How to have uncomfortable conversations

November 9, 2023

We build traditions without even knowing it.  

Ryan knows my love for fall. The change, the transition to cooler days and perfect evenings. It all seems to calm down a bit as the leaves begin to change their colors. This year, my typical inward appreciation for the season has deepened to outward excitement, and Ryan couldn’t help but notice, “I know you love fall, but you almost seem giddy!”  

He was right; I’m really excited about fall, but specifically for Thanksgiving. This made me wonder: where was all this joy coming from? 

After a bit of internal unpacking, here’s what I discovered: This Thanksgiving isn’t going to be a harried discussion about where to go or what side of the family to spend it with. It’s set. I know exactly what it’s going to look like, and it’s become familiar and, dare I say, a tradition.  

We’ll go to Ryan’s parents’ house in Lafayette, the house he grew up in. My girls get to sleep in his childhood room. They have grandma’s toy basket set out for their arrival. His mother Joyce has Pinot Grigio chilling for me in the fridge to open right when I arrive. Wayne, his father sets out my little sign “Anna’s reading corner” in their formal living room so I have my space when the noise gets too much for me. Lifetime neighbors who are family come in and out of the house. 

The evening before Thanksgiving, Ryan’s sister is looking for the perfect sunlight to know where to take pictures before dinner the next day. Ryan and I wake up early on Thanksgiving to run the 10k Turkey Trot in Walnut Creek. We get back to Ryan’s parents and the girls are watching the Macy’s Thanksgiving Day Parade.  

Joyce starts prepping Thanksgiving dinner. We all stay out of the way until she gives us our designated tasks. It’s game playing, laughing, drinking, and just doing life together.  

I know we don’t have many Thanksgivings left this way, but I’m going to soak it all up.

Knowing there will inevitably be an end to this way we spend this holiday helps me to have faith in the next transition. We’ll embrace the change and pray for it to gradually move to the next traditions we didn’t know were forming. For all of this, I am grateful.  

As we think about our current transitions and the next traditions we’ll be moving into, it reminds me how important it is to start a conversation with our families about our estate plans.

When you’re thinking about turkey and stuffing and parades, I know it can feel uncomfortable to even be thinking about a time when those gatherings look different. And yet, I believe fiercely that when approached correctly, these times together are exactly the right time to have conversations about the future. 

I believe the holidays create an important opportunity to talk with your family about where you’re at with your estate plan, whether it’s fully baked or just in the idea stage. The goal is just to start the conversation: let others know we’re starting to think about our will and what we want to have happen with what we have.  

Depending on what stage of life you’re at, these conversations most often come from the perspective of either the adult child or from the parent. If you’ve never talked about your future financial plans before, you may be unsure on how to even begin the conversation. That’s extremely normal and believe me: everybody has experienced this at some point. 

Below, I’ve outlined a few ideas on how to approach these conversations from both points of view.

These are just some starting points, based on my own experience as an adult child, as well as with many Mosaic clients who have shared some of their own family discussions. 

Parents of Adult Children: 

Here’s a tip from an adult child: we really want you to bring up this conversation. We’re thinking about it, and it’s not about how much money we’ll inherit. We just want to know what your plan is as you move forward in life.  

Some topics we wonder about: 

  • What are you concerned about? 
  • What are you excited about? 
  • What’s important to you? Charities you give to and why? 

We also just want to know: 

  • Who’s going to be responsible for you financially? 
  • Will we need to help financially or physically take care of you? 

And finally–we’re secretly okay with you giving us a nudge, too. Feel free to toss it back to us to remind us we also need to get our estate plans in gear. 

Here’s the thing: this is so hard. We know this isn’t easy to think about the future. You may not be able to answer all these questions at once—or even at all—but please know we’re thinking about them.  

Adult Children: 

If your parents haven’t brought it up or feel unsure about how to approach it, here are some ideas on how you can approach it yourself. 

  • Over dessert or a glass of wine, consider some easy questions to start the conversation. Lead with “I” or “we” statements to help your parents know you’re thinking about it, too. 
  • “We have been thinking about putting together our estate plan and wanted to know if you have yours in place?” 
  • “I have been wondering: do you have a favorite charity you donate to regularly?” 
  • Tell a story from a friend about a positive or negative experience they had when a parent passed away. I am sure you have heard stories; share one.  
  • “Recently my friend told me about how her parents sat them down and let them know about their estate plan. They were so relieved to have this conversation started. I would love it if we could talk about your plans.” 

Please know you’re not alone in these questions and starting the tricky conversations. All my friends are in this stage with their parents. I think it is vital to just slowly begin the conversations. Who knows where they can lead, but hopefully gradually over time, it moves your relationships closer as you get intentional about what‘s important to everyone.  

I love hearing stories of how parents have started conversations with their adult children, and also how adult children have initiated the conversation. When families were intentional about what they wanted and talked through what they have in place, the outcomes have always been positive. 

However, I have heard horror stories of families not speaking to each other, relationships broken between siblings, because they only knew about the estate plan after the parents had passed away. It breaks my heart because I know it could have been better.  

I strongly believe in intentional conversations. It’s vital to our relationships to let others know what we want and what we’re expecting from others. Estate planning is a form of collaboration. You think individually about what you want, but others will have to be involved. Letting the people know what they will be responsible for is key to getting the estate plans executed with the original intent. It’s hard in the short term but the work put in upfront will help create your legacy now and onward.  

As we go into the holiday season, I encourage you to think about a time that could work to start a conversation with your parents or adult children.

The first step can just be to see where they’re at. Try not to play the conversation in your head but just figure out when you could initiate the conversation. Then once you start, you can see where it goes.  

I would be honored to talk anyone through how to start a conversation with your children or your parents. Or please send me any ways that you have had these conversations, I would love to hear how you navigated this important topic.

P.S. Veteran’s Day is a special day for the Nelson Family. We celebrate Ryan’s years of service in the Air Force, and I celebrate the girls and myself. I am proud of us. We celebrate our friends and family who have served and who are currently serving all over the world. We acknowledge the current tragedies happening in our world, and we are broken. I am giving the biggest shout-out to my military spouses out there; you are amazing and I am grateful to be included in that bunch.


The opinions expressed herein are those of Anna Nelson and are subject to change without notice. This material is not financial advice or an offer to sell any product. Forward-looking statements cannot be guaranteed. This document may contain certain information that constitutes “forward-looking statements” which can be identified by the use of forward-looking terminology such as “may,” “expect,” “will,” “hope,” “forecast,” “intend,” “target,” “believe,” and/or comparable terminology. No assurance, representation, or warranty is made by any person that any of Anna Nelson’s assumptions, expectations, objectives, and/or goals will be achieved. Nothing contained in this document may be relied upon as a guarantee, promise, assurance, or representation as to the future. Investment Advisory Services offered through Integrated Advisors Network, LLC (Integrated) a Registered Investment Advisor. Registration does not imply a certain level of skill or training.