Every Canadian knows the drill: when winter’s coming, we prepare. We put on the snow tires, wrap the windows, stack the wood, and double-check that everything that protects us is ready for harsher conditions.
Winterproofing isn’t dramatic—it’s practical. It’s human. It’s how we take care of ourselves and the people we love.
And as strange as it may sound, our legal and digital lives deserve the same kind of preparation.
Because winter isn’t just a season. It’s a metaphor for the unexpected moments that arrive, quietly or catastrophically, and ask us, Were you ready?
Why the “Unexpected” Is Bigger Than We Think
For most of us, the unexpected looks like the traditional things we try not to think about:
- a health scare
- incapacity
- the death of someone we love
- the sudden need for someone to step in and speak or act for us
But modern life has added a new layer: digital assets, cloud accounts, passwords, social media, family photos, subscription services, and even the content we create using AI.
Your digital presence is part of your estate. And if you don’t plan for it, you leave behind confusion, inaccessible assets, and unnecessary emotional labour for your family.
Winterproofing means taking those pieces seriously. Not out of fear, but out of love.
Where AI Fits into Estate Planning: Helpful, but Not a Stand-In for Humans
We’re living through the early stages of the AI era, and with it comes a wave of tools promising to streamline or even replace estate planning.
There’s good in this:
- AI can help you gather information faster
- It can help you brainstorm what should go in your “When the Time Comes” Binder
- It can simulate estate scenarios or flag things you might not have considered
- It can make education more accessible
But there’s also risk:
- AI can misinterpret nuance
- It cannot understand family dynamics
- It can’t manage complex Ontario estate law
- It can’t support your loved ones through the emotional reality of incapacity or death
- And—it gets things wrong (sometimes very wrong)
AI is a tool, not a replacement for thoughtful, personalized guidance. It can help you start, but it cannot winterproof your legacy on its own.
At Brown Lawyers, we see AI as a co-pilot. Not the driver. The human matters most. Your story matters most. The relationship matters most.
Tech is helpful; it is not help.
How to Use AI Responsibly When Planning Your Estate
Here’s how to keep AI in its proper place, supportive, not steering:
1. Keep a Human in the Loop
Let AI give you drafts or starting points, but always bring them to a lawyer who understands your life, your relationships, and your intentions.
Legal documents don’t communicate your meaning; you do. Your lawyer helps carry that meaning forward.
2. Guard Your Data
Not all platforms are designed for sensitive information.
Choose secure systems, understand how your data is stored, and avoid uploading private documents to unverified tools.
3. Document the Process
If AI tools generate lists, notes, or instructions, keep them, especially if they reflect what you would have communicated to your family. Store these with your Will or in your “When the Time Comes” Binder.
4. Remember: You Can’t Outsource the Thinking
AI can outline what should go in your plan.
Only you can express your values, intentions, stories, and the “why” behind your choices.
That is what your loved ones actually need.
What Winterproofing Your Legal Life Really Looks Like
Think of it like clearing the driveway before the storm is too deep to shovel.
Winterproofing your estate is ongoing, not a one-time event.
A strong plan includes:
- Clear, current lists of your assets
(What do you own? How do you own it?)
- Up-to-date contact information for the people who help manage your financial and legal life
- Wills and Powers of Attorney that reflect your current relationships and wishes
- Updated beneficiaries on financial and insurance policies
- Corporate records that reflect your actual business reality
- A real human-to-human communication plan, not just a stack of documents
- A “When the Time Comes” Binder filled with instructions, stories, intentions, and wisdom that your legal documents cannot express on their own
This is the heart of winterproofing:
Preparing not because something is wrong, but because something will change.
Winter always comes, eventually. We just don’t know when.
The Brown Lawyers Advantage: Human-Centred, Future-Ready
At Brown Lawyers, we know estate planning isn’t just legal — it’s deeply human.
Your life isn’t static. Your relationships evolve. Technology evolves. Your wishes evolve. And your plan needs to evolve with you.
That’s why our work goes beyond documents. We blend empathetic, values-driven guidance with an understanding of modern tools, digital realities, and the emotional weight that comes with preparing for the unexpected.
And at the heart of this approach is CODA, our signature, human-centred framework for tying your life, values, intentions, and legacy together with clarity and compassion. CODA helps you move beyond “getting your Will done” into understanding why your decisions matter, how they affect the people you love, and what story you want to leave behind.
It’s planning that grows with you — and honours you.
We help you create a plan that feels like you: clear, grounded, practical, and connected to the people you love. Because preparing for the unexpected isn’t preparing for the worst.
It’s preparing for life.
Winterproof Your Legacy for 2026
If you haven’t revisited your estate plan in a while, or if you’ve never created one, now is the perfect moment to start.
Whether you want to update your Will, organize your digital estate, or make sense of how AI fits into your planning, we’re here to walk beside you.
Ensure your estate plan is ready for life’s surprises, and for the AI era.
