These 3 Estate Planning Mistakes Could Cost Your Family
Let’s face it—estate planning isn’t usually dinner party conversation. It can seem overwhelming, uncomfortable, and often gets put off to something you’ll get to “someday.” But none of us can predict what tomorrow will bring, and postponing the work or making assumptions can lead to costly consequences for the people you care about most.
After supporting families and individuals through estate and legacy planning, I’ve seen how a few common mistakes can unravel even the best intentions. Fortunately, they’re all avoidable—with the right conversations, tools, and support. So, with that in mind, here are the top 3 mistakes to avoid.
Mistake #1: Thinking Your Will Covers Everything
Many people breathe a sigh of relief once they’ve finally drafted a will. After all, although it is the cornerstone of your estate planning, most people put off getting it done. But that sense of security can be misleading.
A will is only one part of a complete estate plan. It governs assets that pass through your estate—but not everything you own goes through your estate. Jointly held assets with rights of survivorship (like a home owned with a spouse), registered accounts with named beneficiaries (RRSPs, RRIFs, TFSAs, life insurance), or assets held inside a corporation can bypass your will entirely. And make sure to review your beneficiaries regularly or risk having unintended consequences.
A retired teacher in Alberta had a solid will leaving everything equally to her two adult children. However, her TFSA still listed her ex-husband as the beneficiary—a detail overlooked since their divorce 15 years earlier. When she passed away, the account went directly to her ex. The children were devastated, but legally there was nothing they could do.
Lesson: your will doesn’t control everything—especially if you don’t keep your beneficiary designations up to date.
Another often-overlooked detail is how real estate is titled. For example, if you own a property with an adult child but haven’t clarified whether it’s joint tenancy or tenants-in-common, you could unintentionally trigger capital gains taxes or probate complexities.
What to do: Make a habit of reviewing all your assets—not just what’s listed in your will. Confirm how each account, property, and policy is titled and whether a beneficiary is named. When in doubt, get help interpreting how those designations interact with your estate plan.
Mistake #2: Naming the Wrong Executor – or Leaving the Role Unclear
Choosing your executor (also called an estate trustee in some jurisdictions) is one of the most important decisions you’ll make. Yet too often, people choose someone by default—like a spouse, adult child, or close friend—without considering whether they have the time, skills, or temperament to handle the job.
Executors are responsible for everything from locating the will and applying for probate (where required) to filing tax returns, paying debts, communicating with beneficiaries, and distributing assets. It’s a significant legal and administrative responsibility that can take 12–18 months—or even longer if the estate is complex.
A man in his early 70s was named executor for his brother’s estate. He agreed, out of love and duty, but quickly became overwhelmed. The estate included two properties, multiple bank accounts, a business, and adult children who weren’t speaking to each other. He had no legal background and didn’t know where to start. After months of stress and costly delays, he reached out for help—but the early decisions had already created avoidable complications.
Lesson: being named an executor is often seen as an honour—but it’s also a time consuming job requiring detailed record keeping.
What to do: Choose someone who is trustworthy, organized, and capable of following through—not just emotionally close to you. And always confirm they are willing to take on the role. If your estate is complicated or you want to spare loved ones the burden, consider appointing a professional executor or connecting your chosen executor with professional support.
At NEXsteps, we offer Executor Essentials and Executor Ally Plus—tailored services designed to guide executors through the estate administration process. Remember, your executor doesn’t have to figure it all out alone.
Mistake #3: Keeping Your Plan a Secret
Even the best estate plan can cause confusion or conflict if no one knows where to find it, what’s in it – or why.
Too often, people complete their planning and tuck it away, assuming their loved ones will figure it out when the time comes. But that lack of communication can leave room for assumptions, hurt feelings, and legal challenges.
A widowed father of three left his entire estate to his second wife. The will was legally sound, but he had never told his children—nor explained why he made that decision. When he passed, the children were blindsided. They suspected coercion and launched a legal challenge that took years, drained the estate and destroyed family relationships.
Lesson: open communication and conversations can prevent these types of outcomes.
What to do: You don’t have to share every detail or dollar amount, but it’s helpful to communicate your intentions—especially if your plan might surprise someone. Explain your reasoning and give people a chance to ask questions. These conversations don’t always feel easy in the moment, but they can spare your loved ones tremendous pain and confusion later.
If having that conversation feels too emotional or complicated, a third-party professional can help mediate or guide it. Sometimes just having someone neutral in the room makes all the difference. We offer Estate Conflict Coaching to assist with these discussions.
Bonus! Mistake #4: Forgetting to Update Your Plan
Creating a will and power of attorney is a great start—but life changes, and your plan needs to keep pace.
Have you moved? Married, divorced, or started a blended family? Acquired a business or vacation property? Named someone who is now deceased or incapacitated? These are all reasons to revisit your documents. Laws also change, and what worked five years ago may no longer serve you today.
For instance, recent legal reforms in Ontario mean that marriage no longer revokes an existing will (as it once did), and new rules about separated spouses may change who inherits. These aren’t just legal footnotes—they can completely change how your estate is distributed.
What to do: Make a habit of reviewing your plan every 3–5 years, or whenever a major life event happens. A good review doesn’t just confirm that your wishes are up to date—it ensures your documents still align with current laws and reflect the people, assets, and relationships in your life today.
At NEXsteps, we offer an Annual Estate & Legacy Plan Review designed to make this process simple, accessible, and proactive. It’s a small investment that can prevent big headaches down the road.
Final Thoughts
Estate planning isn’t just about paperwork—it’s about people. It’s about protecting your loved ones from unnecessary stress, preserving your values, and leaving a legacy that reflects who you are. By avoiding these common mistakes—and reviewing your plan regularly—you give your family the gift of clarity and peace of mind when they need it most.
If you’re unsure whether your plan is complete, or if your executor could benefit from guidance, let’s connect. At NEXsteps, we offer trusted, personalized support to help you plan wisely and leave well. Because the best legacy is one that’s built with intention.
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Disclaimer: This content is for general information only and is not legal, financial, medical, or tax advice.
