Tax Season Is Over – Now the Real Planning Begins: A Month-by-Month Guide for High-Earning Women in Leadership

May 16 — 2025
Charitable Giving, Investment Strategies, Stock Compensation Planning, Tax Planning and Optimization, Wealth & Investment Strategies

Estimated reading time: 9 minutes

Tax season may be behind us, but for high-earning women in leadership, the real opportunity to take control of your finances starts now. With complex compensation packages, equity awards, and a fast-paced career, staying ahead of the game requires more than filing on time—it calls for a strategic, year-round tax planning approach.

Please note: tax planning is completely different from tax filing. Many executive women who come to me after receiving surprise tax bills had assumed their accountant was handling the planning, but that’s usually not the case. In reality, financial planners who specialize in serving high-earning executives are often more attuned to proactive tax strategy.

Here’s Your Month-by-Month Tax Planning Checklist:
Crafting a Personalized, Year-Round Tax Planning Strategy
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Here’s Your Month-by-Month Tax Planning Checklist:

May: Reflect and Reassess

Instead of shelving your return until next year, use May as an opportunity to reflect on what worked, what didn’t, and make smarter financial decisions for the months ahead.

Take a quick look at your return. Note any surprises—like a bigger tax bill than expected or deductions you didn’t get to take—so you can avoid them next year.
Chat with your CPA or financial planner. A short tax planning meeting now can help you understand your tax return and identify future savings opportunities.
Estimate your income for the rest of the year. If you’re expecting a raise, bonus, or RSU vesting this year, plan accordingly to avoid a surprise tax bill.

June: Commit to a Mid-Year Financial Check-In

A mid-year review gives you plenty of runway to make meaningful adjustments to your tax planning strategy before year-end.

Consider making estimated tax payments. If under-withholding on RSU income led to a surprise tax bill in April, consider making quarterly estimated payments going forward to avoid penalties and stay ahead of what you owe.
Review your retirement contribution pace. Are you on track to max out your 401(k) or other tax-advantaged accounts? Adjust now while you still have time to spread out contributions.
Plan for life events. Marriage, divorce, a move, or a new child can all have tax implications. Incorporating these into your tax strategy now gives you time to plan accordingly.

July: Review Your Investment and Tax Strategy

July is a great time to make sure your investments are still aligned with your goals. A thoughtful, strategic approach can help you grow your wealth more effectively while minimizing avoidable tax consequences.

Rebalance your portfolio. Adjust your asset mix to stay aligned with your goals and risk tolerance, while also managing potential gains or losses that affect your tax bill.
Review asset location. Certain investments are better suited for tax-advantaged accounts like IRAs or 401(k)s, which can reduce the amount of taxable income your portfolio generates.
Evaluate recently vested equity. If you’ve received RSUs or exercised stock options, now’s the time to assess the tax impact and decide whether it makes sense to sell or hold.

August: Align Your Finances with Your Values and Family Needs

As you gear up for a new school year or a demanding season at work, take time to ensure your finances reflect your values and provide the support your loved ones deserve.

If you’re saving for a child’s or relative’s education, contributions to a 529 plan may reduce your state tax burden and help ease the cost of future education. That said, while 529 plans can be beneficial, simply contributing the maximum amount isn’t always the best strategy for every family. Be sure to consult with your financial advisor to determine whether this tool aligns with your specific goals and financial picture.
Consider your caregiving responsibilities. These roles can impact your financial plan, from needing extra savings to qualifying for certain tax deductions or credits.
Double-check your estate documents and account beneficiaries. Keeping your estate plan up to date can prevent complications and avoid unexpected tax consequences down the road.

how to take advantage of your company benefits and how that impacts your tax planning strategy

September: Optimize Your Equity & Employee Benefits

September typically kicks off open enrollment season—a key opportunity to maximize the value of your equity compensation and employee benefits.

Review your health and workplace benefits. Choosing the right benefits can lower your taxable income and out-of-pocket expenses.
If you participate in an ESPP or hold stock options, understanding when to sell—and how long to hold—can help you minimize taxes and avoid costly surprises.
If you’re paying estimated taxes, make sure to submit your third-quarter payment by the September deadline to stay on track.

October: Kick Off Year-End Tax Planning

As the final stretch of the year begins, October is the perfect time to get ahead of year-end tax planning.

