The Trusty Blog

It’s a story we hear all the time.

Different names, different assets, different family dynamics — but the same pattern: someone passes away, and what follows isn’t just grief. It’s uncertainty. Tension. And too often, conflict.

Not because people are greedy. But because no one wrote down the little things — or when they did, they didn’t make them clear.

Sometimes, the things that cause the biggest rifts aren’t mentioned in the Will at all. And even when they are, there’s no explanation behind the choices. That’s where cracks form.

One family we met had a mother who passed away after years of summers spent at the cottage with her three kids. Her Will was perfectly drafted: the house to be sold, the proceeds divided evenly. But it said nothing about the cedar canoe, or her wedding ring, or the cottage table marked with decades of memories. Each sibling had a different memory of what their mother had said. One recalled a promise about the ring. Another believed the boat was supposed to stay in the family. The third said they’d been the one maintaining the property for years. The conversations started civil, but over time turned emotional. Words were said that couldn’t be taken back.

Another story is personal. When my grandmother passed — at 104 years old — she left behind handwritten notes tucked into drawers, journals, and boxes. She had updated them over the years, sometimes every decade or so. But it wasn’t always clear: were the newer ones meant to replace the old ones? Or were they meant to be read together, layered with nuance?

In our case, we were lucky. My siblings, cousins, and I all got along. Maybe too well — because instead of fighting, we politely stalled. No one wanted to be the one to claim anything. We spent months checking in, making sure someone else didn’t want that vase, or picture frame, or brooch. It dragged out what could have been a comforting process. I remember thinking at the time: If only there were an app for this. Something that offered structure but still left room for the human side of it all.

That idea stayed with me.

It helped shape what eventually became Trusty.

And then there are the families where the stakes are even higher.

An executive at RBC Royal Trust once told me about an estate they were settling that included a significant art collection — pieces worth millions. The Will said the art was to be divided between the three children. But once the parents had passed, all three kids agreed: the art should be donated. All of it — except one piece. It was the painting that hung over the dining room table. The one they’d sat in front of every Sunday for decades. That painting, each child felt, belonged to them.

But there was no further instruction. No video. No note. No explanation. Just silence.

The advisor said, “We imagined what it might have been like if there had been a video. Even a short message. Maybe the parents could have added a condition — that whoever received the painting would commit to hosting Sunday dinners. Or maybe they would have said, ‘This one should go somewhere public — so you all can visit it, together.’”

Without that clarity, the piece remained in limbo. The family couldn’t agree. And that one unresolved item cast a shadow over an otherwise generous and well-intentioned estate.

These stories — rings, boats, artwork, family heirlooms — they sound small. But they hold weight. Emotional weight. And when that weight isn’t balanced with guidance, it leads to conflict.

According to the Financial Planning Standards Council, one in four Canadians has experienced family friction over unclear estate planning. In the U.S., 44% of adults say they worry their family will fight over their estate. That fear? It’s not unfounded.

And it’s not inevitable, either.

That’s where Trusty comes in. Not to replace your lawyer. Not to write your Will. But to support everything around it. With Trusty, you can record video messages for specific assets. You can log what you want passed down — and to whom — with context. You can make your intent clear.

You can also prevent your family from having to interpret, debate, or argue over what they think you meant.

Because sometimes what people want most is not just the thing — it’s the feeling that they were remembered. That they were chosen. That they were understood.

Estate planning isn’t just about dividing assets. It’s about leaving behind peace. And that peace rarely lives in legal documents alone.

It lives in clarity.

In compassion.

In stories told — and wishes made — before it’s too late.

For many advisors, guiding a client through their estate planning checklist ends with the Will. And for decades, that was enough. But today’s families are more complex. Assets are more diverse. And expectations — both emotional and legal — have shifted.

Helping a client “get a Will in place” is no longer the finish line. It’s the starting point.

We regularly hear from wealth advisors, estate planners, and lawyers who say: “I didn’t realize how much was missing until I saw the conflict it caused.” From siblings disputing over heirlooms, to executors lost in paperwork, the gaps in most estate plans aren’t just logistical — they’re deeply personal.

If you’re advising clients on how to plan for what comes next, here’s how to take the conversation deeper.

🔍 Go Beyond the Legal Framework: Key Areas to Explore With Clients

Uncover what’s not in the Will

Most Wills are designed to meet legal requirements — but they rarely reflect the nuance of family dynamics, personal values, or sentimental belongings. Encourage clients to reflect on what matters most emotionally, not just financially.

Document specific and sentimental items

Jewelry, collectibles, art, and family heirlooms often hold disproportionate emotional weight. When these aren’t mentioned — or explained — they become flashpoints for conflict.

Ask about pets and who will care for them

Pets are part of the family, yet many Wills omit who will care for them or how that care should be funded. Clarify who’s willing and what’s expected.

Discuss burial and funeral wishes

Clients often assume their loved ones “will just know,” but these moments are fraught with emotion. Encourage clients to document preferences clearly — from cremation to religious traditions to celebration-of-life details.

Explore digital legacies

We now live part of our lives online. Clients may have cryptocurrency holdings, photo libraries, cloud storage, email accounts, and digital subscriptions. They should leave instructions and passwords, and specify what should be archived, deleted, or passed down.

Identify less typical assets

Airline miles, credit card points, loyalty programs — these are often overlooked but can be valuable. Some can be transferred, others may require named beneficiaries. Ask: What have you accumulated that has value — even if it’s not traditional?

Review life insurance and beneficiary alignment

Life insurance isn’t only about coverage — it’s a core part of legacy transfer and liquidity planning. Ensure policies are up to date and that beneficiaries are correctly named and aligned with the rest of the estate plan.

Start conversations around tax strategy

Clients are often unaware of capital gains exposure, estate tax thresholds, or the impact of charitable giving. Collaborate with their accountant or tax advisor to identify planning opportunities early — not when it’s too late.

Clarify the executor’s role and give them tools

The executor isn’t just a name. It’s a job — and often a hard one. Help your client choose someone capable, and ensure that person has access to the information and guidance they’ll need when the time comes.

Encourage personal messages or Letters of Wishes

Sometimes the greatest gift isn’t the asset — it’s the context. A short written or recorded message explaining “why” can prevent years of family friction.

🛠️ How Trusty Helps Advisors Create Real Clarity

Trusty was built to support everything the Will leaves out. It’s a secure digital hub that helps clients capture the human side of their legacy — and gives you, as an advisor, a way to stay connected to the bigger picture.

With Trusty, your clients can:

• Record and store Letters of Wishes and video messages
• Assign heirs for sentimental and digital assets
• Track pets, collectibles, storage locations, and travel points
• Log where their Will and legal documents are kept
• Organize important digital credentials for their executor
• Give you access, so you can support better — and stay top of mind

Clients don’t need more documents. They need clarity.

And when you help provide that, you’re not just planning for death — you’re preserving peace for the people left behind.