Tax Planning Checklist: Maximize Savings and Minimize Stress

Somewhere between the busyness and the year-end wrap-ups, you probably have a moment when you start thinking about what’s coming next. Maybe it’s the usual stuff — getting back into a routine, taking better care of your health, finding a little more balance. Your finances belong in that same conversation, too.

A bit of (financial) attention now can set you up for a smoother start to 2026 — especially when it comes to tax planning.

Start with your financial picture

Take a full, 360° view of your income — not just your salary, but also bonuses, RSUs, dividends, business income, and side hustles. If your RSUs vested last year or you received a year-end bonus, it could bump you into a higher tax bracket. It’s smart to model that early. 

Next, review expenses that may qualify as deductions: charitable giving, medical costs, or unreimbursed business expenses. For example, if your AGI was $100,000 and you had $15,000 in medical expenses, $7,500 of those costs may be deductible. 

And don’t forget any carryover losses from 2025 could potentially offset 2026 gains and may help lower your taxable income. 

Review your retirement contribution

Retirement accounts remain one of the most effective tax strategies available. The maximum contributions for 2026 are: 

• 401(k): up to $23,500 (or $31,000 if you’re 50+) 
• IRA: up to $7,000 (or $8,000 if 50+) 
• HSA (family): up to $8,550 

If cash flow allows, consider front-loading contributions early in the year. It gives your dollars more time to grow tax-deferred and keeps your savings rhythm steady throughout the year. 

Get ahead of your RSUs and equity compensation

Equity can be an incredible wealth builder — and an unexpected tax headache if not planned for. Review your vesting schedule and decide whether to sell shares immediately or hold for long-term goals. 

Selling at vesting can provide liquidity and diversify your portfolio, while holding may align better with your long-term strategy. 

Keep in mind: companies typically withhold 22% for taxes on RSUs, but if you’re in a higher bracket, that may fall short. Planning ahead helps you avoid an unwelcome surprise next April. 

Plan for major transactions

If you’re considering a business sale, liquidity event, or real estate purchase, start your tax planning early. 

For example, Qualified Small Business Stock (QSBS) may allow you to exclude up to $5 million in gains on a $10 million sale — but only if your structure meets the requirements. 

Personal milestones, like purchasing a vacation home, benefit from early coordination. Understanding deductions for mortgage interest and property taxes can help you plan cash flow and timing more strategically. 

Alternatively, if you’re part of a company heading toward an IPO or liquidity event, your timing decisions can have a massive impact on your tax outcome. When receiving restricted stock or early-stage equity grants, consider whether filing an 83(b) election makes sense. This election allows you to pay taxes on the value of your shares at the time of grant rather than when they vest — potentially locking in a lower valuation and avoiding future appreciation being taxed as ordinary income. 

For instance, if your shares are valued at $1 when granted and $20 at vesting, an 83(b) election means you’d pay ordinary income tax on $1 per share today, and any future growth would be treated as long-term capital gains. Without the election, you’d owe ordinary income tax on the $19 increase at vesting — a significant difference. As the 83(b) election must be filed within 30 days of the grant date, it’s crucial to connect with your advisor and CPA early to determine whether it aligns with your long-term strategy. 

Outline your charitable giving strategy

If charitable giving is part of your plan, be thoughtful about how you give: 

• Donor-Advised Funds (DAFs): DAFs may allow you to contribute appreciated stock to take the deduction now, then decide where to direct funds later.  
• Qualified Charitable Distributions (QCDs): if you’re 70½+, you may be able to donate up to $108,000 directly from your IRA, tax-free. 
• Bunching gifts: consider combining multiple years of donations into one to exceed the standard deduction threshold. combine multiple years of donations into one to exceed the standard deduction threshold and maximize impact 

Fine-tune your tax payments

Raises, bonuses, or RSU vesting can all change your tax picture. Review your W-4 or estimated payments early to avoid underpayment penalties — and the stress of catching up later. 

For high-income earners and business owners, dividing quarterly estimated payments evenly can help maintain steady cash flow and stay compliant throughout the year. 

Revisit your estate & trust plans

Life changes — and your estate plan should evolve with them. If your relationship status has changed, or you’ve added assets, received an inheritance, or created a business interest, it’s time for a review. 

For 2025, the IRS annual gift tax exclusion is $19,000 per recipient. This exclusion may allow individuals to make gifts without incurring federal gift tax, subject to IRS limits and reporting requirements. 

Lean into smart investment moves  

Tax-loss harvesting remains one of the simplest and most effective ways to reduce taxable gains. 

For example, if you realized $50,000 in capital gains last year, realizing a capital loss of $20,000 by selling underperforming investments this year could reduce your taxable gain to $30,000 — while reinvesting in similar assets to maintain diversification. 

Exploring advanced tax strategies

Depending on your goals, a few higher-level strategies might make sense: 

• Roth Conversions: Roth conversions may allow future earnings to grow tax-free, subject to IRS rules. This approach can have different outcomes depending on your income and tax bracket, so it’s important to review with your tax adviser before proceeding.. 
• Opportunity Zone Funds: Investments may offer the potential to defer or reduce capital gains taxes if certain criteria are met, including required holding periods. These investments can involve higher risk and longer time horizons, so consultation with a tax and financial adviser is essential. 
• Section 199A Deduction: Eligible business owners have been able to deduct up to 20% of qualified business income under current law. This provision is scheduled to expire at the end of 2025 unless extended by Congress. 

Don’t go it alone

Tax planning is part of living intentionally and making your money work toward what matters most. Your advisor and CPA can help you synchronize timing, optimize contributions, and capture opportunities before deadlines hit. A proactive plan today leads to a calmer, more confident tax season and fewer “tax-day surprises.”

About the Author: Katy McDonald, CFP®, is a Lead Advisor at Brighton Jones. She helps high-income professionals and families design tax-efficient investment strategies and retirement plans aligned with their values and long-term goals.

Disclosure: This content is for informational and educational purposes only and should not be construed as individualized advice. For individualized advice tailored to your specific circumstances, please consult with your adviser.