As their conversation with Jamie Cain continues, Tracy Reynolds and Chris Maxwell think with Jamie about rejoicing well and grieving well. Many of life’s seasons are painful. Many are just what leaders are experiencing and enduring now. What can leaders learn? How can leaders respond? Leaders need honest, transparent, authentic friends. Leaders must not lead alone. Withdrawal is not the solution. Healing can come through writing, reading, and honest conversations. Shared pain and joy through Christ and His people offer leaders chances to guide others with the deep love of Jesus.