Why Boomers Aren’t Talking About Estate Planning

They say the greatest act of love is legacy planning. Yet for many families, legacy means silence.

The Silent Generation (born 1928–1945) and Baby Boomers (1946–1964) have lived through eras of rapid change—war recovery, prosperity, digital transformation, and longer lifespans than any generation before. But when it comes to estate planning, silence reigns.

If you’ve ever struggled to talk to your parents about their wishes, you’re not alone. Most families haven’t had the conversation, and most Boomers still don’t have a formal estate plan.

Generational Snapshot

The Silent Generation (roughly born 1928-1945) and the Baby Boomers (roughly born 1946-1964) carry decades of life experience. They’ve lived through tremendous change: post-war prosperity, civil rights expansion, rapid tech adoption, shifting retirement norms.

Gen X and older Millennials (born roughly 1965-1994) are now stepping into the roles of caregivers, financial advisors, and family conversation starters — often before our parents are ready to cede the mic.

What the Data Reveal

According to the most recent survey by Caring.com, only 24% of U.S. adults have a will and only 13% have a trust — with more than half having no estate-plan documents at all.
A 2024 survey by AARP of adults aged 45+ found that while 83% said end-of-life transition is important, and 85% said they’re comfortable discussing death and dying, far fewer have acted: only 36% had prepared a last will and 33% had done a living will.
One major reason people give: they don’t feel they have enough assets to warrant a will. In the Caring.com 2024 survey, 40% of those without a will gave that reason.

These statistics help explain our starting point: Many older adults may feel comfortable talking about mortality in the abstract — yet haven’t taken concrete steps, and many haven’t communicated their intent or documentation to their heirs.

Why Older Generations Are Not Formalizing Their Plans

Here are some of the key drivers we see (and some you’ll resonate with when working with clients or your own family).

1. “I’m not rich enough / it’s not urgent”

Many simply believe: “My assets aren’t big enough to worry about a will or trust.” The data backs this: 40% cite asset-size as the reason they haven’t done a will. When people feel they’re not facing wealth or complexity, they deprioritize formal planning.

2. Optimism bias & deferral

Even when health concerns exist, many assume they’ll “get to it later.” The Caring.com 2025 data show that procrastination is the most common reason for having no plan: 43% say “just haven’t gotten around to it.” For Boomers who’ve been working, managing life changes and maybe not facing acute triggers, estate-planning slides down the to-do list.

3. Complexity, confusion & cost

The legal and financial dimensions can feel burdensome: wills, trusts, powers of attorney, titling, beneficiary designations. Some may avoid acting because they don’t feel confident navigating the process. The 2025 Caring.com guide notes that many feel unsure how to even start.

4. Technology and access gap

While younger generations grew up with digital tools for everything, many older adults didn’t. Tech platforms, online portals, digital asset management may feel foreign. Research on older adults’ online adoption and comfort points to diverse levels of readiness. In practice: a parent may have everything in place on paper — yet it’s not digitized, shared or synced.

5. Attitudes of independence & privacy

Older generations often grew up valuing self-reliance. The idea of “inviting kids into my finances and wishes” may feel like a loss of independence. In many families, the parents have been decision-makers, and handing over conversation control feels uncomfortable.

Why They Aren’t Talking About It (Even If They Have a Plan)

It’s one thing to plan; it’s another to share. Here are the reasons the “big talk” often doesn’t happen.

Fear of mortality & conflict

Though older adults say they’re comfortable discussing death in principle, the conversation still triggers dread. According to AARP, while 85% of adults 45+ are comfortable talking about death and dying, 69% say the topic is generally avoided. The tension is real: we avoid the talk because we know it signals change, loss, mortality.

“What if I stir things up?”

Many parents fear that a conversation will open family conflict: about unequal inheritances, perceived favoritism, sibling rivalry or burdens. So silence seems the safer path.

It “hasn’t come up” — meaning no one asked

Often the child-generation (Gen X/older millennials) does not know how to launch the talk; the parent doesn’t know the child will take it up. The stage remains quiet until one of them feels motivated.

It “feels final”

Some older adults resist the talk because it “makes it real.” They are still active, independent, in good health. Talking about long-term care, incapacity or death may feel premature and unsettling.

