Nobody likes thinking about death. It’s uncomfortable, it feels morbid, and honestly, there are about a thousand things you’d rather be doing right now.
But here’s what’s even more uncomfortable: leaving your loved ones scrambling to figure out what you wanted, watching your assets get tangled in legal red tape, or having strangers make decisions about your life when you can’t speak for yourself. That’s the reality for families who put off these conversations.
Estate planning isn’t just for wealthy people with vacation homes and stock portfolios. If you own anything, love anyone, or have preferences about your medical care, you need a plan. These questions will help you get started—or realize what you’ve been missing.
Estate Planning Questions to Ask Yourself
Getting your affairs in order doesn’t happen overnight, and it certainly doesn’t happen by accident. Use these questions as your roadmap to building a plan that actually protects what matters most.
1. Who Will Make Medical Decisions for You If You Can’t?
Picture this: you’re in a hospital bed, unconscious after an accident. The doctors need someone to decide whether to proceed with a risky surgery. Who speaks for you?
Without a healthcare power of attorney, your family might end up in court fighting for the right to make these calls. Even worse, the person who gets appointed might not be the one you would have chosen. Maybe your sister understands your values better than your spouse, or maybe your adult daughter knows you’d never want to be kept alive by machines. Whatever your preference, you need to document it now.
This person needs to be someone who can handle pressure, respect your wishes even when they disagree, and make tough choices in emotional situations. That’s not everyone. Your best friend might be amazing in every other way but fall apart in a crisis. Think carefully about who has the backbone and judgment for this role, then have a real conversation with them about what you’d want.
2. Who Gets Your Digital Accounts and Passwords?
Your digital life is probably worth more than you think. There are bank accounts, investment platforms, cryptocurrency wallets, online businesses, social media profiles with sentimental value, and cloud storage packed with irreplaceable photos. All of it locked behind passwords.
Most people don’t realize that your email account is the master key to everything else. Whoever controls that can reset passwords and access almost anything. But here’s the catch: many platforms have strict policies about account access after death. Some will lock out everyone forever. Others require death certificates and legal documents. A few, like Google, let you set up an inactive account manager who automatically gets access after you’re gone.
Make a secure list of your important accounts, usernames, and passwords. Store it somewhere safe—maybe with your attorney, in a fireproof safe, or using a password manager with an emergency access feature. Don’t just leave a sticky note on your desk or save everything in a document called “Passwords.doc” on your desktop. Your executor will thank you for making this easy instead of forcing them to play detective.
3. What Happens to Your Minor Children?
If you have kids under 18, this question should keep you up at night until you answer it. Who raises them if you and your partner both die? Courts will appoint someone, but it might not be who you’d choose.
Your brother might be fun at family gatherings but terrible with money. Your best friend might have the right values but already has four kids of her own. Your parents might be willing but too old to handle teenagers. There’s no perfect choice, but there’s definitely your choice versus the court’s choice.
Name a guardian in your will. Then actually talk to that person and make sure they’re willing. You’d be surprised how many people name guardians without asking first. Also consider naming a separate person to manage the money you leave for your kids. Sometimes the best caregiver isn’t the best money manager, and that’s okay. You can split those responsibilities.
4. Who Will Manage Your Finances If You’re Incapacitated?
Death isn’t the only scenario you need to plan for. What if you have a stroke? Develop dementia? Get into an accident that leaves you unable to manage your bills?
A financial power of attorney lets someone pay your mortgage, manage your investments, file your taxes, and handle everything else money-related. Without it, your spouse or kids might need to go to court to get control of your accounts, which takes time and money while your bills pile up.
Choose someone trustworthy who’s good with money. This doesn’t have to be the same person who makes your medical decisions. Maybe your husband is great with healthcare choices but your daughter is the spreadsheet wizard who should handle the finances. You can customize this however makes sense.
5. Have You Communicated Your Wishes to Your Family?
Here’s a hard truth: the best estate plan in the world can still cause family drama if nobody knows what’s in it. Surprises breed resentment.
If you’re leaving more to one child than another because they have special needs, tell everyone why. If you’re cutting someone out completely, they should hear it from you, not from a lawyer after you’re gone. If you want your body donated to science, your kids need to know before they start planning a traditional funeral.
