43 Questions to Ask a Retired Person

Retirement is a stage of life that many people look forward to. It is a time to relax, pursue hobbies and spend time with family and friends. For some, however, retirement can come as a shock.

Suddenly, they have so much free time, and they do not quite know what to do with it. If you know someone who has recently retired, here are questions you can ask them to help them adjust to this new stage of their life.

25 Questions to ask a person about their retirement:

  1. How did you know it was time to retire?
  2. What are you most looking forward to now that you are retired?
  3. What plans do you have for your retirement?
  4. How do you think retirement is different from working life?
  5. Do you have any concerns about retirement?
  6. What are your hobbies?
  7. Do you plan to take up any new hobbies now that you are retired?
  8. How do you plan to spend your days?
  9. Do you sometimes feel bored or lonely now that you are no longer working? If so, how do you combat these feelings?
  10. Have you ever thought about volunteering now that you have more free time?
  11. Do you think you will travel more now that you are retired?
  12. What places would you like to visit?
  13. Do you have any relatives or friends you would like to spend more time with now that you are retired?
  14. What advice would you give to someone who is about to retire?
  15. How do you think your lifestyle will change now that you’re retired?
  16. Will retirement allow you to finally have the time to pursue something you are passionate about outside of work?
  17. Do finances play a role in your decision to retire? How so?
  18. Are there any downsides to retirement that you had not considered before retiring?
  19. How do you feel now that retirement has arrived? Excited, anxious, happy, relieved, etc.?
  20. What do you think is the key to a happy and fulfilling retirement?
  21. Is there anything about retirement that you have found unexpectedly difficult to get used to? If so, what is it?
  22. How has retirement changed your daily life?
  23. What sources of income did you have in retirement?
  24. What financial advice would you give to someone approaching retirement?
  25. Do you have any regrets about retiring? If so, what are they?

18 Questions to ask a retired person about their work before:

  1. What did you enjoy most about your job?
  2. What did you dislike most about your job?
  3. Is there anything you wish you had done differently during your working years?
  4. What have you learned from your most challenging experiences at work?
  5. How did you develop such a successful career?
  6. What would you have done differently if you could go back to the beginning of your career?
  7. How did you balance work and life throughout your career?
  8. Did you ever experience any major setbacks or challenges in your career? If so, how did you overcome them?
  9. How did you make important connections in your industry?
  10. Who have been some of the most influential people in your career?
  11. Have you ever experienced age discrimination in the workplace?
  12. Did you ever take a pay cut or make other major sacrifices for your career?
  13. Do you have any funny or memorable stories from your time on the job?
  14. Who have been your favorite people to work with over the years?
  15. Who were some of the most challenging people to work with?
  16. Was there ever a time when you didn’t feel supported by your employer or colleagues? If so, how did you deal with it?
  17. Did you ever have to take on extra duties at work due to staff shortages or other reasons? If so, how did you handle it?
  18. What advice would you give to someone who is just starting in their career?

Frequently Asked Questions

What are the common fears of retirees?

Some common fears of retirees are that they will run out of money, become ill, and not be able to take care of themselves and that no one will be there for them. These fears can keep people from retiring when they want to, or cause them to retire earlier than they planned. It’s important to discuss these fears with a financial planner or advisor to get a better idea of what your specific risks are and how to mitigate them.

What risks or challenges do current or future retirees face?

One challenge for current retirees is that their savings may not be sufficient. This can be especially problematic if they haven’t planned for it and do not have a solid retirement plan. Retirees also face rising healthcare costs, which can be a major burden on a fixed income.

Another challenge is staying healthy and mobile as one gets older, which can be difficult if retirees do not have access to good health care. Finally, some retirees may find themselves isolated and lonely after retiring. This can be particularly challenging if they do not have a solid social network.

What are the negative effects of retirement?

The negative effects of retirement can include social isolation, boredom, and a lack of purpose. Retirees may find themselves without the structure of work and with too much free time. This can lead to a decline in physical and mental health. Retirees may also lose their sense of identity and purpose in life.

What do you need to do before you retire?

The important thing to do before retiring is to create a plan. Determine how much money you need to live comfortably, what your expenses will be, and when you want to retire. Once you have a plan, start saving as much money as you can. Be sure to factor in inflation and unexpected expenses. Retirement may be a long way off, but it’s important to start planning for it now.

Why is retirement planning important?

Retirement planning is important because it allows you to save for your retirement. This way, you have a cushion in case you do not have enough saved when you retire. In addition, retirement planning can help you plan for other expenses that may arise during retirement, such as health care costs.


Retirement is a huge life transition and it’s normal for retirees to feel a range of emotions during this time – from excitement and joy to fear and anxiety. Asking questions about their plans and feelings can help them adjust and make the most of their retirement years!

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