How to talk money (without starting a feud)

We teach kids to say "please" and "thank you," and talk openly about mental health. Some of us even share what we’re earning on TikTok. However, when it comes to talking about money within families — really talking about it — too many of us prefer to stay silent.

This is especially true when it comes to the hot-button topic of leaving an inheritance. According to a recent national study I co-led through the Money Wise Institute, The Age of Broken Conversations, we found that:

• 80% of Canadian parents plan to leave an inheritance
• 52% haven’t discussed their estate plan with their children
• 25% worry their kids aren’t ready to handle the money

Gary Teelucksingh, co-founder of the Money Wise Institute and author of the forthcoming book Roots of Prosperity, puts it plainly: “Families think they’re avoiding conflict by avoiding the topic. What they’re really doing is setting the stage for confusion, resentment, and sometimes even litigation.”

The financial landscape has changed

Today’s financial realities look nothing like they did a generation ago. 

Thanks to longer lifespans, later retirements, and the rising cost of living, many Baby Boomers are rethinking their financial legacies. Some deliberately choose to enjoy the wealth they’ve built — spending more on travel, wellness, and personal fulfillment — rather than preserving it for a traditional inheritance.

This shift is popularly called the "Die With Zero" philosophy, which encourages people to spend their money while they’re still alive to enjoy it.

Some may even choose to make large donations to their favourite charities while they're still living. The logic? Your money can have more impact on your causes and community now, rather than decades from now.

Not to mention that with increasing lifespans, aging parents may require more care for a longer amount of time. Between expenses like home care and retirement homes, there may not be as much inheritance to pass down when the time comes.

Furthermore, aging parents are increasingly helping their children during their lifetimes with down payments, business investments, or even caregiving support. These “living inheritances” often come without formal documentation or discussion, which can lead to confusion or resentment later on.

 “We’re seeing a values shift,” says Teelucksingh. “Legacy is no longer just about assets. It’s about meaning, relationships and values. It’s about what kind of impact you leave behind — not just what’s left in the bank account.”

That’s why clear, ongoing communication matters more than ever. It’s not just about dollars and cents — it’s about ensuring everyone is aligned on expectations, intentions and shared family values.

We need to talk — but how?

When families create a culture of openness around money from a young age — talking about saving for a big purchase, setting shared goals, or making trade-offs together — it becomes easier to carry those conversations into adulthood. 

That’s especially important as adult children often begin to play a more active role in their parents’ finances — whether informally helping with bill payments or when carrying out responsibilities of Power of Attorney or as Executor.

The earlier these conversations start, the less loaded and intimidating they become over time.

Why aren’t families talking about money?

We all know we should have these financial conversations. But when it comes to money, logic often takes a backseat to emotion, and the emotional roadblocks are real. So, why aren’t families talking? 

• Guilt and shame are powerful silencers. Parents may feel embarrassed about not having “enough,” whatever that means within their family. “I don’t want them to know how little I have,” one mother confessed to Teelucksingh during his research for Roots of Prosperity. “They think I’m more secure than I am — and honestly, I don’t want to burst that bubble.”

• Fear of conflict is another common barrier. Many families avoid discussing money because they fear the drama that can arise from such conversations. Family members might think, “If I bring this up, they’ll argue,” or “My siblings will take sides,” or “I don’t want to look greedy.” These are valid fears, but avoiding the conversation often leads to even greater tension in the long run.

• Cultural beliefs also play a role. In some families, money is considered a private matter or even a taboo subject. Talking openly about finances might feel like a betrayal of long-standing values. In Teelucksingh’s interviews, many second-generation Canadians spoke about how their immigrant parents equated silence on the topic of money with love and protection. Some parents operate under the assumption that if they handle all the finances quietly, the rest of the family will never have to worry.

And sometimes, it’s just inertia. “I’ll get to it someday,” people tell themselves. But then life gets busy, family dynamics become more complicated, and "someday" turns into "never."

What’s important to remember is that these feelings are completely normal. Talking about money isn’t easy. The trick is to start small, be honest about the discomfort, and lead with care rather than trying to control people's reactions or the outcome of the conversation.

Staying silent about money has its downsides 

Avoiding these conversations may feel easier in the short term, but silence is rarely neutral. In Roots of Prosperity, Teelucksingh shares the story of a father who thought he was doing the right thing — leaving the family’s beloved lakeside cottage to his three adult children. But he never told them or had a conversation about the details.

Each child made their own assumptions. One thought they’d share the space equally. Another planned to sell her share to help with retirement. The third had already started making renovation plans with his kids. Within a year, they were in court, arguing over logistics and legalities, and inflaming long-held resentments. The result? Tens of thousands of dollars in legal fees, strained relationships, and a rift in a once-close family.

“He meant it as a gift,” Teelucksingh explains. “But because he didn’t communicate, it became a burden.”

Disputes over wills and estates can drag on for years, eroding trust and entrenching emotional wounds that may never fully heal. The financial cost can be staggering — legal fees, court dates, and drawn-out negotiations — but it’s the relational toll that leaves the deepest scars. When there’s no conversation ahead of time, what was meant to be a final act of love can feel like a betrayal. And too often, by the time families try to make sense of it all, it’s too late for clarity, or reconciliation.

