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TaxonTax Advisory Strategy-first tax & estate planning for farm families and business owners – estate freezes, farm succession, executor advisory. PBA, CEA.

Author of TaxOnTax: The 12Event Planning Model.

10/06/2026

Event 9: The resignation letter worth half a million dollars

Two women were assessed for over $500,000 of a failed company's unpaid payroll withholdings. Their husbands had run the business. The wives were on paper as directors.

Their defence: they had resigned as directors more than two years before the CRA came calling, and the law limits director liability to two years after leaving. In 2014, the Tax Court agreed, but the fight took nearly a decade.

This one is personal for a lot of farm and small-business couples. Spouses get added as directors for financing, for shares, for convenience, and then everyone forgets. But a director signature carries real liability: payroll withholdings, GST, and more, personally, even for the spouse who never touched the books.

Whether a resignation was legally effective is a question for your lawyer. What that directorship means for your family's tax exposure is a question for me. Both deserve answers while the business is healthy, not after.

Quick check for every couple in business: do you know exactly which companies you and your spouse are directors of, right now? Many people who signed years ago don't.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

09/29/2026

Event 8: Even famous families get audited. Prepared ones win.

When Ted Rogers, founder of Rogers Communications, passed away, his family's estate tax plan was challenged by the CRA using its most powerful anti-avoidance rule. In 2020, the Tax Court sided with the family. Every step of the plan had used the tax rules exactly as Parliament wrote them, set up well in advance.

Compare that with a company that moved itself offshore just weeks before cashing in a $16 million gain, hoping to escape tax on it. In 2026, the Court took that structure apart. Built in a hurry, right before the money moved, and it read that way.

Here's what matters for the farm families and business owners I work with: the same tools the Rogers family used, freezes, rollovers, reorganizations, are available to you. They're how a farm passes to the next generation without a crushing tax bill, and how a company gets ready for a sale years before a buyer appears.

The pattern from the courtroom is consistent. Plans built early, for real family and business reasons, hold up. Plans built in a panic don't.

If your company or farm structure hasn't been reviewed in five years, it's due.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

09/22/2026

Event 7: The owner who never read the returns

A family-run company's owners lived partly through the business. Personal spending mixed with corporate. Returns signed without being read, because the accountant handled everything.

When the CRA reassessed, it went back beyond the normal limits and added gross negligence penalties. In 2026, the Tax Court gave a split verdict: trusting the accountant helped soften some penalties, but never reviewing the returns failed the standard the law expects of a careful owner, and years the family thought were closed got reopened.

The rule of thumb from decades of these cases is simple. 'My accountant handles it' can save you from penalties. It will not save you from the tax, and it will not keep old years closed if the returns you signed were wrong.

The fixes are unglamorous and cheap. One corporate card that never buys groceries. A shareholder account reconciled yearly. Ten minutes reading the return before you sign it.

Owner-managers: when did you last actually read your corporate return before signing? Honest answers welcome.

We're past the halfway mark of the twelve events. The full model, with all the stories, is in my book, The 12Event Planning Model.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

09/14/2026

Event 6: The doctor whose farm losses hit a wall

A New Brunswick physician also ran a substantial farming operation. In two years, the farm lost over $530,000 and $595,000. When she deducted those losses against her medical income, the CRA capped them at $17,500 a year under a rule called the restricted farm loss.

In 2023, the Tax Court upheld the cap. Because farming wasn't her chief source of income, the Income Tax Act limited how much of the farm's losses could offset her other earnings.

Every farmer and acreage owner in Alberta should know this rule exists. If farming is your main livelihood, real losses are generally deductible in full. But if the tax system sees farming as your sideline, no matter how seriously you take it, the losses hit a wall, and the wall is low.

Where that line falls depends on time, capital, planning, and the way the operation is set up. It is exactly the kind of thing to sort out before the losses pile up, not after the reassessment.

Farming alongside another income? The structure question is worth an hour of your winter. It can be worth six figures.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

09/09/2026

Event 5: The on-reserve business the CRA taxed anyway, until the Court stepped
in

A status Indian ran a brush-clearing business from his home on the Fort Nelson Indian Reserve, working for oil and gas companies. The CRA taxed his business income. He appealed.

In 2012, the Tax Court sided with him. Looking at all the connecting factors, where he lived, where the business was based, where the work was organized from, the Court found the income was situated on reserve and exempt under section 87 of the Indian Act.

For my Indigenous clients, the honest version of this story has two halves. The exemption is real, and it wins in court when the facts genuinely connect the income to the reserve. But the courts read those connecting factors carefully, and arrangements built only on paper have repeatedly failed.

Where your business is based, where the work happens, where decisions get made: these details decide the tax outcome. That's true for every business, and doubly true where section 87 may apply.

