How To Talk About Money, Death & Aging With Your Parents

“Hey mom/dad, at some point in the future, you’re going to pass away. Can we talk about how much money you’re going to leave me?”.

When we’ve asked our clients who have aging parents whether or not they’ve had a discussion with their parents about money, their estate plan, their will, or their eventual passing - this is typically how they imagine the conversation going. And, if we keep playing this out, the assumption is that this conversation won’t go well.

This year in particular, we’ve started to hear questions from more of you about how to actually go about having these conversations because *gulp* these conversations can be so hard.

In today’s post, we’re going to cover:

Why it can be so hard to talk about any/all of these topics.
Ideas for how you can actually make these conversations easier and more productive.
And finally, we’ll share some success stories - positive conversations our clients have had with their parents.

Money, Death & Aging

Money and death are quite possibly two of the most taboo topics in our modern society.

Many of our parents were raised to not talk about money, and especially not outside of the family. As a result, it’s no wonder that, when we ask about early money memories, many people we’ve spoken to don’t remember money ever being talked about during their formative years.

The topic of death is also frequently ignored, because it evokes strong feelings of fear and existential questions that can be uncomfortable to confront. It can be a very challenging topic to face and process, both internally and socially in conversation.

Estate planning, long term care, and insurance decisions generally require us to combine all of these topics into a conversation, and that can get really, really tricky. Here are some common reasons we’ve encountered that can make these conversations difficult to start:

Fear of Role Reversal: For aging parents, discussing estate plans with your children or grandchildren can feel like an awkward reversal of roles. Parents, who are used to being decision-makers, can find it uncomfortable to navigate a space where their children might have strong opinions about outcomes, or may even want to be involved with organization of such plans.

Mortality: As I mentioned before, it’s hard to confront one’s own mortality. Conversations around aging, illness, and end-of-life planning force this confrontation.

Cultural or Personal Taboos: Taboos around death and inheritance vary across and within cultures. Having grown up with a mom raised in Chinese-Filipino culture, I often remember her telling me that discussing death or inheritance was seen as inviting bad luck.

Fear of Uncertainty: It is no question that the future itself is uncertain, and for those who are also uncertain about what they want in life, avoiding conversations can be a coping mechanism that saves them from facing the stress of defining and committing to future goals.

Fear of Conflict or Family Discord: Estate - and in particular, inheritance - discussions can raise concerns about potential family conflicts or hurt feelings. Parents may fear that sharing details of their will or inheritance plans could lead to sibling rivalry or resentment among family members.

Emotional Attachments: Estate planning isn’t just about finances—it often involves emotionally charged decisions, like who will inherit a family home or personal items with sentimental value. These decisions can be hard to discuss without emotional responses.

Fear of Burdening Children: Many parents don’t want their children to worry about their future care or end-of-life plans. We’ve heard from several of our clients that their parents have expressed not wanting to burden their children with their future health needs - especially when their children are taking care of young children at home. Parents may avoid conversations about aging or estate plans to protect their adult children from worry.

Even though these conversations will very likely be challenging and emotionally charged, we can’t stress how important we think they are to have. With the right approach, these discussions can transform from deeply fraught to wildly meaningful.

If you need help starting these conversations with your loved ones, here are some strategies we’ve found that could work for you:

Set the Scene Thoughtfully

Choose a private, peaceful moment (for example, you could plan a weekend morning coffee or walk; absolutely avoid circumstances like chaotic holiday dinners or stressful, time-limited gatherings).
Pick a neutral location, where everyone feels at ease. Sometimes a public place can actually be better for these discussions than someone’s home - especially if that could help you or others keep their emotional activation and responses in check.
Ensure you have uninterrupted time – this isn't a rushed conversation! If you can’t find an entire afternoon to talk, you can break up the topics into shorter sessions.

Lead with Love, Not Logistics

Open with gratitude for one another. Start the conversation with a positive celebration of the life and moments you’ve shared together, wisdom gained, and love for each other.
Acknowledge your loved ones’ role(s) in shaping your values about money and family.
Make it clear: this is about understanding their wishes, not claiming assets.

