6 Conversations About Money to Have With Your Family Over the Holidays

As I get older, I find myself appreciating the winter season more. It’s a time to relax and enjoy being around family and friends. There’s also more time for in-depth conversation about topics that might not normally come up—such as financial planning for members of the family. In this article, I’ll discuss six topics that are worth bringing up with family members, including parents, kids, and partners. I wrote this article from the perspective of someone with a spouse, retired parents, and 20-something kids, but feel free to adapt as needed for your situation.

Conversations to Have With Your Parents

How healthy are their finances?

In many families, money is a taboo topic. But as parents or other relatives age, their adult children often get more involved in their financial lives. One way to broach this topic is to ask if an elderly relative is having any trouble paying their bills (either because of limited financial resources or more difficulty keeping up with complicated tasks if cognitive decline is a potential issue).

If a parent’s financial resources are dwindling, adult children can help them enroll for Medicaid, which provides healthcare coverage and long-term care for individuals with annual income and assets below certain thresholds, which vary by state. If Medicaid is a possibility, it’s important to plan several years ahead to avoid potential issues with the Medicaid look-back period, which is designed to prevent applicants from giving away assets (or selling them at an artificially low price) to meet Medicaid’s asset limits. During the five years leading up to potential Medicaid enrollment, it’s best to avoid gifting money to relatives, transferring the title on a house or car, and even donating vehicles to charity.

Adult children can also help their aging parents get in touch with organizations such as senior services or Departments on Aging offered by state or local governments. These organizations can help seniors access services such as meal delivery, transportation, money management services provided by a qualified volunteer, and help with navigating medical issues and long-term care.

It’s also helpful to make sure aging parents have end-of-life plans in place, including an advanced directive for end-of-life medical care, a will or other estate-planning documents, healthcare power of attorney, and any final wishes for a burial, cremation, or memorial service. It can be difficult to discuss these topics, but it’s better to broach them ahead of time instead of waiting until a loved one is in a medical crisis that turns out to be fatal.

How viable are their living arrangements?

Another difficult conversation focuses on the best living arrangements for an aging parent. A house with two or more floors may be difficult for the elderly to manage, especially as the likelihood of serious falls increases with age. A larger home that was once filled with the hustle and bustle of family life may be difficult to maintain, particularly for an individual living alone after a spouse has passed away.

As parents age, it can also be helpful for them to move closer to adult children or other family members. An elderly parent may initially resist the idea of moving, particularly if they cherish their independence and love being in a certain location. Research indicates that the majority of older adults want to remain in their own homes as long as possible. As people age, though, it can be difficult for them to stay in the place they love if it’s several hours away from the rest of the family.

In my experience, the issue of where to live is particularly fraught, so it’s best to broach the topic early and think about unconventional solutions, such as home-sharing or an accessory dwelling unit that can offer both independence and proximity to younger relatives.

Conversations to Have With Your Kids

What do they need to know about your finances?

As I mentioned above, money remains a taboo topic in many families. But as Cameron Huddleston points out, there are several reasons why it makes sense to share information about your finances with your adult children. For one thing, they’ll likely need information to handle your estate after you’re gone.

As I wrote about previously, it’s helpful for your beneficiaries to have a general understanding of how your finances are set up—which assets do you hold in taxable versus tax-deferred accounts, is your mortgage paid off, and are there certain assets such as a family business that will eventually need to transition to the next generation. Beneficiaries will also need to know the potential tax implications of assets they inherit, such as the step-up in basis for inherited assets for capital gains purposes and details on required minimum distributions from inherited IRAs (which are generally required to be fully distributed within 10 years of the original accountholder’s death for nonspouse beneficiaries).

Many families are less comfortable talking about specific dollar amounts that their beneficiaries may eventually inherit. For one thing, the size of an estate can be largely unknown if your eventual death is decades down the road. Market performance, potential tax-law changes, and the cost of specialized medical care late in life are all huge swing factors that can dramatically change your net worth. However, as your children start planning their own financial futures, it’s helpful to share more information about your plans, such as whether you plan to contribute to education funds for any potential grandchildren or set up a gifting program to take assets out of your estate.

Are they taking the right steps for their financial futures?

As many parents can attest, it can be difficult to encourage teens and young adults to do the right things without slipping into lecturing mode, which isn’t always well-received. (Ask me how I know!)

Nevertheless, your kids will probably appreciate your hard-earned wisdom at some point, even if they don’t always implement it right away. For a young adult just getting started in a career, there are a handful of basics that are worth tending to as soon as possible. Among them:

• Make sure you have health, car, and renter’s insurance.
• Contribute to a Roth IRA or 401(k).
• Set up an emergency fund.

Although certain members of Generation Z might think of these as boring tasks of “adulting,” parents or other adults can reframe them as low-effort ways to take care of your future self. For example, it takes less than 15 minutes to sign up for basic health insurance available under the Affordable Care Act. Getting the financial basics in place doesn’t have to be time-consuming, and there’s no need to overthink anything. Especially early in life, done is better than perfect. With time on their side, the young can worry about fine-tuning their plans later. The most important thing for now is just to start.

Conversations to Have With Your Spouse or Partner

Are we on track with our budgeting plans?

Checking in on day-to-day savings and spending can be worthwhile to do periodically. With the new year approaching, it’s also helpful to have a full year of data to review.

Most online banks and credit card providers can provide a downloadable summary of spending over the previous year. Reviewing this with your spouse or partner can be a good opportunity to see exactly where the money is going and where there might be opportunities to cut back. Monthly subscriptions, for example, can easily add up, especially for services that automatically renew.

Budget issues can also be a source of stress and disagreement, though. To make the process less fraught, try to frame it as a way to make sure your future together is on track. It can also be helpful to think about ways to make potentially stressful budget sessions more enjoyable. At the 2022 Bogleheads Conference, for example, Betterment’s Dan Egan discussed the strategy of temptation bundling. In addition to their regular date nights, he and his wife have periodic “admin nights,” during which they review their finances together, followed by a night out with a cocktail. Linking the potentially boring and stressful budget discussion with something to look forward to can make it more likely that couples will stay on top of mundane but important financial details.

What are our shared goals for our future together?

A regular admin night can also spur broader discussions about longer-term goals. While we don’t plan to retire anytime soon, for example, my husband and I recently talked about visiting a few different locations to scope out where we might want to live during retirement. Especially in the years leading up to retirement, it can be helpful to have a series of discussions about what each member of the couple envisions for the next phase of life. What would each person’s ideal day look like? How much time will the couple spend together when they’re no longer working outside of the home? Where does each person want to live—in the same geographic location as during the work years or somewhere new and different? What type of living arrangement—a house, condo, motor home, or retirement community—would work best for the next phase of life?

A couple might also want to discuss other long-term goals, such as paying off the mortgage, taking a dream vacation, helping out children or grandchildren financially, or contributing to charity. As with any money discussion, it’s possible that the two partners may not have the exact same vision for their future life and goals. But continued discussion and a commitment to understanding what your partner really wants should help clarify the picture of what a shared future might look like.

A version of this article was published on Dec. 19, 2022.