Where Am I Going to Live in Retirement? Making One of Life's Biggest Decisions
- Travis Tsukayama, CFP® CFA

- Jul 31
- 4 min read

Summary:
Deciding where you’ll live in retirement should be planned for in advance. Start the conversation early with your spouse and adult children so you’re not forced to make a rushed decision later.
Choosing where to live is based on a number of factors, including your lifestyle, health, family, cost, and finances.
Explore your options. Understand the differences between different types of senior living facilities. Lean on your family and trusted advisors to help you in this process.
At some point along the retirement planning process, you’ll be faced with a question that may cause discomfort.
It may have to do with your income changing in retirement, and how you’ll afford the expenses that come with aging.
It could be your estate planning – who will inherit your assets?
Here’s one you may not have considered: where am I going to live in retirement?
Many people will want to age in their home. It’s comfortable – you have your favorite chair, the decor you like, familiar neighbors. But it may not be practical or affordable.
We have this conversation with dozens of families each year, as their trusted wealth management firm. In having these conversations, it’s clear that cost is only one piece of the puzzle.
Lifestyle Goals
Start with this.
What do you want retirement to like and feel like?
What activities will you be doing?
How important is it that you are close to your family and friends?
How important is the weather in allowing you to do your favorite activities?
What type of community are you looking for?
Current Living Situation
If you want to age in place, ask yourself what needs to be done to prepare your home.
Is your home designed for an older version of you?
Are there multiple stories? Is there room for a chair lift?
How is shower and bathroom accessibility?
What home repairs and maintenance are needed?
Do you have a large yard or pool that requires regular upkeep?
What are your transportation options to and from your home?
What financial impact will renovation and upkeep have?
Consider Your Health
Your health today versus 10-20 years in the future.
Do you have chronic health conditions?
What level of mobility will you have in the future?
Proximity to your health care professionals
Explore Your Options
Know your living arrangement options. Know the difference in services provided between skilled nursing homes and assisted living. How long is the waitlist for your preferred home? Most people I speak with are surprised at how many senior living facilities there are on Oahu. Evaluate each option based on cost and long-term affordability.
Stay in your current home – age in place
Downsize to a smaller home or condo
Living with adult children or other relatives
Independent living
Assisted living
Skilled nursing homes
Memory care
Long-Term Care Planning
You may eventually need assistance with daily living or ongoing medical oversight.
What happens if me or my spouse needs long-term care?
Can I remain in my home if my spouse needs long-term care?
Can I afford the increased costs of long-term care services?
Family Involvement
Adult children are often involved in some part of the decision-making process.
Do I want to live near children, grandchildren, or siblings?
Will my children be involved in managing my affairs if I’m incapacitated or deceased?
Do my children know my wishes regarding my living situation and finances?
What are the family expectations regarding caregiving responsibilities?
In Summary
The best time to think about where you’ll live in retirement is before you are forced to think about it. Planning and getting everyone on the same page can take a while, not to mention the waitlist spanning years for some of the more popular senior living communities. Start the conversation while it’s not an urgency.
You don’t have to do this alone. Your financial advisor should be encouraging this discussion and serving as facilitator. There are third-party services that will help you think through this and provide a number of homes to consider. Many of these services don’t even charge you a fee, instead getting paid a placement fee from the care facility when you move in. Involve your family in the discussion, if you want to. Your support system is crucial here.
That’s all for now. Talk soon!




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