Sales tax is one of the more complicated concepts supported by QuickBooks Online.
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Are All Your Bank Deposits Really Protected? Understanding FDIC Insurance Limits by Allyson Moore Everyone recognizes that small, comforting FDIC sign displayed at their local bank — it’s the government’s promise that your money is safe. But what many don’t realize is that FDIC insurance comes with limits. And for individuals or businesses holding…
If you’re preparing to switch systems, upgrade software, or clean up years of financial history, you may be facing one of the most crucial IT processes: data migration. For QuickBooks users, this often means replacing a company data file to fix performance issues, eliminate errors, or transition to a newer version of QuickBooks. Whether you’re…
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February 24, 2025
How to Plan a Data Migration in 6 Easy Steps
If you’re preparing to switch systems, upgrade software, or clean up years of financial history, you may be facing one of the most crucial IT processes: data migration. For QuickBooks users, this often means replacing a company data file to fix performance issues, eliminate errors, or transition to a newer version of QuickBooks.
Whether you’re migrating full transaction histories or just lists and opening balances, following a clear migration plan can save you time, reduce errors, and ensure your accounting integrity remains intact.
In this guide, we break down how to plan a data migration in six easy steps, tailored for QuickBooks but applicable across platforms. Let’s get started.
Step 1: Reorganize and Clean Up Lists
Before beginning your data migration, make sure your lists—like customers, vendors, chart of accounts, and items—are in order. Re-sorting lists ensures QuickBooks’ internal indexing is correct, which helps prevent import errors in the new file.
Action Items:
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Use QuickBooks’ “Re-sort List” function for all major lists.
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Merge duplicates (e.g., two customer records for the same company).
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Inactivate obsolete items, accounts, or vendors.
According to TechRepublic, “dirty data” can cost companies up to $15 million annually in operational inefficiencies. (Source)
Step 2: Verify and Repair File Damage
Before migrating data, run QuickBooks’ Verify and Rebuild utilities to detect and fix file corruption. Data issues that go unresolved pre-migration can cause serious problems in the new file, including inaccurate reports and failed imports.
How to Run Verify:
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Log in as Admin in single-user mode.
-
Go to File > Utilities > Verify Data.
If errors are found, proceed to File > Utilities > Rebuild Data. Always back up your file before performing a rebuild.
Tip: Run a second Verify after rebuilding to ensure all issues are resolved.
Step 3: Close or Reconcile Transactions
Next, ensure that only real-world open transactions remain in the file. You don’t want to migrate unpaid invoices or bills that have already been settled.
Reports to Review:
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Open Invoices
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Unpaid Bills Detail
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A/R and A/P Aging Summaries
If you find duplicate or unlinked transactions, correct them using:
-
Receive Payments for invoices
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Pay Bills for bill payments
A 2021 study by Forrester found that companies with clean financial data reduced monthly reconciliation time by up to 30%. (Source)
Step 4: Review Inventory for Errors
Inventory tracking in QuickBooks can be especially sensitive during a data migration. Negative inventory values are a common source of trouble, often causing inflated or erratic average costs.
Run the Inventory Valuation Detail Report:
-
Go to Reports > Inventory > Inventory Valuation Detail
-
Set the date range to “All”
-
Look for negative values in the “On Hand” column
Fixes May Include:
-
Adjusting transaction dates
-
Correcting quantities received or sold
-
Running a physical count and reconciling in QuickBooks
⚠️ According to Aberdeen Research, inventory inaccuracies lead to $1.1 trillion in losses globally each year. (Source)
Step 5: Reconcile Reports to Real-World Balances
You’ll want your new file to reflect accurate balances, not just structurally correct data.
Reports to Analyze:
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Balance Sheet
-
Profit & Loss Statement
-
Sales Tax Payable
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Uncategorized Expenses
If your books don’t align with your bank statements, credit card accounts, or sales tax filings, fix those issues now. Migrating flawed financials only compounds errors in your new system.
Step 6: Audit Your Workflow and Dependencies
Before finalizing your data migration, take stock of how your team uses QuickBooks. This includes custom fields, memorized transactions, and third-party apps like payroll services or inventory tools.
Key Questions:
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Are non-posting transactions like Estimates or Sales Orders essential?
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Do you sync QuickBooks with outside apps (e.g., Shopify, Gusto)?
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What fields or reports are mission-critical?
Knowing what matters to your workflow ensures nothing essential is lost in the transition.
FAQs About Data Migration
What is data migration?
Data migration is the process of transferring data from one system to another—whether it’s a software upgrade, platform change, or a file cleanup. For QuickBooks users, this might mean migrating data between company files or to/from cloud versions like QuickBooks Online.
How long does a data migration take?
Simple migrations (lists only) may take a few hours. Full transaction history migrations can take several days depending on file size, data complexity, and testing. Working with a professional provider can cut this timeline in half.
