October marks the beginning of one of the most important times on the tax calendar: year-end planning season. With just a few months left before December 31, you still have the opportunity to take meaningful steps to reduce your 2025 tax bill, improve cash flow, and position yourself for success in 2026.
The problem? Many taxpayers wait until April to think about taxes — and by then, most of the best opportunities are long gone. Smart planning happens now.
To keep things simple, here are three powerful questions you should be asking your CPA before year-end.
1
Am I on track with estimated tax payments?
One of the most overlooked areas of tax planning is making sure you’re paying the right amount of tax throughout the year.
If you’re a W-2 employee, your employer withholds tax on your behalf — but if you’ve had raises, bonuses, side income, or investment gains, your withholding may not be enough.
For business owners, freelancers, or investors, quarterly estimated tax payments are critical. If you’ve underpaid, the IRS may assess penalties and interest even if you pay in full by April.
Why it matters in 2025:
- The IRS is tightening enforcement with advanced data analytics, meaning underpayment penalties are catching more taxpayers.
- You still have a chance to make adjustments in your final quarterly payment (due January 15, 2026) to avoid surprises.
What to ask your CPA:
- Based on my 2025 income so far, am I underpaid or overpaid?
- Should I increase my final estimated tax payment to avoid penalties?
- Would adjusting my W-2 withholding before year-end be a better option?
Getting this right ensures peace of mind — and can free up cash if you’ve been overpaying.
2
Should I accelerate or defer income and expenses in 2025?
Timing is one of the most powerful tools in tax planning. Whether you’re an individual or a business owner, deciding when to recognize income or expenses can dramatically change your tax bill.
For business owners:
- Equipment purchases: Thanks to the One Big Beautiful Bill Act (OBBBA), businesses can take advantage of 100% bonus depreciation on qualifying assets purchased and placed in service before December 31, 2025. This is a huge opportunity for companies planning major capital investments.
- Operating expenses: Consider prepaying certain expenses (like rent or supplies) before year-end if it makes sense for cash flow.
For individuals:
- Income deferral: If you’re expecting a raise, bonus, or large payout in late 2025, it may be worth exploring whether some can be deferred into 2026 — especially if you expect to be in a lower bracket next year.
- Charitable contributions: Donating before December 31 ensures the deduction counts toward 2025. Strategies like “bunching” contributions or using a donor-advised fund can maximize benefits.
What to ask your CPA:
- Should I accelerate income or delay it based on my 2025 projections?
- Does it make sense to invest in equipment or assets now to capture bonus depreciation?
- How do year-end decisions affect my 2026 tax situation?
3
What deductions or credits am I missing that expire after this year?
The tax code is constantly changing — and 2025 has brought a wave of new opportunities (and temporary ones at that). If you don’t capture them by December 31, they’re gone.
Key examples for 2025:
- SALT deduction cap increase: The state and local tax deduction cap is temporarily raised to $40,000 (from $10,000) through 2029. If you live in a high-tax state, you may benefit from accelerating property tax or state income tax payments into this year.
- New deductions: The OBBBA introduced several unique new deductions, including:
- Up to $12,500 (single) or $25,000 (married) for eligible overtime pay.
- Up to $25,000 in tips for workers in eligible occupations.
- Car loan interest deduction for U.S.-assembled vehicles.
- Retirement contributions: 2025 limits are higher, and contributions must be made by year-end for certain plans (401(k), SIMPLE).
What to ask your CPA:
- Do I qualify for the new overtime, tip, or car loan deductions?
- Can I maximize the expanded SALT cap this year?
- Have I contributed enough to retirement accounts to reduce taxable income?
A year-end meeting ensures you don’t leave money on the table.
Why Act Now (Not Later)?
- Deadlines are real: Once December 31 passes, most tax moves are locked in.
- CPA availability shrinks: October–December is the perfect window to schedule planning sessions before filing season chaos begins.
- Laws are changing: Some favorable provisions could sunset after 2025, meaning this may be your last year to benefit.
Proactive planning can mean the difference between writing a big check to the IRS and keeping more of your hard-earned money.
Next Steps
Schedule a year-end planning session with your CPA before November ends. Bring your income year-to-date, expected changes, and any big financial moves you’re considering. Together, you can map out strategies that protect your bottom line.
At Tusk PCS, we help business owners and individuals identify opportunities, reduce risks, and build strategies tailored to their goals. Don’t wait until April. Let’s finish 2025 strong, together.
Article by:
Kyle Kennedy
Tax Advisor