These conversations are awkward. Your kids might not want to talk about it. Your spouse might get upset. Do it anyway. The short-term discomfort is nothing compared to the long-term damage of family members feeling blindsided or betrayed.
Write a letter explaining your reasoning for major decisions. Your attorney can keep it with your will. Sometimes just knowing why you made certain choices helps people accept them, even if they don’t agree.
6. What Are Your Funeral and Burial Preferences?
Funerals are expensive, emotional, and full of decisions that grieving people don’t want to make. Do you want to be buried or cremated? Religious service or celebration of life? Open casket or closed? Donations to charity instead of flowers?
The average funeral costs between $7,000 and $12,000, and that’s before burial plots, headstones, or cemetery fees. If you want cremation instead, say so. If you want your ashes scattered somewhere specific, put it in writing. If you have a prepaid funeral plan, make sure someone knows where the paperwork is.
Some people feel weird planning their own funeral. Get over it. This is a gift to your family. They’ll be heartbroken and exhausted, and the last thing they need is to argue about whether you would have wanted “Amazing Grace” or something more modern. Take that burden off them.
7. Who Will Be Your Healthcare Proxy?
This overlaps with the medical decision-maker question, but it’s worth emphasizing because many people confuse a living will with a healthcare proxy. A living will says what treatments you want. A healthcare proxy names who decides when situations arise that you didn’t specifically address.
Medical technology creates scenarios nobody can predict. New treatments emerge. Rare complications happen. Your proxy needs to make judgment calls based on what they know about your values and priorities. That’s different from just following instructions.
The best healthcare proxy is usually someone who’s seen you face difficult medical decisions before, or who you’ve had deep conversations with about quality of life versus quantity of life. It might not be your closest family member. It might be the one who can separate their own fears from your wishes.
8. What Debts Will Your Estate Need to Cover?
Death doesn’t erase debt. Credit cards, mortgages, car loans, personal loans—they all get paid from your estate before anyone inherits a penny. If your debts exceed your assets, your heirs might inherit nothing. In some cases, they might even face creditor claims.
Make a list of everything you owe. Include the obvious stuff like your mortgage and car payment, but also the less obvious: medical bills, taxes, business debts if you’re self-employed, and any personal loans from family or friends. Your executor needs this information to settle your estate properly.
Life insurance can cover these debts and then some. A policy worth two or three times your annual income usually does the trick for most families. It’s not glamorous, but it works. Your family won’t have to sell the house to pay off your credit cards.
9. Who Gets Your Sentimental Items?
Your kids don’t care about your money as much as you think. What they’ll fight over is grandma’s wedding ring, your collection of first-edition books, the painting you bought on your honeymoon, and that ridiculous lamp everyone hates but somehow still wants.
Sentimental items cause more family feuds than anything else in estate planning. Three siblings who got along perfectly their whole lives will stop speaking over who gets dad’s watch. It’s irrational, but it’s real.
Make a personal property memorandum—a separate document from your will that lists specific items and who gets them. You can update this anytime without redoing your whole will. Be specific. “My jewelry” is vague and causes problems. “My diamond engagement ring to Sarah, my pearl necklace to Jennifer” is clear.
Better yet, give things away while you’re alive. You get to see people enjoy them, and there’s no confusion later.
10. Do You Have a Living Will?
A living will (also called an advance directive) tells doctors what medical treatments you want or don’t want if you’re terminally ill or permanently unconscious. It’s different from a regular will, which deals with your property.
Be specific about life support, feeding tubes, ventilators, resuscitation, and organ donation. “No heroic measures” sounds clear but means different things to different people. Does that include antibiotics for pneumonia? What about a simple surgery that might extend your life by months?
You can make this as detailed or as simple as you want. Some people write pages covering every scenario they can think of. Others just state basic principles and trust their healthcare proxy to apply those principles. Both approaches work as long as you actually create one.
Most hospitals have free forms you can fill out. So do most state health departments. It takes maybe 30 minutes, and then you’re done. File copies with your doctor, your healthcare proxy, and your attorney.
11. What Happens to Your Business?
If you own a business, your estate plan gets significantly more complex. Businesses don’t pause operations while your estate gets settled. Customers need service, employees need paychecks, and bills keep coming.