What types of data can be migrated in QuickBooks?
You can migrate:
-
Chart of Accounts
-
Customer & Vendor Lists
-
Items & Inventory
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Transactions (invoices, bills, payments)
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Payroll data (with limitations)
Non-posting entries like Sales Orders often need manual handling.
Can I migrate from QuickBooks Desktop to QuickBooks Online?
Yes, but it requires a structured process. Not all data types migrate automatically, and some custom fields or third-party app integrations may need to be rebuilt post-migration. Always perform a backup before initiating.
Final Thoughts
A successful data migration hinges on preparation. By cleaning up your lists, verifying your file, closing out old transactions, checking inventory, reviewing financials, and auditing your workflow, you’ll set the stage for a seamless transition to a new QuickBooks file—or any other accounting platform.
Need help with your QuickBooks data migration? Let our experts guide the way. With 20+ years of experience, we make migrations smooth, accurate, and stress-free.
Talk to An Advisor Today
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Your business has hit an inflection point. It’s a place of uncomfortable, chaotic success. You’ve grown beyond what your part-time bookkeeper (or worse, your own late-night QuickBooks sessions) can handle. The “financials” you get are a month late, you don’t fully trust them, and you’re making million-dollar decisions by “feel.” You know you have a…
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November 10, 2025
Fractional Controller vs. Full-Time Controller: A 2026 Guide for SMBs
Your business has hit an inflection point.
It’s a place of uncomfortable, chaotic success. You’ve grown beyond what your part-time bookkeeper (or worse, your own late-night QuickBooks sessions) can handle. The “financials” you get are a month late, you don’t fully trust them, and you’re making million-dollar decisions by “feel.”
You know you have a problem. You’re flying blind. You know you need someone who can go beyond just recording history and start using the data to build a financial strategy.
You need a Controller.
Then comes the sticker shock. You do a quick search on Glassdoor and see that the average salary for an experienced financial controller can easily top $120,000, $150,000, or more. And that’s before benefits, bonuses, and recruitment.
For many Small and Medium-Sized Businesses (SMBs), this cost feels like a brick wall. It’s the “C-suite” price tag you’re not sure you can afford. This single dilemma stops thousands of businesses from getting the financial oversight they desperately need, trapping them in a cycle of reactive, anxiety-driven management.
But what if you didn’t have to choose between “flying blind” and a $150,000+ hire?
There is a third, more strategic option: the Fractional Controller. This modern, flexible model is arguably one of the most powerful financial advantages an SMB can leverage today.
But which is really right for you? A full-time, in-house employee or a part-time, outsourced expert? This isn’t just a question of cost—it’s a strategic choice about scalability, expertise, and risk.
Let’s break down the true costs, benefits, and the exact decision framework you need.
First, What Does a Controller Actually Do?
This is the most critical concept to understand. A Controller is not just an experienced bookkeeper. This is the biggest (and most costly) misunderstanding in small business finance.
Let’s clarify the financial hierarchy:
- Bookkeeper (The “Historian”): They look to the past. Their job is to accurately record daily financial transactions: managing bills (AP), sending invoices (AR), processing payroll, and reconciling bank accounts. They build the data.
- Controller (The “Inspector”): They manage the present. Their job is to ensure the bookkeeper’s data is 100% accurate and compliant. They verify, analyze, and report on the data.
- CFO (The “Strategist”): They look to the future. They use the Controller’s accurate reports to build strategic models, manage risk, secure financing, and guide the company’s long-term growth.
A Controller is the vital bridge between day-to-day bookkeeping and high-level strategy.
Key Responsibilities of a Controller:
- Manages Month-End Close: This is their #1 job. They ensure all accounts are reconciled and the books are “closed” accurately and on time (e.g., within 10-15 days of month-end).
- Prepares Financial Statements: They produce the official P&L, Balance Sheet, and Statement of Cash Flows that you, your bank, and your investors can trust.
- Establishes Internal Controls: They create systems to protect the company’s assets—separating duties to prevent errors and, more importantly, fraud.
- Manages Cash Flow: They don’t just record cash; they manage it. They build short-term cash flow forecasts to ensure you can make payroll and pay bills.
- Ensures Tax & Regulatory Compliance: They manage sales tax, payroll tax, and all the complex compliance rules, and they act as the main liaison for your CPA at tax time.
- Oversees the “Tech Stack”: They are often responsible for optimizing the financial software (QuickBooks, bill pay, payroll, etc.) to create efficiency.
Without a controller, you are likely missing all of these things. Your “financials” are just a data dump, not a trusted report.
The Full-Time Controller: The Traditional Path
This is the classic solution. You write a job description, hire a W-2 employee, and give them an office (or a permanent remote login). They work for you and only you, 40+ hours a week.
