For millions across the country, the 2026 midyear mark is as much a time for financial planning as it is for celebration. This summer marks America’s 250th birthday — a historic milestone for our country’s independence.
But while the nation was founded on a rebellion against unfair taxes, tossing your computer into the nearest harbor probably wouldn’t work when it comes time to pay the IRS; December 31st is the final deadline for most 2026 tax year money moves.
Instead, you might just want to look to the wisdom of founding father and financial thinker, Benjamin Franklin, this planning season.
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Franklin famously noted that, “nothing can be said to be certain except death and taxes.” And though you can’t escape either, you can control how much you overpay the government.
By applying Ben Franklin’s wisdom to midyear tax planning today, you could help secure your retirement nest egg, fund intergenerational wealth, and potentially lower your tax bill in 2026. Here’s how.
Did you know? Much of the wisdom we associate with Benjamin Franklin was popularized in his annual Poor Richard’s Almanac. Interestingly, he didn’t actually invent most of these famous idioms; rather, his curation of them made centuries-old proverbs more accessible to the working class.
1. “The Doors of Wisdom are never shut.”
Popularized in the 1755 edition of the Almanac, Franklin quoted this proverb to challenge the status quo in how we do things; it’s easy to fall into a routine of wash, rinse, and repeat.
But routinely doing your taxes the same way every year can cost you. Gain a little midyear tax wisdom through the following ways:
- Learn midyear strategy. You don’t have to wait until April to learn a new tax strategy. Platforms like the IRS Video Learning Portal and tax software academy portals offer free, year-round webinars to help you spot planning opportunities before the year-end deadline strikes.
- Revitalize your filing plan. Your revenue streams may change, and so should your taxes. For instance, if your financial situation has simplified, you might no longer need an expensive tax professional anymore. Alternatively, if you’ve bought property or started a business, doing taxes yourself might cause you to overlook certain tax deductions and credits.
- Save with free tax tools. There are several ways to file your taxes for free each year. For example, the IRS reports that millions of taxpayers have saved over a billion dollars collectively using IRS Free File alone. Evaluate free filing tools available to you now, while you’re outside of the chaotic tax season stress.
2. “Beware of little expenses; a small Leak will sink a great Ship.”
(Image credit: Getty Images)
In the Almanac, Poor Richard warns that “a little punch” or extra tea now and then might seem like “no great Matter,” but accumulated tiny expenses can sink your long-term financial ship.
In terms of midyear tax planning, the lesson is simple: Don’t miss the small stuff. Now is the perfect time to audit your tax records before the end-of-year holiday chaos.
- Audit your health accounts. Check your Flexible Spending Account (FSA) or Health Savings Account (HSA) balances. Ensure your medical procedures, prescriptions, and qualifying purchases are properly documented with clean receipts (no matter how small), and budget out your remaining FSA funds if your plan has a strict year-end deadline.
- Track new tax provisions. If you plan on claiming provisions from the 2025 Trump tax bill, tracking documentation is key. For example, the car loan interest deduction allows you to deduct up to $10,000 in interest, but only if the vehicle was bought new, is used primarily for personal use, and had its final assembly in the U.S. Make sure you qualify for all the tax deductions and credits you plan on claiming.
- Organize the paper trail. Start digging through your kitchen junk drawer or email folders. You’ll want to make sure you have your tax mileage log on file if you’re, say, a ride-share driver, or have your gambling tax documentation if you’ve placed a bet this year. Start the family’s designated “tax folder” now to avoid unnecessary stress later.
3. “Early to Bed and early to rise, makes a Man healthy, wealthy, and wise.”
Printed in the 1735 edition of the Almanac, this phrase originally praised the discipline of an industrious lifestyle. Let’s modernize that approach and polish it into a midyear tax mantra:
“Early to check and early to optimize makes you more planned, less stressed, and energized.”
Corny, sure.
