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21 Questions People Ask During Life Transitions

Life transitions are hard. It brings up many questions.

Having worked with over over 1,000 people over the years, here are some of the top questions we explored during our coaching sessions. Some individuals are also considering retirement.

The answers to each of these questions are highly personal and unique, making it impossible to provide a one-size-fits-all solution. Everyone is at a different stage in life, with their own experiences, goals, and dreams.

These are important questions to ask ourselves. If you need support in delving into any of them, please let me know.

Self-Assessment and Exploration:

  1. What do I truly enjoy doing?

  2. What are my strengths and skills?

  3. How do I figure out what I want to do next?

Career Transition:

  1. Should I stay in my current field or switch industries?

  2. What new skills or education do I need?

  3. How do I build a network in a new field?

Job Search and Marketability:

  1. How do I update my resume for a career change?

  2. What are the best strategies for job hunting in a new field?

  3. How do I handle potential gaps in my employment history?

Financial Considerations:

  1. Can I afford to make a career change?

  2. How does this transition impact my retirement plans?

  3. Should I take a pay cut to pursue a new career?

Retirement Planning:

  1. When is the right time to retire?

  2. Do I have enough savings to retire comfortably?

  3. What will I do with my time in retirement?

  4. How do I transition from a full-time job to retirement?

Personal Fulfillment and Well-Being:

  1. What activities will keep me engaged and fulfilled?

  2. How do I maintain social connections in retirement?

  3. How can I stay healthy and active during retirement?

Professional Guidance:

  1. Would a career coach or financial advisor help me?

  2. How do I handle the emotional aspects of retirement?


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