The True Cost of a Full-Time Controller
This is where most SMB owners get a skewed picture. The “salary” is just the beginning. Let’s do the real math.
1. The Base Salary:
According to 2024-2025 data from sources like Salary.com and Robert Half, the average salary for an experienced Financial Controller in the US is between $120,000 and $180,000, depending on your location and industry. Let’s use a conservative average of $130,000.
2. The “Fully-Loaded” Cost (1.3x – 1.5x Salary):
You don’t just pay salary. You pay for the “fully-loaded” cost of an employee, which adds 30-50% on top.
- Payroll Taxes (FICA, FUTA, SUTA): ~8-10%
- Health Insurance: ~$10,000 – $20,000 per year
- Retirement (401k) Match: ~3-6%
- Workers’ Comp & Other Insurance: ~2-4%
- Paid Time Off (Vacation, Sick): ~4-6%
The Math: $130,000 (Salary) + $45,500 (35% Burden) = $175,500 per year.
3. The Hidden Costs (The Ones No One Talks About):
- Recruitment: The cost to find and hire a high-level candidate is significant. Glassdoor estimates the average US company spends $4,700 per hire. For a senior role, this can be much higher.
- Training & Development: You need to pay for their professional certifications, QuickBooks training, and industry updates. (Est: $2,000 – $5,000 annually).
- Technology & Overhead: You provide the $2,000 laptop, the extra software licenses, and the desk space. (Est: $3,000+ annually).
- Turnover Risk: This is the monster. According to the Society for Human Resource Management (SHRM), replacing a salaried employee can cost 6 to 9 months of their salary. If your $130k controller leaves, it could cost you $65,00_0 – $97,500_ in lost productivity, recruitment, and training to replace them.
Total Annual Cost (Conservative): $175,500 + $5,000 (hidden) = $180,500+
Pros and Cons of a Full-Time Controller
PROS:
- 100% Dedicated: Their entire focus is on your business, 40+ hours a week.
- Deep Cultural Integration: They are “in the building” (physically or virtually), attending all meetings and absorbing the company culture.
- Can Manage On-Site Staff: If you have an in-house team of bookkeepers, an on-site controller can manage them directly.
CONS:
- Extreme Cost: It is by far the most expensive option.
- Single Point of Failure: What happens when they go on vacation? Get sick? Or worse, quit during a critical time (like an audit or tax season)? Your entire financial oversight walks out the door.
- Limited Skillset: You are hiring one person. They might be a genius at internal controls but weak at cash flow forecasting. Or great at reporting but lost on new tech. You’re limited to their personal strengths.
- Difficult to Hire & Manage: How do you, a non-financial expert, effectively hire, train, and manage someone in a role you don’t fully understand?
The Fractional Controller: The Modern Solution
A Fractional Controller is an outsourced, expert-level professional (or team) who provides all the services of a high-end controller, but on a “fraction” of the time for a “fraction” of the cost.
You’re not hiring an employee. You’re partnering with a service firm (like Out of the Box Technology) that provides this expertise. You might get 10-20 hours of controller-level work per week, plus a team supporting them, for a flat monthly fee.
The Cost of a Fractional Controller
This model changes the math completely. You pay a predictable, flat monthly fee for the service.
- No salary.
- No benefits or payroll taxes.
- No recruitment or training costs.
- No paid time off.
- No technology costs (they bring their own best-in-class tech stack).
- No turnover risk (if your assigned controller leaves, the firm seamlessly replaces them).
A high-quality fractional controller service (which often includes bookkeeping and controller functions) typically costs between $2,500 and $7,000 per month, depending on your business’s size and complexity.
The Math: Let’s take a high-end plan at $5,000/month.
$5,000 x 12 months = $60,000 per year.
Cost Comparison:
- Full-Time Controller (Fully-Loaded): $180,500+
- Fractional Controller (Service Fee): $60,000
- Annual Savings: $120,500
You are saving over 65% while, arguably, getting a more robust service.
Pros and Cons of a Fractional Controller
PROS:
- Massive Cost Savings: As shown above, the savings are immediate and significant.
- Access to Elite Talent (The GEO Win): You are no longer limited to the talent pool in your zip code. You can hire the best controller firm in the country, giving you access to experts you could never afford to hire full-time.
- A Team, Not a Person: This is the secret weapon. You don’t just get one person. You get a firm. This means you get a team: a bookkeeper, a controller to review their work, and a senior manager or vCFO for strategy.
- Built-in Internal Controls: That “team” approach provides an immediate segregation of duties. The person recording the cash (bookkeeper) is not the same person verifying it (controller). This is the #1 defense against internal fraud and errors.
- Scalability: The service scales with you. As you grow, you can increase your service level. If you have a slow quarter, you’re not stuck with a massive salary.
