What Saves Tax Might Cost You Everything Else

A lot of estate plans get built around a single question: "How do we minimize tax?"

It’s not a bad question. But if it’s the starting point, the whole plan usually ends up off course.

Tax matters. But it’s not the test your plan has to pass.

The real test comes later. After the funeral. When your family is grieving, confused, and left to manage what you’ve set in motion. When the structures you built with your accountant or tax lawyer are suddenly in the hands of people who don’t understand them and never asked for them.

I’ve seen plans that saved a staggering amount in tax and still caused irreparable damage. Because they were built for efficiency, not durability. For optimization, not clarity.

Frozen shares. Multi-tiered ownership. Complex reorganizations. Beneficiaries holding assets they can’t use or sell. Plans that assumed harmony where there isn’t any. Plans that passed tax audits but failed the family.

You don’t get to be in the room when your plan unfolds. But the people you care about will be. And if what you’ve built creates conflict, confusion, or resentment, it doesn’t matter how efficient it was. It failed.

A good plan doesn’t just reduce tax. It reduces risk. It makes things easier to carry. It holds up under pressure. It works when the people executing it are tired, emotional, and uncertain.

That’s why I don’t start with the tax. I start with the structure—and I pressure test it against real life. Not in a boardroom. Not in a glossy binder. And not with the kind of advice that sounds smart but leaves a mess for someone else to clean up. I ask the hard questions upfront, because your family shouldn’t have to answer them after you’re gone.

Who has to manage this? What decisions are they left with? What happens if someone dies early, marries again, gets sick, or walks away? What happens if they all disagree? 

If your plan can survive that, it’s strong enough. If it can’t, the tax savings won’t matter.

Because at the end of the day, you’re not planning for the CRA.You’re planning for the people who will have to live with your decisions.

You won’t be remembered for saving tax. You’ll be remembered for what your plan left behind.

If you’re ready for a plan that holds up in real life, book a call →

**If you’re not ready for legal documents but want a clear read before things get messy, I offer private clarity sessions. No forms. No fluff. Just sharp, strategic thinking—before the real work begins.

This site shares real-world insights from my work as an estate planning lawyer. It’s not legal advice, I'm not your lawyer, and it won’t cover every situation. But it will show you what tends to go wrong—and what usually holds up.