Tax Planning

Managing RSU Withholding Tax: A Guide for Women with Equity Compensation

RSU Withholding

Restricted stock units (RSUs) can be a meaningful source of wealth, particularly if you work for a growing or publicly traded company. The challenge is that the tax treatment isn’t always intuitive, and it’s easy to underestimate what you’ll owe until tax season arrives.

The good news is that you can plan for this. When you understand how RSUs are taxed and take a few proactive steps during the year, you can avoid surprises and make more deliberate decisions about how this equity can support your broader financial goals.

How RSUs Work

RSUs are a form of compensation where your employer grants you the right to receive company stock (or sometimes cash) once certain conditions are met, typically staying with the company for a set period or meeting performance goals. Unlike stock options, there’s no purchase required. When the units vest, the shares are delivered to you.

Most companies use a multi-year vesting schedule, often with quarterly or annual vesting after an initial cliff or service requirement. At each vesting date, the value of those shares is determined by the stock price at that time, and that amount is treated as taxable income.

This is where many people get caught off guard, as the income shows up on your paycheck and affects your overall tax picture.

How RSUs Are Taxed When They Vest

RSUs are taxed as ordinary income when they vest, regardless of whether you hold or sell them. The fair market value of the shares at vesting is treated as “supplemental wages” and shows up on your W‑2, just like a bonus.

That vesting amount is subject to:

  • Federal income tax withholding
  • Social Security and Medicare (FICA)
  • State and possibly local income taxes, depending on where you live

For federal income tax, employers generally follow IRS supplemental wage rules:

  • 22% withholding on supplemental wages up to $1 million in a calendar year
  • 37% on supplemental wages above $1 million

This flat rate is only a withholding method, not necessarily your true marginal tax rate. If you’re in a higher tax bracket, which is common for professionals with significant equity compensation, your actual tax owed may exceed what was withheld.

Common Ways to Cover RSU Withholding Tax

When RSUs vest, your employer typically uses one of several methods to collect the required withholding taxes. The specific approach is dictated by your company’s plan, but the most common methods are:

  • Sell to cover. A portion of your newly vested shares is automatically sold to cover estimated taxes, and the remaining shares are deposited into your brokerage account. This often feels “automatic” and convenient, since you don’t have to write a check. However, it doesn’t guarantee that enough tax has been withheld for the year.
  • Same‑day sale (cash out). All vested shares are immediately sold, the company withholds the estimated taxes, and you receive the remaining cash. This can help with cash flow if you have near‑term goals or want to avoid concentrated stock risk.
  • Cash withholding / share delivery. Your employer withholds the tax due from your regular paycheck or asks you to pay cash, and you receive all of the vested shares in your account. This preserves your full equity position but increases your exposure to the company’s stock.

Most employers default to a variation of sell‑to‑cover or net share settlement, unless you make a different election. Whichever method your company uses, it’s important to remember: the withholding is just an estimate based on IRS rules—not a guarantee you’ve paid the “right” amount of tax for the year.

Why RSU Withholding Often Falls Short

Because RSU income is treated as supplemental wages, most employers use the IRS flat rate for federal withholding. For many mid‑ to high‑income earners, this flat 22% rate is lower than their actual marginal tax rate, which can easily land in the 24–35% range (or higher).

This gap is a common reason people with RSUs end up with a tax bill they didn’t anticipate. Consider a simplified example:

  • If 1,000 RSUs vest at $100 per share, you’ve added $100,000 of ordinary income.
  • At a 22% withholding rate, only $22,000 might be withheld.
  • If your marginal tax rate is 35%, your actual federal liability on that income alone is $35,000 dollars, leaving a $13,000 shortfall.

Other factors that can make under‑withholding more likely include:

  • A spouse or partner’s income
  • Prior RSU vests and bonuses in the same year
  • Investment income and side‑business income
  • Changes in filing status or deductions

The IRS can charge underpayment penalties if your combined withholding and estimated payments don’t meet safe‑harbor thresholds. It’s best to avoid these if possible, since penalties have become more expensive as interest rates have risen.

Options If Your RSU Withholding Isn’t Enough

If you notice your RSU income is pushing your tax bill higher than what was withheld, you generally have three ways to close the gap over the year instead of waiting for an April surprise.

  1. Increase withholding from regular paychecks. You can adjust your Form W‑4 so your employer withholds more tax from your regular wages. This approach spreads the extra tax over each paycheck and is often the easiest to implement.
  2. Make quarterly estimated tax payments. If your income is variable, or you prefer more control, you can send estimated tax payments to the IRS and, if applicable, your state each quarter. This route requires more tracking and discipline but can be very effective, especially if your RSU vests are large or clustered in certain quarters.
  3. Pay the difference when you file. You can choose to do nothing during the year and simply pay any shortfall when you file your tax return. This may work if the gap is small, but if the shortfall is significant, you may face penalties and a large lump‑sum payment—neither of which feel great.

Often, the best solution is a combination: slightly higher paycheck withholding plus modest estimated payments during heavy vesting years.

Best Practices for Managing RSUs Thoughtfully

For many professionals, especially those in tech, finance, or high‑growth industries, RSUs can represent a meaningful share of total compensation. To integrate them smoothly into your financial life, consider these best practices:

  • Know your vesting schedule and values. Track upcoming vesting dates, the number of shares expected to vest, and a reasonable estimate of what those shares may be worth. This allows you to plan ahead for both taxes and cash flow.
  • Avoid over‑concentration in company stock. It’s easy to let vested shares accumulate, especially when things are going well at work. Yet holding too much of your net worth in a single stock can increase risk and tie your income and wealth to the same company. It’s generally wise to set a maximum percentage of your investable assets you’re willing to hold in company stock and rebalance periodically.
  • Set a default “sell versus hold” policy. Instead of making each vesting decision in the moment, decide in advance how you’ll handle new shares. For example, you might choose to sell a set percentage at vest to cover taxes and diversify, while keeping the rest within your agreed‑upon concentration limit.
  • Coordinate RSUs with your broader plan. RSU income can be a powerful way to accelerate progress on long‑term financial objectives. Aligning your equity decisions with your values and goals helps you use this compensation intentionally, not reactively.
  • Document everything. Save your vesting statements, trade confirmations, and year‑end tax forms (W‑2, 1099‑B, etc.) so you and your tax preparer can accurately calculate any capital gains when you eventually sell.

