By mid-summer, most investors have filed last year’s return, seen their 2026 estimated tax vouchers, and moved on. Yet from an advisor’s perspective, July through October is prime time for proactive moves that can reduce taxes, improve portfolio positioning, and align family goals before the calendar closes.
This article offers a “Matter of Tax” checklist—ten action items to consider before December 31—framed for investors and business owners working closely with a financial advisor.
1. Reconcile 2026 Income and Estimated Taxes
Start by reconciling year-to-date income against estimates used for April and June payments.
Changes in bonus timing, investment income, or pass-through distributions can make initial estimates stale. Advisors can work with tax partners to update projections, adjust remaining estimated payments, and avoid both underpayment penalties and unnecessarily high overpayments that tie up cash.
2. Review S-Corp Compensation and Pass-Through Structures
For business owners, 2026 continues the trend of heightened scrutiny around reasonable S-Corp compensation, pass-through entity taxation, and state-level workarounds for SALT limitations.
A mid-year review can identify whether current wage-versus-distribution splits still make sense, whether entity elections remain optimal, and how recent tax law changes affect multi-year planning.
Coordinating these decisions with retirement plan contributions and healthcare benefits amplifies their impact.
3. Maximize Retirement Contributions Under 2026 Limits
Retirement plan limits have shifted again for 2026, and catch-up rules for high-income earners are now tightly linked to Roth treatments.
Advisors should ensure clients are on track to fully utilize employer plans, SEP/SIMPLE arrangements, and IRAs, with particular attention to the tax character of contributions—traditional versus Roth—and how that affects future withdrawal taxation.
Where cash flow allows, increasing deferrals in the second half of the year can meaningfully reduce taxable income.
4. Harvest Losses and Gains Strategically
Volatility across sectors and asset classes has created opportunities both to harvest losses and to manage realized gains.
A summer review can identify positions with meaningful unrealized losses that no longer fit the client’s strategy, enabling tax-loss harvesting while maintaining market exposure via replacement securities.
Conversely, clients with concentrated gains may benefit from deliberately realizing some appreciation within a “capital gains budget,” smoothing the tax impact over multiple years.
5. Optimize Asset Location for Tax Efficiency
Tax-smart portfolios don’t rely only on security selection; they also use asset location—placing tax-inefficient assets in tax-advantaged accounts and tax-efficient ones in taxable accounts.
Advisors can use summer meetings to review whether high-yield bonds, actively traded funds, or tax-intensive strategies are held in IRAs and 401(k)s, while index funds, tax-managed strategies, and municipal bonds sit in taxable accounts.
Aligning location with strategy is one of the most durable tax moves investors can make.
6. Plan Charitable Giving and Donor-Advised Fund Contributions
High-income investors increasingly use front-loaded charitable strategies to manage tax exposure, including donor-advised funds (DAFs), direct gifts of appreciated securities, and qualified charitable distributions (QCDs) from retirement accounts.
Advisors can help clients decide whether 2026 is the right year for a larger DAF contribution, coordinate gifts with portfolio rebalancing, and ensure QCDs are integrated into RMD planning for eligible retirees.
Documenting a multi-year philanthropy plan also reduces last-minute December decisions.
7. Revisit Estate Plans and Lifetime Gifting
Current estate and gift tax rules still provide significant exemptions, but ongoing policy discussion makes it prudent to assume today’s generosity may not persist indefinitely.
A summer review can confirm whether wills, trusts, and beneficiary designations reflect current intent and whether the household should use more of its annual exclusion or lifetime exemption through strategic gifts.
Integrating real estate, business interests, and vehicles like Trump accounts into these plans ensures consistency across assets.
8. Coordinate Real Estate Decisions With Tax Strategy
Investors contemplating property sales, exchanges, or refinancing should coordinate timing and structure with their tax plan.
Advisors can help model the impact of outright sales versus 1031 exchanges, DST investments, or 721 exchanges into REITs, and determine whether 2026 is the right year to recognize gains or defer them.
Linking real estate moves to broader portfolio and estate objectives prevents isolated decisions that create unintended tax consequences.
9. Address Concentrated Positions and Risk Management
Tax considerations often deter investors from trimming concentrated stock positions or legacy holdings, but the risk of inaction can be greater than the tax bill.
Advisors can build staged diversification plans that recognize gains over several years, pair sales with charitable contributions or loss harvesting, and use options or structured products where appropriate to manage downside risk.
Framing tax as one variable among many—not the only variable—helps clients make more balanced decisions.
10. Confirm Documentation, Elections, and Deadlines
Finally, a practical but critical step: confirm that all elections, documentation, and deadlines tied to 2026 strategies are understood and calendared.
This includes retirement plan adoption and funding deadlines for businesses, charity-related paperwork, entity elections, and any actions tied to tax credits or incentives.
Advisors who maintain a shared planning calendar with clients and tax professionals can dramatically reduce the risk of missed opportunities or inadvertent non-compliance.
Bringing the Checklist to Life
The checklist is only valuable if it drives action.
Advisors can use it to structure summer and fall review meetings, assigning each item to a specific month and responsible party. For clients, seeing tax moves integrated into their investment, retirement, and estate conversations reinforces that tax planning is not a separate silo—it is part of the overall strategy.
By December, the goal is not perfection, but progress: fewer surprises, more intentional decisions, and a clearer view of how today’s actions support tomorrow’s outcomes.
