Stress-Free Tax Prep

Tax season doesn’t have to feel overwhelming especially when you have a clear roadmap of what to do before you file. As a small business owner, your tax return reflects the work you’ve done all year, so a little organization now can save you time, money, and headaches later.
Whether you’re filing on your own or working with a CPA, here are the most important steps you can take to prepare for a smooth, accurate, and stress-free tax season.

1. Get Your Bookkeeping Fully Reconciled
This is the #1 most important step and the one most business owners skip until the very last minute.
Before you file, make sure:
All bank accounts are reconciled through year-end
Every transaction is categorized correctly
Any personal expenses are marked as owner draws
All duplicate or uncategorized transactions are cleaned up
Credit cards, loans, PayPal/Venmo, and merchant accounts are reconciled too
Accurate books = accurate taxes. It also ensures you’re not overpaying or missing deductions you’re entitled to.

2. Gather Every Necessary Tax Document
Don’t wait until the deadline to search for missing paperwork. Create a folder (physical or digital) and collect:
1099s received for contractor work
1099-Ks from payment processors
W-2s if you run payroll for yourself or employees
Annual loan statements (interest is deductible!)
Asset purchase receipts
Home office, mileage, or utility records
Any large purchases made for the business
Having everything in one place will save you from the last-minute scramble.

3. Review Your Profit & Loss + Balance Sheet
Before passing information to your tax preparer, check that your financial statements make sense.
Ask yourself:
Does the income match what you actually earned?
Do expenses look accurate and complete?
Does your ending bank balance match your actual bank account?
Do loan balances look correct?
Is owner’s equity positive and realistic?
A quick review now prevents adjustments and extra fees later.

4. Make Sure Contractor 1099s Are Filed Correctly (and On Time)
If you paid any contractor $600 or more, you’ll likely need to issue a 1099-NEC by January 31.

Double-check:
You have completed W-9s for each contractor
Payment amounts match your books
You paid contractors as contractors (not through payroll)
You didn’t accidentally include reimbursements or transfers
Late or incorrect 1099s can lead to penalties — so this step matters.

5. Review Estimated Tax Payments You Made Throughout the Year
Many business owners forget this one.
Pull together:
Quarterly federal estimated payments
State estimated payments
Any taxes withheld through payroll
Your CPA needs these to properly calculate what you owe — or what you’ll get back.

6. Organize Your Receipts and Supporting Documentation
You do not need to hand over a shoebox of receipts. But you do need to keep them.
Make sure your documentation supports:
Meals & entertainment
Travel
Assets & large purchases
Home office expenses
Vehicle expenses
Subscriptions and software
Repairs & maintenance
Digital is fine, just ensure everything is stored in one consistent place.

7. Review Potential Deductions Before the Deadline
Some deductions can only be taken if you planned for them during the year.
Before filing, review:
Retirement contributions
Health insurance premiums (self-employed)
Depreciation for equipment
Startup costs
Professional fees
Software & tools
Business insurance
Education and training
Understanding what’s deductible helps you avoid leaving money on the table.

8. Plan Ahead for Next Year, Not Just This Year
Use tax season as a reset button. Once you get through this year’s prep, ask:
Do I need better bookkeeping support?
Should I switch to an LLC or S-Corp?
Am I tracking things the hard way?
Can I automate invoices, mileage, payroll, or receipts?
Should I schedule quarterly bookkeeping or CFO check-ins?
Your business changes every year, your systems should evolve with you.

Final Thoughts
Tax season doesn’t have to be chaotic. With clean books, organized documents, and the right support, you can approach your filings with clarity and confidence and avoid the costly mistakes that many small business owners make.

If you’re feeling behind or overwhelmed, Valley Bookkeeping LLC is here to help you get organized, stay compliant, and make tax time as
stress-free as possible.

Book a consultation to get your books cleaned up, reviewed, and ready for tax season.

December 6th, 2025