When you think of any family, but especially your own, you likely think of it in an inter-generational, linear fashion. Connecting the eldest members to the youngest probably looks like an org chart, with lines up and down and across.

As you prepare to read what follows, I need you to have a different visual in mind. It would help if you saw your family more as an ecosystem that resembles a circle. The economic realities of the 21st century demand this different viewpoint, because the family’s overall financial wellness, over multiple generations, depends on it.

It also depends on the family members being willing to talk about money!

I was fortunate. My mother and I always talked about money. I was a single child, who grew up with a mother who separated from my father when I was quite young. Since I was two years of age, it was her and me. At 13, she taught me how to balance a checkbook. For us, frank conversations about money didn’t start and end then; they continued until her death in 2014.

Yes, my mother and I had open and honest conversations about money. But that doesn’t mean it was less difficult, uncomfortable or emotional for either of us.

I know my familial experience isn’t unique; single child/single parent. But based on what I know about some of my friends and some of my clients, our family conversations about money were atypical.

Perhaps this is why I am such an advocate for families pushing through the awkwardness and carving out the time to do it.  Especially during the holidays!

Your family & money

If you just rolled your eyes or silently said, “no way, that is not going to work for my family,” I am not surprised. I’m accustomed to these types of reactions. As I’ve said previously, mixing family, money and the holidays can be an emotional landmine. One that requires graceful navigation and maybe even greater negotiation.

But avoiding the “talk” doesn’t make the need for it disappear.

So why not endeavor to get better at it, right?!

Understanding there are many family dynamics and nuances to consider, I share the following below more as a “pick-n-choose” guide.

If your family already has healthy conversations about money, read this for additional ideas about substance and style.

If your family talks about money, but only when there’s a crisis. Or, if your family avoids these types of conversations like a plague, read this both for ideas of what to talk about as well as how to prepare for a meaningful experience.

And just as there’s no one-size-fits-all when it comes to advice about money, there certainly isn’t when it comes to suggesting how families talk about money! But, you do need to begin with the “right” mindset.

To get the most out of these family money meetings, it helps to remember that you don’t positively impact the current and future generations with just one conversation about money.

No, you accomplish this by making a commitment to continuously engage all family members – the elders and younger ones. 

And if you find it challenging to broach these conversations, look to pop culture for easy entry points.

Ironically, songs, scripted and reality television shows, movies, social media and even neighborhood gossip can be used to kick-off or resume a conversation. It can spark a question or the sharing of an experience about everything: like, savings, investing, retirement and retirement planning, spending, earning, health/healthcare, estate planning. You can even use them to talk about habits and expectations. Or, to describe “what you would/would not do” scenarios. 

But like any conversation that involves a thorny topic, you need a strategy. Here’s my suggested game-plan:

Make a proposal

The quickest way for the family conversation about money to fail is to spring it on people. So, propose the idea, in advance. It can look something like this:

“Hey, Everyone, I’m looking forward to seeing you for (the holiday you celebrate). I would love for the family to carve out 30-60 minutes for a family financial meeting. I know, crazy idea! But I think it’s important for us to do this because we’ve never done it and it’ll be good tradition for us to start.” (Or if more appropriate, you can say,”…because we haven’t done it in a while.)

Then tell them why this meeting is important to you. (If you can’t come up with a reason, tell them I suggested it and you wanted to give it a try.)

Choose a single topic for discussion

To make the broadness of money less overwhelming, prepare a list of potential topics to discuss. You can pull from one of the areas noted above, or come up with your own. 

Have the meeting!

Yay…the day is here!! Start your family financial meeting with an agenda. It’ll help set some ground rules – like not interrupting people; or making judgmental comments; or bringing up unresolved conflicts that have nothing to do with the purpose of the meeting. And if necessary, remind people that the purpose of this gathering isn’t to be intrusive. Rather, to be supportive, proactive and strategic.

Determine next steps

What’s a good, productive meeting if there aren’t any next-step actions to be taken, right?!

Based on the discussion, each person should have at least one (1) takeaway or one thing for them to do. Whatever that is, determine what part of it can be done within a week; a month; and the next twelve weeks.

And create a follow-up plan that provides support and self-accountability for each person’s takeaway.

Breaking the silence

If you read “The Road Less Traveled,” then you are familiar with the book’s first sentence: “Life is difficult.”

It might behoove families to adopt a similar stance when it comes to talking about money. Embracing the truth that it will rarely be easy, can then create the space for it to be easier.

Because here’s the deal: Eventually, every family will have to talk about money.

The question becomes how you end up doing it, and whether you do it when things are calm or when you’re in the midst of a crisis. And wouldn’t it be better to do it during the former — rather than the latter?

I sure think so!

Mixing family, money and the holidays helps you individually and collectively plan for the year (and years) ahead. And in my opinion, the benefits far outweigh the emotional discomfort you may experience.

So, that’s why I push for families to use the holiday season to talk about money. Because your family’s overall financial wellness – today and for generations to come – may very well depend on it!

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