You need a succession plan that answers several questions. Who runs things immediately after you die? Who has authority to access accounts and make decisions? Do your heirs keep the business, or should your executor sell it? If there are partners, does the business have a buy-sell agreement funded with life insurance?
Many small business owners are so busy running things that they never plan for this. Then they die, the business collapses, and something they spent decades building becomes worthless. That’s a tragedy for everyone—their family loses an asset, and their employees lose jobs.
Talk to an attorney who specializes in business succession planning. This isn’t DIY territory. The tax implications alone can be complicated enough to require professional help.
12. Who Will Care for Your Pets?
Your pets are family, but legally they’re property. You can’t leave money directly to a dog. You need to name a caretaker and potentially set up a pet trust to fund their care.
Think beyond who loves your pets. Who has the time, space, and financial ability to care for them properly? Your niece might adore your cat, but if she lives in a tiny apartment with a no-pets lease, that’s not going to work. Your neighbor might have a big house and yard, but are they really up for adopting a high-energy dog that needs daily runs?
A pet trust can provide money for food, vet care, grooming, and anything else your pet needs. You can include instructions about diet, exercise, medical care, and what to do when they eventually pass away. Some people even leave money for the next pet their caretaker adopts.
If you can’t find anyone willing to take your pets, research animal rescues that specifically handle estate situations. Some organizations will care for pets long-term using funds you leave for that purpose.
13. What Charitable Causes Matter to You?
Leaving money to charity can reduce estate taxes, create a lasting legacy, and support causes you care about. You don’t need to be wealthy to do this.
Maybe you want to leave $1,000 to your local animal shelter, or maybe you want to establish a scholarship fund at your alma mater. Perhaps you’d rather split a percentage of your estate among several causes instead of specifying dollar amounts. All of these work.
Name specific organizations with their full legal names and addresses. “The cancer foundation” isn’t specific enough. There are hundreds of cancer charities. Your executor needs to know exactly which one you mean.
Some people set up donor-advised funds or charitable remainder trusts that provide income to their heirs for years and then the remainder goes to charity. These get complicated fast, so you’ll need professional guidance. But they can be powerful tools for tax planning while supporting causes you believe in.
14. Have You Reviewed Your Beneficiary Designations?
Here’s something that catches people off guard: beneficiary designations on retirement accounts, life insurance policies, and payable-on-death bank accounts override your will. It doesn’t matter what your will says if the beneficiary form says something else.
This causes problems all the time. Someone gets divorced, remarries, and updates their will but forgets to change the beneficiary on their 401(k). They die, and their ex-spouse gets the retirement money while their current spouse gets nothing. The will can’t fix this.
Pull out every financial account statement you have. Look at who’s listed as the beneficiary. Is it still the right person? Are your kids still minors who would need a court-appointed guardian to manage the money? Did you name your elderly parents who might die before you do?
Update these forms every few years or whenever your life situation changes significantly. Getting married, divorced, having kids, or losing a loved one all trigger the need for updates.
15. What Tax Implications Will Your Heirs Face?
Taxes can eat up a huge chunk of your estate if you don’t plan carefully. Federal estate tax currently only applies to estates over $13.61 million (as of 2024), but state estate taxes often kick in at much lower amounts. Some states tax estates over $1 million.
Beyond estate taxes, there are income taxes on retirement accounts, capital gains taxes on investments and real estate, and potential gift taxes if you try to give away assets before you die. Each type of asset gets taxed differently, and the rules change constantly.
Roth IRAs pass to heirs tax-free. Traditional IRAs force heirs to pay income tax when they withdraw money. Stocks held until death get a “step-up in basis” that eliminates capital gains taxes, but stocks gifted before death don’t. Real estate can be put in trusts to minimize taxes, but the wrong type of trust can backfire.
This is absolutely a situation where professional help pays for itself many times over. An estate planning attorney or CPA who specializes in estate taxes can save your heirs tens or hundreds of thousands of dollars.
16. Who Will Be Your Executor?
Your executor handles everything after you die. They file your will with the court, notify creditors, pay bills, file final tax returns, distribute assets to heirs, and close your estate. It’s a lot of work that can take months or even years.
Choose someone organized, responsible, and willing to handle conflict, because disputes will arise. This person needs to follow your wishes even when heirs pressure them to do otherwise. They also need to be good with paperwork, deadlines, and dealing with attorneys and financial institutions.
