Making Love: Hacking the Holidays with Hard Conversations

A family enjoys Thanksgiving dinner. Image courtesy of Envato Elements

What if we used this holiday season to do something truly transformative and rooted in love? What if we pushed beyond surface-level pleasantries and tackled the conversations we usually avoid? This year, I’m inviting you to “hack” the holidays by leaning into one of the hardest—and most necessary topics— money.

For many families, this year’s hardest conversations will be about politics, especially this post-election season. But the reality is that Donald Trump is the president-elect. Whether you voted for him or not, we all must prepare to live under his administration. And if his presidency underscores anything, it’s America’s deep economic divides. The wealth gap is a glaring reality—and one we can’t afford to ignore. According to the Federal Reserve, as of the end of 2023,  white households held 84.5% of all U.S. wealth while making up only 77% of households. By contrast, Black households held only 3.4%, and Latino households held only 2.3%of national wealth.  

This holiday season, let’s center our family conversations around money. Let’s start talking about the steps we can take within our households to close the wealth gap for future generations.

The Wake-Up Call I Didn’t Want

A little over a year ago, I lost several family members, including my mother. She was vibrant, funny, and full of life. She’d often tell me, “You should get life insurance on me, just in case.” Like many families, we didn’t want to dwell on what felt like a far-off reality. We didn’t plan, even though she had a small policy. When she passed, the financial strain compounded the emotional weight of our loss. There were unexpected costs—things no one thinks about until you’re facing them. I found myself asking, “Why didn’t we do more?”

That experience pushed me to start uncomfortable conversations with my family. We began talking about estate planning, life insurance, and how to make sure we’re prepared for the unthinkable. These aren’t easy topics. Death feels taboo, and money is often seen as a private matter. I’ve learned that avoiding these conversations costs us dearly in the end. Culturally, families with wealth don’t see these topics as taboo. They plan because they know what’s at stake. Trusts, estates, and life insurance are tools they use to ensure their wealth moves seamlessly to the next generation.

For many Black families, the day-to-day hustle often takes priority over long-term planning. But even small steps can have a profound impact. Something as simple as a life insurance policy can be the difference between surviving a tragedy and creating a secure future.

The Wealth Gap Isn’t Just Numbers—It’s Generational

The racial wealth gap in America is a direct result of systemic inequities. For generations, white families have had access to tools and resources—homeownership, higher wages, inheritance—that many Black and Brown families have been denied. The result? Black families have, on average, significantly less wealth to pass down.

While systemic issues require systemic solutions, there’s power in what we can control. We can hack our own family dynamics and culture to make financial planning a priority. This starts with changing the way we talk about money.

Multi-Generation Family Joining Hands And Saying Prayer Before Meal At Home

Three Ways to Hack the Holidays with Money Talks

If you’re wondering how to begin, here are some practical steps to guide your family conversations this holiday season:

  1. Wealth Planning: Start Simple
    Do your family members have life insurance? If not, start there. A simple policy can cover funeral costs, pay off debts, or even provide seed money for a child’s education. For those ready to take it a step further, explore family savings accounts or trusts. Even modest contributions to a savings account can add up over time, creating a safety net for emergencies or shared goals.
  2. Will & Legacy Vision: What Will You Leave Behind?
    This conversation isn’t just about who gets what—it’s about how you want to be remembered. What values do you want to pass on? What traditions should live on in your absence? Drafting a will is a deeply loving act. It ensures your wishes are clear, reduces stress for your loved ones, and protects your assets.
  3. Family Financial Values: Align Around a Vision
    Money isn’t just about numbers; it’s about values. Use this time to talk openly about your family’s relationship with money. What do you prioritize—saving, investing, giving back? Share your financial journey and encourage others to reflect on theirs. These discussions create a culture of responsibility and empowerment that benefits everyone.

 

Breaking the Taboo

For many of us, the idea of discussing death or finances feels uncomfortable—sometimes even shameful, and avoiding these conversations puts our families at a disadvantage. I get it. These conversations can feel overwhelming, especially if you’re starting from a place of scarcity, but we can’t let discomfort keep us from building a secure future.

Here’s the truth: taking even one small step can shift the trajectory of your family’s financial future. Maybe it’s encouraging an elder to draft a will. Maybe it’s setting up a savings account with your siblings. Maybe it’s simply learning about how trusts work so you can educate your family. Progress starts with intention.

Culturally Hacking Wealth Strategies

Black culture has always been defined by resilience and creativity. We innovate, we adapt, and we thrive. It’s time to channel that same energy into wealth-building. That means normalizing conversations about financial planning and celebrating those who are already doing the work. It means sharing knowledge across generations and ensuring that the tools of wealth-building—life insurance, trusts, savings—are accessible to everyone.

One way to hack the culture is by reframing financial planning as an act of love. This isn’t just about money; it’s about ensuring your family’s stability and honoring the sacrifices of those who came before you.

A Love-Rooted Approach

Ultimately, these conversations are about love: they’re about showing up for the people we care about, for years to come, and creating a future where our children and grandchildren don’t have to struggle the way we did.

So, I’m challenging you to do something radical this holiday season. 

Hack the holidays by having hard conversations. Use the time with your family to talk about life insurance, estate planning, and financial goals. Dream together. Plan together. And love each other enough to face the uncomfortable truths that can lead to a more secure future.

This isn’t easy work, but it’s necessary. The decisions we make now will ripple across generations. And in the end, isn’t that what love is all about? It’s not just a feeling—it’s an action. A choice to build something bigger than ourselves. Let’s ‘make love’ by hacking the holidays with hard conversations.

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