Monument Wealth Management Articles

Advice on Talking With Your Aging Parents About Finances, Living Options, and More

Nov 15, 2023 Passing Down Family Wealth

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If you are part of the sandwich generation, chances are you have significant demands on your time. As time for work is squeezed between taking care of your family and often your aging parents too, finding a work/life balance is difficult, and finding time for yourself is near impossible!

How do you provide your loved ones the care they deserve when your time is at a premium? And when conversations with your parents about finances, healthcare needs, and end-of-life care are so difficult? If you find yourself at this common crossroads, we have you covered. Our client experience team Cecelia Gilliam and Cathleen Phelps, along with our co-founder Dean Catino share some guidelines below to help you navigate the process of caring for your aging parents, including helping them with their finances.

Start the Conversation Early

The truth is that many parents and children fail to have a conversation about plans and wishes around living arrangements, healthcare, and other support as time goes on and needs change. It’s a difficult topic to broach – Who wants to talk about aging and death? No one.

Research by Fidelity shows that there’s a huge disconnect between what parents and their kids may think about the roles they will play in the future. Approximately 72 percent of parents expect one of their children to assume long-term caregiving responsibilities, but only 40 percent of kids are aware that this is the plan. Maybe even more pressing is that 70 percent of parents expect one of their children to help manage their investments or retirement resources while only 36 percent of kids are expecting to step into that role.

Legacy planning for families doesn’t happen on its own, and you absolutely must find out what your parents’ plans and wishes are.

The last thing you want is a crisis where you have to make choices without knowing what your parents want, or in a way that makes them feel like a child. It’s better to make important decisions with your parents while they still have full cognitive capacity. Ideally, your parents will be involved in their care and financial management decisions rather than being forced into something they’re unsure or unhappy with during a crisis situation.

But how do you bring up such a sensitive and emotional topic?

Most of the time, it’s easier and more effective to have several smaller conversations over time. You may mention a friend’s experience or share an article, which can provide a segue into a larger and more personal conversation.

Put yourself in your parents’ place, facing the potential loss of independence. Your parents will appreciate maintaining their autonomy during any decision-making. This can be as simple as using phrasing like “Have you considered…?” or “What do you want to do about…?” rather than a more forceful statement like “You need to …..” No one likes to be told what to do.

Some families find it helpful when other professionals, such as doctors or wealth advisors, are part of the conversations as they can provide advice without the emotional involvement that family members have. If your parents are willing to have you attend doctor’s appointments or financial meetings with them, this will enable you to be an additional set of ears in taking in complex information, better understand their situation, and ask questions. And sometimes tough decisions such as “independent living is no longer a safe situation for you,” or “it is no longer safe for you to drive” are better accepted by parents when delivered by a doctor rather than their child.

In short, provide your parents with support and resources to let them know that you’re listening, but allow them to take the lead moving forward. Stay calm during the process and remember that the primary goal is their safety and well-being.

Tips for Providing Oversight to Accounts

Once you understand what accounts, assets, and liabilities your parents have, you can look for ways to provide oversight as their needs change. To start, your parents could add you as a trusted contact for medical purposes which would allow you insight into your parents’ healthcare needs. Your parents could also add you as a trusted contact or interested party to their financial accounts. This way, you can check on the advice they are receiving from their investment advisors to see that it makes sense and is not generating unnecessary fees. You would also be in a position to spot any potential fraud or suspicious activity.

An aging population is a particularly vulnerable group for scams, even for those who still retain full cognitive capacity. Be a resource for your parents to keep their accounts secure and watch for potential fraud. Two ways to do this are to encourage your parents to use a password manager such as Dashlane or 1Password (show them how!) and to help them set up two-factor authentication wherever it is offered.

Essential Documents for Parents

If you can, get copies of your parents’ estate planning documents and take the time to read them. Are they current? Do they express what your parents want today? Documents might have been made decades ago and may need updating to reflect current wishes. It is worth reviewing and discussing these documents with your parents:

  • Will – A will only becomes effective when you pass and must go through probate, which is public and time-consuming. Avoid probate by ensuring your parents’ assets are titled either jointly, in trusts, or have beneficiaries designated.
  • Trust – referred to as a Living Trust – where the grantor/owner decides how assets are managed and distributed during your lifetime and after you die. All assets titled within a trust will pass to the beneficiaries privately — and outside of the probate process.
  • Power of attorney – to allow someone to make decisions on their behalf.
  • Advanced healthcare directives – These include a living will that expresses wishes for end-of-life care if your parent becomes incapacitated, and a healthcare power of attorney.

