Mid-Year Tax Planning Checklist for Busy Professionals

May 28, 2025

By the time June rolls around, most people stop thinking about taxes. But that’s usually when things start slipping through the cracks.

If you’re a busy professional, you already know how quickly the year can get away from you. And when it comes to tax planning, waiting until December—or worse, April—isn’t exactly a winning strategy.

Mid-year is your window to adjust, course-correct, and take action while there’s still time.

Why Mid-Year Tax Planning Matters

You’re halfway through the year. You’ve earned income, probably spent some of it, and maybe made a few big life or work decisions. But how does that translate to your tax picture?

  • Are your withholdings on track?

  • Have you taken advantage of the right deductions?

  • Are you saving enough in tax-advantaged accounts?

Mid-year planning helps you answer those questions before they become problems.

It also gives you time to work with a tax advisor—someone who can identify tax-saving opportunities you didn’t know existed.

1. Check Your Income So Far

Start with the basics. How much have you made this year?

  • Look at your most recent pay stub or year-to-date income statement

  • Add side income, freelance, or 1099 work

  • Compare it with last year’s total to spot changes

If your income has increased, you may owe more than you expect. That could trigger underpayment penalties unless you adjust your estimated tax payments or withholdings now.

Some professionals are also seeing more non-clinical income streams, which can have different tax consequences. Here’s how physicians are managing it.

2. Reevaluate Your Withholding or Estimated Taxes

A mid-year check is the perfect time to ask: Am I withholding too little or too much?

  • Use the IRS withholding estimator

  • If you’re self-employed, review your quarterly payments

  • Factor in bonuses, raises, and investment income

Small adjustments now can help you avoid a surprise bill later.

3. Max Out Retirement Contributions (If You Can)

Retirement accounts are one of the best tax planning tools you have. But many people underfund them or wait too long.

Here’s where you should focus:

  • 401(k): Up to $23,000 in 2025 (plus $7,500 catch-up if over 50)

  • Traditional and Roth IRAs: Up to $7,000 (plus $1,000 catch-up)

  • Compare options if you’re not sure which IRA type fits your strategy

If you’ve only been contributing the bare minimum, now’s a good time to step it up.

Some professionals are also considering less traditional vehicles like private insurance or self-insured strategies for long-term tax savings.

4. Audit Your Deductions

You probably missed something—most people do.

Go back and check:

  • Charitable donations

  • Business expenses (even if you’re W-2, unreimbursed costs matter)

  • Medical expenses (especially if they’re unusually high this year)

  • HSA contributions

  • Continuing education or certifications

If you’re a 1099 contractor, the list gets even longer: home office expenses, mileage, equipment, software subscriptions.

5. Consider Income Shifts or Deferrals

Is your income unusually high this year? Or lower than expected?

Shifting or deferring income can help even out your tax burden across years. For example:

  • Delay a bonus to January

  • Accelerate deductible expenses into this year

  • Shift income into a spouse’s lower tax bracket (in certain structures)

In some cases, professionals are exploring strategies like S corporation setups or best tax structures for doctors to improve efficiency.

6. Revisit Investment Accounts

What has your portfolio done this year?

If you’ve had losses, it might be a good time to harvest them and offset gains. Market downturns can be an opportunity.

Other steps to consider:

  • Rebalance your portfolio

  • Check tax-efficiency of your holdings

  • Set up automatic contributions to stay on track

A tax advisor can help you spot where to pivot and where to wait.

7. Plan Around Big Life Changes

Did you get married, divorced, or have a child this year?

What about moving to a different state?

  • These changes affect filing status, credits, and even how your income is taxed

  • For high earners, moving to a high-tax state can create long-term tax headaches

The earlier you account for these changes, the more time you have to prepare.

8. Think About Required Minimum Distributions (RMDs)

If you’re near retirement age or have inherited an IRA, you may need to plan for RMDs.

Even if they don’t apply yet, it’s worth understanding how they’ll impact your future withdrawals and taxes. Here’s a breakdown.

Some are using strategies like Roth conversions or charitable distributions to reduce their RMD exposure over time.

9. Meet With a Tax Advisor

Mid-year is the best time to schedule a tax check-in. You’re far enough into the year to make projections but still have time to change course.

A good advisor can help you:

  • Spot missed deductions

  • Optimize retirement contributions

  • Restructure income

  • Prepare for year-end opportunities

And if you’re considering selling a business, like a practice, there are tax-saving moves worth planning now.

10. Don’t Wait for December

It’s easy to procrastinate. Maybe too easy.

But mid-year planning puts you in control—not just of your taxes, but of your finances overall. Even if all you do is make one change, it can have a big impact.

Maybe you bump up your 401(k) contribution. Or decide to open an HSA. Or finally talk to someone about your side business.

Either way, you’re ahead of where you were yesterday.

Bonus: Keep Enjoying Your Life, Too

Tax planning doesn’t have to mean cutting back. In fact, the right plan can help you save money without sacrificing enjoyment.

That’s the whole point—work hard, plan smart, and actually enjoy the results.

Frequently Asked Questions

What is mid-year tax planning, and why does it matter?
It’s a check-in to adjust your financial strategy before year-end. It helps you avoid surprises and seize tax-saving opportunities while there’s still time.

Do I need to meet with a tax advisor mid-year?
Yes—especially if you’ve had income changes, started a business, or made big life decisions. Advisors can spot things you might miss and help implement strategies now, not after the fact.

How can I lower my taxes at this point in the year?
You can increase retirement contributions, track deductions, adjust withholdings, harvest investment losses, or restructure income sources.

What if I have multiple income streams?
It’s even more important to plan mid-year. Consider strategies that work for physicians and professionals who juggle clinical, non-clinical, or freelance work.

What about business owners?
You have more levers to pull: income deferral, expense acceleration, entity structure changes, and retirement plan options like solo 401(k)s or SEP IRAs.

Should I be thinking about RMDs or retirement withdrawals?
Yes, especially if you’re near retirement or inherited a retirement account. Mid-year is a smart time to project RMDs and decide if a Roth conversion makes sense.

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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