The Most Common Tax Mistakes and How To Avoid Them
Tax season shouldn’t feel like cleaning up a disaster zone, but for many business owners and individual filers, that’s exactly what it turns into. As tax professionals, we’ve seen it all, and we get it. Bookkeeping isn’t everyone's favorite part of running a business, but messy books can cost you time, money, and peace of mind come tax season. The good news? Many common mistakes have simple fixes.
Whether you're managing your books solo or working with a professional, here are some of the top issues we see, and what you can do now to make next year easier (and less expensive).
We’re going to share out top mistakes we see every year, and quick fixes to avoid this and help you save the headache next tax season
What NOT To Do Next Tax Season
Mistakes We See Every Year (Even from the Pros)
For Business Owners
Owner draws booked as payroll
Capital improvements logged as repairs (<$1500-2000)
Reimbursed expenses showing up as income
Sales tax included in revenue
Scrambling for 1099 contractor info in January
Comingling between business and personal accounts/expenses
For Individuals
HSA contributions mistimed or missed
Overlooked itemizations
ACA credit miscalculations due to inflated income
Estimated payments logged inaccurately or not at all
Smart Bookkeeping Fixes You Can Start Today!
For Business Owners:
Set a monthly checklist for non-bank feed entries (owner draws, loans, reimbursements)
Use project/class tracking for better reporting
Implement receipt rules (ex: Home Depot = review for CapEx)
Schedule quarterly reviews
Document your S-Corp salary logic (for audit protection)
For Individuals:
Keep a “tax events” list (life changes, large sales, etc.)
Drop tax docs into one digital folder as they arrive
Use a mileage tracker like MileIQ
Confirm your estimated payments mid-year
Why Does This Matter?
Good bookkeeping and tax support isn’t just about checking boxes and balancing books, it’s about having clarity, confidence, and systems that actually support your goals.
At T&O Strategic Advisory, we work with people who are capable and committed, but don’t always have the time or tools to manage their financials effectively. Whether you’re catching up, cleaning up, or trying to grow with more intention, we’re here to help you do that with less stress and more strategy.
We take a thoughtful, personalized approach to ensure you are making the best moves for your business, and we’re always happy to have a conversation, even if it’s just to point you in the right direction.
Not sure where to start? Reach out anytime. We’re here when you’re ready
