A Simple Guide for Entrepreneurs and Small Business Owners
Tax season doesn’t have to mean late nights, last-minute scrambling, or piles of receipts scattered across your desk. In fact, with just a little planning and support, you can head into tax time with confidence—and maybe even a bit of calm.
At Your Bookkeeper On Call, we help small business owners and solopreneurs stay organized all year long with live, on-demand bookkeeping services and DIY coaching. Whether you’re doing it yourself or working with a tax pro, here’s how to prepare for tax season—without the stress.
Step 1: Start Early (Yes, Now)
The earlier you begin preparing for tax season, the easier it becomes. Waiting until the last minute often means:
- Missing out on deductions
- Making costly mistakes
- Filing extensions you didn’t plan for
- Feeling overwhelmed and rushed
What to do:
✔️ Set a reminder to begin prep in Q4
✔️ Block out time weekly or biweekly to update your records
✔️ Get your tax documents organized as they arrive
Starting early doesn’t mean doing it all at once—it means giving yourself room to breathe.
Step 2: Organize All Your Financial Records
Your tax return is only as good as your financial documentation. Keeping clean, accurate records isn’t just smart—it’s required.
Here’s what you’ll want to have ready:
- ✅ Income statements (invoices, sales reports)
- ✅ Business expenses (receipts, bills, subscriptions)
- ✅ Bank and credit card statements
- ✅ Payroll records, if applicable
- ✅ 1099s or W-2s you issued
- ✅ Loan documents, asset purchases, and depreciation records
Pro Tip: Use cloud-based accounting software like QuickBooks or Xero to keep everything in one place—and link scanned receipts directly to transactions.
Step 3: Reconcile All Accounts
Reconciling your bank and credit card accounts ensures your financial records match your actual transactions. It’s one of the most common areas where small business owners fall behind.
Why it matters:
- Identifies duplicate entries or missed expenses
- Catches errors early
- Ensures your tax numbers are accurate
If you haven’t reconciled lately (or ever), don’t worry—we offer catch-up bookkeeping to get your books clean before tax season hits.
Step 4: Separate Personal and Business Expenses
If you’ve been using one account for both business and personal spending, now’s the time to clean that up.
Why?
- It makes tax filing much harder
- You could miss deductions or trigger an audit
- It muddies your financial reporting
Going forward:
✔️ Open a dedicated business checking account
✔️ Get a separate credit card for business use
✔️ Reimburse yourself properly instead of co-mingling funds
Need help sorting it all out? That’s what our DIY coaching is for—we’ll walk you through it.
Step 5: Work With a Bookkeeper or Coach
Even if you’re a hands-on business owner who likes to keep things in-house, tax prep is not the time to guess. A bookkeeper can:
- Help you identify missing documents
- Ensure your books are tax-ready
- Coordinate with your tax preparer or CPA
- Maximize deductions and reduce risk
- Save you hours (or days) of time
At Your Bookkeeper On Call, we offer flexible support—from quick check-ins to full-service monthly bookkeeping. You get expert help only when you need it.
Step 6: Understand What You’ll Owe (Before You File)
One of the worst parts of tax season? Surprise bills.
Avoid sticker shock by:
- Reviewing your estimated quarterly taxes
- Running a year-end profit report
- Factoring in new deductions, like home office or equipment purchases
- Talking with a pro about potential tax strategies before December 31
Want to know where you stand? Let us help you generate the right reports and review them together—so you’re never left guessing.
Step 7: Plan for Next Year (Right After This One Ends)
Once you’ve filed this year’s taxes, take a moment to review:
- What went smoothly?
- What caused delays or stress?
- What could be automated, outsourced, or improved?
Then set a plan for the new year—ideally with a bookkeeping routine that supports you year-round.
Need help building a system that works for you? That’s exactly what our coaching and monthly support services are for.
You Don’t Have to Do This Alone
Preparing for tax season doesn’t have to be a solo mission. Whether you want to learn how to do your own books properly, or you’re ready to hand it off entirely, Your Bookkeeper On Call is here to help.
We Offer:
✅ Live, on-demand bookkeeping support
✅ DIY coaching for business owners who want to learn
✅ Tax season cleanup and prep
✅ Stress-free systems that work year-round
Final Word
You started your business to create freedom—not to spend tax season buried in spreadsheets and receipts. With a little structure and the right support, you can face tax time feeling clear, confident, and in control.
👉 Want a stress-free tax season? Book a free consultation with Your Bookkeeper On Call today and let’s get you prepared.
