Most families don't avoid estate planning because they don't care. They avoid it because they don't know where the conversation begins.
There's no natural opening. Nobody sits down to dinner and says, "Pass the bread and let's talk about what happens when I die." The conversation gets delayed for years, sometimes decades. Then something happens: a parent forgets a PIN, a spouse gets a diagnosis, a close friend dies and leaves behind a mess of paperwork and unanswered questions. Suddenly, the conversation that felt optional becomes the one everyone wishes they had already had.
If you've been putting this off, you're not alone. According to a 2024 Caring.com survey, only 32 percent of Americans have a will. The numbers drop further when you ask about powers of attorney, healthcare directives, and documented final wishes. Most people have nothing written down at all.
Starting is not as hard as most people expect, and you don't have to do it alone.
Why the Conversation Feels So Hard
The obvious reason is that estate planning forces you to think about death. That's genuinely uncomfortable, and most of us are wired to avoid it.
There's a less obvious reason too. Most people don't know what they're supposed to be gathering, documenting, or deciding. The process feels vague and overwhelming. When something feels overwhelming, the easiest response is to put it off until later.
What actually helps is having a clear picture of what you need, and knowing that you don't have to get it all done at once.
What to Gather Before You Meet with an Attorney
Estate planning attorneys bill by the hour. Arriving prepared makes your meeting shorter, cheaper, and more focused on decisions rather than on organizing paperwork.
Here's what to have ready before you walk in.
Your Assets
Start with a complete inventory of what you own. This includes:
- Bank accounts (checking, savings, money market)
- Investment and brokerage accounts
- Retirement accounts (401k, IRA, pension)
- Real estate (primary home, rental properties, land)
- Vehicles
- Business interests or ownership stakes
- Life insurance policies, with policy numbers and insurer names
- Valuable personal property (jewelry, art, collectibles)
You don't need precise valuations for everything at this stage. You need a complete picture so nothing gets missed.
Your Beneficiaries
A beneficiary is anyone you want to receive something when you die. Before meeting with an attorney, think through who gets what and in what proportion, what happens if a beneficiary dies before you, and whether any beneficiaries have special circumstances such as a minor child, a person with a disability, or someone who struggles with financial management.
One thing worth knowing: beneficiary designations on retirement accounts and life insurance policies typically override what's written in your will. Keeping those designations current is just as important as the will itself.
Your Fiduciaries
A fiduciary is someone you trust to act on your behalf. You'll need to name:
- An executor, who carries out your will after you die
- A financial power of attorney, who can manage your finances if you're incapacitated
- A healthcare proxy, who can make medical decisions for you if you can't make them yourself
- A guardian for any minor children
These are among the most consequential decisions in estate planning. The people you choose need to be trusted, capable, and willing to take on the responsibility.
Your Healthcare Directives
A healthcare directive, sometimes called a living will or advance directive, documents your wishes for medical care if you can't speak for yourself. This includes under what circumstances you'd want life-sustaining treatment continued or discontinued, your preferences around pain management and palliative care, organ donation wishes, and any specific medical conditions or procedures you feel strongly about.
Many families find this section the hardest to complete. It requires honest conversations about mortality and personal values. Take whatever time you need.
Your Final Wishes
This section covers what happens at and after death. It includes:
- Burial or cremation preferences
- Service or memorial preferences (religious, secular, private, public)
- Any specific requests for music, readings, or eulogies
- Instructions for digital accounts (social media, email, subscriptions)
- Personal letters or messages you want passed on
- Instructions for pets
Final wishes are not legally binding in most states, but putting them in writing spares your family from having to guess. That clarity is a genuine gift to the people who love you.
The Documents You'll Eventually Need
Once you've organized your wishes, an attorney will help you turn those decisions into binding documents. These typically include a last will and testament, a durable power of attorney, a healthcare proxy or healthcare power of attorney, a living will or advance directive, and potentially a trust depending on the size and complexity of your estate.
You don't need to understand every document before you start. You need to understand your own wishes. The documents are the mechanism.
Where Most People Get Stuck
The checklist above is useful. But a checklist alone rarely gets people moving.
The real obstacle for most families is the emotional weight of the process. Deciding who gets the house. Naming the person who will make medical decisions for you. Writing down what kind of service you want. These aren't tasks. They're conversations that force you to face your mortality, your relationships, and your values all at once.
Most people are navigating all of this without any guidance. That's where things tend to stall.
How a Guided Conversation Changes Things
BestFarewell offers every new member a complimentary 30-minute onboarding session with a real specialist. Not a chatbot, not a support ticket. A person.
In that 30 minutes, your specialist will walk you through the platform, help you understand which parts of the checklist you've already addressed, and identify what still needs attention. They'll answer your questions at whatever pace feels comfortable.
If talking about death is hard for you, say so. BestFarewell's specialists work with families at every stage of readiness, from people who have been thinking carefully about this for years to people opening the conversation for the first time.
The platform itself keeps everything organized in one secure place: your asset inventory, your beneficiary designations, your healthcare directives, your final wishes, and the documents you'll bring to your attorney. Family members can be given access to exactly what they need, when they need it.
The goal isn't to replace your attorney or your financial advisor. It's to help you arrive at those conversations prepared, so you're spending their time on decisions rather than on disorganization.
A Note on Timing
There is no perfect time to start this. Every year you wait is a year your family is less protected if something unexpected happens.
The good news is that you don't have to finish everything in one session. Most people build their plan over several weeks or months, coming back to add pieces as they go. Progress saves automatically, so you can return whenever you're ready.
The harder truth is that waiting too long means making these decisions under pressure instead of with care.
Starting today, even with one small step, is worth something.
Where to Begin
Create a free account, and schedule a complimentary onboarding session with one of our specialists. Sessions run 30 minutes and are available on a first-come, first-served basis. We hold a limited number each week.
The checklist above isn't meant to overwhelm you. It's meant to show you that this is manageable. People do it every week, often with more fear going in than coming out.
Your family is worth the conversation.