If your income touches reserve land and nobody has ever walked through the connecting factors with you, that conversation is overdue. It can change everything.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

09/05/2026

Event 4: Two investors, two very different endings

A B.C. investment advisor grew his TFSA from $15,000 to over $600,000 by rapidly trading penny stocks. The CRA said that much trading isn't saving, it's running a business, and business income is taxable even inside a TFSA. In 2023, the Tax Court agreed.

Meanwhile, in 2026, an investor claimed credits for the foreign tax withheld on her overseas dividends. The CRA denied them. She won her appeal, because her account statements were clean enough that the judge could recalculate every dollar from scratch.

One investor's account became a tax bill. The other's records became a victory.

For my semi-retired clients especially, this is Event 4 in a nutshell: the tax system cares how you invest and how you document it, not just what you earn. Which investments sit in the TFSA, which in the RRSP, which in the open account. How actively you trade. Whether your paper trail can answer questions years later.

When did someone last review your portfolio through a tax lens instead of just a returns lens?

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

09/01/2026

Event 3: Retired doesn't mean finished with the CRA

A retired federal public servant, almost thirty years of service, ended up in Tax Court over a deduction connected to how her employment ended. She represented herself. In 2015, she won.

What made the difference? Her paperwork. Years after retirement, she could still show what happened, when, and why.

Retirement changes your relationship with the tax system, but it doesn't end it. Pension income. RRIF withdrawals. The credits that begin at 65. The decisions that echo for decades: when to start CPP and OAS, which account to draw down first, how to split pension income with your spouse.

The withdrawal order alone can change a retirement's lifetime tax bill by tens of thousands of dollars. Same savings. Different sequence. Very different result. And the decisions cluster in a narrow window around the retirement date.

If you or your parents are within five years of retiring, that's the planning window. It closes quietly, one election at a time.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

08/29/2026

Event 2: The Edmonton woman who fought for her tuition and won

An Edmonton woman went back to school mid-career, an online MBA through a U.S. university, while keeping her life running here at home. When she claimed her tuition and education credits, the CRA denied them.

She appealed to the Tax Court. In 2011, she won. The Court confirmed her online program qualified, and the credits stood.

Mid-career retraining is one of the biggest financial moves people make, and one of the least planned. Tuition credits. RRSP room. The timing of a low-income year, which can be the perfect year for certain moves. A year of school changes your whole tax picture, usually in our favour, if someone is paying attention.

And a caution from the same court, in 2026: a taxpayer who pulled money from her TFSA and put it back the same calendar year got hit with a monthly overcontribution tax. The room doesn't come back until January 1. Small rule, exact edge.

Planning a return to school, a first home, or any big move this year? The tax plan belongs beside the budget, not after it.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

08/20/2026

A lot of people tell me they've got their estate planning handled. Then it turns out what they actually have is a will. Those aren't the same thing.

A will does one job. It says who gets what after you're gone, and who's in charge of carrying it out. That's it. It only kicks in after death, and everything it covers still has to go through the estate.

An estate plan is the bigger picture. It's how you actually move assets, minimize the tax hit, decide who steps in if you're alive but can't make decisions, and make sure the transfer happens the way you want with as little cost and conflict as possible. It works while you're living, not just after you're gone.

Here's the part that matters. A will without a plan behind it can still leave your family with a big tax bill, assets tied up, and decisions nobody prepared for. And a plan without a proper will has gaps too. They're built to work together.

If you've got a will and you're assuming that means you're covered, that's worth a second look. Especially if there's a farm or a business involved, where the numbers and the stakes are higher.

Derik Godbout, PBA, CEA
taxontax.com

08/19/2026

Event 1: The medical expenses the CRA said didn't count

A retired couple paid for regular acupuncture treatments. When they claimed the cost as a medical expense credit, the CRA denied it, because the person providing the treatments wasn't a licensed medical practitioner.

The taxpayer took it to the Tax Court himself, no lawyer, and in 2012 he won. The Court looked at how the provincial rules treated acupuncture at the time and let the credit stand.

Here's why this story matters to so many people. If you're managing a serious illness, caring for a spouse, or supporting an aging parent, the medical expense credit is real money. Travel for treatment. Attendant care. Home modifications. Some claims are allowed, some aren't, and the line moves depending on the year and the province.

Most families claim far less than they're entitled to, because nobody ever sits down and goes through eighteen months of receipts with the rules open.

If your household had a hard health year, don't guess at what counts. Ask. The answer is often better than you expect.

Real cases from the Tax Court of Canada. General information, not advice for your situation.
TaxOnTax Advisory Ltd. | Edmonton, Alberta | taxontax.com

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