The Mid-Year Financial Planning Checklist for High Earners

Because building wealth isn’t about working harder—it’s about planning smarter.

If you're a high-income professional, the middle of the year is the perfect time to zoom out and assess whether your financial strategy is still aligned with your long-term goals. A few smart tweaks in July can lead to thousands of dollars in tax savings, optimized investments, and a more confident close to the year.

Here’s your mid-year financial planning checklist—tailored specifically for high earners in 2025.

1. Review Your Income and Optimize for Tax Brackets

If your income has changed this year—due to bonuses, commissions, equity vesting, or business profits—it’s time to re-evaluate your tax picture.

Ask yourself:

• Am I on pace to cross into a higher federal tax bracket?

• Should I front-load deductions (charitable contributions, business expenses, etc.)?

• Do I need to increase estimated tax payments to avoid penalties?

2. Maximize Retirement Contributions (and Beyond)

By mid-year, you should be on track to max out tax-advantaged accounts. These are the foundational building blocks of your wealth.

Check your progress:

• 401(k): $23,500 (plus $7,500 catch-up if 50+)

• Traditional/Roth IRA: $7,000 (plus $1,000 catch-up)

• HSA: $4,300 individual / $8,600 family (plus $1,000 catch-up if 55+)

Business owners and self-employed? This is the perfect time to evaluate:

• Solo 401(k) or SEP IRA contributions

• Whether a defined benefit or cash balance plan makes sense to supercharge savings and lower your taxable income

3. Revisit Your Equity Compensation

If you’ve had RSUs vest, exercised options, or participated in an ESPP this year—don’t let the tax planning fall through the cracks.

Mid-year actions:

• Estimate your tax liability from vested/exercised shares

• Consider 83(b) elections on early-exercise stock options

• Review your concentration risk (are you too exposed to employer stock?)

• Prepare for year-end sales and potential AMT exposure on ISOs

Equity compensation is one of the most under-optimized areas for high earners. A mid-year check-in can make a big difference.

4. Use Tax-Loss (and Gains) Harvesting to Your Advantage

With a volatile market this year, there may be strategic losses to harvest—or opportunities to sell appreciated assets tax-efficiently.

Tax-smart strategies:

• Harvest capital losses to offset gains (or up to $3,000 of ordinary income)

• Reinvest into similar—but not “substantially identical”—positions to stay invested

• If your income is lower than usual, consider harvesting gains in the 0% or 15% capital gains bracket

Also: If your modified AGI is over $200,000 (single) or $250,000 (married), the 3.8% Net Investment Income Tax may apply. Plan accordingly.

5. Reevaluate Your QBI Strategy

If you're self-employed or own a business, the Qualified Business Income (QBI) deduction can potentially reduce your taxable income by up to 20%.

Mid-year QBI checklist:

• Are you on track to qualify for the full deduction?

• Should you switch to or optimize your S-Corp election?

• Are your W-2 wages structured appropriately using the 2/7 rule?

Getting QBI right is a game-changer—but it requires advance planning and coordination with your CPA or financial planner.

6. Review Insurance and Estate Planning

Often overlooked—but critically important. If you’ve had a lifestyle or income change, this is a good time to reassess your risk management strategy.

Key areas to review:

• Disability insurance: Would it replace enough of your income?

• Umbrella coverage: Still enough liability protection?

• Term life: Do your coverage amounts reflect your current obligations?

• Estate docs: Are your will, trust, and beneficiary designations still aligned with your wishes?

Your financial plan isn’t complete without proper protection.

7. Final Thoughts: Is It Time to Level Up Your Planning?

High earners face a unique set of financial challenges—and opportunities. From AMT exposure to optimizing equity compensation, from harvesting tax losses to structuring income for QBI, the stakes are higher and the strategies more nuanced.

If you’ve hit a point where you’re making good money but feel like you’re missing something—or you're unsure how to tie it all together—a second set of eyes can go a long way.

At WealthBound Advisors, we specialize in helping high-income professionals design tax-savvy, long-term financial plans that don’t just build wealth—but help you use it with purpose.

Not sure if you’re on track? Let’s talk. Book a free intro call here.

Disclaimer: This blog is for educational purposes only and does not constitute financial advice. Please consult with your advisor, tax professional, or mortgage lender before making a major purchase decision.