A Simple RSU Planning Routine

To make RSU planning feel more manageable, it can help to use the same basic steps each year.

  1. Forecast your RSU income
    • List your upcoming vest dates and expected share counts.
    • Apply a conservative stock price to estimate how much taxable income those vests might create.
  2. Compare your projected tax to withholding
    • Look at your paystub and equity portal to see your RSU withholding method and rate.
    • Compare the expected withholding (for example, 22% federal) to your estimated marginal tax rate for the year.
    • Identify any likely shortfall early.
  3. Decide how you’ll handle the gap
    • Adjust your W‑4, schedule estimated payments, or do a mix of both so you stay ahead of potential underpayment.
    • Consider directing part of your vest proceeds to a separate “tax and goals” savings account to avoid accidentally spending them.
  4. Set your sell/hold rules and revisit annually
    • Choose a default approach to selling and diversifying, along with a cap on company stock concentration.
    • Revisit these decisions at least once a year, or sooner if your stock’s performance or personal circumstances change.

RSUs and Your Financial Plan

RSUs are more than just another line on your paystub. For many hard-working women, they’re part of your life story: the late nights, the risks you’ve taken in your career, and the future you’re building for yourself. When you understand how RSU withholding works and proactively plan for taxes, you give yourself permission to enjoy the rewards of your hard work instead of worrying about what might happen next April.

If you’d like help weaving your equity compensation into a clear, values‑aligned financial plan—one that supports your independence, your goals, and the life you want to live—consider partnering with Curtis Financial Planning. We understand the nuances of RSUs and can help you turn complex equity decisions into a simple, repeatable strategy that works for you. Connect with us to learn more.

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Making the Most of Your Charitable Giving Before OBBBA Changes Take Effect

Americans have always shown incredible generosity. In fact, charitable giving reached an astounding $592.50 billion in 2024, according to Giving USA. If giving is already woven into your financial life, now is a great time to revisit your approach. Starting January 1, 2026, the One Big Beautiful Bill Act (OBBBA) will introduce permanent changes to how charitable gifts are treated for tax purposes, with the biggest effects felt by those who itemize deductions.

What’s Ahead in 2026: Updates to Charitable Deduction Rules

Beginning in 2026, the One Big Beautiful Bill Act (OBBBA) introduces permanent revisions to how charitable contributions are treated for tax purposes. Below is an overview of the key changes you’ll want to keep in mind:

Above-the-Line Deductions for Standard Deduction Filers

Starting in 2026, taxpayers who don’t itemize will still be able to claim a charitable deduction. The allowance is:

  • Up to $2,000 for couples filing jointly
  • Up to $1,000 for individuals

This deduction applies only to cash donations made directly to eligible public charities. It does not extend to gifts contributed through donor-advised funds (DAFs) or to non-cash contributions.

Reduced Charitable Deduction for Itemizers

Starting in 2026, those who itemize deductions will see a small but permanent reduction in the charitable deduction they can claim. The new rule trims 0.5% of adjusted gross income (AGI) from the total amount deductible, lowering the tax benefit of giving.

For instance, with an AGI of $400,000, the 0.5% reduction equals $2,000. Therefore, if you contribute $20,000 to charity, only $18,000 would count as a deductible expense under the updated rules.

Deduction Limits for High-Income Taxpayers

Beginning in 2026, individuals in the highest tax bracket will see a reduced benefit from charitable giving. The maximum value of deductions will be capped at 35%, compared to the current 37%. This change comes in addition to the new rule that trims 0.5% of adjusted gross income (AGI) from the amount eligible for deduction.

For example, if your AGI is $1 million in 2026 and you donate $50,000:

  • The 0.5% AGI reduction removes $5,000, leaving $45,000 as the deductible portion.
  • Applying the 35% limit, your tax savings would be $15,750.

Under today’s rules, the full $50,000 would qualify at 37%, resulting in $18,500 of tax savings. That’s a difference of $2,750, illustrating why it may be wise to plan charitable contributions before these new rules take effect.

What Stays the Same

Qualified charitable distributions (QCDs) from IRAs will remain one of the most tax-efficient ways for retirees to give. These gifts are still fully deductible, excluded from adjusted gross income (AGI), and untouched by the upcoming law changes.

5 Charitable Giving Moves to Consider Before 2026

While the OBBBA will soon bring lasting changes to charitable giving tax rules, there’s still time to take advantage of the current, more favorable framework. Here are a few strategies to consider putting in place before year-end:

#1: Accelerate Giving into 2025

If you anticipate making large charitable gifts in the coming years, it may be wise to move some of that giving into 2025. Doing so allows you to lock in today’s more favorable deduction rules before they change.

This approach can be particularly advantageous if:

  • You plan to itemize deductions in 2025.
  • Your income or deductions are likely to be lower in future years.
  • You’re in the top tax bracket and want to benefit from the current 37% deduction rate.

#2: Bunch Contributions to Boost Tax Efficiency

If you typically spread out your charitable gifts, consider grouping several years’ worth into 2025. By “bunching” donations, you may push your total contributions above the standard deduction limit, making itemizing worthwhile and increasing your overall tax savings.

For instance, rather than donating $10,000 in both 2025 and 2026, you could give $20,000 in 2025, itemize that year, and then take the standard deduction the following year. This way, you maximize deductions without altering the total amount you give.

Using a donor-advised fund can make this strategy even more effective. You claim the full deduction in 2025 while retaining flexibility to distribute funds to charities over time.

#3: Give Non-Cash Assets Before the Rules Change

Under the OBBBA and its new charitable giving rules, non-itemizers won’t be able to claim an above-the-line deduction for non-cash contributions such as clothing, household goods, or appreciated securities. In other words, unless you itemize, these gifts won’t provide a tax benefit.

If you currently itemize but expect to take the standard deduction in future years, consider making your non-cash donations in 2025 so you can still deduct their value under the existing rules.

