Top 10 Questions to Ask Someone Stuck in Transition.

August 7, 2021

Top 10 Questions to Ask Someone Stuck in Transition.

May 29, 2023

Currently, we’re in a collective transition that may be more profound than anything I’ve seen in my life. People are quitting jobs and changing careers. They’re moving from their homes or apartments. Ending relationships. Taking up new spiritual interests.

There’s a growing sense that time is of the essence, and we need to seize the day before it’s too late.

And while there may be those around you who seem to have the whole transition game mastered, there are many more who are feeling a crisis of confidence—wondering how to take that next step. Fortunately, with the right questions, it’s possible to not only become unstuck but to use these transitions to transform our lives into opportunities for growth and deeper meaning.

Whether you’re the one feeling stuck or you have a friend or family member who is, here are ten empathetic questions you could ask to get started (some of them based on the Appreciative Inquiry method of catalytic curiosity):

  1. What are the transitions you’re currently dealing with—what are their biggest obstacles, and how do you feel about each? Getting tangible about what you’re facing is the first step to working through your transitions. One of the chief findings in Bruce Feiler’s book “Life is in the Transitions” is that the top three emotions people struggle with during their transitions are fear, sadness, and shame. Guilt, anger, and loneliness also come up regularly.

  2. Do you have a friend who has successfully transitioned who could mentor you or be your role model? It often feels like we’re all alone when we’re going through transitions, but there are people who both care about you and may have some transition best practices they could share.

  3. Are you in the caterpillar, the cocoon, or the butterfly stage when it comes to your transitions? Cultural anthropologists studying rites of passage rituals distilled transitions into three stages: the ending; the awkward, liminal middle; and the new beginning. MEA’s Anatomy of a Transition lays this out based upon the insightful scholarship of Joseph Campbell, William Bridges, and others. Understanding the transition landscape might help you understand which stage you’re in, which will give you the awareness to be patient with yourself while you look for the right tools to navigate that particular stage.

  4. Who are you living for? Most of us have people renting space in our head giving us direction, and, often, it’s around midlife that we evict those squatters. Stop living someone else’s idea of how you should live. Follow the breadcrumbs to interests that bring up curiosity and passion and forget about what it looks like to others. They’re dealing with their own squatters.

  5. Is this a change or a transition you’re going through, and do you know the difference? Change is situational and circumstantial. Transition is psychological and spiritual. Change your boss or spouse, and two years later, you may be reciting the same complaints. Make a conscious, internal transition, and you won’t likely repeat the past.

  6. What are the things that brought you to where you are today but no longer serve you going forward? Is there a habit or mindset that is holding you back? Old tapes? Outdated ideas? Make peace with the identity or mindset that brought you to this place in your life, and then allow those that no longer serve you to drift away.

  7. What do you know (or have done) that you wish you’d known or had done ten years ago? Similarly, what’s something you can pursue now that, ten years from now, you’ll regret you didn’t learn or do now? Anticipated regret is a painful but powerful motivator.

  8. Is perfectionism or impatience getting in your way? Feiler’s work shows that the average adult transition takes three to five years, so don’t expect to emerge from the cocoon overnight. But there are tricks to accelerating the metamorphosis process, and being perfect isn’t one of them.

  9. How can you ritualize your progress? Two steps forward, one step back. Knock me down seven times, get up eight. It’s easy to get disappointed by setbacks. Yet, few of us practice celebrating our progress, especially with those who are here to support our transition. Rituals can be cathartic and energizing.

  10. Paint the picture of what your life will look and feel like when you’re on the other side of this transition. Would you be open to writing a parable of your life moving forward, starting with “Once upon a time…?” Sometimes, we need to be the “first-class noticer” of our own lives, the enlightened witness and prognosticator. And, when we infuse that storytelling with our passion and dreams, it can be a powerful combination. Trust what your intuition conjures up.


For those of you eager to dive into the concept of transitions in a more structured format, our MEA Online course, Navigating Midlife Transitions, starts Oct 2 and will help you navigate the most common transitions in your work, relationships, health and more.

Our 8-week course can easily go with you if you’re traveling or we can bring the world to you at home. With live and recorded sessions, you get the best of both worlds with a new community to support you through the biggest transitions we all face.

Take advantage of our early bird pricing of $750 before the price climbs to $999. Learn more and reserve your early bird spot here.

Go deeper with a workshop, in person or online.

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