In my practice as a career coach I recently saw a client who was considering leaving her 30-year career. She said, “I don’t know how to even begin thinking about moving on.” She is a talented professional who has had a lot of career success and is accustomed to feeling clear-headed about making decisions. Facing a transition after a successful career, she needed to know where she was heading rather than just what she was leaving.

I find that people are rarely as genuinely confused as they feel. Facing a transition, even the most successful professional can be feeling uncertain – UNclear – about their future and the next steps they want to take. Sometimes it’s a matter of asking yourself the right questions. When you’re considering a major transition – going from a successful full-time career to a post-career lifestyle –  these questions can help you find answers:

Social Questions

  • Where do I want to live?
  • Do I want to move to a new geographic location?
  • What impact will that have on my family and my network of friends?

People in transition have the opportunity to ask themselves if they’d like to move closer to family, to move to their second home or just to get a cheaper and more convenient house. Geography matters, but it’s only part of the picture. Many people move happily and create a wonderful new life. But others struggle to replace their supportive social network, familiar doctors and local church or synagogue.

Physical Questions

  • What is my current health situation?
  • Do I need a physical tune-up?

A transition after a successful career takes physical and emotional stamina. Most people who come to see me are more physically tired than they realize. Many people have put off visits to health professionals and neglected any regular exercise. Too bad. Exercise releases endorphins that increase a sense of well-being.

Spiritual Questions

Transitions often suggest issues of identity, meaning, and purpose. “Who am I now” is a spiritual question and is particularly relevant for my baby boomer clients who are leaving long-term careers. People who are leaving first careers with 20-30 productive years ahead of them often want to look at the “why” of their lives. Meaning matters.

Psychological Questions

  • Am I ready to leave?
  • Do I have a clue about how I am going to feel during the transition?
  • Do I have a passion for something I want to do or am I just bored?

One of the smartest people on the issue of transition is the author William Bridges. He says that change is an event, but that transition is a psychological process because it involves a shift in identity. After thirty years in a career, it is easy to get attached to your title, your agency, or position. Leaving behind that kind of validation is by definition anxiety provoking.

Financial Questions

  • Can I afford to retire?
  • Do I have a solid financial retirement plan?

Money is essential, but not the whole story. My advice is to get a part-time job that you love. It takes some creativity to figure out what you love to do, but getting paid to do it is the best hedge against financial worries. There are lots of different ways to be part-time. Be creative.

Success Factor Questions

  • Will I love what I am doing?
  • Am I competent to do this new work?
  • What additional education or preparation do I need?

Success at this stage of life is about being happy and useful in a way that makes sense to you. There is no one right way. There’s only a way that works for you. Don’t think small about your next stage. There are going to be 78 million stories in the naked city. Make sure that yours is one you’ll enjoy telling.

Peter Sherer is a nationally recognized career coach who offers clarity and confidence to mid-career and senior executives in transition. His rigorous assessment tools enable his clients to identify a meaningful assignment that uses all of their skills and experience in just two short days. Learn more and get in touch with Peter today.