Examples of non-cash contributions to consider this year include:

  • Gently used clothing and household items
  • Vehicles
  • Appreciated stocks or other securities
  • Collectibles or other tangible property

Remember to keep proper records of your donations, particularly for items worth more than $500.

#4: Take Advantage of QCDs at Age 70½+

For retirees, qualified charitable distributions (QCDs) remain one of the most tax-efficient ways to give. If you’re 70½ or older, you can transfer up to $108,000 in 2025 (inflation-adjusted) directly from your traditional IRA to a qualified charity, and the amount counts toward your required minimum distribution (RMD).

QCDs offer several advantages:

  • They don’t increase your AGI, which may help you avoid higher Medicare premiums and other income-related taxes.
  • They are unaffected by the OBBBA, meaning the tax benefits stay intact beyond 2025.
  • You can donate to multiple charities in one year while keeping your tax reporting simple.

Important: the transfer must go straight from your IRA custodian to the charity. If you withdraw the funds first, the amount will be treated as taxable income and won’t qualify as a QCD.

#5: Consider a Donor-Advised Fund (DAF)

A donor-advised fund lets you make a large, deductible gift now while giving you the flexibility to distribute the money to charities gradually. This can be an effective way to bunch donations or lock in today’s more favorable deduction rules while still supporting causes over time.

With a DAF, you can:

  • Claim the deduction in the year you contribute.
  • Decide later when and how to recommend grants to charities.
  • Contribute appreciated assets, such as stock, to avoid capital gains taxes while still receiving the full deduction (if you itemize).

One key note: starting in 2026, DAF contributions won’t qualify for the new above-the-line deduction available to non-itemizers. If you expect to use the standard deduction in future years, opening or funding a DAF before the rules change can help maximize your tax benefits.

Maximizing Your Charitable Giving Ahead of OBBBA Changes

With the OBBBA changes on the horizon, this is a good moment to be more intentional with your charitable giving. If generosity is part of the future you’re building, taking action before year-end can help you make an even bigger difference while taking advantage of today’s more favorable tax rules.

Explore our free resources for helpful tips, tools, and educational content to support your financial journey.

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What the One Big Beautiful Bill Act Could Mean for You

One Big Beautiful Bill Act

On July 4, President Donald Trump signed a sweeping new tax and spending bill, the One Big Beautiful Bill Act (OBBBA), into law. At nearly 900 pages long, it’s one of the most ambitious policy packages of his presidency.

The bill includes roughly $4.5 trillion in tax cuts, major changes to federal spending, and significant investments in border security and defense.

Supporters see it as a continuation of Trump-era tax relief and a bold move to bolster national security. Critics, however, point to its steep cuts to safety net programs and the potential $3.3 trillion increase to the federal deficit over the next decade.

The bill’s provisions are likely to affect individuals, families, and businesses across the country. Here’s a closer look at what’s inside and how it could impact you.

One Big Beautiful Bill Act: Key Tax Provisions

Tax Rates and Brackets Made Permanent

The tax brackets introduced by the 2017 Tax Cuts and Jobs Act (TCJA) were originally scheduled to expire in 2025. The OBBBA makes these lower tax rates permanent, keeping the 10%, 12%, 22%, 24%, 32%, 35%, and 37% brackets in place indefinitely (or until changed by future legislation).

Standard Deduction Increases Under the One Big Beautiful Bill Act

The standard deduction amounts, which the TCJA nearly doubled, are now permanent and slightly higher for 2025:

  • Single Filers: $15,750
  • Married Filing Jointly: $31,500

Additional standard deductions for those 65+ also remain, increasing annually with inflation.

New $6,000 Deduction for Older Adults

People 65 and older may qualify for an additional $6,000 personal exemption between 2025–2028. However, this benefit phases out:

  • For single filers, the deduction begins to phase out at $75,000 and goes away completely by $175,000 MAGI.
  • For joint filers, it phases out between $150,000–$250,000 MAGI.

SALT Deduction Temporarily Expanded

From 2025 to 2029, the State and Local Tax (SALT) deduction cap increases from $10,000 to $40,000, with a phaseout beginning at $500,000 MAGI. The base cap of $10,000 becomes permanent starting in 2030.

New Deductions for Workers

Temporary tax breaks from 2025 through 2028 include:

  • Up to $25,000 of tip income excluded from federal income tax (phased out starting at $150,000 MAGI for singles, $300,000 for couples).
  • Up to $12,500 of overtime pay excluded for individual filers, and up to $25,000 for joint filers (same income thresholds as above).
  • Up to $10,000 of auto loan interest is deductible if the car is U.S.-assembled and the loan originated after 2025 (phased out for singles earning over $150,000, couples over $250,000).

Changes for Retirees and Estate Planning in the One Big Beautiful Bill Act

Social Security Still Taxable

Despite some confusion, the One Big Beautiful Bill Act does not change Social Security taxation. However, with expanded standard deductions and senior-specific exemptions, more retirees may see lower overall taxable income.

ACA Credits Not Extended

Enhanced Affordable Care Act (ACA) premium tax credits—originally introduced during the pandemic—are set to expire at the end of 2025.

Beginning in 2026, income eligibility rules will revert to pre-2021 levels, meaning many households that previously qualified for subsidies may no longer be eligible. According to an analysis from KFF, the average enrollee could see their premiums rise by 75%, making health insurance substantially less affordable for millions of Americans.

However, starting in 2026, all bronze and catastrophic plans purchased on the ACA exchange will qualify the policyholder to contribute to a Health Savings Account (HSA), which could offer a new tax-advantaged savings opportunity for early retirees.

Estate and Gift Tax Exemption Increases

The current estate and gift tax exemption of $13.99 million per person will increase to $15 million in 2026 and remain indexed to inflation going forward. This makes long-term legacy and gifting strategies even more important for high-net-worth families.

Charitable Giving Rules Adjusted

Beginning in 2026, if you don’t itemize deductions, you’ll be able to claim a charitable deduction of:

  • $1,000 (single filers)
  • $2,000 (joint filers)
    Note: Applies regardless of income, but donations to donor-advised funds are not eligible for this deduction.

