So, you want to start talking about estate planning. Cue the awkward silence. Now, it’s not exactly the topic that has people leaping out of their chairs…we get it. Multiple conversations that focus on money? Death? Who gets your vintage record collection? (Your favorite child, of course). Yeah, it’s not the first dinner conversation topic people gravitate to. But here’s the hard truth: avoiding the conversation can cause (everyone) way more stress than biting the bullet and having it now.
Why we dodge the conversation (And why that’s a problem)
Despite being blessed with the capacity for existential thought, most humans don’t like contemplating their mortality. Add a dash of financial planning (and all its challenges) and some ripe family dynamics—it’s a recipe for discomfort. And the best way to decrease stress or anxiety immediately? Avoidance. It works like a charm, but it doesn’t solve the problem. It just shoves the feelings into a metaphorical bag until they overfill.
Another reason we may delay estate planning? Because people may think it’s only for the wealthy or older adults. Spoiler: it’s not. If you have any assets, children, or just an opinion about what should happen to your stuff (and your healthcare decision), estate planning is for you.
Having a plan can help reduce anxiety and stress for you and your loved ones at a time that tends to be one of the most stressful times.
Setting the stage (Without making it awkward)
Alright, so you’re ready to have the talk. Timing and setting matter. Bringing up estate planning during your granddaughter’s birthday party is probably not ideal. Instead, be intentional and choose a calm, private setting where everyone can focus. Coffee at home on a Sunday morning is perfect. During a casual drive around town? Surprisingly effective (no one can escape!).
Need some ideas to break the ice? Try something like:
- “Hey, I read an article about how important estate planning is, and it got me thinking…”
- “I know this isn’t the most fun topic, but I think we should find a time to talk about plans just in case.”
- “Remember how Auntie Billie’s estate turned into a mess? I want to avoid that and set things up so we don’t have to worry about that later.”
- “I’m not going anywhere soon, but just in case I get abducted by aliens, let’s chat about my will.” (Humor can always help jump-start the conversation!)
Handling emotional reactions (Because feelings happen)
Estate planning conversations will stir up emotions. With our partners, family members, friends, and even within ourselves. Fear, sadness, anxiety, or even anger can pop up. You’ll see the full range of coping strategies, too. Someone might try to joke their way through it while another family member gets teary-eyed every 5 minutes. It’s all normal!
Acknowledge the feelings without letting them derail the conversation. Here are some comments you can make to help acknowledge the feelings:
- “I know this is uncomfortable to talk about, but it’s important.”
- “I know this can be tough, but I want to talk about it now and not regret missing this chance to do so.”
- “This is important, and I want to check in to see how we’re both feeling as we talk more about it.”
If someone’s emotions are too overwhelming for them, which can show up as distraction, resistance, or anger, don’t feel the pressure to force it. Even just initiating the conversation or sharing your intention to have the conversation is enough for the first step. Offer to revisit the topic later when they have time to process the conversation you’ve started.
Key points to cover
You don’t have to cover everything in one sitting. And it helps to plan out what points to cover so you don’t forget anything important, and you can plan out what to talk about next if you don’t (and you probably won’t) cover in one sitting. Estate planning usually involves several things:
- Wills: Who gets what? Who takes care of any minor children? Who will take ownership of any pets?
- Trusts: Helpful in deciding how assets are distributed if you want more control.
- Healthcare Directives: Outlining certain medical decisions for yourself and appointing a medical proxy to help make decisions on your behalf. (Do you want to stay on life support? How do you want to treat pain management?)
- Power of Attorney: Who handles your finances if you can’t make those decisions? What about legal decisions?
- Beneficiaries: Are they up to date on your retirement accounts and life insurance policies?
Dump it all out and then break it into chunks. To help make each discussion manageable for everyone involved, you can set an agenda.
When family dynamics get…Interesting
Family dynamics can turn estate planning talks into a minefield. Maybe there’s sibling rivalry, a blended family, or someone who thinks they deserve more than their fair share. Be honest and fair, and remember: clarity is kindness. It will help prevent conflict later.
Know when to pause the conversation. Set the intention of when to return so things can cool off. Sometimes, work harder, not smarter— involve a neutral third party (like a financial advisor, estate attorney, or family therapist) that can help diffuse tension or share some of the logistics. It may also help prevent the more… difficult family members from getting too out of hand.
Keep the conversation going
Even though you are trying to prepare for the future, life changes constantly. As life progresses—marriages, divorces, children, new assets—make it a point to revisit your estate plan to ensure it still aligns with your wishes. For example, you may want to update your will beneficiaries if there are new grandchildren in the mix. Or maybe you are now estranged from your daughter. Or maybe you won the lottery. Whatever the case is—you’ll want to update your estate plan.
Final thoughts
While talking about estate planning isn’t anyone’s idea of a good time, it doesn’t have to be a grim or “avoid-at-all-cost” experience. Planning the conversations with intention, approaching them with honesty (maybe a bit of humor), and a lot of empathy can go a long way. As you initiate the conversations and get the ball rolling, you’ll probably notice a (metaphorical) weight being lifted off your shoulders. Or, even if it doesn’t feel that way, your future self (and family) will thank you for your foresight.
Dr. Vivian Oberling is a licensed clinical psychologist with degrees from UCLA, Harvard, and Stanford. In her private telehealth practice, she works with adults navigating anxiety, identity shifts, and relationship dynamics—whether they’re dating, partnered, or parenting. She also provides executive coaching and behavioral health advisory support to tech startups and legal tools reshaping how we think about love, marriage, and psychological safety. Dr. Oberling combines 10+ years of clinical expertise with modern, real-world insight to help people move through uncertainty with clarity and connection.
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