Four Seasons
My Reunion Tour is a group-based, faith-grounded program for people in midlife and the second half of life who are navigating an identity transition. It is not a curriculum to complete. It is a companioned pilgrimage — held in small groups, paced by the Spirit, and designed to give every person exactly what they need to move at their own pace toward wholeness.
The journey moves through four seasons. Each is a complete experience. No one is rushed between them.
Season One
REMEMBER
Mapping the terrain of your life. Discovering what formed you.
Season Two
RECOGNIZE
Naming what no longer fits. Seeing beneath the surface of the identity you have carried.
Season Three
RELEASE
Honoring what was — and committing to what will be. Moving toward a ceremony of release.
Season Four
REUNION
The ceremony. The life beyond it. An ongoing community with no graduation date.
What the Journey Looks Like
My Reunion Tour is a group-based, faith-grounded program for people in midlife and the second half of life who are navigating an identity transition. It is not a curriculum to complete. It is a companioned pilgrimage — held in small groups, paced by the Spirit, and designed to give every person exactly what they need to move at their own pace toward wholeness.
The journey moves through four seasons. Each is a complete experience. No one is rushed between them.
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Small Groups: Cohorts of 6–8 people, held in a group spiritual direction model — listening without fixing, present without advising. The community itself is the container.
- Your Pace: Month-to-month enrollment. No contracts. No pressure to advance before you're ready. Off-ramps are not failures — they are honored pauses with a standing invitation to return
- Daytime Sessions: Sessions are offered during daytime and late afternoon hours. This is a program designed to honor the energy of both guide and participant.
- Winston's Presence: Not a course delivered from a distance. Winston is a companion first, a teacher second. He is still on this journey. You will know that from the first conversation.
It's your tour. Your journey. You're right where you're supposed to be.
Spiritual Direction
Not everyone arrives ready for the group journey. Some people need a quieter on-ramp — a season of one-to-one companionship before stepping into community. Others simply desire the gift of spiritual direction on its own, separate from any program.
Both are welcome here.
What Is Spiritual Direction?
Spiritual Direction is a sacred conversation — not coaching, not counseling, not a checklist. It is a space created for one purpose: to slow down, listen deeply, and notice where God is already at work in your life.
Sessions begin in stillness rather than agenda. Instead of advice or problem-solving, you are gently invited to pay attention to the still, small Voice that is always present — and often unheard in the noise of a busy life.
Winston discovered spiritual direction during the same season that gave rise to My Reunion Tour. It changed the way he listened — to God, to others, and to himself. He brings that same quality of unhurried presence to everyone he companions.
How Spiritual Direction and the Journey Relate
Spiritual direction and My Reunion Tour are deeply connected — but they are not the same thing.
Here is how they fit together:
As a Bridge into the Program
Some participants finish Season One and feel the restlessness — but aren't yet ready for community. A season of individual spiritual direction with Winston provides the one-to-one space for recognition to deepen before stepping into the group.
Alongside the Program
Individual spiritual direction or coaching is strongly encouraged as a companion support during Seasons Two and Three. Winston can offer this directly, or connect participants with trusted directors from his own network.
On its Own
Spiritual direction is available to anyone, independent of the group program. If you are not sure whether the full journey is right for you — or if you simply desire a steady, contemplative companionship — this is a meaningful place to begin.
Your journey back to God's heart begins with a single conversation. Winston offers a complimentary overview session for anyone curious about spiritual direction — no commitment, no pressure. Just a first, honest conversation.
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