“What You Wish Was Deductible vs. What Actually Can Be — A Smarter Look at Tax Strategy”

Financial Horizons: Insights for Building Wealth and Securing Your Legacy

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

Every year, tax season invites a wave of wishful thinking — and as this meme cheekily points out, it’s easy to daydream about what should be deductible:

• A. Travel Expenses
• B. Expenses for Hobbies
• C. Money Spent on Personal Development
• D. Entertainment Expenses

Here’s the truth: While the IRS isn’t handing out deductions for binge-watching Netflix or collecting comic books just yet, there are strategic ways to structure your life and business so that many of these “wish list” items become legitimate, legal deductions. Let's unpack it.

What You Wish Was Deductible… Can Be, With the Right Structure

A. Travel Expenses

Yes, personal vacations are off the table — but business travel is absolutely deductible. Here’s the key: if you own a business or side hustle, and your travel is ordinary and necessary in the course of doing business (like attending a conference, visiting a client, or scouting investment property), it could qualify. Even better? With proper planning, you can combine business and leisure into a "bleisure" trip and legally write off a portion.

B. Expenses for Hobbies

Hobbies are for fun, not for deductions… unless you turn that hobby into a revenue-generating business. By meeting the IRS criteria for a business (intent to make a profit, consistent record-keeping, marketing efforts), you unlock legitimate deductions for things like supplies, equipment, and even home office use.

C. Money Spent on Personal Development

Education expenses often fall into a gray area — but if they directly relate to maintaining or improving skills required in your current business or profession, they may qualify. Entrepreneurs, consultants, and advisors can often deduct coaching, training, certifications, and even books as continuing education. Structuring your professional development through a business entity unlocks the door.

D. Entertainment Expenses

This one’s tough — the IRS has cracked down on entertainment deductions in recent years. But there’s a nuance: meals during business discussions or client outings may still be 50% deductible (or 100% in special cases). It’s all about documentation and intent.

How Wealth Builders Use the Tax Code Differently

Here’s the truth that separates the wealthy from the overtaxed: they don’t find loopholes — they build strategies.

Using an LLC, S-Corp, or C-Corp, paired with tax advisory, can transform everyday expenses into wealth-building tools. This is exactly the type of insight we share during our tax assessments.

Ready to Turn Wishful Thinking Into Strategic Deductions?

Our tax planning process helps uncover opportunities most tax preparers miss — because they’re focused on compliance, not strategy.

👉 Book a Tax Assessment and let us show you how to turn travel, education, and lifestyle expenses into legally optimized tax strategies.

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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