Ask, Don't Tell

Try these conversation starters:

"What values about money do you hope to pass down?"
"What would make you feel most at peace about the future?"
"How can I help ensure your wishes are honored?"

Navigate with Empathy

Watch for signs of discomfort.
Validate their emotions (remember to pause and acknowledge, "I understand this isn't easy to discuss…").
Offer to take breaks or continue another time. Do this when emotional responses begin to arise, before they escalate.
Share your own feelings of vulnerability about the topic.

Keep It Structured But Flexible

Start with each party’s general values before diving into specifics.
Set expectations and guardrails for each topic, e.g., if you want to talk about a long term care plan, don’t let the conversation derail into proposing elements of a will. Keeping things focused will help everyone feel better.
Break the conversation into manageable chunks.
Have a rough outline in mind, but be willing to compromise on pace and ordering of topics.
Be prepared to pivot if certain topics feel too sensitive. You can always come back to them later.

As we’ve guided more clients through these discussions, we’ve found that folks who initiate these conversations with curiosity, and the simple intention to understand (vs. make immediate decisions) have the most success. Remember: if you begin broaching these topics early enough, the conversations can unfold more gently, over time.

We’ve also discovered strategies that don’t work so well: Ambushing parents with paperwork, bringing up specific assets early in the discussion, or making assumptions about their plan can often result in total shut down, hurt feelings and unnecessarily strained relationships.

We wanted to share a few memorable anecdotes from client experiences, that may personally inspire you or resonate in some detail:

A client asked us how we’d recommend bringing up their concerns around a parent’s memory loss. We worked together to draft an agenda for a family meeting that prioritized creating a safe space for the older parents to talk about their wishes for the future. In their family meeting, their mom acknowledged that she had Alzheimer's for the first time. In the meeting they discovered that their mom’s greatest fear was managing her finances after her husband had passed. There is now a plan in place to introduce a daily money manager (someone who can be paid to play this role) should this time come.
A client and his siblings were feeling stress around their mom’s ability to live on her own in the future, and the siblings didn’t know how to begin having these conversations. We facilitated a meeting among the siblings where we asked questions to better learn their collective concerns and desired outcomes. The result of this meeting: our client and his siblings agreed to have lunch with mom every other week as a family, and begin bringing up some of the topics they shared together.
A client’s parent received a terminal medical diagnosis, and there was no clarity around the resources available to support the surviving parent. Even though money was historically never discussed between the parents and children, we guided our client to approach the conversation in a way that demonstrated the love and respect that existed between the generations. The client now not only has clarity about how many years of top quality care can be afforded, they also know what their parent’s trust says about how assets will be distributed after both parents pass.

Most parents have spent a lifetime making decisions with the family’s best interests in mind. These conversations are your chance to share in handling their legacy with the same care and thoughtfulness they've always shown. Remember: these discussions are not just about tactics and inheritance – at their core, they are about strengthening relationships, facing uncertainty together with greater strength, and ensuring everyone’s wishes are honored.

Pro Tip: If the conversation stalls, try sharing a story about how their financial wisdom has already helped you in life. Personal anecdotes can help break the ice and show your appreciation for guidance.

By approaching this conversation with patience, empathy, and respect, you're not just planning for the future – you're creating an opportunity for meaningful connection in the present.

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Stephanie Bucko and Cristina Livadary are fee-only financial planners based in Los Angeles, California. Stephanie is the Chief Investment Officer and Cristina is the Chief Executive Officer at Mana Financial Life Design (FLD). Mana FLD provides comprehensive financial planning and investment management services to help clients grow and protect their wealth throughout life’s journey. Mana FLD specializes in advising ambitious professionals who seek financial knowledge and want to implement creative budgeting, savings, proactive planning and powerful investment strategies. As fee-only fiduciaries and independent financial advisors, Stephanie and Cristina never receive commission of any kind. Stephanie and Cristina are legally bound by their certifications to provide unbiased and trustworthy financial advice.