EP. 24 | Ending Well: How to Navigate the Closing Chapters of Discipleship

In this episode of the Ordinary Discipleship Podcast, Chris, Jacob, and Jessie dive into a topic many avoid—how to navigate the endings of discipleship relationships. While the beginning of a mentoring journey is often exciting, knowing when and how to conclude a season of discipleship can be challenging.

Together, they explore these key questions:

  • How do you discern when a discipleship relationship should change or end?
  • What does a healthy, fruitful ending look like?
  • How can you redefine the relationship without losing the good work God has done?

With personal stories and practical wisdom, Jessie shares insights on recognizing when a season is shifting and the importance of marking endings with intentionality—what she calls a “rite of passage.” Whether you’re a seasoned disciplemaker or just beginning, this conversation will equip you to navigate these transitions with grace and clarity.

ORDER Jessie’s newest book, Ordinary Discipleship: How God Wires Us for the Adventure of Transformation → https://a.co/d/51j86DG

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Jessie Cruickshank is a disciple-maker, wilderness guide, and ordained minister. She has trained thousands of people how to survive when their life depended on it and earned a Master’s degree in experiential education at Harvard to learn how the brain works to help people train more effectively.

The key to discipleship is not more information, but learning how to create intentional environments where people can learn and grow. By working with the brain and treating individuals as whole persons, you too can discover how God wired our brains for transformation. You already have all the tools you need, it is time to activate them in you and your church.

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