For itemizers, donations must now exceed 0.5% of AGI before becoming deductible. For example, if your AGI is $100,000, only donations above $500 will count toward your itemized deduction.

Clean Energy Rollbacks

Several clean energy provisions from the 2022 Inflation Reduction Act are rolling back:

  • EV tax credits will end after September 30, 2025.
  • Home energy efficiency upgrades and clean residential energy systems (like solar or geothermal) must be installed by December 31, 2025 to qualify for tax credits.
  • New tax credits are now available for metallurgical coal, a move critics argue slows the transition to greener energy.

Introducing “Trump Accounts” for Children

Starting in 2026, new savings accounts will be available for children under 18. Key details include:

  • Named “Trump Accounts,” these operate similarly to Roth IRAs.
  • Annual contributions are capped at $5,000, with no upfront tax benefit.
  • The federal government will contribute $1,000/year to accounts for children born between 2025–2028.
  • Investment options are limited to low-cost index ETFs or mutual funds.

These accounts are designed to encourage early saving, but the complexity of distribution rules and limited utility for most taxpayers means it may take time to understand how widely they’ll be used.

One Big Beautiful Bill Act: The Bottom Line

The One Big Beautiful Bill Act brings sweeping changes to the tax code, health care system, and energy policy. While the full long-term effects are still unfolding, many provisions should deliver short-term savings, particularly for older adults, working families, and small business owners.

That said, the impact will look different for everyone depending on your income, age, and filing status. If you’re unsure how these changes could affect your tax bill, retirement strategy, or estate plan, now is a great time to revisit your financial plan. We’re here to help you cut through the complexity, make informed decisions, and plan confidently for what’s ahead.

Explore our free resources for helpful tips, tools, and educational content to support your financial journey.

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How to Choose the Right Withholding on Your W-4

W-4 Withholding

One of the most common questions I get is: “How many deductions should I take on my W-4?” The truth is, the IRS no longer uses “allowances” on the W-4 form. This changed in 2020, when the IRS redesigned the W-4 to make withholding calculations more accurate and easier to understand. Instead of allowances, the form now asks for specific income amounts, deductions, and credits to determine the right withholding. Here’s how to navigate these changes and ensure you’re withholding the right amount.

Step 1: Why the W-4 Changed

Before 2020, the W-4 form used allowances to determine how much tax to withhold. The more allowances you claimed, the less tax was withheld, and the fewer allowances, the more tax was withheld. However, this system often led to confusion and incorrect withholdings.

The change was driven by the 2017 Tax Cuts and Jobs Act (TCJA), which eliminated personal exemptions. Since allowances were tied to personal exemptions, they were no longer relevant, and the IRS needed a new approach. The new W-4 form now asks for specific financial details instead of an arbitrary number of allowances, making it easier to withhold the correct amount.

Step 2: Who Has to Fill Out a W-4?

Employees must fill out Form W-4, Employee’s Withholding Certificate, to determine how much federal income tax should be withheld from their paycheck. The following groups need to complete a W-4:

  • New Employees: Anyone starting a new job must fill out a W-4 so their employer knows how much tax to withhold. If you don’t submit a W-4, the employer will default to withholding at the “single with no adjustments” rate, which may result in higher withholding.
  • Employees Adjusting Withholding: If you owed a large tax bill last year or received a big refund, you may want to update your W-4 to better match your tax liability.
  • People Experiencing Life Changes: If you marry, divorce, have a child, or buy a home, your tax situation changes, and updating your W-4 ensures the correct withholding.
  • Employees with Multiple Jobs or a Working Spouse: The W-4 includes a section to help prevent under- or over-withholding for those with more than one income source.
  • Employees with Additional Income: If you earn side income (freelancing, dividends, rental income) but don’t want to pay estimated taxes, you can adjust your W-4 to have more withheld.

Step 3: Who Has to Fill Out a W-9 and When?

Unlike employees who fill out a W-4, independent contractors, freelancers, and self-employed individuals must complete Form W-9, Request for Taxpayer Identification Number and Certification. Here’s why and when you need a W-9:

  • Who Needs to Fill Out a W-9?
    • Independent contractors and freelancers
    • Self-employed individuals providing services to a company
    • Vendors receiving payments from a business
    • Anyone receiving non-employee compensation exceeding $600 in a tax year
  • When Do You Fill Out a W-9?
    • A business will request a W-9 before paying you for services.
    • You provide your Social Security Number (SSN) or Employer Identification Number (EIN) so the business can report payments to the IRS using Form 1099-NEC or 1099-MISC.
    • Unlike a W-4, a W-9 does not determine tax withholding—contractors are responsible for paying their own taxes, usually through quarterly estimated tax payments (Form 1040-ES).

Step 4: Review and Adjust Annually

Life changes quickly, and so can your tax situation. Review your W-4 at least once a year or when you:

  • Marry or divorce
  • Have a baby
  • Buy a home
  • Start a new job or change income levels
  • Owe a significant tax bill or receive a large refund

Final Thoughts

Many people still think they need to decide on the number of allowances for their W-4, but that system went away in 2020. Now, getting your W-4 right means more financial control—whether that means taking home a bigger paycheck or avoiding an unexpected tax bill. If you’re unsure, using the IRS calculator and reviewing your situation annually is the best way to keep things on track.

For those who work as independent contractors or freelancers, remember that you need a W-9 instead, and you are responsible for making your own tax payments.

Still have questions? Let’s talk! I’m happy to help you navigate your tax strategy so you can make the best financial decisions for your future.

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Pretty Soon, It’ll Be Tax Time: Are You Ready?

Tax Season

As tax season approaches, it’s almost time for that annual ritual: gathering your W-2, 1099s, and other financial documents. Your accountant will send their trusty checklist—or maybe you’ll take on the task yourself, cramming like it is finals week to beat the deadline.

Or perhaps you’ll file an extension, hoping for a bit more breathing room. (A reminder: filing an extension doesn’t extend the deadline to pay tax. You must make an estimated payment by April 15 and then true it up when you officially file).  Some of us might miss the deadline entirely—something I highly recommend avoiding.

When I was single, I always filed my taxes on time. It felt like a huge weight lifted from my shoulders.