Why It’s So Hard for Gen X / Older Millennials to Raise the Topic

If you’re the “kid” in the conversation, here are the common barriers you’re likely up against (and how to navigate them).

You’re already under pressure

Many Gen X and older Millennials are dealing with the “sandwich” — aging parents and growing children. According to AARP’s “Caregiving in the U.S.” data, many in this age band are juggling multiple roles. AARP When you’re exhausted, initiating conversations becomes one more item on your to-do list.

Role reversal discomfort

You grew up being parented. Now you’re in a position where you might feel you’re “managing” your parent’s future. That shift in dynamics is emotionally loaded: you may fear coming across as bossy, or worry about pushing your parent.

Blended assets, generational issues & complexity

Parents may have houses, accounts, digital legacy, multiple marriages, step-children. It adds complexity — and you may feel under-prepared or unqualified. Also: different generations have different communication styles (in-person, phone, texting) and risk tolerances.

Lack of clarity on whose job it is

Does the parent initiate the talk? Does the child? Often neither does. And the longer no one does, the more awkward it becomes. Many children report, “If only someone had asked, I would have.” But the parent may not want to “tell me what to do.”

Fear of “pushing” or causing distress

You might want to respect your parent’s autonomy — but you also worry: what if something happens tomorrow and wishes weren’t shared? It’s a tension between honoring independence and protecting the future.

What Families Think They’re Covering vs. What They Actually Are

There’s a gap between what gets talked about and what actually gets done.

Many believe “we talked about it” — but the details aren’t documented or accessible.
Key areas often get missed: naming a successor trustee, digitizing account access, clarifying titles or joint accounts, retiring share-ownership, explaining home deed issues, designating pet guardians, reviewing beneficiary designations.
The lack of clarity can leave executors and heirs unprepared — a major risk both for peace of mind and financial cost.

Why It Matters Now

This isn’t just “nice to have.” Here’s what’s at stake if we delay.

The projected wealth transfer from Boomers (and the Silent Gen) is enormous: some estimates put it at $124 trillion through 2045.
Without proper planning and communication, families face: longer probate, unintended tax consequences, sibling conflict, asset losses, lost value in real estate, missed philanthropic opportunities, and emotional stress on the next generation.
The sooner you start these dialogues — while parents are well, mentally engaged, and decisions can be made without crisis — the smoother the transition will be.

How to Shift the Dynamic: Conversation Starters for Gen X / Older Millennials

Here are practical approaches that feel natural rather than forced:

Lead with values, not documents.
Instead of “Did you set up a trust?” start with: “What do you want your legacy to be?” or “What are the things you want us to remember about you?” This opens a lighter, value-based conversation that can lead into details.
Break it into micro-talks.
One evening: discuss digital asset access (passwords, cloud storage). Another: talk housing/home repairs and how ownership is titled. A third: health care proxy/power of attorney. These small conversations are less threatening than a full “estate plan” talk.
Use a neutral third-party tool or guide.
Share an article or checklist you found helpful (e.g., “I read this short guide about wills — want to glance at it together?”). Sometimes it’s easier when you are the messenger of the guide, not the topic.
Schedule a casual but specific time.
“Hey Mom/Dad — could we set aside 30 minutes next Tuesday afternoon to go over one thing: what happens to digital accounts and passwords when you’re gone?” Framing it as short, specific, and collaborative helps.
Invite the professional later.
Let the conversation start at home, then suggest: “Would it help if we had your advisor talk through this with you?” That avoids making you the gatekeeper — you’re just helping facilitate.
Focus on the upside.
Emphasize what good planning can give: peace of mind, smoother transitions, less burden on you or other siblings, greater freedom for the parent to enjoy the present.

Our parents have given us so much: life lessons, security, support. And now many of them want the freedom to enjoy the years ahead without worrying about what happens next. As their children — the Gen Xers and older Millennials — we have a unique role: not to take control, but to stand beside them, facilitate their wishes, and ensure that what matters most to them doesn’t get lost in silence or confusion.

That’s why legacy planning isn’t cold or transactional — it’s a profound act of love. It says: I see you. I respect you. I want your story and your wishes carried forward.