When Do You Start Preparing for Tax Season?

By Dr. Jose G. Cardenas | Chief Tax Strategist, The C & R Group, LLC
Published in Financial Horizons: Insights for Building Wealth and Securing Your Legacy

Introduction: Timing Isn’t Everything—But It’s Close

Tax season always seems so far away—until it’s suddenly breathing down your neck. Whether you’re someone who kicks off the year with a fresh spreadsheet or the kind of taxpayer who’s printing forms the night before the deadline, your approach to tax prep can make or break your financial peace of mind.

Let’s be honest—most people fall into one of the four camps illustrated in the image above. But only one of those groups sleeps easy while others reach for coffee and chaos. The question is: Which one are you?

Section 1: The Four Filing Personas (And Their Consequences)

A. “At the Start of the New Year”
These are the early birds. They gather documents, track deductions, and meet with their tax strategist before February even begins. This group avoids the April rush and often unlocks greater tax savings thanks to strategic planning time. If you’re in this group—well done. If not, keep reading.

B. “A Month Before the Deadline”
Still better than most, this group thinks they’re ahead… but they’re not. March may seem early, but by then, windows for certain tax-saving strategies have closed. You’re mostly limited to damage control rather than opportunity.

C. “A Week Before the Deadline”
Cue the stress sweats and printer jams. At this stage, you’re reacting—not planning. Mistakes are more likely, documents get missed, and you’re stuck hoping the IRS doesn’t mind sloppy math.

D. “I Hire a Professional So I Don’t Worry About It”
This is the gold standard. It’s not about doing it early—it’s about doing it strategically. This group outsources the stress, gains proactive planning, and benefits from year-round guidance—not just seasonal filing.

Section 2: The Real Cost of Last-Minute Filing

Procrastination has a price. Filing late or under pressure can lead to missed deductions, penalties, and even IRS scrutiny. But beyond that, you’re leaving money on the table.

Let’s take a hypothetical example:

• Client A started planning in January. They structured income, made deductible purchases for their business, and funded their retirement accounts—resulting in $18,600 in tax savings.
• Client B waited until April 10th. They filed a basic return, didn’t maximize deductions, and paid an extra $6,800 in taxes unnecessarily.
• Client C hired our firm in November the prior year. Their plan included business restructuring, a retirement contribution strategy, and implementing the Augusta Rule—leading to $32,000+ in legally reduced tax liability.

This is the difference between checking a box and changing your financial life.

Section 3: Why You Should Never Face Tax Season Alone

A solid tax strategy is not just about filing. It’s about planning your income, deductions, credits, retirement contributions, and even business structure throughout the year. When you hire a tax strategist, you're not just preparing a return—you’re building a tax-saving game plan.

Think of it this way: Would you rather defuse a tax deadline bomb on your own with a pair of kitchen scissors… or hire the EOD (Explosive Ordinance Disposal) team?

Our team at The C & R Group, LLC is trained to uncover legal tax savings, design custom strategies, and help you keep more of what you earn. It's not just about avoiding penalties—it's about building wealth.

Section 4: Pro Tip—The IRS Doesn’t Reward Procrastinators

Contrary to popular belief, the IRS isn’t “chill” about late or sloppy returns. They might process your return and send a refund… or they might flag it for audit. And guess what? DIY returns filled with errors or missed deductions are audit magnets.

When you wait too long to prepare, you rob yourself of options. But when you plan ahead with a professional, you gain the power to control outcomes. In tax planning, time really is money.

Final Thoughts: D Is the Real Power Move

If you picked answer D—hiring a professional—you’re already ahead. And if you didn’t, don’t worry. There’s still time to switch lanes.

At The C & R Group, LLC, we specialize in helping high-income earners and business owners build legally sound, forward-thinking tax strategies. You don’t have to stress over tax season ever again.

Ready to Prepare the Smart Way?

✅ Let’s talk strategy—not survival. Book your tax advisory session today:
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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. He helps business owners and high-income professionals reduce tax burdens and build lasting wealth. He is also the author of the Financial Horizons series, empowering readers to master every stage of their financial journey.

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.