Financial Planning
November 15, 2022

Holiday Conversations

Holiday gatherings are all about family, food and football, but they’re also a great time to talk about finance!
Stewart Willis

The holidays are often the only time extended families get together in person, which makes them a great time to have serious discussions about things that matter. That doesn’t just mean football! Many financial conversations are best held in person.


Good holiday financial conversations run the gamut from teaching kids how money works to talking with older relatives about their plans as they enter retirement. How you approach talking with a relative about money depends on their age.


Teach Your Children

Young kids benefit immeasurably from being taught about money early on. The concept of money is fairly advanced. Before the Mesopotamians invented it about 5,000 years ago, the idea of a token being a go-between to represent value was a foreign concept. After all, on its own, money is essentially valueless. It’s only because it represents value and can be used to obtain valuable things that it has any value at all.


Because that’s not very intuitive, kids need to be taught the concept that doing work earns you money, which you can then use to get things you want. A great way to do this is to make a game of it. If a child helps clear the table, give them a token of some sort. If the child then wants a second helping of pie, have them give you back the token in exchange for it. This teaches kids the lesson that doing work gets you something which you can then exchange for something else.


Increase Sophistication with Age

As kids grow older, start talking with them about more advanced financial matters. Teaching kids about saving money from an early age is vital to their financial future. A classic way is to play the penny-doubling game.  


Ask a child if they’d rather you give them $1,000 per day for a month, or 1 penny now, then double it every day for a month. Many kids will pick the $1,000, and you can then show them that picking the penny will get them their $1,000 just over halfway through the month, and by the end, they’ll get more than $5 million!  That’s a very effective way to get kids to understand more advanced concepts like compounding interest.


Uncomfortable Conversations

Turning to the other end of the spectrum, holiday gatherings are also a great time to have conversations with older family members about their future plans. As we age, it’s important to spend time making sure our financial affairs are in order.


We need to know what our retirement income will be, and create a plan to make sure it will see us through retirement. We need a long-term care plan. How will we pay medical bills if we require high levels of medical care due to a chronic illness or dementia? And we need an estate plan, not only to make things easier on our loved ones when we pass away, but also to establish important documents like living wills, which give directives for medical care should we be unable to express our wishes due to injury or illness.


People don’t often like thinking about such things, which means it’s frequently up to relatives to open the conversation. But because people don’t like thinking about it, finding the right approach to broaching the topic is key. General MacArthur once famously said “A tactic known is a tactic blown.” In other words, don’t try to “sell” your family members on retirement, estate or long-term care planning. They'll likely see you coming and shut you down!


Instead, casually work the topics into conversations so that discussing these issues becomes normalized. You need to strike the delicate balance between having the talks that need to happen and making your relatives uncomfortable to the point they don’t want to engage at all.


It’s Not a Handout

Younger relatives too often dislike having these conversations. They frequently feel as though they’re asking for handouts when discussing estate plans with aging parents. It’s important for families to create a culture of generational wealth- one of the family taking care of itself.


Part of taking care of your children is to pass assets you no longer need on to them; you can’t do that effectively without a good estate plan! At Asset Preservation Wealth & Tax, we help clients negotiate their golden years and beyond. We know from years of experience that the process is difficult, from starting conversations to the detail-oriented work that comes after. Once you’ve begun talking with relatives about these issues, it’s important to seek guidance from a financial advisor with experience in estate planning.


Proper planning can save you and your heirs a lot of money, from not having to pay unnecessary taxes to avoiding probate and the legal costs associated with it. This holiday season, give yourself and your family the gift of having those important financial conversations. It may be uncomfortable now, but it can save you a lot of stress and heartache in the future.

By structuring charitable giving properly, you not only help yourself, but the recipients of your donations as well. You benefit by not having to pay unnecessary taxes, and the charity also benefits by getting more value from your donation than might otherwise be possible.

Stewart Willis is the founder and president of Asset Preservation Wealth & Tax, a financial planning firm in Phoenix, Arizona. Investment advisory services offered through Foundations Investment Advisors, LLC, an SEC registered investment adviser.

The commentary on this blog reflects the personal opinions, viewpoints and analyses of the author, Stewart Willis, providing such comments, and should not be regarded as a description of advisory services provided by Foundations Investment Advisors, LLC (“Foundations”), an SEC registered investment adviser or performance returns of any Foundations client. The views reflected in the commentary are subject to change at any time without notice. Nothing on this website constitutes investment, legal or tax advice, performance data or any recommendation that any particular security, portfolio of securities, transaction or investment strategy is suitable for any specific person. Personal investment advice can only be rendered after the engagement of Foundations for services, execution of required documentation, including receipt of required disclosures. Any mention of a particular security and related performance data is not a recommendation to buy or sell that security. Foundations manages its clients’ accounts using a variety of investment techniques and strategies, which are not necessarily discussed in the commentary. Any statistical data or information obtained from or prepared by third party sources that Foundations deems reliable but in no way does Foundations guarantee the accuracy or completeness. Rates and Guarantees provided by insurance products and annuities are subject to the financial strength of the issuing insurance company; not guaranteed by any bank or the FDIC. Investments in securities involve the risk of loss. Any past performance is no guarantee of future results. Advisory services are only offered to clients or prospective clients where Foundations and its advisors are properly licensed or exempted. For more information, please go to and search by our firm name or by our CRD # 175083

Ready To Get Started?

You spent all your working years accumulating this wealth. Now it’s the time to make the most of it.