6 Tax Deductions You’re Probably Ignoring (That Could Be Saving You Money)

Financial Horizons: Insights for Building Wealth and Securing Your Legacy

By Dr. Jose G. Cardenas, Chief Tax Strategist at The C & R Group, LLC

Here’s the uncomfortable truth—a lot of people overpay the IRS not because they did something wrong, but because they didn’t claim everything they’re legally entitled to.

You’re busy. You’re juggling work, family, business, health, and a thousand other things. So when it’s time to file, you just want it done. The problem? That “just get it over with” mindset is exactly how deductions get missed and money gets left on the table.

In this edition of Financial Horizons, we’re going to shine a light on six tax deductions people routinely ignore:

1. Home office deduction
2. Health insurance premiums (in certain situations)
3. Medical expenses above certain limits
4. “Unusual” business expenses
5. Educator expense deductions
6. Charitable donations

Let’s break each of these down so you can stop tipping the IRS and start keeping more of what you earn.

1. Home Office Deduction: Your Workspace Might Be Working for You

If you run a business, side hustle, or freelance work from home, you may qualify for a home office deduction. The key concept is exclusive and regular use of a specific area for business.

Depending on your situation and current tax rules, the deduction may allow you to allocate a portion of:

• Rent or mortgage interest
• Property taxes
• Utilities
• Certain repairs or maintenance

…to your business use of the home.

What scares people off?

• They think taking a home office deduction is “a red flag.”
• They don’t understand the rules, so they avoid it entirely.

The reality: if you legitimately qualify and document it properly, it’s a normal, legal deduction. The key is to apply the rules correctly and keep good records.

2. Health Insurance Premiums: A Major Cost That Sometimes Gets Overlooked

Health insurance is one of the biggest expenses for many families—especially:

• Self-employed individuals
• Small business owners
• Early retirees not yet on employer coverage or Medicare

In certain situations, health insurance premiums (and sometimes dental or long-term care premiums within limits) can be deductible, either:

• As an above-the-line deduction for self-employed people, or
• As part of medical expenses if you itemize and exceed specific thresholds.

People often miss this because:

• They assume it only counts if they itemize.
• They don’t realize self-employed health insurance has separate rules.
• Their premiums are paid through multiple places (marketplace, private plans, etc.) and don’t get captured cleanly at tax time.

If you’re paying for your own coverage, it’s worth having a professional review your situation to see where those dollars may be working for you on your return.

3. Medical Expenses: More Than Just Copays and Prescriptions

Most people only think of medical deductions when they have a massive hospital bill. But the rules around qualified medical expenses can include much more than just doctor visits, such as:

• Certain dental and vision expenses
• Some medically necessary procedures or treatments
• Certain travel costs related to medical care
• Equipment or supplies prescribed by a professional

Medical expenses are subject to floor rules (you generally must exceed a percentage of your income before they count), which is why many people ignore them.

However, in years where:

• You have a major procedure
• A family member has ongoing treatment
• You’ve had multiple surgeries, therapies, or specialized care

…those costs can add up fast, and suddenly you’re well above that threshold.

This is where planning matters:

• Keep every receipt and bill related to medical care.
• Don’t assume “it won’t be enough” until you actually run the numbers.

4. “Unusual” Business Expenses: The Things That Don’t Look Like Deductions (But Are)

If you’re a business owner or self-employed, the tax code generally allows you to deduct ordinary and necessary expenses related to your trade or profession.

Here’s where people leave money on the table:

• They only think about the obvious items—software, office supplies, etc.
• They ignore expenses that feel “unusual,” even though they are directly tied to earning income.

Depending on your line of work, “ordinary and necessary” might include:

• Professional association dues or subscriptions
• Specialized tools or equipment
• Training, certifications, or continuing education
• Marketing and advertising (including certain online costs)
• Certain travel, meals, and client-related expenses under current rules

The key is not whether the expense is common for everyone, but whether it is reasonable and ordinary for your business.

This is where a good tax strategist will ask, “Walk me through your day. What do you pay for that helps you make money?” The answers often uncover deductions that software alone will never find.

5. Educator Expense Deductions: For the Teachers Who Pay Out of Pocket

Teachers and educators are famous for reaching into their own wallets for:

• Classroom supplies
• Books
• Educational materials
• Professional development

The tax code recognizes this reality and allows certain educator expenses to be deducted, up to limits, if you meet the definition of a qualified educator and work a minimum number of hours in a qualified setting.

The problem?

• Many educators don’t even know this deduction exists.
• They throw away receipts or don’t track their spending.
• They assume, “It’s just part of the job,” and never get any tax benefit for it.

If you or your spouse is a teacher or eligible educator, you should absolutely be tracking these expenses. Every little bit matters—especially when you’re already underpaid for the impact you make.

6. Charitable Donations: Giving With a Strategy, Not Just Emotion

You’re probably giving more than you think:

• Cash donations to nonprofits
• Contributions at religious services
• Online gifts to support causes or disaster relief
• Donated clothing, furniture, or household items

Charitable contributions may be deductible if you itemize and give to qualified organizations. But even if you don’t itemize, charitable planning can still integrate with other strategies.

Common reasons people lose out:

• No receipts or documentation
• Not tracking non-cash donations
• Confusing personal gifts with tax-deductible charity
• Assuming “it doesn’t add up to much”

Wealthy families often go a step further:

• Donor-Advised Funds (DAFs)
• Gifting appreciated stock instead of cash
• Integrating charitable planning with estate and retirement strategies

Even at a smaller scale, you can still think strategically: keep records, group gifts in certain years, and align giving with your larger financial goals.

Stop Ignoring Deductions That Are Trying to Help You

The IRS is not in the business of reminding you what you could have deducted. If you don’t claim it, you lose it.

These six deduction categories are places I routinely find missed opportunities when reviewing new clients’ prior returns. The goal isn’t to “get cute” with the tax code—it’s to use the rules as they were designed so you stop overpaying.

If you:

• Work from home
• Pay your own health insurance
• Had a year with high medical expenses
• Run a business or side hustle
• Teach or are married to a teacher
• Give to charity in any form

…there’s a good chance at least one of these applies to you.

The question is: are you capturing it?

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About the Author

Dr. Jose G. Cardenas is a retired U.S. Army Finance Officer and the Chief Tax Strategist at The C & R Group, LLC. With a Doctorate in Business Administration and over 20 years of experience in tax planning and financial strategy, Dr. Cardenas helps individuals, families, and business owners legally reduce taxes, maximize deductions and credits, and turn reactive tax filing into proactive wealth building. Learn more at thecrgroupllc.com

📌 Disclosure

This article is for educational and informational purposes only and is not intended to serve as personalized legal, tax, or investment advice. Deduction rules, thresholds, and eligibility for home office expenses, health insurance premiums, medical costs, business expenses, educator deductions, and charitable contributions change over time and depend on your specific situation. You should consult with a qualified tax professional or review current IRS guidance before relying on any particular deduction. Dr. Jose G. Cardenas, DBA, provides tax advisory services through The C & R Group, LLC. Insurance and investment strategies may be offered through his role as a licensed financial professional affiliated with Experior Financial Group.

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