Retirement questions — Cortea Coaching and Consulting

Rewiring for Your Third Act – Top 10 Questions

Every transition into a new life stage starts by letting go parts of what you used to be, while exploring your interests, values, strengths and sensibilities that you want to explore and build on. It can also be useful to list all the things you did not enjoy and use their opposites as a way to narrow down preferences for your third act.

Free offer: Below are the top 10 questions to guide you through this process. I invite you to take a little time out of your busy day to write down the answers. If you click the send button and share them with me, I offer you a free 50 minute coaching session to help you start your journey.

If you prefer to simply download them, consider to discuss your answers with friends and family members, as their feedback may provide useful insights in to your next move.

1. Who inspires you? Why?

Look for a handful of people that were role models for you or that you admire, and describe why you admire them. Is it their social activism, sense of beauty, kindness, creativity? Find commonalities among them that explain your choices.

2. How would you like to be remembered?

Imagine you are 90 years old and tell your niece or grandchild about the things you did in your life that made you proud. Although we don’t want to think about our legacy yet, it’s a good way to drill down to the things that matter most.

3. Where does your sense of personal meaning come from now? Are you living in a way that is aligned with your values?

Personal meaning is often experienced as a sense of being part of a larger whole, and leaving our jobs can create a vacuum where we experience the loss of purpose. Reflecting on what gives us meaning is helpful for designing our next steps.

4. Which benefits among the 6 ‘S’ of working - structure in your day, salary, socialization, stimulation (intellectual) sense of purpose or status - will you miss most? Why?

Identifying what it is that you appreciate most about work can help you explore how to retain these benefits in your transitions to the third act.

5. What in your current job and day to day life gives you energy?

Consider activities that put you in the flow, meaning that you lose a sense of time and space when you do them (painting, listening to music, woodworking, writing, teaching etc). Which people and social situations energize you? Identifying what gives you a sense of vitality and agency will reveal what you are passionate about.

6. What are some of the things you’ve most enjoyed doing in your professional and personal life, and what do they suggest about what you might do next?

These don’t have to be big things. For example, if resourcefulness is your attribute and you enjoy helping other people, you may have enjoyed building connections and linking people with resources that were useful to them.

7. What activities did you like as a child?

One aspect of exploring new things during a transition is to dig for those that we liked in the past. Think about your favorite childhood activities - reading, playing games, piano, or spending time with your dog - and find those that still appeal to you today. They may become a joyful addition to your third act.

8. What would you do next if you knew you could not fail?

This question, originally attributed to First Lady Eleanor Roosevelt, acknowledges our fears and limiting beliefs that prevent us from exploring and trying out new tings. You might be surprised by the exciting possibilities for a third act that surface once doubt and fear fall to the wayside.

9. What are your strongest skills and expertise, and can you blend them with your personal interests?

There might be a novel way to use your professional skills in a totally different way. An example are angel investors who take a small stake in a start up in a field they feel passionate about in return for sharing their expertise and advice.

10. Which types of people do you most enjoy spending time with?

Most activities can become enjoyable when you do them with people you like, and conversely, interesting activities can be ruined by difficult people. What types of people do you like to be around the most? Young or old? Men or women? Funny or serious? Intellectuals or artists? Make a note of those whose company you have enjoyed the most and how you met them.

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