September is almost over.

And this is usually the point in the year when I start thinking less about tax returns and more about what can still be changed before December 31.

Because there is a big difference between preparing a tax return and actually planning for taxes.

A tax return answers:

What happened this year?

Tax strategy asks:

What can we still do about it?

Those sound similar.

They are not.

A perfectly accurate return can still be a bad outcome

Imagine an agent has a great year.

Income jumps.

Their S-Corp salary has not been reviewed in three years.

They are making the same retirement contributions they made when income was half as high.

Estimated taxes are based on last year's numbers.

Nothing is technically “wrong.”

But nobody stopped during the year to ask whether the plan still made sense.

That is the gap I see all the time.

Real estate creates the same problem

An investor buys a rental and hears about cost segregation.

Great.

But before ordering the study, I want to know:

• Is the activity passive or nonpassive?
• Can the resulting loss actually be used?
• Are material-participation hours being documented?
• Is the property short-term or long-term?
• Is there a sale or refinance planned?
• Does accelerating depreciation make sense this year?

The cost segregation study is the easy part.

Knowing how it fits into the rest of the tax return is the strategy.

Business owners have their own version of this

Maybe the business has grown significantly.

But the entity structure has not changed.

The owner's compensation has not been revisited.

There is no retirement-plan strategy.

Business expenses are still being paid personally with no clean reimbursement process.

The books get cleaned up once a year when the tax return is due.

Again, the return may still get filed correctly.

But filing correctly and planning well are two different things.

Why Q4 matters

Some decisions can still be made in October, November, and December. After the year closes, many of them can't.

Here are the four I check first:

Retirement plan design. Some plans have to be set up, and payroll deferrals elected, before December 31 to count for this year. Miss it and that room is gone.

S-Corp salary. If your income jumped and your salary didn't, the fix runs through payroll. That means you need enough pay periods left to make the change.

Estimated taxes. If they're based on last year's numbers, you may be overpaying or heading for a penalty. Both are easier to fix now than in April.

Real estate timing. A cost segregation study, a purchase, a sale, or a refinance can all change the picture. The property generally has to be placed in service by December 31 for it to count this year. And if you're counting on your hours to qualify as material participation, they have to be documented as you go. You can't rebuild them in March.

There's more on the list, like equipment and vehicle purchases, charitable planning, and income and expense timing. But not every strategy applies to every taxpayer, and that's the point of planning.

Not every strategy applies to every taxpayer.

And that is exactly why planning matters.

The goal is not to chase every deduction you see online.

The goal is to figure out:

What actually makes sense for your income, business, and investments this year?

The bigger point

If the first serious tax conversation of the year happens when you upload your documents in February or March, most of the year has already been written.

At that point, your CPA is mostly reporting the result.

I would rather have the conversation now — while there are still decisions left to make.

Waqas “Vic” Hussain, CPA
Whitestone CPA
Based in Chicago. Serving clients nationwide.

P.S. This is the time of year when we start reviewing what can still be improved before December 31 — entity structure, compensation, retirement planning, real estate, estimated taxes, depreciation, and other planning opportunities.

That is the kind of work we do through ongoing tax strategy.

If you want a second set of eyes on this before year-end, grab 30 minutes with me and I'll walk through what I'd want to review in your specific situation.