But after I got married, my husband took over tax prep, and suddenly, we were always filing extensions. It drove me crazy! These days, we have an accountant, and yes, they often file extensions too. It turns out there are valid reasons for this:

Reasons for Filing an Extension

  • Late K-1s: If you own alternative investments or receive trust income, you’ll need a Schedule K-1. These forms are notorious for being issued late, delaying your entire return.
  • Missing Information: Sometimes, clients don’t get all their documents to the accountant in time. (Guilty as charged?)
  • Overwhelmed Accountants: Some accountants take on too many clients and use extensions as a way to manage the workload.

If I were an accountant, I’d try to get everything done by April 15 just so I could take a long, well-earned vacation!

Unfortunately, there are consequences for not filing taxes on time…(by the way, filing an extension is a completely legitimate way to get more time to do your taxes, and it will not trigger an audit as many think. It is much better to file an extension than to do nothing and file late!

Not filing your taxes on time or failing to file altogether can lead to significant penalties and headaches. Here’s a quick rundown:

IRS Penalties

  • Failure-to-File Penalty: The IRS charges 5% of the unpaid taxes for each month (or part of a month) your return is late, up to 25% of your unpaid taxes.
  • Failure-to-Pay Penalty: If you don’t pay your taxes on time, you’ll be charged 0.5% of your unpaid taxes each month, up to 25%.
  • Interest Charges: The IRS also charges interest on unpaid taxes, which accrues daily from the original due date of your return.

Example: Suppose you owe $10,000 and don’t file or pay anything for three months. When you finally file, the interest and penalties would add an additional $1,850.00 to your tax bill.

The IRS penalties don’t stop there. Here are a few lesser-known reasons to stay on top of your tax obligations:

Beware of These Red Flags This Tax Season

  1. Solo 401(k) Filing Requirements: If you’re self-employed and have a Solo 401(k) with more than $250,000, you must file Form 5500 by July 31 or be subject to a $250-per-day penalty until you file. If this seems onerous, it is—the penalties were designed primarily to enforce compliance for large employer-sponsored retirement plans and prevent employers from mismanaging employee retirement funds. Unfortunately, Solo 401(k)s fall under the same penalty structure, even though they don’t pose the same risks.
  2. State Tax Nexus Issues: Working remotely or in multiple states might mean owing taxes in more than one state. Failing to file the correct state returns can lead to penalties and interest.
  3. Capital Gains Misreporting: Forgetting to report stock sales or underestimating the basis of your investments can trigger an IRS audit or unexpected tax bills.
  4. Health Savings Account (HSA) Mistakes: Overcontributing to an HSA or using HSA funds for non-qualified expenses can result in taxes and penalties.
  5. Gift Tax Filings: If you give someone more than $19,000 in a year (as of 2025), you need to file a gift tax return (Form 709), even if no taxes are due. Missing this step can complicate estate planning down the line.
  6. Failure to Report Cryptocurrency Transactions: The IRS is cracking down on unreported cryptocurrency gains. If you’ve traded or sold crypto, you must report it on your tax return.
  7. If you inherited an IRA and don’t take the correct distributions, the IRS imposes a 25% excise tax. They lower the excise tax if you correct the mistake within a correction window.
  8. IRA Rollovers: If you need cash for a short period of time and tap your IRA for it, there is no problem as long as you redeposit the money back into the IRA within 60 days. However, you can only do this once within a 12-month period. If you do more, the full amount is taxable; if you are under age 59 ½, there is also a 10% penalty.

Make Tax Season Work for You

Instead of scrambling at the last minute or risking penalties, consider these steps to make tax season easier:

  • Start Early: Gather your documents as soon as they’re available and set aside time to review them.
  • Work with a Professional: A CPA, Enrolled Agent, or financial advisor can help you navigate complex situations and minimize your tax burden.
  • Double-Check Everything: Avoid errors by reviewing your return carefully before filing.

Tax season may not be fun, but it’s a lot easier when you stay ahead of the deadlines and know the rules. Filing on time, avoiding penalties, and understanding your options can save you time, money, and stress. And isn’t that worth it?

For more financial planning tips and best practices, check out our free resources page.

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Why Procrastinating on Finances is a Bad Idea

Procrastinating on Finances

Let’s face it—money is hard. Few people relish the thought of sitting down to deal with their finances. It ranks right up there with dental visits, pap smears, and mammograms. Unlike healthcare, however, there’s no friendly reminder postcard urging you to get it done. It’s easy to procrastinate, and before you know it, years have passed without any financial planning.

Could things still work out despite the neglect? Sure, it’s possible. But chances are, something will go wrong, or you’ll miss opportunities to optimize your finances. And what does “optimizing your finances” mean? Let’s break it down.

1. Review Your Investments

Take a good look at your investments at least once a year. Are you overexposed to stocks? Underexposed? Stocks are the engines that drive long-term returns—just look at the S&P 500’s historical 10% average annual return over the past 20 years.

But too much of a good thing can backfire. If you’re too heavily invested in stocks, a market downturn might tempt you to panic and sell, locking in losses. Bear markets (defined as a 20% or greater drop from recent highs) are inevitable. The key is staying invested for the long haul to benefit from eventual recoveries.

2. Be Tax-Smart

No one enjoys watching 25–30% of their paycheck disappear into taxes. While taxes fund essential services, there are perfectly legal ways to reduce your tax burden. Here are a few strategies:

  • Donate appreciated shares to a donor-advised fund to align your charitable giving with tax savings.
  • Open a Health Savings Account (HSA) with a high-deductible health plan to deduct contributions directly from your income.
  • Boost your Roth savings with strategies like a Backdoor Roth or Roth Conversion.
  • Max out contributions to your 401(k), 403(b), or other retirement plans.
  • Engage in tax-loss harvesting to offset gains and reduce taxable income.

3. Define Your Goals

Set your short-, medium-, and long-term goals—and write them down. Studies consistently show that writing down goals increases the likelihood of achieving them.

For example, one of my big goals is to own a home in Sonoma County—ideally in Sebastopol or Healdsburg—within the next five years. Having this goal in writing makes it more tangible and actionable.

