What Will They Remember? The Emotional Side of Your Legacy Planning

Sep 1, 2025 | Blog

Talking about wealth can make people uncomfortable, especially when it involves end-of-life planning. For many families, it’s a conversation that never happens. Yet, when we avoid these discussions, we also miss the opportunity to ensure clarity, protect relationships, and shape a legacy that reflects not just our finances, but our values.

Legacy planning is not just a financial task; it is an emotional one, and it deserves just as much care and attention as any other part of your life plan. To explore this often-overlooked emotional side of wealth planning, we sat down with two RaeLispkie wealth professionals for an honest conversation about what legacy truly means and how to navigate the complexity, emotion, and responsibility that comes with it.

Wills And Trusts as Messages of Intention 

Wills and trusts are so much more than paperwork; they’re acts of care. As one advisor shares, “Worrying that talking about wills, end-of-life care or estate decisions will upset or stress other family members” is a common reason people delay these important conversations, often until it’s too late.

A will outlines who receives what, who will care for dependents, and can even include personal wishes. A trust can go further, offering more control over timing, purpose, and asset protection, sometimes helping avoid the probate process entirely. Both give you the chance to tell your loved ones: “I have thought this through, so you don’t have to.”

Without clear direction, families can often be left guessing at an already emotional or overwhelming time. Giving your loved ones a thoughtful plan to hold onto when the waters get rough, purposefully designed wills and trusts bring clarity to the confusion and light to the darkness. 

These important documents aren’t just about inheritance, they’re about showing up for loved ones and protecting the relationships that matter most, even when you’re gone. 

A New Era of Complexity 

“Legacy planning is a loaded word,” one RaeLipskie advisor notes. Another adds, “People can have concerns about whether their executors, trustees, or heirs will handle their money responsibly.”

Today’s families are increasingly complex. According to Statistics Canada, in 2021, one in ten couples with children were identified as stepfamilies. Canada is also the G7 country with the highest proportion of common-law couples, at 23%. On top of all of this, we’re currently living through the largest intergenerational wealth transfer in history, as baby boomers pass down significant assets to their heirs.

These complexities make planning even more essential. Without a well-articulated plan, questions about who inherited what– whether it’s a biological child and a stepchild, or a spouse and a common law partner– can become a source of conflict and confusion. 

“I’ve rarely seen family cottages end amicably,” one RaeLipskie advisor shares candidly. When people assume their children will feel the same way about their beloved assets, chances are they will not. Planning with your eyes open is paramount, and so is a thoroughly planned estate document, paired with clear communication. 

The Power of Open, Ongoing Dialogue 

At RaeLipskie, we encourage clients to prioritize three key principles when discussing wealth transfers: starting early, speaking often, and being open.

Even though legal control remains with the wealth owner, the best outcomes are created when all key parties, children, spouses or potential executors are brought into the conversation. As one advisor puts it, “Encourage people to share why decisions were made, rather than only sharing the outcome of their decision,” an advisor notes. 

The advisor also shares, “Frame it as an act of love and responsibility, not just a legal formality.” When everyone understands their role ahead of time, there is no room for confusion or mystery. 

This doesn’t need to happen in a boardroom; in fact, wealth transfer conversations are best done in familiar and comfortable settings. Whether it be around the dinner table, at the cottage, or over a relaxed meal, when the environment is safe, openness is bound to follow. 

“Start small,” a RaeLipskie advisor suggests. “Begin with values, – ‘What matters most to me in how I’m remembered?’ – before diving into technical details.” This nurtures clarity, builds trust and ensures your legacy reflects both your vision and your family’s evolving needs.

Guidance That Is Emotional and Professional 

While collaboration with family is important, involving a trusted professional adds a valuable perspective and helps ensure plans are thoughtful, clear and well executed. 

Our team of experts bridges the emotional and financial aspects of legacy planning by guiding meaningful conversations and identifying strategies to elevate your wealth plan to its fullest potential. 

Working with clients who want their plans to be intentional, personal and enduring, RaeLipskie understands and values the importance and prioritization of family dynamics, long-term vision and effective execution. While setting goals is important, ensuring those goals are also realistic and well-communicated makes all the difference.

To us, it is so much more than getting the paperwork done. With years of experience leading individuals through the stages of life, from marriage, to children, to retirement and eventually legacy planning, we make sure your stories, values and vision for the future are honoured and respected with clarity and care.  

Learn more about our services and multifaceted team here:  https://raelipskie.com/