What Most Estate Plans Miss and Why It Matters

Cheryl Maloney from Caldwell Securities with Elena Iacono, Founder, LegacyNex

People don’t just find strength in documents.
They find it in the stories, perspective, and clarity their loved ones share — the kind of guidance you can return to anytime, long after a will has been read.

That came into sharp focus this week at an evening event hosted by Caldwell Securities Ltd., where advisor Cheryl Maloney, CPA, CMA, CEA spoke about executors, wills, and estate planning.

What stood out wasn’t the paperwork.
It was what’s missing from most estate plans.

We spend so much time deciding who gets what, listing assets, and preparing executors. But Cheryl highlighted something we rarely talk about: the emotional side.
The context.
The reasoning.
The “why” behind decisions.
The pieces that help people understand each other — and stay connected.

I’ve seen this firsthand.
I’ve sat in will readings where someone’s entire life was reduced to numbers and lists. Their perspective, values, and stories… nowhere to be found. No guidance for the living. No continuity to draw from.

Meanwhile, Canada is approaching a $1 trillion wealth transfer, and for the first time, we have more people over 65 than under 15. That’s an enormous amount of lived experience — and an enormous opportunity to preserve it before it disappears.

Cheryl also noted that more Canadians are choosing to give financially while they’re alive.

But what about giving something even more valuable?

The clarity.
The meaning.
The guidance.
The human inheritance.

This is why I built LegacyNex.
A meaningful estate plan includes more than financial assets; it includes you — your stories, your lessons, your perspective — so the people you love can draw on your wisdom for years to come.

Money transfers wealth. Stories transfer wisdom.

If this resonates, let’s talk.
I help people preserve the meaning, clarity, and guidance that a will alone can’t capture.

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