Tax season and March Madness have one thing in common: strategy. Just like filling out a bracket, preparing for tax season requires planning, smart choices, and a little bit of foresight. Whether you’re filing early or racing against the clock, having a game plan is key.
In this edition of Money Courage, we’ll walk you through a Tax Season Bracket, breaking down key tax preparation steps, offering strategies to maximize deductions, and helping you score financial wins.
🏀 Round 1: Building a Winning Tax Game Plan
Preparation is Everything
“The will to succeed is important, but what’s more important is the will to prepare” – Bob Knight
Just like the first round of the tournament, this stage is about getting organized and setting the foundation for a strong finish. Without the right preparation, you could miss deductions, credits, or even file with errors. Here’s how to start:
✅ Gather Your Documents – Collect W-2s, 1099s, investment statements, mortgage interest forms, charitable donation receipts, and any other necessary paperwork. IRS Tax Forms
✅ Check for Life Changes – Did you get married, have a child, buy a home, or start a business? These events can significantly impact your tax return. IRS Life Events & Taxes
✅ Review Last Year’s Return – Use it as a guide to ensure you don’t overlook key items.
🏆 Bracket Tip: The teams that prepare well in advance have the best chance of making it to the final rounds—your tax prep should follow the same rule!
🏀 Round 2: Maximizing Deductions & Credits
Scoring Tax Savings
The second round is where things get competitive. The goal here is to make sure you’re taking advantage of every opportunity to lower your tax burden.
✅ Retirement Contributions – Contributions to IRAs and 401(k)s may be tax-deductible. Retirement Contribution Limits
✅ Education & Student Loan Deductions – Take advantage of credits like the American Opportunity Credit and Lifetime Learning Credit. Education Tax Benefits
✅ Medical & Business Expenses – If your medical expenses exceed 7.5% of your income, you may qualify for deductions. Self-Employed Tax Deductions
✅ Charitable Contributions – Donations to qualified charities could be deductible. IRS Charitable Contribution Rules
🏆 Bracket Tip: Cinderella stories happen in March Madness—unexpected teams make deep runs. Similarly, small deductions can add up to significant savings when combined.
🏀 Final Four: Avoiding Common Mistakes & Filing on Time
Stay on Top of Your Game
The Final Four is all about execution. You’ve put in the effort—now it’s time to finish strong and avoid costly mistakes.
✅ Double-Check Everything – Ensure accuracy in Social Security numbers, bank account details for direct deposit, and all income and deduction entries. Common Filing Errors
✅ Standard vs. Itemized Deduction – Choose the one that benefits you most. Standard vs. Itemized Deductions
✅ Watch for Red Flags – Large, unusual deductions can increase the risk of an IRS audit. IRS Audit Triggers
✅ Consider an Extension if Needed – File for an extension if you need more time. Filing an Extension
🏆 Bracket Tip: A strong team doesn’t fall apart in the final stretch. Take your time and review everything carefully to ensure a smooth finish.
🏀 Championship Round: Winning the Tax Season Tournament
Sealing the Deal
You made it to the championship round, and now it’s time to secure the win. Whether you file on your own or work with a tax professional, finishing the season strong means being confident in your filing and planning ahead for next year.
✅ E-File for Speed & Accuracy – Filing electronically can get you your refund faster. E-File Options
✅ Plan for Next Year Now – Adjust withholdings, increase retirement contributions, and track deductible expenses year-round. IRS Tax Withholding Estimator
✅ Consult a Professional – If your situation is complex, a tax professional can help.
🏆 Bracket Tip: Championship teams don’t just celebrate and forget about next season—they start planning immediately. Apply the same mindset to your taxes for an even smoother filing process next year.
📌 Resources for More Help:
🔹 IRS Free File – For those who qualify, file your taxes for free.
🔹 Taxpayer Advocate Service – Independent organization to help with tax issues.
🔹 Where’s My Refund? – Check the status of your refund.
🔹 State Tax Information – Find your state’s tax agency for local filing requirements.
By taking a strategic approach to tax season, you can minimize stress, maximize your return, and keep more money in your pocket. Just like in March Madness, a well-planned bracket (or tax filing strategy) can lead to big wins. Ready to file with confidence? Let’s get started!
#MoneyCourage #TaxSeason #MarchMadness #SmartFinances
Disclosure: Tradewinds, LLC is an investment adviser registered under the Investment Advisers Act of 1940. The information presented in the material is general in nature and is not designed to address your investment objectives, financial situation or particular needs. Prior to making any investment decision, you should assess, or seek advice from a professional regarding whether any particular transaction is relevant or appropriate to your individual circumstances. Although taken from reliable sources, Tradewinds cannot guarantee the accuracy of the information received from third parties. The opinions expressed herein are those of Tradewinds and may not actually come to pass.
