As the calendar flips to June, most taxpayers and advisors have long put tax season in the rearview mirror. But for proactive individuals and business owners, June is the perfect time for mid-year tax planning. This mid-point in the year offers a valuable opportunity to assess your financial health, implement tax-saving strategies, and avoid unpleasant surprises come April.

In this article, we’ll explore key mid-year tax strategies for individuals, families, and business owners, covering income, deductions, retirement planning, charitable giving, and estimated tax payments.

1. Review Year-to-Date Income and Withholding

The first step in any mid-year review is to evaluate your income and tax withholding.

Check Your Pay Stub

Pull your most recent pay stub and review:

• Year-to-date earnings
• Federal and state tax withholding
• Retirement plan contributions (e.g., 401(k), 403(b))

Use the IRS Withholding Estimator

The IRS offers a Withholding Estimator Tool to determine whether you’re on track. Adjust your W-4 if:

• You’ve received a raise or bonus
• You’ve had a change in family status (marriage, divorce, dependents)
• You anticipate capital gains, stock sales, or other investment income

Avoiding under-withholding now may prevent underpayment penalties later.

2. Maximize Retirement Contributions

June is an ideal time to assess retirement plan contributions and make catch-up plans.

Contribution Limits for 2026:

• 401(k), 403(b), most 457 plans: $24,500 (+$8,000 catch-up if age 50+ & ages 60-63 catch-up +$11,250 & after age 63 back to the +$8,000 catch-up)
• Traditional or Roth IRA: $7,500 (+$1,100 catch-up if age 50+) total combined subject to income phaseout
• SEP IRA: Up to $72,000 or 25% of compensation, whichever is less

Strategic Considerations:

• Higher-income individuals should consider Roth conversions in a low-income year.
• Small business owners should explore Solo 401(k) or defined benefit plans.
• Monitor income limits if contributing to Roth IRAs directly (Modified AGI phase-outs apply).

A mid-year increase to retirement contributions can meaningfully reduce your taxable income.

3. Estimate Capital Gains and Tax-Loss Harvesting Opportunities

If you actively trade stocks, real estate, or other assets, start reviewing your capital gains position.

Strategies:

• Harvest Tax Losses: Sell underperforming assets to offset gains, subject to IRS rules and individual circumstances.
• Depending on an investor’s tax situation, realized capital losses may be used to offset realized capital gains.
• Hold for Long-Term: Assets held over 12 months benefit from favorable long-term capital gains rates (0%, 15%, or 20%) depending on income.

June is a low-pressure time to rebalance portfolios and take advantage of intentional asset location or harvesting opportunities before year-end volatility.

4. Plan Charitable Giving with a Tax-Efficient Lens

Charitable donations are a cornerstone of many tax strategies, especially for those itemizing deductions.

Options to Consider:

• Bunching Donations: Group 2–3 years of donations into one year to exceed the standard deduction.
• Donor-Advised Funds (DAFs): Make a large contribution now, then distribute to charities over time.
• Qualified Charitable Distributions (QCDs): IRA owners age 70½+ can donate up to $111,000 (single filer or up to $222,000 married filers) directly to charity—reducing both AGI and RMDs.

If your income is spiking in 2026 or a liquidity event is expected, plan a giving strategy now to secure a deduction this year.

5. Take Advantage of Health-Related Tax Benefits

Mid-year is a smart time to evaluate healthcare-related savings tools:

Health Savings Account (HSA):

• 2026 limits: $4,400 for individuals, $8,750 for families (+$1,000 catch-up if age 55+)
• Triple tax advantage: Contributions are tax-deductible, grow tax-free, and distributions are tax-free if used for qualified medical expenses

Flexible Spending Account (FSA):

• Check your use-it-or-lose-it status—mid-year is often your last chance to spend wisely.
• Some employers allow a carryover or grace period—know your rules.

Don’t miss out on pre-tax savings for medical, dental, vision, or dependent care expenses.

6. Reassess Estimated Tax Payments

If you are self-employed or receive income without withholding (e.g., rental, K-1, capital gains), then estimated taxes matter.

The second quarterly estimated tax payment for 2026 is due June 15. Make sure:

• You’re following the safe harbor rules: 90% of current year tax liability or 100% (110% if AGI > $150,000) of last year’s liability.
• Payments are properly allocated between spouses if filing separately in community property states.

Tip: Safe Harbor Strategy

Even if you expect higher income in 2026, consider paying based on last year’s tax liability to avoid penalties—then true up in April (this is the safe harbor rule in action).

7. Evaluate Tax Credits and Deductions

Mid-year is ideal for tracking eligibility for tax credits, which can directly reduce your tax bill.

Common Mid-Year Credit Opportunities:

• Child Tax Credit (up to $2,200 per qualifying child under age 17)
• Child and Dependent Care Credit (based on childcare expenses & income)
• American Opportunity and Lifetime Learning Credits (for education expenses)

Now is the time to gather documentation, track qualifying expenses, and budget for additional spending to maximize these credits by year-end.