Many people name their spouse or oldest child. That’s fine if they’re up for the job, but it’s also okay to name someone else. A trusted friend who’s good with administrative tasks might be better than a family member who gets overwhelmed easily. You can also name a professional executor like an attorney or trust company, though they’ll charge fees.
Name a backup executor too. Your first choice might die before you, become too ill to serve, or simply decide they can’t handle it when the time comes.
17. Do You Need a Trust?
Wills go through probate, a court process that’s public, slow, and sometimes expensive. Trusts avoid probate, keeping your affairs private and getting assets to heirs faster. But trusts cost more to set up and require more maintenance.
For many people, a simple will works fine. If your estate is straightforward and you don’t mind the probate process, save your money. But trusts make sense if you have significant assets, own property in multiple states, have minor children or heirs with special needs, want to control how and when heirs receive money, or value privacy.
Revocable living trusts are the most common. You control the trust while you’re alive and can change it anytime. After you die, it becomes irrevocable and distributes according to your instructions. You can also create trusts that reduce taxes, protect assets from creditors, or provide for a disabled loved one without disqualifying them from government benefits.
Talk to an estate planning attorney about whether a trust makes sense for your situation. Don’t let anyone pressure you into complex trust strategies you don’t understand or need.
18. What Happens to Your Retirement Accounts?
Retirement accounts like 401(k)s and IRAs are often people’s largest assets, but they come with special rules. Your spouse usually has automatic rights to these accounts unless they sign a waiver. Non-spouse beneficiaries face different withdrawal rules that affect taxes.
The SECURE Act changed how inherited retirement accounts work. Most non-spouse beneficiaries now must empty inherited accounts within 10 years, paying income tax on withdrawals. This can push heirs into higher tax brackets and cost them a fortune if not planned carefully.
Some strategies can help. Roth conversions while you’re alive move money from traditional IRAs to Roths, eliminating future income taxes for your heirs. Charitable remainder trusts can stretch out distributions while supporting causes you care about. Naming a trust as beneficiary gives you more control but requires expert setup.
The rules keep changing, so review this area regularly with a financial advisor who understands estate planning. What worked five years ago might not be optimal today.
19. Have You Documented Your Asset Locations?
Your executor can’t distribute what they can’t find. You’d be amazed how often families discover forgotten bank accounts, insurance policies, safe deposit boxes, or investment accounts years after someone dies.
Create a master list of everything you own and where to find it. Include account numbers, financial institution names, and contact information. List the location of important documents like deeds, titles, insurance policies, and passwords. Note any safe deposit boxes and where the keys are.
Don’t forget about unusual assets. Do you have valuable collections? Money owed to you by others? Frequent flier miles or credit card points? Mineral rights or royalty payments? Storage units? Timeshares? All of this needs to be documented.
Update this list annually or whenever something major changes. Keep copies with your attorney, your executor, and in your home safe or filing cabinet. This simple document will save your family countless hours of searching and potentially thousands of dollars in lost assets.
20. When Was the Last Time You Updated Your Plan?
Estate plans aren’t “set it and forget it.” Laws change. Your life changes. Assets grow or shrink. People die or get divorced. An estate plan that worked perfectly 10 years ago might be completely wrong for your situation today.
Review your plan every three to five years at minimum. Review it immediately after major life events: marriage, divorce, births, deaths, large inheritances, buying or selling a home, starting or selling a business, moving to a new state, or significant changes in your financial situation.
Many people create estate plans in their 30s or 40s when their kids are young, then never look at them again. Fast forward 30 years, and those kids are now adults who don’t need guardians, but the old plan still names grandparents who died 15 years ago as guardians and executors. Meanwhile, assets have multiplied, and nobody’s thought about tax planning.
Set a reminder on your calendar to review your estate plan every few years. It only takes an hour or two, and it might save your heirs from massive headaches later.
Wrapping Up
Estate planning feels like homework for a test you hope never comes. But skip it, and you’re not just failing yourself. You’re failing everyone who depends on you.
Start with these questions. You don’t need all the answers today. Pick three, make some decisions, and document them. Next month, tackle three more. Before you know it, you’ll have a real plan that protects the people and things you care about most.
The peace of mind is worth every minute you spend on it.