During my years working as a hospice physician, I witnessed the exact same tragedy play out in hundreds of living rooms and hospital wards.
When a parent is entering their final days, the family should be gathered around the bedside. They should be holding hands, sharing old stories, and finding closure. Instead, I usually found the adult children standing out in the hallway. They were frantically whispering into their cell phones, trying to track down a lawyer, arguing over who had the login to a bank account, or desperately trying to figure out how to pay for a sudden transition to memory care.
Financial silence creates immense, unnecessary suffering. The administrative scramble piled on top of deep grief is enough to break a family apart.
So why do we wait until a crisis to have these conversations with our parents?
This week on the Earn & Invest podcast, I sat down with AJ Ayers. She is a certified financial planner, the CEO and co-founder of Brooklyn FI, and the author of Creative Money. AJ sees the financial and legal fallout of this avoidance every single day in her practice.
We avoid talking to our parents about their estates because it forces everyone to confront mortality. It requires looking at the people who raised you and acknowledging they are in the final third of their lives. Furthermore, it completely flips the traditional parent-child dynamic. Parents feel uncomfortable being questioned by the kids they used to diaper, and adult children are terrified of overstepping or looking greedy.
AJ shared a brilliant strategy for breaking the ice: blame a third party. Do not march into Sunday dinner and demand to see their bank statements. Instead, approach them under the guise of your own planning. Say, “My financial advisor gave me homework this week to look into getting a will, and I realized I have no idea how you guys handled yours. Can I get your advice?” Alternatively, you can blame me. Tell them a podcast host you listen to assigned you the task of asking these questions.
Once you have opened the door and asked for a time to sit down, here are the ten essential questions you need to cover before a health crisis arises.
1. Do you have a will, and who can act on your authority if you cannot? People often confuse a will with a durable power of attorney. A will only takes effect after death. But the time before death can involve months or years of cognitive or physical incapacity. You need a power of attorney so someone has the legal authority to talk to doctors, pay the mortgage, and manage accounts. This is especially critical for unmarried partners who have absolutely no legal standing without formal paperwork, even if they have lived together for thirty years.
2. Who are your professionals, and can you introduce them to me? Contact lists tucked into emergency binders often become outdated as accountants retire or lawyers change firms. Ask for a warm introduction now. Establishing a direct relationship with their professional team allows you to assess if those advisors are actually acting in your parents’ best interest.
3. What is your plan for long-term care? There is a massive misconception that Medicare covers long-term custodial care. It does not. While most people will require manageable out of pocket expenses, about fifteen percent will face astronomical costs. Quality nursing facilities or private memory care can run between $15,000 and $30,000 per month. Because long-term care insurance is often prohibitively expensive, you need to talk about how home equity or dedicated savings will be used.
4. Are there debts, loans, or reverse mortgages tied to your property? Uncovering encumbrances early prevents nasty surprises during probate or estate settlement.
5. Where are your assets, and is there an organized digital list? A handwritten note stuffed into a desk drawer is a dangerous strategy. Adult children need a secure, digital document listing all bank accounts, retirement plans, and assets. Otherwise, forgotten 401(k) accounts or old insurance policies will simply be lost to state unclaimed property divisions.
6. What do you want your money to do after you are gone? Does your family want to support specific charities, causes, or leave a legacy? This is also the time to discuss intergenerational gifting. AJ and I both heavily advocate for giving money while you are alive. It is far more impactful to help your children in their twenties or thirties when they are facing rent, student debt, and raising toddlers, rather than leaving them an inheritance when they are already in their sixties.
7. Do you feel financially secure for retirement? Many parents prioritized their children’s education over their own retirement savings and feel deep shame admitting they are falling short. In many immigrant and diverse cultural households, unstated expectations about children eventually supporting their parents financially can collide with modern economic realities. Early transparency prevents resentment.
8. If I need financial help in the next decade, is there money you could spare? This goes both ways. Knowing whether a parental safety net actually exists allows adult children to make realistic career, housing, and life choices without operating on false assumptions.
9. Are you living in the right place? Do not wait for a broken hip to force a crisis move. Selling a multi-story family home early, on their own timeline, prevents fire sales and allows home equity to be leveraged effectively for their future care.
10. Are there bucket-list items you still want to do right now? Retirement spans the go-go, the slow-go, and the no-go years. Families need to plan their shared experiences, like that big family cruise or cross-country trip, during the go-go years before health and mobility inevitably decline.
If there is one thing you take away from this conversation, let it be this: facing mortality does not have to be a morbid exercise. In fact, it can be profoundly life-affirming. If you stick around for our after-show segment, AJ shares her own story of being diagnosed with a heart condition in her twenties and receiving a pacemaker at thirty-three. Facing her own mortality early is exactly what pushed her to prioritize her planning, protect her time, and build a life of purpose today.
Do yourself and your family a favor. Listen to this episode, take notes, and then blame me when you call your parents this weekend.
The Happiness Code: My next book, The Happiness Code, officially drops on March 9, 2027.
