January Tax Questions to Ask Before Filing

January 21, 2026

You can file taxes fast.
Or you can file taxes right.

For physicians, “right” usually means one thing.
You don’t just report what happened last year.
You spot what you missed.
You fix what you can.
And you build a plan before the year gets away from you.

January is the best time to do that.
Because it’s early enough to adjust.
But close enough to last year’s numbers that the gaps are obvious.

This guide is a practical list of tax questions to ask before you file.
Not later.
Not after you get the surprise bill.

1) Did my income structure change this year?

A small change in how you earn can change how you get taxed.

Ask yourself:

Even one new income stream can create:

  • under-withholding

  • missed quarterly payments

  • incorrect payroll settings

  • unexpected state tax exposure

Your tax return needs to reflect your real earning picture.
Not the simplified version in your head.

2) Did I have any 1099 income that didn’t get tracked properly?

Many physicians earn income outside their main job.

That might include:

  • locums work

  • expert witness work

  • consulting

  • teaching

  • speaking

  • medical director roles

  • telehealth side work

January question:

  • Do I have a list of every payment source and date received?

Because “I’ll remember it later” rarely works.
Not when 12 months of deposits are mixed into the same bank account.

A clean list now saves hours later.
And helps prevent under-reporting.

3) Was my withholding actually correct?

Physicians often overestimate how “safe” withholding is.

Especially if you had:

  • a new job mid-year

  • multiple W-2 incomes

  • big bonuses

  • stock compensation

  • spouse income changes

  • 1099 income layered in

Ask:

  • Did I owe last year?

  • Did I owe more than expected?

  • Did I pay penalties?

  • Did I get a huge refund that could’ve been invested?

A big refund can feel like a win.
But it usually means you overpaid all year.

A surprise bill feels worse.
But it’s usually fixable.

4) Did I pay estimated taxes when I should have?

If you have meaningful income not covered by withholding, you may need quarterly estimated payments.

Ask:

  • Did I have self-employed income?

  • Did I have a large K-1?

  • Did I have significant investment income?

  • Did I sell something with a gain?

  • Did I receive a large signing bonus without enough withholding?

If you missed estimates, January is still useful.
You can:

  • adjust withholding now

  • increase estimated payments for the year

  • plan for safe harbor rules

Avoiding penalties usually comes down to planning early.

5) Did I max out the right retirement accounts?

A lot of physicians “contribute.”
Few physicians maximize the right strategy.

Ask:

  • Did I max my employer plan?

  • Did I use the right type of account for my tax bracket?

  • Did I miss a backdoor Roth opportunity?

  • Did I run into income limits unexpectedly?

Retirement planning isn’t just saving money.
It’s controlling taxable income.

And many retirement moves have deadlines.
Some are still open in January.
Some are not.

That’s why reviewing in January matters.

6) Did I make a mistake with Roth conversions?

Roth conversions can be great.
They can also be mistimed.

Ask:

  • Did I convert in a high-income year without planning?

  • Did I trigger higher Medicare-related premiums later?

  • Did I push myself into a higher bracket unnecessarily?

  • Did I forget about state tax impacts?

The goal isn’t “do a Roth conversion.”
The goal is to do the right amount.
In the right year.

January is when you look back and decide if that move was clean or costly.

7) Did I trigger any surprise taxes from investments?

Investments can create taxes you didn’t feel until filing time.

Ask:

  • Did I have large capital gains?

  • Did I sell any crypto?

  • Did I exercise stock options?

  • Did I receive RSUs?

  • Did I get hit with large mutual fund distributions?

These show up on tax forms later.
But you can spot them now by reviewing activity and planning the next move.

Sometimes the best fix is:

  • harvesting losses

  • timing future sales

  • adjusting withholding

  • rebalancing more strategically

8) Did I track business deductions correctly?

If you have a 1099 side practice or medical business activity, deductions matter.

Ask:

  • Did I keep a record of expenses monthly?

  • Did I separate business and personal spending?

  • Did I track mileage correctly?

  • Did I document education, licensing, and subscriptions properly?

The problem isn’t that physicians don’t have deductions.
It’s that deductions are often:

  • scattered

  • forgotten

  • not documented

  • mixed into personal accounts

That leads to either:

  • missed savings

  • or audit risk

You want neither.

9) Do I have the right entity setup for my side income?

Many physicians operate side income informally.
And that can be expensive.

Ask:

Entity strategy can reduce taxes.
But only if it matches your real income, effort, and goals.

This is a January question because it takes time to implement correctly.
You don’t want to rush it in December.

10) Did I qualify for any credits or deductions I overlooked?

High earners can still miss savings.

Ask:

  • Did I capture charitable giving correctly?

  • Did I miss deductible HSA contributions?

  • Did I qualify for energy credits?

  • Did I overlook education-related deductions?

  • Did I track dependent care costs correctly?

Tax software won’t find strategy for you.
It only reports what you enter.