8. Business Owners: Accelerate or Defer Income and Expenses depending on accounting method

If you’re a sole proprietor, S Corp [“S corporation status” is a federal tax election that allows an eligible corporation or LLC to be taxed as a pass-through entity], or partnership owner, you have more flexibility with tax timing.

Mid-Year Actions:

• Accelerate Expenses: Purchase equipment, software, or prepay services before year-end.
• Defer Income: Push invoices into January if you expect lower rates next year.
• Review Entity Structure: Ensure you’re using the most efficient business entity (S Corp, LLC, partnership) based on income levels.

Consider a mid-year meeting with your CPA to run profit-and-loss projections and re-evaluate your compensation structure and reasonable salary rules.

9. Coordinate Estate and Gift Planning

With the lifetime federal estate and gift tax exemption at $15 million per person in 2026—and will be indexed for inflation until 2029 -- now is the time for strategic gifting.

Strategies:

• Use your $19,000 annual gift exclusion per recipient
• Consider intra-family loans, grantor retained annuity trusts (GRATs), or spousal lifetime access trusts (SLATs)
• Mid-year reviews are ideal for initiating or refining wealth transfer strategies in coordination with your estate planner

10. Schedule a Mid-Year Review with Your Advisors

Finally, put a meeting on the calendar with your:

• CPA or enrolled agent
• Financial planner or wealth advisor
• Estate planning attorney

Bring documents including:

• Pay stubs, investment statements, retirement account summaries
• YTD income and expense reports (for businesses)
• Recent tax return

Mid-year check-ins offer time to make meaningful changes, implement savings strategies, and lower your total 2026 tax burden.

Tax planning doesn’t end on April 15—it’s a year-round discipline. By taking stock in June, you give yourself the time and flexibility to make smart tax decisions while there’s still time to act. Whether you’re a W-2 employee, retiree, business owner, or investor, these mid-year strategies can help you optimize your taxes, enhance retirement readiness, and align financial decisions with your long-term goals.

For Informational Purposes only and not for legal or tax advice.

About the Author – Marie Feindt, JD 

Marie Feindt is the Planning Specialist – Estate Attorney at Members’ Wealth, a boutique wealth management firm that offers a comprehensive and holistic approach to serving individuals, families, business owners, and institutions. The firm’s goal is to preserve and grow its clients’ wealth to endure over time, while thoughtfully evolving its strategy to suit an ever-changing world. With over 20 years of estate planning experience, Marie and the Members’ Wealth team thrive on bringing clarity and confidence to clients’ unique situations. She believes everyone, young adults and older, need the essential documents to conserve and preserve and transfer assets accumulated during lifetime to the next generation.

Marie received her JD from Widener University School of Law, her bachelor’s degree from Penn State University, University Park and is currently enrolled in the Villanova University Charles Widger School of Law Graduate Tax Program.

Marie is an Adjunct Faculty at the Villanova University College of Professional Studies Paralegal Professional Certificate Program where she teaches Estates & Trusts and Civil Procedure & Litigation and Torts & Personal Injury Law.

Marie volunteers for a monthly legal clinic at The Salvation Army in Chester, PA facilitated by the Christian Legal Clinic of Philadelphia. She has served on the Women’s Commission of Delaware County and as a Board Member for the Delaware County Literacy Council.

Marie enjoys biking, reading, yoga and walking in her free time with her husband and three children.

To get in touch with the Members’ Wealth team today, I invite you to email info@memberswealthllc.com or call (267) 367-5453. 

You can learn more about how we serve our clients by tapping the button below.

Investment advisory services are offered through Members’ Wealth, LLC., a Registered Investment Advisory Firm.

Registration with the SEC does not imply a certain level of skill or training. We are an independent advisory firm helping individuals achieve their financial needs and goals

Members’ Wealth does not provide legal, accounting or tax advice. Please consult your tax or legal advisors before taking any action that may have tax consequences.

This commentary reflects the personal opinions, viewpoints and analyses of the Members’ Wealth, LLC employees providing such comments, and should not be regarded as a description of advisory services provided by Members’ Wealth, LLC or performance returns of any Members’ Wealth, LLC client. The views reflected in the commentary are subject to change at any time without notice. Nothing in this commentary constitutes investment advice, performance data or any recommendation that any particular security, portfolio of securities, transaction or investment strategy is suitable for any specific person. Any mention of a particular security and related performance data is not a recommendation to buy or sell that security. Members’ Wealth, LLC manages its clients’ accounts using a variety of investment techniques and strategies, which are not necessarily discussed in the commentary. Investments in securities involve the risk of loss. Past performance is no guarantee of future results

Copyright © 2023 Members' Wealth LLC