Charting the Course: How Five Below Employees Can Navigate the New Senior Tax Deduction

“Five Below employees who leverage strategic income coordination and Roth conversion timing can fully benefit from the 2025 senior bonus deduction and increased standard deductions—though they should consult a tax advisor for individualized guidance.” – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

“By modeling various income scenarios—balancing part-time earnings with Roth conversions and RMD timing—Five Below employees can optimize their benefit from the four-year senior bonus deduction window.” – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

1. The new four-year “senior bonus” deduction and increased standard deduction.

2. Tax exclusions for part-time employment and strategic income coordination.

3. Roth conversion timing and RMD considerations to optimize MAGI.

President Donald Trump’s 2025 Tax Law

President Donald Trump signed a historic tax policy into law on July 4 that takes effect in 2025, providing taxpayers age 65 and older with a significant planning opportunity. Instead of fully exempting Social Security benefits from taxes, the law preserves existing rules while introducing a temporary, increased standard deduction to lower seniors’ taxable income.

New Senior Bonus Deduction

Five Below employees who qualify can claim a $6,000 “senior bonus” deduction for each eligible individual through the 2028 tax year, provided their modified adjusted gross income (MAGI) stays within specified limits.

Increased Income and Deduction Caps

Single filers with a MAGI up to $75,000 can claim the full $6,000 bonus deduction; the benefit phases out entirely once MAGI reaches $175,000. Married couples filing jointly may each deduct $6,000 if their combined MAGI is under $150,000, with the deduction phasing out by $250,000. ¹  Wealth Enhancement financial advisor Tyson Mavar notes, “This is a meaningful opportunity.” Every dollar of tax reduction directly strengthens retirement assets for those on fixed incomes.

Increases in Standard Deduction

Beginning in 2025, the basic standard deduction rises to $15,750 for single returns and $31,500 for joint returns, ²  in addition to any senior bonus deduction. Retirees age 65+ already receive age-based increases—$2,000 for single filers and $3,200 for married couples. As a result, a married couple under the income threshold could deduct up to $46,700 before any itemized deductions.

Exclusions from Taxes for Part-Time Employment

The legislation also provides sector-specific limits for hourly and tipped workers. Certain service roles may exclude up to $25,000 in tip income and $12,500 in overtime pay from taxable income. Retirees who continue part-time work in service or hospitality may find this particularly transformative, as Tyson Mavar suggests, since it allows additional earnings without jeopardizing deduction eligibility.

Considerations for Roth Conversion

While converting traditional IRA assets to a Roth IRA can yield long-term benefits, it increases taxable income in the conversion year. Five Below retirees may inadvertently exceed MAGI limits, negating the $6,000 deduction. Patrick Ray, a financial advisor with Wealth Enhancement, suggests carefully structuring any Roth conversions to avoid exceeding limits, or potentially postponing the conversion until after the senior bonus phases out in 2028.

Required Minimum Distributions with Roth Accounts

RMDs from traditional IRAs begin at age 73 and fully count as taxable income, raising AGI. In contrast, Roth IRA withdrawals are tax-free and have no distribution mandate. Brent Wolf at Wealth Enhancement emphasizes that “the tax-free feature is crucial” for supporting flexible income planning through Roth accounts.

Management of Strategic Income

Coordinating revenue sources is essential to leverage this four-year window. Five Below employees might ask, “Can we adjust withdrawals and earnings to keep MAGI below the cutoff and capture substantial tax reductions?” as Mavar frames it. 

Next Actions

Five Below retirees should forecast income streams—including earned income, Social Security, IRA distributions, pensions, and Roth conversion schedules—and model scenarios to identify optimal withdrawal ranges and part-time earnings. Engaging tax and wealth planning specialists helps confirm that plans are in place when the law takes effect.

The Bigger Picture

At a time when living costs may be rising, this four-year boost to the standard deduction offers a rare chance to lower tax bills. Over 2025–2028, disciplined planning—balancing MAGI against new thresholds, leveraging tip-income exclusions, and judicious Roth use—could yield tens of thousands in savings for those prepared to chart their course.

Personalized Guidance

Five Below employees seeking tailored strategies should consult advisors at Wealth Enhancement today to craft a retirement plan optimized for the enhanced deduction and broader tax changes.

Managing Medicare Surcharges

The same MAGI limits for the senior bonus also apply to Medicare premium surcharges. For instance, a single filer whose MAGI exceeds $106,000 by just $1 may face IRMAA penalties that add over $1,000 to annual Part B and Part D premiums. 

In Summary

Examine the 2025 tax law’s retirement-planning options—including the $6,000 bonus deduction, higher standard deductions, MAGI thresholds, Roth timing, and tip-income exclusions—to optimize after-tax income through 2028.

Analogy

Navigating this new tax landscape is like steering a sailboat through a series of canal locks: you must time your income withdrawals and Roth conversions precisely to avoid rising water levels (MAGI phase-outs and Medicare surcharges), harness every current (the enhanced deductions and higher standard deduction) for forward motion, and explore side channels (tip-income and overtime exclusions) to gain extra distance. By keeping that careful course, Five Below employees can sail smoothly through 2025–2028 with optimal savings.

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p data-start='4780' data-end='4932' data-is-last-node='' data-is-only-node=''> Sources:

1. Tax Foundation. “ How Does the Additional Senior Deduction Compare to No Tax on Social Security? ,” by Alex Durante, 4 July 2025.

2. Bipartisan Policy Center. “ The 2025 Tax Bill: Additional $6,000 Deduction for Seniors, Simplified. ” by Emerson Sprick, 12 June 2025.

3. CBS News. “ Does the ‘Big, Beautiful Bill’ Eliminate Taxes on Social Security? ” by Mary Cunningham, 9 July 2025.