Retirement Answer Man

On this episode of Retirement Plan Live: Flying Solo Edition we tackle a challenging question. Is retiring single risky? This episode is all about risk and the special or riskier situations that retired singles may find themselves in. Single people have different considerations than married people and may need to plan their retirement in more detail. I ask Sam, my guest, and case study for this edition of Retirement Plan Live, about what types of concerns she has retiring single. You’ll want to make sure that you listen to this episode so that you can begin to think about all of the circumstances you may encounter when retiring single.

Should you embrace risk or hide from it?

There are risks to everything in life, but to live a full life you have to take on a certain amount of risk. If you run away from risk entirely you end up living a smaller life. The more you embrace risk the more it can broaden your life. There is a certain amount of freedom that comes with being a single person. You don’t have anyone that you need to check in with, you can travel whenever and wherever you want. But there are situations that a single person needs to prepare for more than a married person. Listen to this episode of Retirement Answer Man to start thinking about how much risk you are willing to take in your retirement and your life.

What are some of the normal risks that are increased for singles?

Retired singles have an increased chance of loneliness as they age. You can begin to combat loneliness in your elderly years by establishing a strong network of friends now. Making friends with similar interests is easy to do. There are groups and clubs for just about every hobby, even solo activities like knitting and fishing can be enjoyed with others. Another consideration you may not have thought of is whether or not you have someone to use as a sounding board for big decisions. Making life altering decisions can be a challenge and it is always helpful to have someone you trust to help you talk things out. Listen to this episode to hear several considerations that you may not have thought of that you will need to plan for as a single person.

How do you plan your estate when you’re single?

If you don’t have any heirs you may think that what happens to your estate doesn’t really matter, but you do need to think about who you would like to be the executor of the estate. There are professionals that can be hired to do this job if you don't have anyone to ask. Long-term care insurance is a good option when thinking about what will happen when to you when you are no longer able to care for yourself. But have you considered who will have power of attorney and can handle the personal medical decisions that may be faced if you are incapacitated? This episode may not be as fun as the dreaming big episode, but it is important nonetheless. Listen in to hear many of the significant considerations that you may not have thought of when retiring single.

What are Sam’s worries about retiring single?

Sam has been considering retirement for quite some time and has put a bit of thought into many things. She has been working with a financial planner whom she trusts for many years. He has helped her weather the financial upheaval of 2008. Sam thought it was important to purchase long-term care insurance, so as not to burden her daughters with caring for her if she becomes unable to care for herself. Sam considers herself pretty conservative and not much of a risk taker, so listen to her concerns as she considers retiring single on the practical planning segment of this episode.


  • [2:42] The live results webinar is on Thu June 7


  • [6:22] What are some of the normal risks that are more heightened for singles?
  • [17:22] How do you plan your estate when you’re single?


  • [21:21] How does she handle her investment accounts?
  • [27:21] What are her worries as a single person?
  • [32:03] How did she find her investment professional?


  • [40:02] How do you balance taking risks and staying safe?


  • [42:39] What risks am I allowing to restrict my life?

Resources Mentioned In This Episode

Roger’s YouTube Channel - Roger That

BOOK - Rock Retirement  by Roger Whitney

Ask Roger a question

Work with Roger

3-video Series: 5 Minute Retirement Makeover

Roger’s Retirement Learning Center

The Retirement Answer Man Facebook Page

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Direct download: RAM222.mp3
Category:general -- posted at: 6:00am CDT