By Michael Henley, CFP®, CPWA®, CRPC®, RMA®

Tax season may be a few months away, but for high earners, real tax planning has little to do with April. Some of the most impactful tax decisions happen ahead of key deadlines, contribution windows, and estimated tax payment dates in January, June, and October.

For high earners, effective tax planning means taking a proactive approach. If your income comes from multiple sources, if you’re managing equity compensation, or if your financial picture involves charitable giving and legacy goals, it’s worth rethinking the idea that tax planning is a once-a-year event.

The Numbers Have Changed, Your Strategy Should Too

With the passage of OBBBA in 2025, some favorable contribution and exemption limits remain in place for wealthy households, making 2026 a key part of a multi-year tax strategy.

A few notable numbers:

401(k) contributions: Employees can contribute up to $24,500, and total contributions (with employer match) can reach $72,000. For those age 50 or older, an additional $8,000 catch-up is available, bringing the total to $80,000. For those aged 60-63 in 2026, a super catch-up of $11,250 is allowed instead of the standard $8,000, bringing the maximum possible to $83,250 for this age range.

For individuals who made more than $150,000 in FICA wages in 2025, you must now make all catch-up contributions as Roth (after-tax) rather than pre-tax. This means you’ll pay taxes on the income in the year it was earned, rather than receiving an up-front deduction for the contribution. While this changes the timing of the tax benefit, it creates tax-free growth going forward and allows for tax-free withdrawals in retirement.

Estate tax exemption: The exemption rose to $15 million per person in 2026, with the option to double to $30 million for married couples. You can gift $19,000 per recipient per year without incurring any tax. For a family with three children and six grandchildren, that totals $171,000 in potential tax-free wealth transfer each year.

Charitable contributions: And for those considering charitable giving, 2026 also marks a significant shift in deduction rules. New limitations could reduce the tax efficiency of future gifts. Brandywine Oak published an article last month reviewing how these changes could affect you.

Why Tax Planning for High Earners Requires Year-Round Coordination

What happens when you want to diversify a concentrated stock position but face a significant capital gains bill?

Consider a hypothetical couple: both executives, combined W-2 of $850K, sitting on $1M in stock that has appreciated drastically over several years. They want to diversify but selling triggers significant capital gains.

The reactive approach is to sell all the shares in November, pay the tax, and diversify. A coordinated approach could look something like this:

  • January: Fund a donor-advised fund with appreciated stock, creating a large charitable deduction.
  • December: Sell part of the concentrated position, offsetting some gains with losses realized from other positions if available
  • The following January: Sell more of the stock in the new tax year. Chipping away at a large stock position can require a multi-year strategy

This kind of coordination can potentially save significant taxes, but it only works when decisions are made proactively throughout the year rather than reactively in March.

Strategies Worth Considering Throughout the Year

1. Manage RSUs and concentrated positions strategically.

When RSUs vest, they trigger ordinary income. But what happens next (whether you hold, sell, diversify, or donate) carries tax implications. If you are facing a large vest or sitting on concentrated company stock, gifting appreciated shares to a donor-advised fund can reduce your position while creating a current-year deduction. This is especially effective in high-income years when you need the deduction most.

2. Time capital gains.

When you are holding positions with significant unrealized gains, timing matters. Monitoring short-term versus long-term treatment and selling strategically to stay in favorable brackets can make a meaningful difference. For example, selling appreciated stock before the 1-year mark results in ordinary income taxes, while selling it after at least 1 year results in preferential long-term capital gains rates (0%,15%, or 20%).

3. Utilize a health savings account.

Health savings accounts, or HSAs, remain one of the most underutilized planning tools. If available through your employer and paired with a high-deductible health plan, they can offer triple tax advantages. These include tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. In retirement, you can tap these funds strategically to cover medical costs such as Medicare premiums.

4. Implement tax-efficient asset location.

The type of account you hold your investments in can matter just as much as what you invest in. Different accounts have different tax treatment, so putting the right types of investments in the right accounts can help reduce taxes over time. For example, keeping higher-growth investments like stocks in Roth accounts allows future growth to come out tax-free, while holding income-producing investments like bonds in tax-deferred accounts can help avoid paying high taxes on interest each year. Thoughtful asset location can improve your after-tax results without changing your overall investment strategy.

