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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?

Brooke O. Erol
Brooke O. Erolhttps://www.purposeful.business/
Brooke O. Erol started her career at IBM following the traditional path she was given to be "successful". She quit her "great job" on paper after 11 years, feeling she is not aligned with it. She started her journey to find her purpose in life. She started her first business in 2003; Your Best Life to help professionals who don’t like their jobs and want to find more meaning at work. After being around so many unhappy people at work as her clients, she decided to help the organizations and leaders who employed them. She started her second business; Purposeful Business to help leaders catch up with our times and grow their businesses without sacrificing the well-being of their people; where profit becomes a by-product rather than the main goal. She believes life is too precious to live only for weekends and retirement. She is the author of Create a Life You Love. She is also the co-author of "From Hierarchy to High Performance: Unleashing the Hidden Superpowers of Ordinary People to Realize Extraordinary Results" that became an International Best Seller in 2018. She speaks and writes about Leadership, Purpose-Driven Life and Organizations, Future of Work in the US, and abroad.

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