4. Plan for Retirement

Think about when you want to retire—or when you’d like to leave your current job to pursue something more meaningful. This kind of transition requires thoughtful planning, clear goals, and detailed number crunching. The earlier you start, the better positioned you’ll be to make it a reality.

Why Start Now?

Every one of these actions underscores why procrastination is a financial mistake. Planning gives you a clear picture of where you’re headed and what you need to do to get there.

January is a natural time for fresh starts, so why not begin today? Whether it’s reviewing your investments, setting goals, or planning for retirement, even small steps can make a big difference. Take action now—your future self will thank you.

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The Intricate Dance of Charitable Giving and Taxes: What You Need to Know

Charitable Giving and Taxes

Charitable giving is about more than just supporting causes you care about—it’s also an opportunity to make a tax-savvy move. But like most things tax-related, it’s rarely simple. Let’s unravel the complexities of charitable giving and taxes to help you maximize your generosity and tax benefits.

Federal Tax Rules: What Changed After 2017?

Remember the Tax Cuts and Jobs Act (TCJA) of 2017? It nearly doubled the standard deduction, which is great for simplifying taxes but complicated things for deducting charitable contributions.

Standard Deduction for 2024:

  • $14,600 for single filers
  • $29,200 for married couples filing jointly

Note that there is an additional standard deduction of $1,950 for single filers and
1,550 for married filing jointly for those 65 and older.

Here’s the catch: if your total itemized deductions (like mortgage interest, state and local taxes, and charitable donations) don’t exceed the standard deduction, you can’t claim a federal tax break for your contributions.

And Even If You Itemize…

The IRS limits how much of your Adjusted Gross Income (AGI) you can deduct:

  • Cash Donations: Deductible up to 60% of your AGI.
  • Appreciated Securities: Deductible up to 30% of your AGI.

Donations exceeding these limits can carry over for up to five years, but the rules are precise and unforgiving.

The Bunching Strategy: A Smart Workaround

Here’s a clever approach: bunching. Instead of donating $5,000 annually, donate $15,000 every three years.

  • In “bunching” years, itemize to claim the deduction.
  • In off-years, take the standard deduction.

Donor-advised funds (DAFs) make this even easier. Contribute a lump sum to a DAF in your itemizing year for the tax break, then distribute donations to your favorite charities over time.

Donor-Advised Funds (DAFs): A Strategic Giving Tool

Think of a DAF as your personal charitable giving account. You can contribute funds—or better yet, appreciated securities that you’ve held for more than one year.

Why the “long-term” holding period? It’s key to maximizing your tax benefits. When you donate appreciated securities that you’ve held for over a year, you avoid capital gains taxes and get a deduction for the full fair market value of the asset.

Example:
Let’s say you bought stock for $5,000, and now it’s worth $15,000. By donating it to a DAF:

  • You bypass capital gains tax on the $10,000 growth.
  • You get a charitable deduction for the full $15,000.

But here’s the golden rule: if the stock was held for less than one year, the deduction is limited to your cost basis—not its market value. Timing is everything.

Once the funds are in your DAF, you can invest them for growth or distribute them over time to your favorite charities. Just remember: don’t let your DAF become a parking lot for charitable dollars. Charities need support now, so make it a habit to grant funds regularly.

Qualified Charitable Distributions (QCDs): A Game-Changer for Retirees

If you’re 70½ or older, QCDs offer a unique advantage. You can donate up to $100,000 directly from your IRA to a charity.

  • QCDs count toward your Required Minimum Distribution (RMD).
  • They don’t increase your taxable income.

This is perfect for retirees who don’t itemize but still want to give strategically.

Non-Deductible Donations

Not all giving qualifies for a tax break.

  • GoFundMe or Crowdfunding: Usually not deductible unless the recipient is a 501(c)(3) nonprofit.
  • Political Donations: Contributions to candidates, PACs, or ballot initiatives are never tax-deductible.

Why Giving Feels Good Beyond the Tax Break

Don’t lose sight of the real reward: the joy of giving. Studies show that charitable acts enhance emotional well-being and deepen community connections. Tax benefits are just the cherry on top.

Final Thoughts on Charitable Giving and Taxes

Charitable giving is about more than tax strategy—it’s about making a real difference. Whether you’re supporting food banks, funding medical research, or championing the arts, every gift matters.

So, give with your heart—and maybe a little strategy, too.

Want to dive deeper into the intricacies of charitable giving? Check out our four-part blog series.

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Estate Planning Considerations Ahead of Potential TCJA Expirations

The Tax Cuts and Jobs Act (TCJA) of 2017 brought significant changes to estate planning, notably increasing exemptions for estate, gift, and generation-skipping transfer taxes. These changes have provided high-net-worth individuals and families with greater opportunities to transfer wealth to their beneficiaries while mitigating taxes.

However, with key provisions of the TCJA set to expire in 2025, it may be time to revisit your estate plan. Even if your portfolio is way below the exemption amounts (below), compounding returns are a powerful wealth builder, and your future values could quite possibly reach and exceed the limits.

 It must be noted though, that Congress will debate the expiration of these tax provisions, and we do not know the outcome yet.

Key Tax Changes Under the TCJA of 2017

The Tax Cuts and Jobs Act (TCJA) of 2017 meaningfully reshaped the tax landscape, offering wealthy individuals and families a way to pass more assets to beneficiaries tax-free. Key legislative changes included:

It’s important to note that these TCJA estate planning provisions are set to expire at the end of 2025 unless Congress votes to extend them. Depending on your individual circumstances, taking advantage of the current high limits, you can potentially preserve more of your estate from tax.

Estate Planning Strategies to Be Aware Of

With the expiration of the TCJA approaching, now is an opportune time to explore strategies that align with your values and long-term goals.

