10 Smart Tax Questions That Can Save You Thousands This Year

Financial Horizons: Insights for Building Wealth and Securing Your Legacy 

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

When it comes to tax planning, the questions you ask can be more powerful than the forms you file. Whether you're an individual taxpayer or a small business owner, asking the right questions early in the year—and revisiting them often—can uncover thousands in tax savings, protect your financial future, and help you stay compliant.

Here are 10 essential tax questions that every proactive taxpayer should be asking their advisor:

1. Am I Withholding Enough Taxes?

Underpayment can result in costly penalties. Overpayment means giving the IRS an interest-free loan. A quick paycheck review or estimated tax assessment can fine-tune your strategy.

2. Am I Taking Full Advantage of Tax Credits?

Credits reduce your tax dollar-for-dollar. From education to energy efficiency to child care, many credits go unclaimed. Ask your advisor to audit your eligibility.

3. Are There Any Deductions I'm Missing?

Many taxpayers overlook deductions related to home office use, business mileage, continuing education, or medical expenses. It’s time to stop leaving money on the table.

4. How Can I Lower My Taxable Income?

Contributing to retirement plans, investing in a Health Savings Account (HSA), or strategically timing income and expenses can all help. Smart planning here can shift your entire tax bracket.

5. Have There Been Any Tax Law Changes That Affect Me?

Tax laws evolve constantly. Don’t assume what worked last year will apply this year. Proactive reviews can help you avoid surprises.

6. Am I Structuring My Business or Side Hustle Efficiently?

Choosing the right entity structure (LLC, S Corp, etc.) can massively impact your tax liability. This isn’t a one-time decision—it's something to evaluate annually.

7. Should I Be Making Estimated Payments?

If you're self-employed, a freelancer, or earning income outside a W-2, this is a must. Avoid penalties and ensure you’re not caught off guard come April.

8. Is My Retirement Strategy Tax Efficient?

Tax-deferred accounts (like traditional IRAs and 401(k)s) vs. tax-free options (like Roth accounts) each have pros and cons. Balancing both could be the ultimate retirement tax hack.

9. What Can I Do to Prepare for a Potential Audit?

Keeping your books clean, your records tight, and your advisor in the loop dramatically lowers audit risk—and gives you peace of mind.

10. How Can I Plan Better for Next Year?

The best time to fix tax mistakes is before they happen. Mid-year reviews and tax planning sessions ensure you stay ahead, not behind.

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 financial strategy, tax planning, and life insurance, Dr. Cardenas helps individuals and business owners protect their wealth and build a legacy. Learn more at www.thecrgroupllc.com.

📌 Disclosure:
This article is for educational and informational purposes only and is not intended to serve as personalized legal or investment advice. Dr. Jose G. Cardenas, DBA, provides tax advisory services through The C & R Group, LLC. Insurance strategies, including Indexed Universal Life (IUL) and annuity products, may be offered through his role as a licensed financial professional affiliated with Experior Financial Group.

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