Encourage your parents to keep their important papers in one easy-to-find location such as a red binder or folder. At some point, you will need to be able to find and review these documents.

Care Needs as Your Parents Age

Financial planning for the aging isn’t the only thing to consider. You need to start talking with your parents about their care needs as they age. These needs can be difficult to gauge, especially if you don’t see them often. They might be safe and comfortable in their own home, but what if you take them out of this environment? They may need additional assistance. And consider your parents’ mental health and social needs. If they are lonely, a retirement community may provide a sense of belonging.

If a retirement community seems like a potential solution, scope out the options ahead of time. Don’t wait for a crisis to force your parents into a facility you haven’t evaluated and where your parents may not be happy. There are so many questions to ask during your research…here are a few to start:

  • What types of living arrangements are a fit for your parents (standalone cottage vs townhome vs apartment format)?
  • What social, wellness, and other amenities are important to your parents in a new community?
  • What level of care do your parents need now and in the future? (independent vs. assisted living vs nursing home communities)?
  • Is there a waitlist?
  • Are there medical evaluations required to establish or qualify for the type of care they need?
  • How does the facility handle resident security and safety?
  • What are the upfront costs, down payments, and ongoing costs (adjusted for inflation)?
  • Is there a Care Manager who can be the eyes and ears for your family and report back?
  • What will the move-in process look like?

These facilities are expensive, and a high price does not guarantee quality of care. Talk with residents, talk with the staff, eat some meals there, check licensing, and visit often and outside of visiting hours to see if there are any surprises.


Eventually, there will be a need to downsize. You and your parents will need to donate, discard, and give away things to fit into a smaller living space, and the experience will likely be overwhelming after decades of accumulating “stuff.”

Many local companies, such as Great Falls Organizers, work with families on senior transitions and downsizing. They help you sort out what to keep, send to auction, haul away, or donate, and then make all of the “stuff” go where it needs to go. They can even help you pack, arrange movers, and unpack. It can be expensive to farm out all of these tasks, but having some help can save a lot of time and emotional turmoil. Make sure the group you hire is certified by the National Association of Senior and Specialty Move Managers and check their references.

Support is KEY

Everyone needs help and support. Who is in your parents’ support network besides you? Think about their neighbors or church friends who are willing and able to provide emotional and practical support, like meals or taking them to appointments. Even more importantly, make sure that your parents are comfortable using their support system.

And who is in your support network? If you will be doing caregiving, you will need help – especially if you have kids, a career, and other responsibilities. Don’t be afraid to reach out. Your friends WANT to help you, and you will get your turn to help them in time.

Taking the First Step

Figuring out how to talk to aging parents about finances and care as they age is no easy endeavor, but the best thing you can do is to simply start. If you procrastinate, the decision may end up being made for you.

Allow your parents to lead as you serve as a supportive copilot. They may find it hard to ask for help, so try to empower them to make these decisions on their own.

Each person has a unique relationship with their parents so the process will be different for everyone. But the goal is the same: providing the safety, security, dignity, and happiness that your parents deserve.

Get Professional Help

Navigating the intricacies of an unfamiliar portfolio, like the one your parents have built over decades, can be overwhelming. At Monument Wealth Management, we understand that wealth planning requires strategic planning alongside a compassionate touch. As fiduciaries, the well-being of your family is always a top priority. We’ll help you build a personalized wealth plan that takes into account your parents’ wishes to facilitate a smooth transition into their next phase of life.

Wealth transfer and family legacy are important considerations that should be handled by a wealth advisor who understands and considers the big picture. Do you have a wealth partner to help you navigate the process?  See if we’re a fit for you in just 30 seconds.

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Dean J. photo

Dean J. Catino, CFP®, CPWA®

President & Co-Founder

Pretty much everything in Dean’s life revolves around his family and friends. Dean married his high school sweetheart, Sheila, and they have three accomplished daughters that he is immensely proud of. For fun, Dean enjoys the serenity of fly fishing and the thrill of crushing the “cyber competition” on his Peloton bike. Of course, scoring better than Dave on the golf course always makes his day!

Learn more ...

Cathleen D. photo

Cathleen D. Phelps

Client Experience Manager

Cathleen has two big drivers-–a challenge and a love of learning. She cannot resist a challenge or a problem to solve, and cannot rest until she’s conquered it. Every morning, Cathleen runs or works out at Crossfit for an energy boost that gets her mind awake and going, ready to face whatever the day brings. She admits there’s always something that needs figuring out, and if she needs to learn something new to do it, that’s even better!

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