#1: Lifetime Gifting

To make the most of the current elevated exemptions before the Tax Cuts and Jobs Act (TCJA) expires, several gifting strategies can help transfer wealth efficiently while minimizing tax burdens:

  • Creating Irrevocable Trusts. By transferring assets into an irrevocable trust, you effectively remove them from your taxable estate, which helps shield them from estate taxes when the TCJA exemptions potentially decrease in 2026. Additionally, you can structure an irrevocable trust to retain control over how and when beneficiaries access the assets, providing peace of mind that they’ll use your wealth according to your wishes. Keep in mind that irrevocable means that once the trust is executed, it cannot be changed.
  • Direct Payment of Medical or Educational Expenses. Payments made directly to medical institutions or schools aren’t subject to the annual gift tax exclusion or the lifetime exemption, meaning they don’t count against your gifting limits. This is a tax-efficient way to provide significant financial support to your loved ones without reducing your lifetime exemption, and it allows you to give in a meaningful way without adding to their taxable income.
  • Transferring Appreciating Assets. Another key strategy is to transfer appreciating assets, such as stocks, real estate, or business interests, while their value is still growing. By gifting these assets before they appreciate further, you can reduce your taxable estate while allowing the recipient to benefit from future growth.

Each of these approaches offers unique advantages and can be tailored to fit your financial goals and family’s needs.

#2: Dynasty Trusts

If you have grandchildren or great-grandchildren, advanced estate planning strategies like dynasty trusts can be highly effective for preserving wealth across multiple generations.

A dynasty trust is a long-term trust that enables the transfer of wealth from one generation to the next, often over several decades or even centuries. This type of trust not only helps protect your legacy but also shields the assets from potential risks such as creditors, lawsuits, and divorces, ensuring your family’s financial security for years to come.

You can also structure the trust in a way that minimizes or eliminates estate taxes, gift taxes, and generation-skipping transfer (GST) taxes, allowing your family to benefit from the full value of the assets you’ve transferred. By establishing the trust while the current elevated exemptions are in place, you can lock in these favorable tax treatments before the TCJA provisions expire in 2026.

#3: Grantor Retained Annuity Trusts (GRATs)

For those seeking more sophisticated estate planning strategies, Grantor Retained Annuity Trusts (GRATs) can be an effective tool for transferring future appreciation of assets in a tax-efficient manner ahead of potential TCJA expirations.

A GRAT allows you to place high-growth assets, such as stocks or real estate, into a trust while retaining the right to receive fixed annuity payments over a specified term. The key benefit is that any appreciation in the assets above the IRS’s assumed growth rate passes to your beneficiaries tax-free at the end of the trust’s term.

This strategy works particularly well in a low-interest-rate environment, where the hurdle rate is low, allowing more of the appreciation to avoid gift taxes. Since the grantor retains the annuity payments, the initial gift value is minimal, often resulting in little or no taxable gift.

#4: Charitable Lead Trusts (CLTs)

Charitable Lead Trusts (CLTs) offer a unique way to support charitable causes while also benefiting your heirs in a tax-efficient manner.

In a CLT, you transfer assets to the trust, which then provides regular payments to a charity of your choice for a specified period. After this term ends, the remaining assets in the trust pass to your heirs, often with little or no gift or estate tax.

This strategy not only enables you to make a meaningful impact on the causes you care about, but it also helps reduce the taxable value of your estate. Because the value of the charitable payments is deducted from the overall gift, the remaining value that eventually goes to your heirs can be significantly discounted for tax purposes.

#5: Family Limited Partnerships (FLPs)

Family Limited Partnerships (FLPs) can be a powerful estate planning tool ahead of potential TCJA expirations.

An FLP allows you to transfer ownership of assets, such as real estate, investments, or a family business, to a partnership structure. Typically, senior family members (parents or grandparents) act as general partners, maintaining control over the management of the assets, while younger family members become limited partners with ownership interest but without decision-making authority.

The primary benefit of an FLP is the ability to transfer wealth to heirs at a discounted value. Because limited partners lack control and marketability, the IRS often allows a discount on the value of the partnership interests for gift and estate tax purposes, effectively reducing the taxable value of the transferred assets.

FLPs also offer the added benefit of asset protection, as creditors may find it difficult to access assets held within the partnership. This structure helps ensure long-term wealth management and continuity within families.

Estate Planning and the TCJA: Recommitting to Your Plan

Estate planning is never a one-size-fits-all solution. The most effective strategies are those tailored to your unique circumstances, financial goals, and family dynamics. A thoughtful estate plan strikes a delicate balance between tax efficiency, asset protection, and—most importantly—caring for the people and causes that matter most to you.

Regularly revisiting and updating your plan ensures that it evolves with changes in your life, such as new financial situations, family additions, or shifting priorities. By engaging in open discussions with your family and trusted advisors, you can craft a plan that truly reflects your values and ensures your legacy endures for generations.

For more financial planning tips and best practices, check out our free resources page.

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Making the Most of Your Medical Expenses: A Tax Savings Opportunity for 2024

Deductible Medical Expenses

Deductible medical expenses are an often overlooked tax savings opportunity that can substantially lower your tax bill.

With healthcare costs on the rise, it’s easy for medical expenses to accumulate quickly. From preventive care to unforeseen medical emergencies, these costs can have a significant impact on your financial well-being.

However, there’s an often-overlooked aspect of these expenses that deserves attention: their potential to provide tax relief. The Internal Revenue Service (IRS) offers provisions that allow eligible individuals to deduct qualified medical expenses, potentially resulting in considerable tax savings.

If you, your spouse, or your dependents have incurred noteworthy medical expenses this year, you may be in a position to take advantage of these tax deductions. Here’s what you need to know to make the most of this potentially valuable tax benefit.

Why Track Your Medical Expenses?

If you plan to itemize deductions on Schedule A of Form 1040 instead of taking the standard deduction, you can potentially reduce your taxable income through deductible medical expenses. For the 2024 tax year, the IRS allows you to deduct the portion of your out-of-pocket medical expenses that exceeds 7.5% of your adjusted gross income (AGI).

If your medical costs have been considerable, these deductions could substantially lower your tax bill. For example, if your AGI is $100,000 and you’ve incurred $10,000 in qualified medical expenses, you could deduct $2,500 (the amount exceeding 7.5% of your AGI, which is $7,500 in this case).

What Qualifies as a Deductible Medical Expense?

The IRS provides a broad definition of deductible medical expenses that encompasses a wide range of health-related costs. These include costs for diagnosing, treating, or preventing disease, as well as treatments affecting any part or function of the body.

