Is there another financial conversation people avoid more than long-term care?
Retirement? We talk about it ad nauseam.
Life insurance? A little morbid, but we do it.
Estate planning? Eventually we get there. Kinda no choice.
But long-term care?
That’s the conversation almost every family knows they should have—and almost nobody does. And, by the way, older parents aren’t exactly helpful (Baby Boomers, I am looking straight at you).
I know more than one parent whose response to the long-term care conversation was, “Just take me out back and shoot me.”
For us kids, it’s already a tough conversation because it forces us to reckon with our parents getting older right before our eyes. Maybe it’s because the costs feel outrageous. Maybe it’s because none of us really knows where to begin until we’re already in the middle of a crisis. Or maybe it’s because, deep down, we’d rather believe our parents will either live forever or just pass away peacefully in their sleep without ever needing care at all.
As an elder millennial (eeep!), I’ve been noticing this topic creeping into my own life more and more. Like so many of us, I’ve watched friends begin navigating aging parents, coordinating doctors’ appointments, and trying to figure out what happens if Mom or Dad can’t live independently anymore. The more people I talk to, the more I realize there isn’t exactly a dynamite playbook for this stage of life.
That’s why I was so excited to sit down with Lily Vittayarukskul, founder and CEO of Waterlily.
Lily’s story begins in an unexpected place: aerospace.
She started college at just 14 years old and was interning at NASA by the time she was 16. Her future seemed destined for aerospace engineering.
Then everything in her life flipped on its head.
That same year, her aunt—the woman who helped raise her—was diagnosed with terminal cancer. Overnight, Lily’s family found themselves navigating not only a devastating diagnosis, but also the financial, emotional, and logistical realities of becoming caregivers.
The cost of care changed their lives.
So did the stress.
The uncertainty.
The impossible decisions.
Ultimately, the strain permanently fractured relationships within her family.
Everyone seems to have a family falling-out story that stems from caregiving.
This experience was so life-altering that instead of continuing down the path toward aerospace, Lily redirected her entire career. She studied genetics and data science at UC Berkeley, spent years building AI products, and eventually founded Waterlily with one mission: helping families prepare for long-term care before it becomes a crisis.
On the surface, this conversation may look like it’s about insurance.
It isn’t.
It’s about families. And protecting them.
It’s about daughters who silently slip into becoming caregivers. Parents who don’t want to burden their children, but also don’t want to confront their own mortality. Siblings trying to divide responsibilities without a plan. And the emotional weight of financial worries when the people you love need help the most.
Of course, we also dive into the practical, financial side of long-term care, and let’s just say I took a lot of notes.
Lily explains why traditional health insurance typically doesn’t cover long-term care, why so many families underestimate the true cost of caregiving, and why relying on national averages often leads people to make financial decisions that don’t actually fit their circumstances.
One of the most fascinating parts of our conversation was learning how Waterlily uses AI to build personalized long-term care projections. Instead of asking families to guess when care might be needed—or how much it might cost—the platform analyzes an individual’s unique circumstances to help them prepare for their own long-term care journey rather than relying on generic statistics.
This level of accessibility is incredibly important because uncertainty and fear are what keep people from planning at all.
We also talked about something I hadn’t really considered before: how dramatically our family structures have changed.
Previous generations often lived together or nearby. Grandparents helped raise their grandchildren, and adult children were naturally closer when their parents began to need help. Today, many of us live across the country, have demanding careers, and are raising our own children. Some of us still have young kids when our parents get sick and need more care. The financial and emotional toll on today’s families looks very different than it did a generation ago—and not for the better.
In this episode, we also chatted about:
Why long-term care isn’t covered the way most people assume—and why so many families discover that too late.
The real cost of caregiving and why waiting until there’s a crisis often makes every decision harder.
Why caregiving responsibilities still disproportionately fall on women—and how that affects careers, finances, and family dynamics.
How AI is helping families move beyond generic statistics to create personalized long-term care plans.
Why planning ahead isn’t just about protecting your savings—it’s about protecting your relationships.
How to get started with long-term care if you don’t currently have a plan.
Lily said something in our interview that has stuck with me.
Families often think caregiving conflicts happen because people don’t care enough.
In reality, she believes many of those conflicts happen because families never had the chance to prepare.
Mic drop, Lily.
As if money isn’t an emotional enough topic on its own. Add illness, aging parents, siblings, grief, and impossible decisions, and suddenly this becomes one of the most personal financial conversations any family will ever have.
I hope this conversation helps you and your family come up with a plan if you need one. More than that, I hope that preparation brings your family a little more peace of mind.
Until next time,
Jenny
Connect with Lily:
If you’re building something that’s changing the future of financial services and want more people to know about it, Pink Shark PR currently has two open spots on our agency roster. Send Jenny a message to get in touch.
💌 jenny@pinksharkpr.com
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