Most people who speak to me about tax decisions start with a very similar question:
“Is this claimable?”
It’s a fair question.
It’s also usually the wrong one to start with.
Over the years, I’ve learned that many tax problems do not arise because someone was trying to be aggressive or dishonest. They arise because decisions were made too quickly, with incomplete thinking, and without considering how those decisions would look later — during a tax audit, a review, or when explanations are required long after the original context is gone.
That is why, before making any tax decision, I now pause and ask a different question:
Is this defensible?
Claimable vs defensible: why the difference matters
Something can be technically deductible under tax law, yet still become problematic if questioned.
This often surprises business owners.
Tax is not assessed only on whether an expense is claimable on paper. It is assessed based on facts, behaviour, consistency, timing, and explanation.
A deductible expense may satisfy a technical requirement, but if the reasoning behind it is unclear, inconsistent, or poorly documented, it can still raise questions during a tax audit or review.
Defensibility asks a broader and more practical question:
- Can this tax decision be explained clearly?
- Does it align with how the business actually operates?
- Is it consistent with past tax filings and behaviour?
- Would the explanation still make sense one or two years later?
When those answers are weak, even a claimable expense can become difficult to defend.
Why defensibility matters over time
Tax decisions do not live only in the moment they are made.
They live on in records, tax returns, and supporting documents long after memories fade.
By the time a question is raised:
- the decision-maker may not remember why something was done
- staff may have changed
- circumstances may have evolved
- documents may be incomplete
What remains is the story told by the records.
Defensible tax decisions tend to share a few quiet characteristics:
- they are consistent with the overall structure of the business
- they make sense without elaborate explanations
- they do not rely on clever interpretations to stand
- they can be explained calmly, without defensiveness
This is why I often say that tax planning is rarely about cleverness.
It is about clarity and consistency.
How this thinking shapes the way I write my guides
Many of the guides I’ve written came about after conversations that started after something had already gone wrong.
In hindsight, the issue was often not the tax rule itself, but the thinking that led to the decision:
- assumptions made too quickly
- focus on outcomes rather than reasoning
- decisions taken without considering how they would later be viewed
When I write about tax, I try not to provide shortcuts or tricks.
Instead, I focus on helping readers slow down, understand the moving parts, and think through tax decisions before they are locked in.
Because once a tax decision is made, the opportunity to improve its defensibility often disappears.
A quieter way to approach tax decisions
Asking whether something is defensible does not mean being overly cautious or avoiding legitimate tax deductions. It means being intentional.
It means choosing tax positions that you are comfortable standing behind — not just today, but later, when circumstances change and questions are asked.
That single shift in thinking has made a significant difference in how I advise clients, how I approach tax planning, and how I write.
And in my experience, it is a question worth asking — before every tax decision.
Some of these ideas are explored further in my guides, written for business owners and investors who prefer clarity over complexity, and understanding over shortcuts.