Whether your family gathers around a brisket, a turkey or a tofurkey this holiday season, the time-honored dinner table advice is to avoid talking about politics, religion — and money. But new Fidelity research illustrates why breaking the taboo around family money conversations can benefit your loved ones now and for generations to come.

Pull up a chair and get… uncomfortable

There’s no denying that it can sometimes feel awkward and even uncomfortable to discuss issues like older family members needing more care or eventually passing away — let alone tackling questions surrounding who will get what once they’re gone, or the legacy parents would like to leave behind. But everyone in the family stands to benefit from having a plan in place.

The challenge is that planning conversations may not be happening. In fact, the Later-in-Life Conversations Study¹ from the Fidelity Center for Family Engagement finds that both baby boomer parents and their next generation children say that achieving “peace of mind” is one of the most important goals of having later-in-life conversations — yet 61 percent of boomers aren’t actively talking with their families about how they plan to achieve it!

Next gen in the dark

Fidelity’s 2025 Family and Finance Study found nearly half of parents haven’t told their kids what — or even if — they’ll inherit. Plus, fewer than half (48 percent) of parents have told their adult children what their net worth is.

Even among parents who anticipate their adult children becoming executor of their estate, only 13 percent have been fully open and specific about what their heirs are likely to receive. When it comes to health care decisions, more than half of both groups anticipate an adult child having power of attorney — but only about 1 in 3 say they’ve actually had a conversation about it.

Opinions differ on when to talk

The Family and Finance Study also found that 81 percent of adult children said conversations with parents should happen before a parent retires — but just 61 percent of parents agreed. Some parents recognize this as a problem: over a quarter (27 percent) say they talked or anticipate talking to their adult children later than these parents think they should.

The Later-in-Life Conversations Study also provides some revealing statistics about what’s not being discussed. For example, 76 percent of the next generation say they want to know if they are named as a beneficiary, yet only 35 percent of baby boomers say they feel a need to talk to the person they are naming.

All of this means that families may unintentionally make things more difficult by delaying conversations they could be having today and waiting until “someday.”

Sure, we talk—but not about that

Family members may assume that having a “great relationship” means they’re talking about the right things — but Fidelity’s research shows that’s often not the case. The Later-in-Life Conversations Study found 98 percent of baby boomers and 94 percent of the next generation say they are comfortable talking about important later-in-life topics.

But a closer look reveals that only 17 percent of the senior generation are actively talking to their adult children about the later-in-life topics they deem most relevant. The numbers show that both parents and adult children overestimate their comfort with later-in-life topics and are not talking as much as they think.

Start small with a “micro-meeting”

Dr. Timothy Habbershon, Managing Director and Founder of the Fidelity Center for Family Engagement, offers some coaching suggestions. First, he says, “If we think of planning as one big problem, we tend to shut down. So, tease it apart into smaller topics. Then you can decide what to talk about right now versus what you can talk about later.”

Habbershon says he started hosting “micro-meetings” with his own family: one-hour gatherings focused on just one topic. For example, he and his wife have a beach house. So they held a micro-meeting to hear their children’s views on what should happen with the property once they are gone.

Talk about wishes and fears

When it comes to starting conversations, Habbershon says talking about wishes — and their flipside fears — is often a good place to begin: “Our later-in-life planning is often dominated by fears, so we don’t talk about them.” He encourages people to flip the fear to a wish. For example, ask, “What are your wishes for your retirement lifestyle, or a dependent care situation, or how we address family heirlooms?”

Habbershon adds that parents often worry that inviting their children to have a voice in decisions means giving up the final vote. He suggests sharing verbal boundaries up front so people know how to participate. When his family talked about the beach house, he started by saying, “This is a voice, not vote, discussion.”  And he reminded them they didn’t need to debate each other’s wishes. They just needed to share their views as individuals.

Lean into the “cringe” to build confidence and closeness

In the words of baby boomers’ Generation Z grandchildren, having later-in-life conversations can often feel “cringe-y,” something grandparents themselves recognize. The overwhelming majority (87 percent) of baby boomers in the Later-in-Life Conversations Study identified at least one emotional resistor keeping them from talking about planning. What was their number one resistor? “I don’t feel prepared to talk about it.”

Here’s why leaning into the discomfort matters: The study also found that parents who are more actively talking to their children about later-in-life topics have greater confidence their plans will be carried out seamlessly. They are also more likely to believe their plans will create closeness in their family. Just by starting the conversation, you show you care and understand that setting your family up for success begins with planning together.

The bottom line

Money doesn’t guarantee your family happiness. But having open, honest and ongoing financial planning conversations can bring closeness, confidence and peace of mind — and that’s priceless.

For those unsure of where to start, Fidelity offers access to licensed advisors who can help you create a personalized plan designed around the things that matter to you and your family — from retirement and estate planning to managing around taxes and the rising costs of health care. Insights from Fidelity Wealth Management^SM are also available for those looking to educate themselves on various wealth topics — including ideas on how families can get critical money conversations started. 

Fidelity does not provide legal or tax advice, and the information provided is general in nature and should not be considered legal or tax advice. Consult an attorney, tax professional, or other advisor regarding your specific legal or tax situation.

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The Fidelity Center for Family Engagement is an affiliated business unit of FMR, LLC and operates externally from Fidelity’s broker dealer and registered investment adviser entities (“Affiliated Entities”). Services available through FCFE are neither brokerage nor advisory products or offerings of the Affiliated Entities.

Fidelity advisors are licensed with Strategic Advisers LLC (Strategic Advisers), a registered investment adviser, and registered with Fidelity Brokerage Services LLC (FBS), a registered broker-dealer. Whether a Fidelity advisor provides advisory services through Strategic Advisers for a fee or brokerage services through FBS will depend on the products and services you choose.

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