Coaching
Circle

The Retirement Rehearsal

Preparing for more than just financial freedom.

Thursday's
/
November 19, 2026
-
December 17, 2026
/
5:30-7:00 PM
The Retirement Rehearsal is a 6-week coaching circle for people approaching retirement or asking deeper questions about what comes next. Together, we explore identity, purpose, relationships, health, structure, and meaning beyond work. Through guided conversation, reflection, and practical exercises, participants begin designing a next chapter worth arriving into.

About this circle:

Preparing for more than just financial freedom.

Most people spend decades planning financially for retirement.
Far fewer spend time preparing emotionally, relationally, or practically for the life that follows.

And yet, one of the biggest transitions of adulthood is rarely talked about honestly.

Who am I beyond my work?
What will give my days shape and meaning?
How do relationships change when schedules do?
What happens when achievement is no longer the primary driver?
What kind of life do I actually want to build now?

The Retirement Rehearsal is a guided six-week coaching circle for people approaching retirement, semi-retirement, or simply sensing that the next chapter of life deserves more intention.

This is not a financial planning seminar.

It is a thoughtful, practical, and deeply human conversation about identity, purpose, relationships, health, rhythm, contribution, and what it means to create a life worth arriving into.

Over six weeks, participants will explore:

  • the emotional side of retirement and transition
  • redefining identity beyond career
  • creating meaningful structure and rhythm
  • relationships, friendship, and community
  • purpose, contribution, and curiosity
  • health, energy, and longevity
  • unfinished dreams and postponed parts of self
  • what a fulfilling “third act” could actually look like

Each 90-minute session includes:

  • a short teaching or reflection
  • facilitated conversation
  • coaching questions
  • practical exercises
  • peer discussion in a trusted small-group setting

Participants can expect thoughtful conversation, meaningful reflection, practical insight, and the rare opportunity to explore these questions alongside others asking similar things.

Inspired by the ideas and thought leadership found in From Strength to Strength (Arthur C. Brooks), Falling Upward (Richard Rohr), The Good Life (Robert Waldinger & Marc Schulz), and Life Is in the Transitions (Bruce Feiler), this coaching circle explores what it means to navigate the second half of life with greater intention, meaning, and courage.

Thursday's
/
November 19, 2026
-
December 17, 2026
/
5:30-7:00 PM

You are:

  • approaching retirement
  • recently retired
  • considering semi-retirement
  • navigating questions of meaning, identity, or next steps
  • wanting to be intentional about the second half of life

This circle could be for you if ...

The format: Here's how it unfolds

  • 6 Weeks
  • 90-Minute Sessions
  • Small Group Coaching Circle
  • Guided Reflection Exercises Included
  • The Benefits

    What you'll walk away with

    ABOUT Coaching CircleS
    Our six-week coaching circles are designed for honest, insightful conversations that help us rethink, recalibrate, and grow.

    Each week, for 90 minutes on Zoom, you’ll be part of a small group of 6-10 people, all here to explore ideas, challenge assumptions, and support each other’s learning.

    With both day and evening options, everyone has the space to contribute, reflect, and leave with practical takeaways that reshape how we approach work, relationships, and life’s bigger questions.

    Facilitated by

    Peter Reek
    Peter Reek is the author of SHIFT and the founder of ShiftInto.Life and The SHIFT Sessions. With decades of leadership and coaching experience, his work focuses on helping people navigate midlife as a season of clarity, meaning, and possibility. Through coaching, community, and shared language, he supports individuals in making thoughtful, deliberate choices for the second half of life.
    Coaching Circle
    The Retirement Rehearsal
    Preparing for more than just financial freedom.
    Thursday's
    /
    November 19, 2026
    -
    December 17, 2026
    /
    5:30-7:00 PM
    $
    350
    +
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