Retirement Series #4: Building a Lasting Legacy
Why families avoid retirement conversations and how to change that
The Quick Hit
Most families agree retirement planning matters. Most families also avoid talking about it.
Research consistently shows that parents rarely share meaningful details about their retirement plans with loved ones, leaving adult children guessing, assumptions hardening, and risks compounding quietly over time.
This silence isn’t caused by apathy or ignorance. It’s driven by discomfort, uncertainty, and a persistent misunderstanding: that retirement is a private, financial milestone rather than a shared, relational transition.
The good news? Engagement doesn’t require spreadsheets, sermons, or sudden transparency. It requires reframing the conversation and approaching it as a family system rather than a solo act.
Below, we explore what the data reveals about the engagement gap, then offer ten practical, human ways to close it.
Building Legacy Thru Narrative
Over the decades I had numerous conversations with clients whose greatest aim was to “leave a legacy.” But more often than not, they spoke in terms of their account balance.
But, in the end, isn’t one’s bank balance just a marker?
I’ve often wondered whether one’s “legacy” is how they are known, and not what they have accomplished or accumulated.
Legacy should be defined by who you are, not by what you have (or end up with). Your possessions are not You.
And, if that is true, then the greatest legacy one can give is to engage one’s loved ones in a narrative that encompasses both one’s journey and the stewarding of that journey into future.
Unfortunately, there is a narrative gap when it comes to discussing retirement…and a missed opportunity to develop a legacy.
The Quiet Gap: What the Research Reveals
The data is remarkably consistent and quietly alarming.
Large national surveys show that more than 50% of Americans report their parents never discussed money with them at all, let alone retirement planning. Among families who do talk, the depth is often shallow: only a small minority of adult children describe those conversations as detailed or actionable.
Even more telling is the mismatch in perception. Parents frequently believe they’ve “covered the basics.” Adult children, meanwhile, report uncertainty around fundamentals:
When retirement income begins
Whether long-term care has been planned for
Who steps in if cognition or health falters
Whether financial support might someday be expected
In other words, silence isn’t neutral. It creates narrative gaps; and those gaps tend to fill themselves with anxiety.
Ironically, studies show that when parents did talk about finances while growing up, adult children were more likely to develop financial skills and think bout retirement planning.
This avoidance persists despite near-universal agreement that these conversations are important. Families know they should talk. They just don’t know how or fear what the conversation might surface.
Which brings us to the real problem.
The Obvious Mistake
Most families treat retirement as a personal financial achievement.
A finish line. A number. A private ledger.
That framing is tidy, but wrong.
Retirement is not merely a change in income. It’s a reordering of time, energy, dependency, geography, and expectations. It reshapes family roles long before money runs out or never does. Avoiding the conversation doesn’t preserve harmony; it simply postpones reckoning.
The other side of obvious?
Engagement works best when retirement is treated as a shared future endeavor, not an individual accounting exercise.
Ten Ways to Engage Family, Without Turning It Into a Trial
1. Start with stories, not statements
Ask how retirement was imagined decades ago or how it’s imagined now. Memory and imagination soften defenses in ways balance sheets never will.
2. Name the family system
Say out loud what everyone already knows but rarely articulates: retirement decisions ripple outward. Housing, caregiving, proximity, inheritance timing - it’s all connected.
3. Replace predictions with “what ifs”
Certainty intimidates. Scenarios invite participation. “What if health holds?” “What if it doesn’t?” “What if markets disappoint?” Planning becomes collaborative rather than confrontational.
4. Lead with humility
Admitting uncertainty isn’t weakness; it’s an invitation. Families engage when no one is posturing as a know-it-all.
5. Translate money into lived experience
Convert dollars into time, flexibility, and dignity. Those currencies resonate across generations and reflect true legacy.
6. Share frameworks, not instructions
Explain how you think, not what others should do. People resist prescriptions but adopt mental models.
7. Make it recurring and boring
One calm, annual check-in beats a single dramatic summit. Familiarity lowers emotional cost.
8. Separate values from mechanics
First align on what matters: independence, generosity, security. Only then discuss accounts and tactics.
9. Borrow neutral voices
Sometimes a third party - an advisor / planner, article, or podcast - carries messages families struggle to deliver themselves.
10. End with openness, not closure
The goal isn’t resolution. It’s continuity. Leave room for reflection and response.
Why This Matters More Than Ever
Longevity is stretching. Families are more geographically scattered. Medical complexity is rising. And yet many households are still navigating retirement planning as if it were a solitary endeavor.
The cost of avoidance isn’t just financial inefficiency. It’s misaligned expectations, last-minute decisions, and preventable stress during moments that already carry emotional weight.
Engagement, done early and gently, is a form of care.
Call to Action
If you’re waiting for the right moment to talk about retirement with your family, here’s the uncomfortable truth: it doesn’t arrive. It’s made.
So don’t start with numbers. Don’t start with solutions.
Start with one question, asked calmly, without agenda:
“How do you imagine the next chapter unfolding for all of us?”
Then listen.
Because the most important retirement asset isn’t a portfolio.
It’s alignment - earned slowly, through conversation, before urgency takes over.
Up Next:
Sunday - The Politically Agnostic Investor
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