Transition creates possibility and vulnerability. Whether someone is moving toward retirement, a career pivot, empty nest, or a new phase of life, they're likely experiencing both excitement and fear. Your role is to help them dream honestly—not the sanitized version they think they should want, but the version that actually calls to them. Then help them identify what has to change for that dream to happen.
What excites you most about the next decade? What do you actually want to do or become?
Listen for energy. The answer might be specific ("I want to write a novel") or expansive ("I want to have the freedom to say no to things I don't care about"). Let them speak without interruption first. Then ask follow-up questions: "What makes that exciting to you? How long have you wanted this? Why now?" Sometimes their excitement points toward something they've been dismissing as impractical. Don't dismiss it. Sit with it.
What terrifies you about this transition? What could go wrong?
Fear is information. It points toward what they care about and what they need to address. Maybe they're afraid of irrelevance, or of letting people down, or of not having enough money, or of discovering they don't like themselves without their role. Don't try to talk them out of the fear. Instead, ask: "If that thing you're afraid of happened, how would you handle it? What would you need?" Sometimes the fear is realistic and needs planning. Sometimes it's imagined and needs examining.
In this next chapter, what do you want to be known for? What's the one thing you'd be proud to be remembered for doing?
This is legacy with a specific time horizon. Not "What do I want people to say at my funeral?" but "What do I want this chapter to mean?" They might say "being a good mentor," "solving a problem I care about," "being fully present for my family," "creating something beautiful." There's no hierarchy. But knowing this helps organize everything else. Ask: "What would it take to make that happen? What would have to change?"
What do you need to let go of to move into this next chapter? What are you still holding?
Identity, status, achievement narratives, old versions of themselves, people-pleasing, the belief that they need to earn their worth—these are the things people carry unnecessarily into new chapters. Ask: "What beliefs about yourself might not be true anymore? What are you proving? Who are you trying to impress?" Sometimes letting go is practical (stopping a role). Sometimes it's psychological (grieving an identity). Both matter. Help them understand what's being released and why.
Who do you want around you in this next chapter? What kind of people and what kind of relationships?
Transition is a time when relationships often shift. Some people drift; others become essential. Some new people enter. They might need different people than they've had before—people who challenge them, or people who are more present, or people who share new interests. Ask: "Do you have those people in your life now? If not, how could you build that? Who might you let go of?" This is personal; hold it gently. But it's also crucial for the next chapter to actually work.