High income amplifies small mistakes. A missed deduction, poor timing, or improper account setup can cost five figures over time.

The solution isn’t a scramble once a year; it’s a steady cadence of planning, documenting, and executing throughout the year to minimize tax leakage.

Act Year-Round

Most tax opportunities expire on December 31, not on filing day. “It’s not what we do once in a while that shapes our lives. It’s what we do consistently.”– Tony Robbins. Build a cadence: quarterly check-ins for income shifts, RSU vests, business profits, and harvestable losses. Adjust withholding, estimated payments, and contribution levels while the window is still open.

Misusing SALT

The state and local tax (SALT) deduction is capped and complicated. High earners often mis-time property tax or state estimates, losing deductibility. Coordinate payments with your itemizing vs. standard deduction years, and watch phaseouts tied to adjusted gross income (AGI). Timing alone can rescue thousands.

Ignore PTET

Own an S-corp, partnership, or multi-member LLC? Many states offer a Pass-Through Entity Tax (PTET) election that converts nondeductible personal SALT into deductible business expense at the entity level, often paired with a state credit. Miss the election window and the benefit is gone for the year.

Wrong Entity

The “default” sole proprietorship can be expensive. Evaluate whether electing S-corp status improves after-tax results once profits justify reasonable wages plus distributions. Confirm Qualified Business Income (QBI) eligibility, wage/capital thresholds, and retirement plan options before year-end—not after.

Roth Missteps

Backdoor and mega-backdoor Roth moves are powerful, but paperwork errors are common. Pitfalls include the pro-rata rule (existing pre-tax IRA dollars dilute the conversion), late 8606 forms, or rolling to the wrong account first. Roth conversions also demand bracket management so you don’t trigger surtaxes or credits loss.

Charity Timing

“Bunching” two or more years of donations into one tax year can push you above the standard deduction and unlock larger write-offs. Donor-Advised Funds help pre-position several years of giving, especially with appreciated stock. You grant to charities later while realizing a bigger deduction now.

Harvest Losses

Tax-loss harvesting isn’t just for December. Throughout the year, swap into similar (not “substantially identical”) holdings to realize losses that offset gains and up to $3,000 of ordinary income. Track wash-sale windows across all accounts—yours and a spouse’s—to avoid disallowance.

Bad Location

Asset location mistakes quietly erode returns. Place tax-inefficient assets (REITs, high-yield bonds, actively traded funds) in tax-deferred or tax-free accounts when possible. Keep broad equity index funds and long-term growth names in taxable for better qualified dividend and capital gains treatment.

Health Overlooked

High-deductible health plan? Max the HSA—triple tax-advantaged and a stealth retirement account. Self-employed? Above-the-line health insurance deductions are often missed, including Medicare premiums in the right situations. Confirm eligibility rules and keep documentation tidy for any IRS inquiry.

Cost Basis

Equity compensation can wreak havoc. Misreported basis on ESPP, ISO/NSO exercises, or RSU sells often creates phantom gains. Keep grant docs, Form 3922/3921, and broker confirmations. For private deals and K-1s, track capital accounts and suspended losses so carryforwards don’t disappear with a preparer switch.

Estate Blindspots

Estate thresholds and state regimes change. Review beneficiary designations, titling, and powers of attorney. Consider lifetime gifting, 529 front-loading, or trusts where appropriate. If approaching future lower federal exemptions, advanced planning (e.g., SLATs, GRATs) can mitigate exposure without losing control.

CPA Strategy

Compliance isn’t strategy. The most common miss for high earners is disjointed advice: investments in one office, taxes in another, no shared playbook. Coordinate your advisor and tax pro to align cash flow, equity comp timing, charitable plans, and retirement contributions before year-end.

Build Playbook

Create a one-page, repeatable calendar:

• Q1: Adjust estimates/withholding, plan equity sales, set HSA/401(k) rates.

• Q2: Midyear bracket check, Roth conversion modeling, PTET decisions.

• Q3: Charitable bunching/DAF funding, education funding, TLH review.

• Q4: Finalize bonuses, capital gains, RMDs/QCDs, and retirement plan top-offs.

Common Misses

Frequent high-earner errors include: forgetting capital loss carryforwards; skipping foreign tax credits; missing home-office or health insurance deductions for businesses; poor estimated tax planning after a liquidity event; and letting RSUs vest into an already high-tax year without offsetting moves.

Conclusion

Big portfolio wins grab headlines, but executing tax strategies effectively compounds just as significantly. Plan early and document everything. Which two actions—timing SALT/PTET, bunching donations, or fixing asset location—will you schedule this quarter to keep more of what you earn?