Connecting With Family Over the Holidays

An Opportunity For Meaningful Conversations About Finances

Gathering with family throughout the holiday season presents a perfect opportunity to have important, albeit potentially difficult, conversations about the future of your affairs. Having a plan in place in case of death or disability – while not enjoyable to think about – can alleviate administrative pains, minimize family disputes, and ensure assets are protected. When you’ve established that plan, it’s of the utmost importance that it is properly communicated to your loved ones.

We’ve put together a few strategies to help you have — and continue — these critical conversations:


If you haven’t had the chance to discuss these issues yet, our Having the ‘Money Talk’ piece provides tips and a checklist to help you broach the subject with confidence.

Once you’ve had conversations about these sensitive topics, it’s important to make sure communication does not end there.

Read: Having the ‘Money Talk’.


Consider filling out a copy of the What My Family Should Know document and using it as a prompt to revisit these conversations at least once a year.

This document creates a central repository for all important information related to your life, including where important items are located. Review this information and make any necessary changes. You should also set aside time to review your estate plan, insurance policies, powers of attorney, and other important legal documents to ensure they still meet your goals and wishes.

Don’t forget – Cassaday & Company, Inc. clients can take advantage of memorializing this document by uploading it to their secure client portal.

Read: What My Family Should Know.


If you have not declared a Client Advocate yet, you may want to bring this up in conversation as well.

As an additional layer of protection, Cassaday and Company’s clients have the opportunity to declare a trusted person in their life as their Client Advocate –someone your advisory team may communicate with in the event you begin to exhibit signs of cognitive decline. This is not designating Power of Attorney. More about our Client Advocate initiative can be found here. If you have questions about declaring an advocate, or are ready to name one, contact your advisor.

Read: Declaring A Client Advocate.

Conversations about death or disability can sometimes be uncomfortable, however having these discussions early will help you feel reassured that your finances and affairs are in order and being managed according to your wishes.

Whether you’re a parent bringing up these topics with your adult child, or a child bringing these topics up with a parent, always remember to be sensitive to the other’s concerns.

Your advisor can also help facilitate these conversations or help at any point in the process. Please contact your advisor if you would like to set up a family summit for these purposes or have any additional questions.


Contact Michelle Tigani

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