Mid-Year Tax Planning Moves to Make Now
Mid-year tax planning moves that matter most in 2026 — Roth conversions, tax-loss harvesting, capital gains planning, and more.
Most tax planning happens in April — or worse, at year-end when options are limited. But the middle of the year is one of the best windows for proactive tax strategy.
At Windward, our CPA heritage means tax planning is a year-round discipline. Here are the conversations we are having with clients right now.
1. Assess Your Roth Conversion Opportunity
By mid-year, we have a reasonably clear picture of your income for 2026. That allows us to model how much room you have in your current tax bracket — and whether converting a portion of your traditional IRA to Roth makes sense this year.
Roth conversions are often most valuable when done strategically over multiple years — filling up lower brackets without pushing into higher ones. Mid-year is an ideal time to make that calculation while there is still time to act.
2. Review Estimated Tax Payments
The third quarter estimated tax payment is due September 15th. If your income has changed significantly since you made your first and second payments — a large distribution, a business sale, unexpected investment gains — you may need to adjust.
Underpaying can result in a penalty. Overpaying is an interest-free loan to the government. A mid-year review keeps both outcomes from sneaking up on you.
3. Harvest Tax Losses Where Available
If you have taxable investment accounts, mid-year is a good time to review positions for tax-loss harvesting opportunities. Selling positions at a loss to offset realized gains elsewhere can meaningfully reduce your tax bill — and markets often create these opportunities when you least expect them.
The key is to act deliberately — not reactively. Tax-loss harvesting should be part of a plan, not a response to short-term market anxiety.
4. Plan for Capital Gains Events
If you are considering a significant asset sale in 2026 — real estate, a business interest, a concentrated stock position — mid-year is when we want to model the tax impact. Options like installment sales, opportunity zone investments, or charitable strategies work best when planned well in advance.
The difference between an unplanned sale and a carefully timed one can be substantial.
5. Review Your Charitable Giving Plan for the Rest of the Year
If you plan to make significant charitable contributions in 2026, now is the time to coordinate strategy. Should you use your Donor-Advised Fund or give directly? Should you donate appreciated stock instead of cash? Would bunching make sense this year?
These decisions are most effective when made before the year-end rush — not in December.
The Windward Approach
The most effective tax planning happens when investment decisions, retirement distributions, and charitable giving are all reviewed together — not in silos. Our integrated approach, combining financial planning with deep CPA expertise, is designed to identify opportunities that a single-discipline advisor may miss.
Ready to put these moves into action? Download our free Mid-Year Tax Planning Checklist — a quick-reference guide to the five moves worth making before Q3 arrives.
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