Why “Tax Strategy” Usually Doesn’t Work the Way People Expect
Every tax season, we hear some version of the same question, “What strategy can I use to lower my taxes?” It’s a reasonable question — and one that’s heavily promoted online. It’s just that… in practice, tax strategy rarely works the way people expect it to. Here’s why.
Tax strategy is not step one
Most tax strategies only apply after a few fundamentals are already in place. Before any strategy matters, you need to know:
what income actually came in
how it was earned
what expenses are legitimate and supported
and whether prior years were handled correctly
If those pieces aren’t solid, “strategy” doesn’t fix the problem — it usually just hides it.
Strategy doesn’t override math
There’s no deduction, election, or loophole that changes the basic math of income and tax rates.
If income goes up, taxes usually go up with it. If withholding is low, balances due happen. If expenses aren’t real or documented, they don’t count. Most disappointment around taxes comes from expecting strategy to override those fundamentals.
Online advice skips the boring parts
A lot of tax content focuses on advanced tactics without mentioning the prerequisites. What rarely gets discussed:
clean bookkeeping
timing issues
prior-year carryovers
or whether someone even qualifies for the strategy being promoted
Without context, those ideas sound far more powerful than they actually are.
What actually helps
In most real-world situations, the biggest improvements come from:
fixing reporting issues
correcting assumptions
planning withholding more accurately
and understanding how income flows through the return
It’s not flashy. In fact, it’s opposite and very boring. And why? Because it freaking works.
Our approach
When we prepare tax returns, we focus on getting the foundation right first. If there is a legitimate opportunity to plan or adjust going forward, we’ll explain it clearly. If there isn’t, we’ll say that too. And this goes for both our once a year tax return only clients and our year round advisory clients. Hopefully you have an accountant already that you like and is doing all this for you :)