Tax Planning Isn’t About Avoiding Taxes, It’s About Managing Them

At this level of wealth, taxes are a given. The difference comes down to how and when you plan. Are your decisions made reactively, in the rush of tax season? Or proactively, with the full picture in view?

When your plan coordinates taxes with investments, retirement income, equity compensation, and legacy goals, tax efficiency becomes a byproduct of strategic planning, not a once-a-year scramble. The goal isn’t to minimize taxes in any single year; it’s to reduce your lifetime tax bill by making strategic decisions across multiple years.

At Brandywine Oak Private Wealth, we work closely with families to coordinate tax planning across all aspects of their financial lives. Through our private tax advisory service, our team of tax professionals collaborates with your wealth advisor to implement tax-saving strategies, file returns, and handle IRS correspondence on your behalf.

For guidance on coordinated financial and tax planning, call (484) 785-0050, email contact@brandywineoak.com, or schedule a consultation online at brandywineoak.com/get-started.

Curious what it’s like to work with us? Visit our client testimonials page to hear from the families we serve.

Frequently Asked Questions About Tax Planning for High Earners

What is the best time of year to do tax planning if I have RSUs and a high income?

Tax planning is necessary for most individuals year-round, not just in March or April. The most effective strategies require timing throughout the year: Roth conversions in low-income years, charitable contributions in high-income years, and tax-loss harvesting during market volatility. Waiting until tax season means reacting to what already happened rather than proactively shaping your tax outcome.

How is tax planning different from just filing my taxes?

Tax filing is backward-looking. It reports what happened last year. Coordinated tax planning is forward-looking and involves your CPA, financial advisor, and estate attorney working together throughout the year. For example, your advisor should know about upcoming RSU vests so they can plan accordingly for a high-income year. Your estate attorney should work with your financial advisor to ensure assets are retitled properly to avoid future probate expenses. When these professionals work in isolation, opportunities get missed, and tax bills get larger than necessary.

Can I reduce taxes when my RSUs vest this year?

Yes, but it requires planning ahead. When RSUs vest, the value is taxed as ordinary income, which can push you into a higher tax bracket. To help offset that tax hit, consider strategies like:

  • Gifting appreciated stock to a donor-advised fund (DAF): If your RSUs have grown in value, donating some of them in the same year they vest can create a charitable deduction to offset the income.
  • Selling strategically: If you decide to hold RSUs after they vest, future gains will be taxed at favorable long-term capital gains rates only if the shares are held for at least 1 year after vesting.

The key is to know your vesting schedule in advance and build your tax plan around it. Waiting until tax season usually means missed opportunities.

About Michael

Michael Henley is the Founder and CEO of Brandywine Oak Private Wealth, a private wealth management and registered independent advisory firm headquartered in Kennett Square, PA. Over the course of his 20-year career, Michael has been dedicated to helping wealthy individuals and families plan and manage all aspects of their finances and investments. With a passion for helping others look behind the curtain and understand the complex world of finance, he develops close relationships with clients as he helps them progress toward their financial goals. Michael loves to provide clarity and alleviate financial anxiety, help prevent families from overpaying in taxes, and give wealthy families permission to enjoy their life savings. He says, “No work is more gratifying than giving families outcomes to what matters most to them.”

Michael holds the CERTIFIED FINANCIAL PLANNER®, Certified Private Wealth Advisor®, Chartered Retirement Planning Counselor℠, and Retirement Management Advisor® designations. Residing in Chadds Ford, PA, with his two children, he enjoys outdoor activities, particularly maintaining trails on his property, hiking with his dogs, and being an actively engaged dad, always taking his kids everywhere. Michael’s latest hobby is tennis and he recently started ice skating to join his daughter Savannah. He can also be found moving logs to the firepit with his son Maverick on the tractor. Michael serves on the board of United Way of Southern Chester County and loves mentoring younger advisors. Great mentors helped him succeed, and he’s convinced that every leader needs to both have mentors and be a mentor. To learn more about Michael, connect with him on LinkedIn.

Brandywine Oak Private Wealth is a registered investment adviser. Registration does not imply a certain level of skill or training. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and, unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance.