Cashless Charitable Contributions

Cashless Charitable Contributions, form 8283

Not everyone can make large charitable contributions. But there are ways to be charitable without spending your discretionary income while at the same time lowering your tax bill. Even those who can make large donations benefit from the tax advantages of a cashless donation. The following are ideas for cashless contributions to causes you are passionate about.

Tax Rules

The main thing to remember is that charities are not required to pay taxes on donations (cashless or otherwise). This can make your donation more valuable to them than it would be to you. Note, too, that if your itemized deductions are below the Standard Deduction for your tax filing status, gifting a high-value asset can put you over that cap and provide substantial savings on your tax bill.

The IRS sets limits on deductions for non-cash donations. Contributions of appreciated long-term assets such as stocks or real estate are subject to a limit of 30 percent of adjusted gross income, while other types of non-cash property donations have a 50 percent limit. Cash donations, on the other hand, have a higher limit at 60 percent of AGI. Even so, if the value of the contribution is higher than your deduction limit, you may carry over the excess for up to five years, subject to those same AGI limitations.

Non-cash donations are particularly beneficial for donors in a year they receive a windfall or unexpectedly high income.

Securities

If you own highly appreciated stock, you can donate it to a 501(c)(3) charity and claim the fair market value as a tax deduction. You won’t have to pay taxes on the earnings because you gifted them, nor will the charity once the stock is liquidated for its needs. Consider gifting stock to a charity when you rebalance your portfolio to both reduce the potential tax bill on earnings and reposition the overall portfolio to your target allocation.

Equity Compensation

You may have received employer company stock as a bonus or through an Employee Stock Purchase Plan (ESPP). Consider transferring one or more shares to a charity as a donation. Note that with ESPP shares, you need to have held them for more than two years from the grant date and one year from the purchase date to optimize your tax deduction.

Qualified Charitable Distribution

Traditional IRA owners are required to begin taking an annual minimum distribution (RMD) starting at a specific age. As of 2025, the rules are:

  • 72 if born before Jan. 1, 1951
  • 73 if born between Jan. 1, 1951, and Dec. 31, 1959
  • 75 if born on or after Jan. 1, 1960

However, some people may still be working or have a high income for which RMDs place them in a higher tax bracket. What they can do is make a qualified charitable distribution (QCD) up to $100,000,so that all or a portion of their RMD is sent directly to the charity of their choice. While this tactic does not offer a tax deduction, it does satisfy the IRA owner’s RMD requirement, which essentially reduces their income tax burden.

Real Estate

If you purchased or inherited a piece of property, be it a residential home, undeveloped land, a commercial building or rental property, there are benefits to granting it as a cashless charitable donation. The strategy is best optimized if you’ve owned the property for more than one year, enabling you to avoid capital gains taxes and claim a fair market value charitable deduction for the tax year of the gift.

Automobile

Perhaps you have a spare car you never drive but continue to maintain and insure. Instead, consider donating it to a charity. First, ensure that the charity of your choice will accept a vehicle donation. In some cases, a charity may not even require that the car be in working condition, as it may sell or auction it to raise cash. While most charities will arrange to have the automobile picked up, you will need to remove the license plates and sign over the car title to the organization. You can determine the fair market value (to claim as a tax deduction) by researching pricing guides like Kelly Blue Book or Edmunds.

Collectibles/Art

Some folks collect or inherit items they don’t want anymore. Instead of selling them on Facebook, consider donating them to a charity. First, establish a value for the item(s); for items worth more than $5,000,you’ll need to get a qualified appraisal to determine your tax deduction. Also, make sure the charity of your choice will accept the collectible.

Life Insurance

For an individual who no longer needs their permanent life insurance policy, transferring policy ownership to a charity may be more advantageous than surrendering it and paying taxes on the policy’s appreciation. Donating the policy eliminates your tax liability and qualifies for a deduction. The deduction is the lesser of the policy’s cash value or the cost basis (i.e., premiums paid to date).

Another option is to simply change the beneficiary on your life policy to the charity you choose. You won’t receive a tax deduction until the policy pays out after your death, at which point your estate can claim it.

Time

Don’t forget that in many cases you can donate your time instead of money. Seek out charities that need volunteers, from specific skills and expertise to help with cleaning, delivering, and organizing events.

Navigating Worker Classification: The Critical Difference Between Employees and Independent Contractors

Difference Between Employees and Independent ContractorsRunning a small business often means working with a mix of people: some full-time staff, part-time helpers, seasonal workers or project-based contractors. While this flexibility helps manage costs and workload, it creates a crucial decision point that many business owners underestimate: properly classifying each worker.

The stakes couldn’t be higher. Companies like FedEx have paid nearly half a billion dollars for getting this wrong, and even tech giants like Microsoft and Lyft have faced costly legal battles over worker misclassification.

Why Classification Matters More Than You Think

The difference between an employee and an independent contractor goes far beyond semantics; it fundamentally changes your legal and financial obligations.

When someone is your employee, you must:

  • Withhold income taxes, Social Security, and Medicare taxes
  • Pay the employer portion of Social Security and Medicare taxes
  • Potentially provide benefits like health insurance and retirement plans
  • Consider offering stock options or other incentive programs
  • Pay severance or unemployment compensation when appropriate
  • Comply with wage and overtime requirements

When someone is an independent contractor, you:

  • Simply pay them for their work
  • Issue a 1099-NEC form at year-end
  • Have no tax withholding obligations
  • Owe no employment benefits
  • Face no severance obligations

The Control Test: Your North Star for Classification

The Internal Revenue Service uses one primary principle: control. The more control you exercise over how, when, and where work gets done, the more likely that person is your employee.

Think of it this way: if you’re micromanaging the work process, you’re probably dealing with an employee. If you’re only concerned with the end result, you’re likely working with a contractor. The 20 factors identified by the IRS in Revenue Ruling 87-41 can be found in full here.

The IRS Three-Factor Framework

Rather than getting lost in complicated checklists, focus on these three core areas:

1. Behavioral Control – Do you dictate not just what work gets done, but how it’s performed? Employees typically receive training, follow company procedures, and work within established systems. Contractors bring their own methods and expertise.

2. Financial Control – Who controls the business aspects of the work? Independent contractors typically:

  • Invest in their own tools and equipment
  • Handle their own business expenses
  • Have multiple clients or income sources
  • Set their own rates and payment terms

3. Relationship Type – What does your working relationship look like? Employee relationships typically feature:

  • Written employment contracts
  • Ongoing work arrangements
  • Benefits packages
  • Work that’s central to your business operations

Beyond Taxes: The Broader Impact

Worker classification affects more than your tax bill. The Department of Labor’s 2024 updates to the Fair Labor Standards Act mean misclassification can trigger wage and overtime violations. State labor departments are also cracking down, with some states presuming workers are employees unless proven otherwise.

When Things Go Wrong: Your Options

If you realize you’ve made a mistake, don’t panic. You have several paths forward:

  • Get an Official Determination: File Form SS-8 with the IRS for an official ruling on a worker’s status. While it takes at least six months, you’ll have certainty going forward.
  • Claim Safe Harbor Protection: If you had a reasonable basis for your classification and treated similar workers consistently, you may qualify for tax relief under Section 530.
  • Use the Voluntary Settlement Program: The IRS Voluntary Classification Settlement Program lets you reclassify workers prospectively while receiving some tax relief.

The Bottom Line

Your worker classification isn’t just an administrative detail – it’s a fundamental business decision with major financial implications. When in doubt, err on the side of caution or consult with employment law and tax professionals.

The cost of getting expert advice upfront is minimal compared to the potential cost of getting it wrong.

Why AI Falls Short for U.S. Tax Guidance

Why AI Falls Short for U.S. Tax GuidanceThe rise of artificial intelligence tools like ChatGPT and Grok has transformed how Americans seek information. From meal planning to complex financial questions, these platforms offer instant answers to virtually any query. But when it comes to U.S. tax advice – especially international tax matters – relying on AI can lead to serious and costly mistakes.

The Allure and Limitations of AI Tax Help

The appeal of AI for tax questions is understandable. However, AI’s limitations become glaringly apparent in international tax matters. This specialized field combines extraordinary complexity with constant change, creating a perfect storm that exposes AI’s weaknesses. The landscape shifts regularly through regulatory updates, IRS interpretations, and court decisions – changes that AI systems struggle to incorporate in real-time.

Consider the IRS Practice Units, internal training materials for tax examiners that became public in 2020. From January through early May 2025 alone, the IRS released 35 new Practice Units, with 22 addressing intricate international tax topics such as foreign tax credit computations, base erosion anti-abuse tax, and treaty provisions. These rapidly evolving resources represent just one stream of constantly changing tax guidance that AI models could fail to capture, leading to outdated or incomplete advice.

How AI Gets Tax Advice Wrong

AI’s accuracy problems stem from its fundamental design. Large language models like those powering ChatGPT and Grok train on vast amounts of text from diverse sources – online forums, books, articles, websites, and public records. This training produces responses that sound authoritative and conversational, but this polish masks significant limitations.

The core issue is what experts call “simplexity” – AI’s tendency to oversimplify complex tax law. When AI presents intricate regulations as straightforward concepts, it fundamentally misrepresents the law itself. This problem has already surfaced with the IRS’s own Interactive Tax Assistant chatbot.

AI systems also suffer from interpretation errors, reliance on outdated information, and conflation of similar but distinct tax concepts. For instance, an AI might confuse the Foreign Tax Credit with the Foreign Earned Income Exclusion – similar-sounding but entirely different provisions with vastly different implications.

The Real-World Cost of AI Errors

Mistakes in international tax compliance carry severe consequences. The IRS considers international tax enforcement a top priority, and errors in reporting foreign income or assets trigger substantial penalties. A late FBAR or foreign information return like Form 8938 or 5471 carries a $10,000 penalty. Errors involving foreign assets can result in a 40 percent accuracy-related penalty on unpaid taxes.

Importantly, relying on AI advice won’t qualify as “reasonable cause” to avoid these penalties. Last year, the U.S. Taxpayer Advocate Service highlighted a Washington Post analysis showing that AI chatbots from major tax preparation companies provided incorrect advice up to 50 percent of the time on complex questions. Beyond financial penalties, taxpayers face the stress of audits and the time-consuming burden of correcting mistakes.

Why Human Expertise Remains Essential

While AI continues to advance, it currently falls far short of replacing human expertise in international tax matters. Experienced tax professionals bring irreplaceable skills that algorithms cannot match. They stay current on evolving IRS guidance, monitor treaty updates, and analyze new case law. Most importantly, they apply professional judgment to each unique situation.

International tax planning rarely follows a one-size-fits-all approach. Professionals provide strategic thinking and contextual analysis that optimize outcomes for specific circumstances. They understand when exceptions apply, how different rules interact, and what documentation requirements must be met. These nuanced judgments remain beyond AI’s current capabilities.

Conclusion

This doesn’t mean AI has no role in tax planning. It can serve as a useful starting point for understanding basic concepts or generating initial questions to discuss with a professional. However, treating AI as a substitute for qualified tax advice is a risky gamble.

The appeal of instant, free tax guidance is strong, but the cost of getting it wrong can be devastating. Until AI can match the precision, current knowledge, and professional judgment of experienced tax professionals, taxpayers would be wise to view it as a supplement to – not a replacement for – human expertise.

Pre-Retirement Planning Guide – Finding Purpose In Life

Pre-Retirement Planning Guide - Finding Purpose In LifeStep 7: Find Your Raison d’Etre

What do you consider to be your purpose in this world? Few people think about their life that way. In Japan, they call it your ikigai. In France, they refer to your raison d’etre. For Americans, that roughly translates to your purpose in life or your reason for being.

It’s easy to consider your family or even your career as your reason to live. But true embracement of the ikigai concept is more of a lifestyle, not a specific person, place or thing.

Your purpose may not even be something you’ve pursued in your adult life. Many of us follow the socially expected path: higher education, a good job, a rewarding career, marriage, home, and family. But those things are not everyone’s raison d’etre. They might wake up one morning thinking that once they’ve achieved all those goals, they will finally get the chance to do the one they’ve always wanted. What is that?

The older we get, the more we lose a spouse or life partner, siblings, or children – and those who retire no longer have work to feel fulfilled. As part of your retirement planning effort, consider life without any of those things. How would you bear it? If you outlive your career and loved ones, what would you do?

Note that your ikigai does not insulate you from bad things happening. Instead, it’s the thing you look forward to when the smoke clears: the light at the end of the tunnel. On balance, it’s the thing that helps get you through the pain and restores happiness. In fact, discovering your raison d’etre can help you better cope with stress and loss. People who pursue their ikigai tend to have better mental health, experience fewer chronic diseases, and are more likely to live longer.

Oftentimes ikigai is felt as part of a process. For example, the joy of mixing ingredients to prepare baked goods or a meal. Planting a garden. Rebuilding an engine. It can be the process of writing or painting or playing an instrument, but not necessarily finishing a novel or singing in public. It can be as simple as finding joy in daily activities, nurturing relationships or doing community service.

Another advantage to ikigai is that it can connect you with other people who share your passion, which can be very important as you grow older and more isolated. By leaning into your ikigai, you could expand your social network with connections that are meaningful and fulfilling.

For some people, their raison d’etre is spiritual. A belief and perhaps a greater connection to a higher being. They may wish to spend more time becoming involved in church activities, reading scripture that supports their religion, or even exploring other religions.

The Japanese culture believes that each individual has an inherent ikigai based on their personal values and beliefs. One way to think about it is as your philosophy on life. Since this step is a part of retirement planning, it is fortunate that you have lived long enough to have developed some philosophies on life.

For example, some people discover that family does not just consist of blood relatives. Instead, their concept of family is people who are there through good and bad times, who always show love and respect, who you can rely on. Those things might not always be true among family members who meet the traditional definition. This type of ikigai may help you recognize that the death of loved ones does not necessarily mean you lose your family. You can always build and add to your family (e.g., neighbors and friends, fostering children or pets, big brother/big sister programs).

How Do You Find Your Ikigai??

Many times, the hustle and bustle of life keeps us from finding our true purpose. We proceed as loyal soldiers down a path prescribed by society instead of pursuing things that may bring us greater happiness. There’s nothing wrong with a career and family, but there is likely something more that each of us can pursue that is personal and soul-enriching. Sometimes, you can discover your raison d’etre by exploring your passions, values, strengths, and skills. For example, ask yourself the following questions:

  • When I was a child, I loved doing…
  • If money didn’t matter, I would be…
  • If I believed I could not fail, I would…
  • I completely lose track of time when I am…
  • I am most happy with who I am when I…
  • I am really good at…
  • If I didn’t care what others thought, I would…
  • In my free time, I love to…
  • If I had only six months to live, I would spend my time…
  • If I were to die tomorrow, I would regret that I did not…

Consider hobbies or classes that you’ve always wanted to try or past experiences or achievements that gave you a sense of satisfaction and fulfillment. Recall where you have found inspiration in the past, and pinpoint what lies at the cross-section of doing what you love and doing what you’re good at.

Remember that your reason for living is more of a journey, not a destination. Finding your ikigai may take a lifetime to discover, so don’t be afraid to try out different pursuits. In fact, your reason for being may simply be to try new things.