Contrast that with another story: a woman in her 70s called a family meeting after revising her will. She sat down with her adult children, walked them through her decisions, and explained her reasoning. “I know it might not be what you expected,” she told them gently, “but here’s why I chose to do it this way.” She invited questions and listened to concerns.

The outcome? When she passed, her children weren’t left with confusion or conflict. They were left with clarity — and the space to grieve, not guess.

These stories highlight a crucial truth: money unspoken becomes money misunderstood. And when expectations clash with reality — especially in times of grief — the emotional toll can be steep. Misunderstandings can unravel relationships.

A word of caution: transparency has its limits 

Sometimes, even well-intentioned honesty can backfire. In one family, a grandfather proudly announced at a holiday dinner that he’d be leaving each grandchild a sizeable inheritance — but added that one grandchild would be getting more “because he’s more responsible.” 

What was meant to be a moment of generosity quickly unraveled into conflict. Tension filled the room, and that side of the family hasn’t gathered together since.

Handled carelessly, even good news can create lasting rifts. That’s why these conversations require more than just disclosure — they demand empathy, thoughtfulness, and timing.

While open communication is essential, it’s important to recognize that talking about money — especially inheritance — can be emotionally charged. Transparency, handled poorly or prematurely, can sometimes stir up tension rather than prevent it.

Some parents worry that sharing inheritance plans too early might demotivate their children. 

“If I tell them now, they’ll stop working hard,” one father admitted. “Or worse, they’ll start making decisions based on money that isn’t even theirs yet.” 

But there’s another side to that dynamic too. Some aging parents feel pressure to not spend their money — even when they want to — because they know their children are expecting to inherit it. This can create quiet resentment, sacrifice well-being, and lead to decisions made out of guilt rather than desire.

Family mediators and estate planners have seen all sides of this issue. Even in families that had open discussions, conflict can still arise. Sometimes, children misunderstand verbal agreements. Other times, disagreements over fairness — especially in blended families or with unequal support during life — can reignite old wounds, no matter how clearly the wishes were communicated.

That’s why thoughtful planning matters just as much as open dialogue. Timing, tone, and documentation all play a role. And sometimes, bringing in a neutral third party — like a financial planner, estate lawyer, or family mediator — can help keep the conversation grounded, fair, and forward-focused.

How to start a conversation about finances with your family

The solution begins with a single, honest human conversation. Because the real legacy isn’t just what you leave behind — it’s the peace you create by preparing your family for what’s to come. Not sure how to initiate a challenging conversation about finances? Try these entry points:

1. Use moments that already have financial context

• Tax season (“Hey, I just organized my paperwork — want to see where I keep the will?”)
• Spring cleaning (“Let’s make sure someone besides me knows what’s in the safety deposit box.”)
• Mortgage renewals or downsizing talks
• Retirement and pension/investment income discussions 

2. Focus on values. Instead of “What am I getting?” try:

• “What matters most to you in the years ahead?”
• “What legacy do you want to leave — financial or otherwise?”

3. Start small. Even one conversation about where to find key documents is a step forward. Create a list of essential documents, including wills, mortgage information, banking paperwork, Power of Attorney, insurance policies, online passwords, and safety deposit boxes. Share where they are, and who is named in what role.

4. Suggest bringing in a third party. A financial planner, estate lawyer, or even a legacy coach can help keep things neutral. If that feels too formal, you can even use this article as a conversation starter. 

5. Set clear expectations. There’s often no guarantee of what children will inherit — or when. But sharing a full picture of the family financial situation (including any debt, mortgages, expected retirement funds and expenses, etc.) can prevent assumptions and resentment. Try language like: “We hope to leave something behind, but things may change depending on health, the market, or what we need later in life.” Or, if you’re the adult child: “I don’t expect anything, but it helps to understand what plans you’ve made so I can support your wishes.”

Handled thoughtfully, these conversations can build trust, reduce confusion, and save your family heartache later on. However, this won't be a one-and-done chat. Financial and estate planning is a series of ongoing, evolving conversations. And that’s okay.

What financial professionals wish you knew

In researching Roots of Prosperity, Teelucksingh interviewed dozens of families, lawyers, accountants, and estate planners — people who’ve seen firsthand what happens when families avoid the tough conversations.

Here’s what financial professionals often wish they could say more bluntly:

• If your family doesn’t talk, your plan won’t work.
• Your estate plan should be revisited every few years — especially after major life changes, like a remarriage, a move to a different province, or even when a child turns 18 and becomes a legal adult.
• Your values matter. And they can be built into your legacy, not just your balance sheet — like choosing to support a grandchild’s education, donating to a cause that reflects your beliefs, or passing down a family story or tradition that money can’t capture.

Talk about money early, talk about money often

This isn’t just about inheritances. It’s about making sure the people you love are cared for, informed, and aligned. Even if you don’t have a large estate or complex investments, having money conversations with your loved ones and your financial professionals can prevent confusion, conflict, and unnecessary costs down the road.

You don’t need to have all the answers. But you do need to break the silence. As Teelucksingh says: “Legacy isn’t just what you leave. It’s how you live — and how you prepare the next generation to carry it forward.”