Purposeful Conversations during the Holidays

Dec 22, 2025

We are well within the festive season, and on behalf of everyone at Forward, however you choose to celebrate, we wish you and yours a lovely holiday. If your family and friends are anything like mine, there will be too much food and too much good times together.

And while this spirit is part of the foundation of the holidays, there is also the opportunity to have purposeful and meaningful conversations with our families about what matters most, about legacy, and about how the family can be better in the year(s) ahead.

These conversations can seem daunting at first, but with a little preparation and forethought as to the best approach, you can create the space and environment to explore these ideas. We summarized five different approaches to these conversations a few weeks back, and they helped me during Thanksgiving. And then we fleshed out the five approaches as well.

Forward’s goal is to help keep more money in the family, and this starts with good communication and planning. Mom and Dad should celebrate their legacy while wanting to help. The Next Generation wants to prove it can not just carry on but raise the family levels. Everyone wants to move the family forward, and we’re here to help…