If you don’t ask the questions, you won’t catch the gaps.

11) Did I move states or work in multiple states?

Physicians often travel for work.
Locums makes this even messier.

Ask:

  • Did I work in multiple states?

  • Did I receive income from different locations?

  • Did I move mid-year?

  • Did I properly track residency status?

State tax mistakes are common.
And they’re costly.

This is one of those areas where it’s smart to slow down.
Filing fast doesn’t help you here.

12) Did I take distributions or withdrawals that changed my taxes?

Large cash events can change everything.

Ask:

  • Did I take money from a retirement account?

  • Did I cash out an old plan?

  • Did I take a loan against something?

  • Did I receive an inheritance or settlement?

  • Did I take a distribution from a business?

These create taxes or reporting requirements.
Sometimes both.

If you’re not sure what it was, don’t guess.
Get the forms.
And get it reviewed.

13) Did I have a major life change that affects filing status?

Life changes show up on tax returns.

Ask:

  • Did I get married?

  • Did I get divorced?

  • Did I have a child?

  • Did I start supporting a parent?

  • Did my spouse stop working or return to work?

Your filing status impacts:

  • brackets

  • deductions

  • credits

  • phaseouts

Physicians can miss this because income feels like the “main thing.”
But life changes can move the tax needle fast.

14) Do I know what my real effective tax rate was?

Most physicians know their income.
But not their tax rate.

Ask:

  • What percent of my income went to taxes last year?

  • Did it increase?

  • Why?

  • Was it avoidable?

This is a powerful January exercise.

Because once you see the real number, you stop guessing.
And you start planning.

15) Am I filing early for the wrong reason?

Some people file early because they feel behind.

Ask:

  • Am I rushing because I want it off my plate?

  • Am I filing before I have all forms?

  • Am I skipping a tax strategy review because I assume it’s “too late”?

Many tax-saving decisions happen before filing.
But the review must happen early enough.

January is not too late.
It’s a window.

Use it.

16) What would I change if I could rerun last year?

This question matters more than most people realize.

Ask:

  • What caused the biggest tax surprise?

  • What felt messy?

  • What do I not want to repeat?

This is where real planning starts.

Not with deductions.
With decisions.

How a tax advisor helps physicians in January

A lot of physicians try to DIY this process.
It’s understandable.

You’re smart.
You’re capable.
And you’ve handled harder problems.

But taxes aren’t about intelligence.
They’re about timing.

A strong tax advisor helps you:

  • review last year for missed planning opportunities

  • fix withholding early so the rest of the year runs smoother

  • project your full-year income (not just W-2 income)

  • manage estimated taxes without panic

  • plan retirement contributions with tax impact in mind

  • structure side income in a smarter way

  • prevent penalties and reduce surprise bills

The goal isn’t just to file.
It’s to file with control.

The January filing checklist for physicians

If you only do one thing this month, do this.

  • Gather every income source (W-2, 1099, side income)

  • List major financial events (bonuses, sale, move, distribution)

  • Review withholding and estimated tax payments

  • Confirm retirement contributions and deadlines

  • Identify deductions you may have missed

  • Run a quick projection for the current year

  • Decide what you want to change before income piles up

January is when the year is still flexible.
That flexibility disappears fast.

FAQ

Should physicians file taxes as early as possible?

Not always. Filing early is fine if you have every tax document and your return has been reviewed for missed strategy opportunities.

What tax forms should physicians look for in January?

Most physicians will need W-2s, 1099s (including 1099-NEC or 1099-MISC), investment forms, and any documents tied to side income or business expenses.

What is the biggest January tax mistake physicians make?

Rushing to file without reviewing withholding, side income, or estimated tax needs for the current year.

Do high-income physicians need to pay estimated taxes?

Many do, especially if they have meaningful 1099 income, K-1 income, investment gains, or bonuses with insufficient withholding.

Can I still make tax-saving moves in January before filing?

Yes. Some moves may still be available depending on your situation, especially around retirement contributions and planning adjustments for the new year.

Why does withholding matter so much for physicians?

Physician income often includes bonuses, multiple jobs, and side work. That combination can lead to under-withholding if not reviewed early.

Should physicians with side income consider an S-Corp?

Sometimes. It depends on income level, consistency, and administrative overhead. It’s worth reviewing in January because setup and payroll take time.

How do I avoid a surprise tax bill next year?

Start with a January review. Adjust withholding, plan estimated taxes, track deductions monthly, and project income early rather than waiting until Q4.

Ready to talk strategy? Start here.

Visit contact physiciantaxsolutions.com to schedule a consultation and learn how we can help you take control of your tax strategy today.

This post serves solely for informational purposes and should not be construed as legal, business, or tax advice. Individuals should seek guidance from their attorney, business advisor, or tax advisor regarding the matters discussed herein. physiciantaxsolutions.com assumes no responsibility for actions taken based on the information provided in this post.

 

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