What You Should Be Doing Right Now: Tax and Retirement Planning Mid-Year
We’re halfway through the year. That weird middle ground—too late to say “I’ll deal with it later,” but not so late that you’ve run out of options.
If you’ve ignored your taxes or haven’t touched your retirement plan since January, now’s your window. Mid-year is when your numbers are real, not just guesses. And with six months left, there’s still room to fix, adjust, or even pull off something smart you didn’t think you’d have time for.
Let’s talk about the mid-year strategies that actually move the needle.
Rethink Your 401(k) and IRA Contributions
Start with the obvious. Are you contributing to retirement at all this year?
If yes—great. But are you on track to hit the limits?
What about Roth contributions? Or employer matches you’re missing out on?
If your income is high, look into Mega Backdoor Roth 401(k) strategies. It’s not mainstream, but it’s one of the few ways to push more tax-advantaged dollars into retirement when you’ve already “maxed out.”
Run a Mid-Year Tax Projection (Even If It’s Rough)
Get your tax software. Or call your accountant. Or at the very least, open your spreadsheet.
Estimate your income so far, project what the second half might look like, and see where you land.
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Did your income go up from a side business?
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Are you withholding enough?
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Will you owe in April?
1099 contractors and business owners can’t afford to ignore this. Not unless you enjoy unexpected tax bills.
Planning now gives you time to make adjustments—whether it’s saving more, spending less, or even shifting how your income is structured.
Consider a Roth Conversion (You Might’ve Ruled It Out Too Early)
Maybe you skipped the Roth conversion conversation in January. Too much income. Not the right timing.
But it’s worth revisiting.
What’s changed?
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Maybe your business had a slower start this year.
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Maybe your portfolio dropped in Q1.
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Or maybe you’re semi-retired and sitting in a lower bracket this year.
If so, a partial Roth conversion could be smart. Convert some traditional IRA money now, pay taxes at your current rate, and let it grow tax-free from here on out.
Just make sure it doesn’t bump you into the next bracket. That’s where working with a tax advisor makes all the difference.
If You’re Over 73, Check Your RMDs
Required Minimum Distributions (RMDs) are like expiration dates. Ignore them, and you pay penalties.
Don’t wait until December. Figure them out now.
And if you recently inherited an IRA or other retirement account, you might be subject to different RMD rules than you think. Here’s the IRS breakdown.
The worst outcome is scrambling to meet a December deadline and accidentally taking out too little. Or worse—too late.
Adjust Your Business Structure If It Still Doesn’t Fit
If you’re still operating as a sole proprietor or general partnership, mid-year gives you the perfect chance to evaluate a change.
Like forming an S corporation.
It could:
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Cut down your self-employment tax
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Let you take distributions beyond your salary
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Give you access to tax-free reimbursements
Not every business benefits, but for high-income earners or growing practices, it might make sense. This guide walks you through the “why” and “when.”
Revisit Health Savings Accounts (They’re Still Underrated)
If you’re eligible for an HSA, max it out.
You won’t find many places where:
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Contributions are tax-deductible
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Growth is tax-free
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Withdrawals for medical costs are tax-free too
That’s a triple benefit.
And if you’re self-employed, look into setting up a health reimbursement plan too. It’s a legit way to cover premiums and expenses with pre-tax dollars. This strategy helps you get there.
Start Looking for Investment Losses (Tax-Loss Harvesting Isn’t Just a December Thing)
Here’s the thing about the markets: if you’ve taken gains, you should be looking for losses.
Selling underperforming investments can help offset:
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Capital gains
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Up to $3,000 in ordinary income
Most people only think about this in December. But if you harvest losses in June or July, you’ve got more flexibility—and more time to reinvest wisely.
This article breaks down how to do it cleanly.
Look at Risk Management Through a Tax Lens
Are you overpaying insurance companies?
Some business owners are switching to private or self-insurance models, which can reduce risk and create tax-advantaged structures.
It’s niche. But for doctors, consultants, and private practice owners pulling in solid revenue, it could be worth exploring.
Start with this guide if the idea’s new to you.
If You’re Selling Something Big—Start Structuring Now
Thinking of selling your practice or a property? You can’t afford to wait until Q4 to plan.
Here’s what you might want to explore:
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Dealer vs investor rules
(explained here)
The earlier you start, the more options you have.
Deductions You’re Probably Ignoring (But Still Have Time to Use)
This is the part where most people roll their eyes—but some of these really add up:
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Business-related travel (yes, even part of your vacation)
→ Like this example -
Heavy vehicle deduction (like for an SUV or truck used in your business)
→ Check eligibility -
Home office write-offs—if used regularly and exclusively
You have six months left to structure expenses in a tax-smart way. Why not take a look?
Keep an Eye on 2025 Compliance Rules
This year, the Corporate Transparency Act rolled out some new requirements. Small businesses need to file BOI reports—beneficial ownership info.
And yes, ignoring it could lead to fines.
Get the full breakdown here.
Better to file now than deal with the fallout later.
FAQ: Tax and Retirement Planning Mid-Year
What’s the benefit of planning in the middle of the year?
You get actual data from the first half, plus time to fix or adjust before December. It’s your best shot at being proactive.
Is it too late to change my 401(k) contributions?
Nope. You’ve still got time. Just contact HR or update your payroll settings.
Should I still consider a Roth conversion in 2025?
Maybe. If your income is lower than usual, or if the market dipped, it could be the right time.
What’s a Mega Backdoor Roth again?
It’s a way for high earners to contribute more than the usual Roth limit—using after-tax 401(k) contributions and in-plan conversions. This guide explains it.
Can I still set up an S corporation mid-year?
Yes, though the clock is ticking. If it makes sense, now’s better than waiting.
Is tax-loss harvesting worth it before year-end?
Absolutely. Waiting until December limits your options. Start pruning now.
What if I’m already behind on savings?
Then this is your moment to catch up. Set up automatic contributions, trim unnecessary expenses, and explore ways to save money without sacrificing enjoyment.
Does this apply to doctors with multiple income streams?
Yes. Especially them. This article covers why.
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.