Update your projected total income for the year, including salary, bonuses, and equity comp, to spot opportunities to reduce taxable income or avoid a higher tax bracket.
If you’re planning tax-deductible expenses—like energy-efficient home improvements or unreimbursed medical costs—completing them before year-end can help increase your credits and deductions for the current tax year.
Plan any Roth conversions thoughtfully. If you’re considering converting pre-tax retirement funds to a Roth IRA, doing so in a lower-income year—or before potential tax hikes—can be a smart move.

November: Give Purposefully and Gift Strategically

As the season of giving begins, November offers a meaningful opportunity to align generosity with smart tax planning.

Make charitable donations before year-end to ensure they qualify for this year’s tax return and give yourself plenty of time to organize the necessary documentation.
Consider donating appreciated stock to a donor-advised fund (DAF) or qualified charity to avoid capital gains taxes while maximizing the value of your contribution.
Take advantage of the annual gift tax exclusion—up to $19,000 per recipient in 2025—to transfer wealth tax-free and avoid filing a gift tax return.

tax planning in december with charitable giving

December: Finish Strong with Smart Year-End Moves

December 31 marks your last chance to take advantage of many key tax planning opportunities for the current tax year.

Use up any remaining FSA funds. Most flexible spending accounts have a “use it or lose it” rule. So be sure to spend down eligible balances before they expire.
Confirm you’ve met any required distributions. If you’re subject to RMDs or plan to make a Qualified Charitable Distribution, make sure it’s processed before year-end to avoid penalties.
Review your financial wins and lessons from the year. Take stock of what worked, what didn’t, and what you want to do differently. This reflection is a powerful tool for shaping your goals and tax planning strategy in the new year.

January: Start Fresh with Intention and Focus

January is the time to reset, review, and lay the groundwork for a strong year ahead.

Update your income, savings, and investment automations. Align recurring contributions, paycheck withholdings, and estimated tax payments with your goals and expected income.
Review your equity compensation calendar. Note vesting dates, expiration deadlines, and blackout periods so you can plan your tax strategy accordingly.
If you’re paying estimated taxes, make sure to submit your fourth-quarter payment by the January deadline.

February: Plan Ahead for Equity Milestones and Career Moves

February tends to be a quieter month financially, which makes it the perfect time to strategize without the pressure.

Evaluate your exposure to company stock. If a large portion of your net worth is tied up in your employer’s shares, work with your financial planner to build a tax-efficient diversification plan.
Check your withholding elections. If you’ve had a significant change in income or equity compensation, update your W-4 before the February 15^th deadline.
Book a proactive check-in with your financial planner or CPA. A strategy session ahead of tax season can help you stay organized, identify opportunities, and reduce surprises later on.

March: Get Organized for Tax Filing Season

With tax deadlines approaching, March is all about preparation. Whether you’re filing in April or planning to extend, organizing now will save you stress later.

Organize your tax documents, especially those related to equity compensation. Make sure you have W-2s, 1099s, and stock transaction summaries—including cost basis and sale dates.
Review last year’s final pay stub. Look for unreimbursed expenses or missed FSA/HSA contributions that could affect your tax return or prompt updates for this year.
Evaluate whether you should file early or extend. Filing early may expedite a refund, while an extension gives you time to gather documents. Just don’t delay payment if you owe.

April: File Your Return

April marks the end of one tax year and an opportunity to fine-tune your strategy for the year ahead.

Submit your return or file an extension if needed. But be sure to pay any taxes owed by April 15 to avoid penalties.
Make prior-year IRA or HSA contributions. You can still make contributions for the previous year until the tax filing deadline and potentially lower your tax bill.
Revisit your tax planning strategy. Meet with your financial planner to assess what worked, identify gaps, and make strategic adjustments for the year ahead.

Crafting a Personalized, Year-Round Tax Planning Strategy

When you’re a high earner, navigating the demands of a fast-paced career, tax planning can’t be a once-a-year event. It requires a year-round approach to make the most of your income and turn your hard work into lasting wealth.

Many of the strategies I mentioned above can be too complex to implement on your own. Or you simply might not have enough time or bandwidth to study them thoroughly right now. And that’s totally fine. That’s why we are here to figure them out together with you.

At Align Financial Solutions, we help not only with optimizing your RSUs but also with your broader financial lives. Our goal is to help you simplify your finances, eliminate surprises, and build a work-optional life with clarity and ease.

If you’re ready to stop reacting and start planning with intention, we’re here to help. Let’s build a tax strategy that supports your goals—not just during tax season, but all year long. Reach out today to get started.