When Sarah’s father died unexpectedly last winter, her family assumed his modest estate would be simple to settle. Instead, they found themselves navigating months of probate hearings, legal fees, and confusion over who should manage his affairs. With no Will in place, Ontario’s intestacy laws dictated how his assets were divided — a rigid formula that rarely reflects a family’s real needs. The experience left Sarah’s family emotionally exhausted and financially strained.
Stories like Sarah’s are far more common than most people realize. Nearly half of Ontarians still do not have a legally valid Will, despite the fact that the consequences of dying without one are well‑documented. Many people continue to believe persistent myths — that they are too young, that they don’t own enough to justify a Will, or that their family will “figure it out.” As Tim Hewson, founder and CEO of Legal Wills, puts it, “People think they’re too young, don’t have assets, or don’t want to think about dying. They assume everything will just fall into place, but that’s rarely the case.”
December is a natural moment for reflection. Families gather, conversations turn to the future, and people take stock of what matters most. It is also a time when the gap between intention and action becomes painfully clear. Many Canadians know they should have a Will — they simply haven’t gotten around to it. For decades, the process was expensive, intimidating, and time‑consuming. But as Hewson explains, that world no longer exists.
“Earlier in my career, I was out for drinks with colleagues — about fifteen of us — and not one person had a Will,” he recalls. “We all knew it was important, but affordability and accessibility were huge barriers. That was the genesis of the idea to start LegalWills.”
Founded in Ottawa more than twenty years ago, LegalWills was built on a simple premise: if the process were easier, clearer, and more affordable, more Canadians would protect their families. Hewson’s background in human‑computer interaction shaped the platform’s design. “We wanted to remove the fear factor,” he says. “People imagine a Will as this complicated legal document, but when you break it down step by step, it becomes manageable. Today, you can do it at home, after the kids are in bed, without the cost or pressure of a legal appointment.”
The shift has been profound. What once required multiple meetings with a lawyer can now be completed online in under an hour. The platform guides users through decisions they may never have considered — guardianship for children, care for pets, charitable gifts, and instructions for digital property. “It’s an educational process,” Hewson explains. “People realize there are things they haven’t thought about. If you don’t make those decisions, a judge or the court will make them for you, and that may not be what you wanted.”
Digital assets, in particular, have transformed the landscape. “If your parents wrote a Will, they probably had two bank accounts and a few documents,” Hewson says. “Today, people have dozens of online accounts — crypto, gaming, cloud storage, social media. Executors have the right to adjudicate those matters, but only if you give them guidance.” He points to the common sight of a deceased person’s social media profile remaining active for years. “Why isn’t the account closed down? Often it’s because nobody knew the login information or what the person wanted done with it.”
The myths surrounding Wills — that they are only for the wealthy, that they are complicated, that they require a lawyer, or that they can wait until later in life — continue to prevent Canadians from taking action. Hewson hears these misconceptions every day. “One of our key markets is people who have just dealt with an estate that didn’t have a Will,” he says. “They come to us saying, I’m not putting my family through that stress.”
The truth is that a Will is not about assets — it is about people. It is about clarity, compassion, and responsibility. It is about ensuring that the people you love are not left to navigate a legal maze while grieving. “You’re thinking about the people you’re leaving behind,” Hewson says. “You’re never too young to write a Will. It’s part of responsible financial planning. And you can always update it as your circumstances change.”
He also stresses the importance of choosing the right executor. “Being an executor is a job,” he says. “They need to know where the Will is stored and what your wishes are. And the spouse isn’t always the best choice for obvious reasons.” Without a Will, the court must appoint someone — a process that can create conflict at the worst possible time.
LegalWills continues to expand its services, offering Canadians a secure, guided, and affordable way to prepare their Wills and Powers of Attorney. The company also provides a free downloadable Will Writing Toolkit to help people understand the process before they begin. “Our goal has always been to remove barriers,” Hewson says. “Cost, complexity, fear — those are the things that stop people. We want to make the process simple, secure, and accessible.”
As families gather this December, the message is clear: estate planning isn’t just about protecting assets — it’s about protecting the people you love. The tools now exist to make the process easier than ever. The myths that once held people back no longer apply. And the cost of waiting can be far greater than the cost of acting.
“There’s never a perfect time,” Hewson says. “But there’s always a right time — and that time is now.”
Visit Legal Wills online at www.legalwills.ca and follow them on Instagram @legalwills and LinkedIn @legal-wills
Photo: iStock