This comprehensive definition covers many common healthcare expenses, including:

  • Health insurance premiums, including Medicare premiums (keep in mind that any premiums you deduct from your paycheck on a pre-tax basis aren’t eligible)
  • Out-of-pocket costs for doctors, dentists, and hospital stays
  • Diagnostic tests and prescription drugs
  • Medical equipment and supplies
  • Long-term care insurance premiums

However, the list doesn’t end there. Many taxpayers are unaware of additional eligible expenses that could further reduce their tax liability. These lesser-known deductible expenses might include:

  • Travel costs related to medical care, including mileage, parking, and tolls
  • Home modifications for medical reasons, such as wheelchair ramps or stair lifts
  • Newborn care, including breast pumps and certain prescription baby formulas
  • Diabetes-related costs, such as blood-testing kits and insulin
  • Certain alternative treatments like acupuncture or chiropractic care
  • Prescription glasses, contact lenses, hearing aids, and even LASIK surgery.

It’s important to note that cosmetic procedures, general health supplements, and over-the-counter medications typically don’t qualify unless your doctor prescribes them for a medical condition.

Easily Overlooked Medical Expenses

It’s easy to inadvertently leave money on the table by overlooking less obvious eligible medical expenses. Being aware of these often-missed deductions can significantly impact your tax savings.

Here’s an expanded list of easily overlooked expenses that may qualify for deduction:

  • Service animals: The costs associated with buying, training, and maintaining service animals for individuals with disabilities are deductible.
  • Comprehensive dental care: Beyond routine cleanings, expenses for orthodontics (such as braces), dentures, dental implants, and even certain cosmetic dental procedures deemed medically necessary are deductible.
  • Substance use disorder treatment: Costs for inpatient treatment at therapeutic centers, outpatient programs, and transportation to and from support group meetings (like Alcoholics Anonymous) may qualify.
  • Reproductive health expenses: This category is broader than many realize, encompassing fertility treatments, in vitro fertilization, birth control, pregnancy tests, and vasectomies.
  • Wigs for medical conditions: Patients who experience hair loss due to medical treatments or conditions like alopecia can deduct the cost of wigs when prescribed by a physician.
  • Special education: Tuition for children with learning disabilities at specialized schools, as well as tutoring fees recommended by a doctor, may qualify.

Remember, proper documentation is key to claiming these deductions. Be sure to consult with a tax professional to ensure you’re maximizing your eligible expenses while staying compliant with IRS regulations.

Standard Deduction vs. Itemizing: Which is Better?

For the 2024 tax year, the standard deduction amounts are:

  • Single Filers and Married Filing Separately: $14,600
  • Head of Household: $21,900
  • Married Filing Jointly or Surviving Spouse: $29,200

Before opting to itemize, it’s essential to calculate whether your total itemized deductions would exceed these standard deduction amounts. The most common itemized deductions generally include:

  • Medical expenses (exceeding 7.5% of your AGI)
  • Mortgage interest
  • State and local taxes (SALT), including income and property taxes (capped at $10,000)
  • Charitable contributions

To determine which option is more beneficial:

  1. Sum up your potential itemized deductions, including medical expenses, mortgage interest, SALT (up to the $10,000 limit), and charitable donations.
  2. Compare this total to your applicable standard deduction amount.
  3. Choose the higher of the two figures to maximize your tax benefit.

It’s worth noting that the IRS requires some taxpayers to itemize, such as married individuals filing separately (if your spouse itemizes). Given the complexities involved, it’s advisable to use tax preparation software or consult a tax professional to ensure you’re making the most advantageous choice for your situation.

Approaching Healthcare Expenses Strategically

As the year draws to a close, consider your healthcare situation strategically. If you’ve already met your insurance deductible, it might be financially prudent to schedule any pending medical procedures or appointments before the year ends. This approach could increase your deductible medical expenses for the year, pushing you over the threshold for claiming deductions.

Additionally, take this opportunity to organize your medical receipts and documentation. Diligently tracking your healthcare costs can help you take full advantage of available deductions, potentially reducing your tax liability for the 2024 tax year.

Lastly, while tax savings are important, your health should always be the primary concern. Always make medical decisions based on your healthcare needs first and consider the tax implications as a secondary benefit.

By being proactive and informed about medical expense deductions, you’re not just potentially lowering your tax bill—you’re taking a step towards more comprehensive financial management. Your future self (and your wallet!) will thank you for the foresight and careful planning.

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S5E2: Here’s What Savvy Donors Need to Know About Strategic Charitable Giving

Strategic Charitable Giving Tips for Savvy Donors

Strategic Charitable Giving Ideas to Maximize Your Tax Savings

Cathy shares her strategic charitable giving tips, from deciding how much to give to maximizing your tax savings.

A lot of my clients are charitably inclined and want to include giving in their financial plan. 

Of course, I thoroughly understand my client’s personal finances. Thus, I can provide specific guidance as to how they should think about giving and how to incorporate it into their financial plan.

However, if you’re listening to this podcast episode because you’re also looking for answers to these questions, I can still offer some nuggets of wisdom without knowing the details of your financial life.

In this episode, we’re going to talk about:

  • How much to give to charity
  • Which charities to support with your donations
  • Strategic charitable giving methods to maximize your tax savings.

Naturally, everyone’s goals and personal finances are unique. Therefore, it’s best to consult a financial professional if you have specific questions on this topic.

Nevertheless, I hope this episode gives you a framework for how to think about giving, so you can continue to make an impact while also reaping the associated financial benefits.

Episode Highlights

  • [01:36] How much should you give to charity?

  • [03:17] Which charitable organizations should you support with your donations?

  • [06:52] Who can reap the tax benefits of donating to charity?

  • [07:51] How to use “bunching” to increase your tax savings from charitable giving.

  • [10:06] How donor-advised funds (DAFs) can support your strategic charitable giving goals.

  • [13:04] Why donors who have reached RMD age may want to consider making qualified charitable distributions (QCDs).

  • [15:44] The potential advantages and drawbacks of a charitable gift annuity.  

  • [16:46] Why you may want to consider a charitable remainder trust (CRT).

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