How to Have Hard Financial Conversations with Your Parents (And Why You Need To)

Photo by Jeremy Bishop on Unsplash

The holidays can already be a bit strained, are we really suggesting you add tough financial conversations to the mix? Maybe. Hear us out. 35-40% of Stash’s H.E.N.R.Y.s™ tell us they are planning to help financially care for their parents to some degree as they age. Typically, this means they are planning on supporting their parents to the tune of about $10,000 per year for 10 or more years. This is not an insignificant commitment, so beyond having a plan yourself, it is important to know what their plan is. Having these conversations can be difficult, so here’s our guide to helping make them as smooth as possible.



The biggest reason to have these conversations around the holidays is proximity. It’s best to have these conversations in person, and many people go home for the holidays. If the holidays are particularly strained for you and your parents, file this information away for a time when you can sit down with them when tensions are lower.


You know your parents best. Some parents will be open to you bringing these topics up during the holidays, others really won’t be. Trust your gut. If they’re not ready to have this kind of conversation, you might want to try respectfully asking when might be the right time. If they respond with “never,” you can pivot and ask them if there is someone else that is close to them they have shared some of this information with, and ask if they would be comfortable with you talking with that person.


Which brings us to probably the biggest hurdle and question regarding this conversation: How do I start it!? Here’s what we suggest: talk about Stash Wealth or whoever your financial advisor is (even if it’s just a more knowledgeable friend). Here’s what that might look like: “I was talking with my financial advisor the other day and we were discussing my retirement account and setting up my beneficiary, it got me wondering, how do you and Dad/Mom/Name have things set up?” Starting from a place of asking open questions and getting a dialogue going is a great way to test the waters and see what they’re open to sharing. You also might get some great advice!



Here are a few of the big questions you might want to cover:


  • Do you have a will? Would you like me to keep a copy of it?
  • Have you thought about whether you want any life-sustaining measures taken if anything happens to you? If so, are those updated in your living will? And do you have a living will?
  • Are your beneficiaries on your accounts up to date?
  • Do you have life insurance?
  • Would you prefer to remain independent and live in a nursing home or assisted care facility, or would you want to live with me or one of my siblings?


Yep. They’re heavy. But the alternative of not asking these questions means that you will be in the dark when something happens. So start opening the door to talk about these things. You don’t necessarily need to bring a checklist and get every question answered in a single conversation, it’s about feeling out what your parents are open to sharing, and starting to get a picture of their finances and end-of-life plans. There’s a chance they haven’t really started planning for these things, which can get tricky, so it’s important to stay present with them as they talk through things. They may not have all the answers, and that can be frustrating and emotional.  


Important note: Don’t just jump into these conversations cold. Think of it like making an appointment. Let your parents know you’d like to have a serious conversation about these things and set a time and a place that is supportive of that conversation. Maybe not in public (things can get emotional), no pets or kids to distract you, involve or exclude any partners of SOs per your best judgement. End-of-life planning is complicated, families are complicated, money is complicated, that is a lot of complications. Try to honor how mixed up and sticky all of it has the potential to get, while also realizing what you do and don’t need to shoulder in the process.


We also suggest you take some notes either during or after the conversation. Use your best judgement about whether your parents might be put off by you bringing a notebook and pen, but regardless of whether it’s during or after, it is going to be a lot of information, take some time to write it all down. The moments when you need this type of information are highly charged already, get it out of your brain and onto paper, and then put it where you can find it.



Are you one of many siblings and are all of you are partnered or married?

Make sure you touch base with them before you bring up these topics with your parents.


Only child with a parent or parents who might both be counting on you? That’s a lot of responsibility, start these conversations as soon as you can, and loop your partner or SO into them.


Estranged from your parents, but your SO is super close with theirs? You may need to step up and help with your new chosen family.


Did one or both of your parents remarry? That adds a whole new level of complexity.


Do your parents have pets? Dogs, cats, birds, horses? Pets outlive people pretty regularly. Are you ready to take on the responsibility or do the work to re-home their beloved animals?


Family dynamics are unique, frustrating, and wonderful. This information is to help you plan out the conversation, decide who needs to be involved, and make sure to come into the conversation as prepared as possible.


And get ready for some disagreements. “4 in 10 families disagree on the roles children will play as parents age, in terms of who will be their caregiver, who will be the executor of the estate and who will manage the finances,” according to the 2016 Fidelity® Investments Family & Finance Study Executive Summary. (Check out the full report summary to see just how much people disagree about all this stuff and just how important it is to get some clarity with your family.)



Swedish Death Cleaning

Beyond money, your parents probably also have a bunch of stuff. Enter Swedish Death Cleaning. It’s really not as morbid as it sounds. And it’s #trending. Many cultures aren’t as prudish as Americans when it comes to death. The topic of death and dying can be pretty taboo in the United States, but in other cultures, it isn’t seen as morbid or uncouth to discuss these things. One of the popular Nordic trends taking America by storm right now is the notion of cleaning out your things as you age. It’s kind of like Marie Kondo meets the Minimalists meets We’re  All Going to Die.


Swedish Death Cleaning is about getting rid of stuff a little at a time as you get older. Essentially, this is so your kids and loved ones have less to go through after you die. You aim to get rid of a certain amount in your 50s, 60s, 70s, 80s, and 90s. Depending on how the financial conversations goes (or doesn’t go, sometimes these things take multiple tries), perhaps bring up the conversation about stuff. Some parents will find this to be easier to talk about, it’s more tangible after all, and much of their stuff has value, so it’s an important conversation to have not only for the logistics of cleaning out and divvying up things after they pass, but also because of the monetary value of those items combined with sentimental value.


If you’re ready to get this conversation started, but are still super nervous, here are a few other fantastic resources we’ve found: Having The ‘Money Talk’ With Aging Parents and How to talk to your parents about their estate without seeming like a greedy jerk. Both have great insights and some fascinating statistics.   

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