Running a business is all about balance—between growth and operations, hustle and rest, and yes, saving money and spending it wisely. That’s why many entrepreneurs and small business owners take a DIY approach to bookkeeping. It seems straightforward: track income, log expenses, and stay organized. Right?
Well… sometimes.
At Your Bookkeeper On Call, we fully support small business owners who want to take the reins of their financial records—but we also know where things often go sideways. Bookkeeping is more than data entry; it’s about accuracy, consistency, and compliance.
So if you’re wondering, “What can I handle on my own, and what should I leave to a pro?”—this blog is for you.
Why Some Entrepreneurs Choose DIY Bookkeeping
DIY bookkeeping can be a great option when:
- You’re just starting out and want to understand your finances intimately
- You have a limited budget for outsourcing
- You enjoy working with numbers and learning new systems
- Your transactions are relatively simple and low volume
But as your business grows (or your time shrinks), keeping your books can quickly shift from smart move to stressful burden. That’s when strategic outsourcing makes all the difference.
What You Can Do Yourself
If you’re confident with basic finance and bookkeeping software, here are a few tasks you can realistically manage in-house:
✅ 1. Recording Daily Transactions
Logging sales, expenses, payments, and transfers is something you can do with accounting software like QuickBooks or Xero. It’s a habit that’s easy to build—and critical to your financial hygiene.
✅ 2. Managing Invoices and Payments
Creating and sending invoices, tracking payments, and issuing reminders can all be handled through your accounting platform. Automation can help, too.
✅ 3. Storing Receipts and Documentation
Keeping digital copies of receipts and linking them to transactions is a good DIY task. Apps like Dext or Hubdoc can simplify this.
✅ 4. Reconciling Bank Accounts (If You’re Comfortable)
If you’re detail-oriented and consistent, monthly reconciliations can be done yourself. But if you’re skipping steps or guessing your way through—this might be one to outsource.
✅ 5. Basic Financial Reports
Running basic Profit & Loss and Balance Sheet reports is possible with most accounting software. Understanding them, however, is where a coach or advisor can be helpful.
What You Should Consider Outsourcing
Even the most driven DIYers benefit from outsourcing certain parts of the bookkeeping process. Here’s what we recommend handing off:
❌ 1. Initial Setup of Your Accounting System
If you don’t start with the right chart of accounts and settings, you’re setting yourself up for confusion and cleanup down the road. A professional can help set your system up correctly from day one.
❌ 2. Payroll Processing
Payroll is heavily regulated and time-sensitive. Mistakes can lead to penalties or unhappy employees. It’s one of the most commonly outsourced functions for a reason.
❌ 3. Tax-Ready Financials and Year-End Prep
You want your books to be clean and accurate before handing them off to your tax preparer. Outsourcing monthly or quarterly reviews (or at least a year-end cleanup) ensures you won’t overpay—or miss deductions.
❌ 4. Sales Tax Filing
Sales tax compliance is a minefield, especially with multi-state or eCommerce businesses. A pro can help you avoid costly missteps.
❌ 5. Catch-Up and Cleanup Work
If your books are behind (or you’re unsure how accurate they are), it’s best to let an expert clean things up so you can move forward with confidence.
Finding Your Sweet Spot: DIY + Expert Support
The truth is, you don’t have to choose either DIY or outsourcing. With Your Bookkeeper On Call, you get the best of both worlds:
- 💡 DIY Bookkeeping Coaching – Want to learn how to manage your books the right way? We’ll walk you through the tools, workflows, and reports so you’re not left guessing.
- 👩💻 Live, On-Demand Support – Hit a wall? Have a quick question? Need a second set of eyes? We’re available when you need us—without the overhead of a full-time bookkeeper.
- 🧹 Cleanup, Setup, and Review Services – Whether you’re just getting started or need to fix what’s already there, we’ll help you get your books back on track.
Final Thought: Know When to DIY—and When to Delegate
Bookkeeping is the financial foundation of your business. Done right, it gives you clarity, confidence, and control. But it’s okay to admit when you’re out of your depth—or when your time is better spent running your business, not buried in spreadsheets.
So ask yourself:
Is DIY bookkeeping saving you time and money—or costing you both?
When you’re ready for support, Your Bookkeeper On Call is here with flexible solutions that fit your business and your budget. Whether you’re a hands-on entrepreneur or ready to offload the books entirely, we’ve got your back.
👉 Ready to get started? Contact us here or schedule a free consultation today.
