Last week I hosted our latest Dining with Purpose dinner, a curated evening where women from across our Annapolis community gather around one table to talk about something that matters. This time, the topic was planning ahead: wills, advance directives, trusts, and the conversations most of us keep putting off.
I expected a practical evening. What I didn't expect was how many people at that table had a story. A will sitting unsigned in a drawer for three years. A parent who insisted "it's all taken care of" when it wasn't. A family that ended up in mediation because no one knew what Mom wanted.
In nearly 20 years of helping families buy and sell homes here, I've seen the same thing again and again. When the paperwork isn't in place, the people we love are left making hard decisions in the hardest moments. If you're 55 or older, this is the season to get it settled, not for you, but for them.
Here's what I took away from that evening, in plain language.
The five documents your family will need
A signed will. It sounds obvious, but a will only counts once it's properly signed and witnessed. If you pass away without one, Maryland's intestacy laws decide who inherits, not you.
An advance directive. This spells out the medical care you do and don't want if you can't speak for yourself. Everyone 18 and older should have one.
A healthcare agent. This is the person who speaks for you with doctors. It doesn't have to be your spouse. Choose the person most able to honor your wishes under pressure.
A durable power of attorney. This lets someone you trust handle your finances if you can't. Ask your attorney whether yours is "springing," meaning it only takes effect after doctors certify incapacity. That extra step can stall a family at exactly the wrong moment.
Current beneficiary designations. The beneficiaries named on your life insurance, retirement accounts, and bank accounts generally override what your will says. A beneficiary form you filled out 25 years ago may send money somewhere you never intended.
The mistakes that cost families most
The stories shared around our table were personal, so I'll keep them anonymous. The lessons, though, belong to all of us.
The trust that held nothing. One woman's father assured her for years that his trust was set up. When she finally called his attorney, the trust existed on paper but held no assets. A trust only works once your accounts and property are actually transferred into it.
The document no one could find. A beautifully drafted plan does nothing if your family doesn't know it exists. Your attorney won't call your children. Tell the people who need to know where your documents are and who prepared them.
Waiting too long. One guest shared that most people living with dementia don't recognize it in themselves. By the time the signs are obvious, putting legal documents in place can become far harder, sometimes requiring guardianship.
Forgotten money. After a loss, one family searched their state's unclaimed property database and found old accounts the surviving spouse never knew existed.
"Someday." More than one guest admitted a will had been on the list for a decade. Good intentions are not a plan.
Where your home fits in
For most of the families I work with, the home is the largest asset they'll pass on, and often the most emotional one. A few things worth thinking through:
How your home is titled matters. Whether it's owned jointly, individually, or held in a trust affects whether it passes through probate. Probate takes time, adds cost, and makes your estate a matter of public record. Ask your estate attorney which approach fits your situation.
A plan makes a future sale smoother. When the right documents are in place, a trustee or agent can step in to sell or manage a property without waiting on the court.
Paper is the first thing to tackle. If you're thinking about downsizing in the next few years, sorting decades of files now is a gift to yourself. Start by thinning out what's no longer needed, then decide what to keep and where.
As a Seniors Real Estate Specialist, I help clients plan a move around their life, their timeline, and their family, rather than the other way around. Getting your paperwork in order is often the very first step.
Free resources to get started
The Conversation Project offers a free workbook with prompts and language for starting conversations about the end of life with the people you love.
MyDirectives lets you create a free digital advance directive, supported in Maryland through the Department of Health. You can add personal touches too, like a video message or the music you'd want at your service, and choose exactly who can see it.
Everplans works like a digital filing cabinet for your will, accounts, passwords, pets, and wishes.
MissingMoney.com is a legitimate search, endorsed by the states, for unclaimed property. Search your own name and those of loved ones who have passed.
Choose one thing
This topic can feel overwhelming. The best advice from our evening was simple: don't try to do it all at once. Choose one thing this week.
Sign the will that's been waiting in the drawer.
Complete your advance directive and name your healthcare agent.
Pull up your beneficiary forms and make sure they still reflect your life.
Tell one person where your important documents are kept.
Then choose the next thing. Your plan can change as your life does; what matters is that one exists.
If you're thinking about what your next home looks like, or how your current one fits into your family's future, I'd love to talk it through. You can reach me here jennifer.chino@compass.com.
This post shares general information from a community conversation and is not legal or financial advice. Please consult a qualified estate attorney and financial advisor about your own situation.
