Quarterly Tax Review Checklist for Business Owners

1) Income Check

• Confirm your year-to-date (YTD) income from your bookkeeping reports (or bank deposits if you’re still catching up).
• Compare this quarter to last quarter and note any unusual spikes or dips.
• Identify “one-time” income (launches, bonuses, large projects) so it doesn’t distort your tax expectations.
• Check for missing income sources (Stripe, PayPal, Etsy, Amazon, affiliates, 1099s, platforms).

Quick note: If your income is trending higher than expected, your estimated tax payments may need to increase.

2) Expense & Deduction Review

• Scan your expense categories for obvious mis-categorizations (meals, travel, software, supplies, contractors).
• Confirm receipts are saved for higher-dollar purchases and anything that looks “personal-adjacent.”
• Review software and subscriptions and make sure they’re being tracked consistently.
• Home office check: If you qualify, confirm you’re tracking a consistent method (and not mixing personal and business use).
• Vehicle / mileage check: If you claim mileage, confirm you are logging trips and have a method (app, calendar notes, mileage log).

If your books are messy or incomplete, you may still be able to recover deductions — but it’s best to fix the system now, not in April.

3) Estimated Tax Payment Alignment

• Confirm what you’ve paid so far (federal + state) and record the dates and amounts.
• Compare payments to your current income trend to see if you’re underpaying or overpaying.
• Check your cash flow plan for the next payment so you’re not scrambling at the deadline.
• Note any withholding changes (W-2 job, spouse income, new employment) that affect your overall tax picture.

Underpayment penalties are avoidable in many cases — but only if you catch issues early.

4) Business & Operational Changes

• New income streams? (new offers, affiliates, marketplaces, consulting, digital products)
• Contractors added or increased? Confirm you’re tracking payments and collecting W-9s where needed.
• Any major purchases? (equipment, computers, software, vehicles) — these can affect tax planning.
• Entity structure still fits? If profits are rising, it may be time to revisit your setup.

5) Strategy Adjustments (Small Moves, Big Impact)

• Review your year-ahead plan: Are you on track, or have priorities changed?
• Timing check: Are there expenses you can plan intentionally (instead of randomly)?
• Retirement / benefits check: If applicable, confirm contributions and plan limits.
• Red flags: If you’re unsure how something should be treated, write it down now.

Quarterly reviews are about staying aligned — not being perfect. The goal is fewer surprises and more control.

6) When to Get Help (Consult Signals)

Consider getting support if any of the following are true:

• You don’t know what you’re likely to owe (or you’re guessing).
• Your income has increased significantly and you haven’t adjusted estimated payments.
• Your books are behind, inconsistent, or you’re mixing business and personal spending.
• You added contractors, started payroll, or expanded into multiple states.
• You have crypto or digital asset activity and don’t have clean exports or records.
• You’re wondering if your entity structure still fits your profit level.