But a midyear checkup ensures you aren’t accidentally giving Uncle Sam an interest-free loan — or worse, setting yourself up for an IRS underpayment fee or penalty. Here’s the phrase broken down:
|
Planning Action |
What to Look For |
|---|---|
|
Check your income |
Use the IRS Tax Withholding Estimator to see if your W-2 withholding matches your actual 2026 liability. Adjust your Form W-4 if you’ve married, had a child, changed jobs, etc. |
|
Optimize your pay |
Retired or drawing from multiple income streams? Double-check that your automatic withholdings on side hustles, pensions, or Social Security taxes are fine-tuned for your federal tax bracket. |
|
Plan your tax payments |
If you’re subject to self-employment taxes or pulling retirement income, verify that your quarterly estimated payments match what the government expects to help avoid underpayment penalties. |
For more information on how to plan your tax payments and optimize your withholdings, check out Kiplinger’s reports on Estimated Tax Payments and 13 Things Every Worker Needs to Know About Withholding.
4. “Having been poor is no Shame, but being ashamed of it is.”
Printed in 1749, this quote reminds us that financial struggle is often a consequence of shifting circumstances, not a lack of virtue. In tax planning, knowing how to handle these financial pivots — and leveraging the IRS code to protect your downside — can be a key tool in your tax toolbelt.
Here’s how we can relate that to our midyear tax planning strategy:
- Harvest your investment losses. Know when a position isn’t working out. Through tax-loss harvesting, you can sell underperforming equities to counteract your capital gains. If your losses exceed your gains, you can use them to offset up to $3,000 of ordinary income, carrying the rest over to future years.
- Strategize charitable giving. If you want to support a cause close to your heart, plan those donations now rather than scrambling in December. Strategizing early helps you maximize itemized charitable deductions and navigate the new 2026 rules on charitable giving.
- Utilize a QCD. If you’re age 70½ or older, you can make a qualified charitable distribution (QCD) directly from your IRA to an eligible charity. This counts toward your required minimum distribution (RMD), the minimum annual amount you must withdraw after reaching a certain age, and also helps keep that money out of your AGI, potentially lowering your tax bill.
5. “Money can beget Money, and its Offspring can beget more.”
(Image credit: Getty Images)
Moving away from the Almanac, this quote comes from Franklin’s 1748 essay, “Advice to a Young Tradesman.” Franklin was explaining compound interest, noting that money is of a “prolific generating nature.”
Retirement accounts and legacy planning are perfect examples of compounding wealth while avoiding high taxes. And midyear is a great time to double-check that your savings vehicles are on track.
- Maximize pre-tax contributions. If you’re currently working and in a higher tax bracket than you expect to be in retirement, maximize your traditional 401(k) or other traditional IRA contributions now. It lowers your taxable income today and gives you more immediate cash flow to save or invest. Later, when your federal tax bracket is (hopefully) a little lower, you’ll be taxed on the contributions when you withdraw them.
- Plan the “perfect” Roth conversion window. If you anticipate an upcoming low-income year — maybe you’re freshly retired but haven’t started drawing Social Security or reaching your RMD age yet — plan a potential Roth IRA conversion ahead of time. Converting traditional retirement funds into a Roth during a low-income year allows you to pay a low tax rate on the conversion, but while there are six reasons to convert to a Roth, there are reasons not to.
- Evaluate your estate tax plan. Check in with your financial advisor about your new estate tax exemption amount. Are you optimizing for the stepped-up basis of inherited assets, leaving appreciated equity without capital gains after death? Also, review whether you should use the annual gift tax exclusion to pass tax-free assets to children or grandchildren in 2026.
From shifting brackets to new legislative bills, tax planning is typically a moving target that requires at least a bi-annual checkup.
While a great financial professional can help you tailor these moves to your specific roadmap, keeping these five pieces of financial wisdom in mind may help you avoid being caught off guard and keep you focused on what matters most this summer — celebrating.
Happy planning!
This article is for informational purposes only and does not constitute professional tax or financial advice. Tax laws (including state taxes) are subject to change and vary by individual circumstances. Consult with a qualified tax professional regarding your specific situation.