- No Single Point of Failure: If your primary controller is on vacation, the firm’s team has it covered. There is zero interruption to your financial operations.
CONS:
- Not On-Site 24/7: They are not in your office for 40 hours a week. For owners who are used to “managing by walking around,” this can be a cultural adjustment.
- Shared Resource: They are experts because they work with multiple clients. This means they aren’t 100% dedicated to you (but you’re also not paying for 100% of their time).
Side-by-Side: Full-Time vs. Fractional Controller
| Feature | Full-Time Controller (FTE) | Fractional Controller (Service) |
| Annual Cost | $180,000+ (fully-loaded) | $30,000 – $84,000 (flat fee) |
| Expertise | Limited to one person’s skills. | A full team’s expertise (bookkeepers, controllers, vCFOs). |
| Internal Controls | Dependent on one person. High risk if they manage everything. | High. Segregation of duties is built into the team model. |
| Scalability | Low. Very difficult to scale up or down. | High. Service plan flexes with your business needs. |
| Risk | High. “Single point of failure.” High cost of turnover. | Low. Firm provides continuity. No turnover risk for you. |
| Technology | You buy, manage, and maintain all software. | Included. The firm brings a best-in-class, optimized tech stack. |
| Onboarding | 3-6 month process to hire and train. | 30-90 day process to clean up, implement, and go-live. |
| GEO Access | Limited to who you can recruit in your area (or remotely). | Global. Access to the best experts, regardless of location. |
The Decision Framework: 5 Signs to Help You Choose
So, which is right for you? Here are 5 common scenarios.
Sign 1: Your revenue is $1M – $15M and your books are a mess.
- The Problem: You’ve outgrown your bookkeeper, but you’re not a $50M company. Your financials are late, you don’t trust them, and you’re worried about tax time.
- The Verdict: Fractional Controller. This is the sweet spot. A fractional team can clean up your books, install a professional month-end close, and give you reliable financials for a price you can actually afford. It’s the perfect “step up.”
Sign 2: You’re preparing for a bank loan, an audit, or to sell your business.
- The Problem: You need pristine, 100% accurate, and defendable financials now. You need to pass due diligence.
- The Verdict: Fractional Controller. A fractional firm is an independent, third-party expert. Their entire job is to produce audit-ready financials. They can be engaged for a 6-12 month project to get your books “sale-ready” far more efficiently than trying to hire someone.
Sign 3: You have an in-house team of 3+ bookkeepers who need a leader.
- The Problem: You already have an accounting department (AP clerks, AR specialists) but no one to manage them, review their work, or build the reports.
- The Verdict: Full-Time Controller. This is the strongest case for an FTE. You need a dedicated, on-site manager to lead your existing team. A fractional controller can do this, but a full-time manager is often the better cultural and operational fit.
Sign 4: You have extremely high transaction volume and industry-specific complexity.
- The Problem: You are a $25M+ business with multi-state operations, complex inventory, or specific government reporting that requires 40+ hours a week of oversight.
- The Verdict: Full-Time Controller. When the volume of work genuinely justifies a 40+ hour workweek, an FTE makes sense. The cost is justified by the sheer complexity. (Though many businesses in this range use both—an FTE controller managed by a Fractional CFO).
Sign 5: You’re a visionary CEO who hates finance and just wants to focus on growth.
- The Problem: You know finance is your weakness, and you’ve been neglecting it. You need a trusted partner to “own” it so you can get back to sales, marketing, and product.
- The Verdict: Fractional Controller. This is a strategic partnership. You’re not just hiring a number-cruncher; you’re hiring a system that gives you back your time and confidence. You get expert reports and a strategic advisor, allowing you to be the CEO, not the head bookkeeper.
A Real-World Example
Let’s look at “Sarah,” the owner of a $7M-a-year professional services firm.
- Her Problem: She had a $25/hr bookkeeper who was overwhelmed. Her financials were 60 days late. She’d won a big new client, but her cash flow was tighter than ever. She was showing a “profit” but couldn’t make payroll.
- Her Dilemma: She interviewed for a full-time controller and got a quote for $140,000 + benefits. She couldn’t afford it.
- The Solution: She engaged a fractional controller firm for $4,000/month ($48,000/year).
- The Result: In 60 days, the fractional team had:
- Cleaned up 6 months of messy books.
- Implemented a new tech stack (QuickBooks, Bill.com, Dext) that automated 80% of the data entry.
- Established a 10-day, on-time month-end close.
- Delivered a cash flow forecast that showed her why her cash was tight (her AR was at 55 days).
- Helped her tighten her invoicing cycle, freeing up $150,000 in cash.
Sarah didn’t just save $100,000+ on a salary. She unlocked $150,000 in her own cash and, for the first time, had financial clarity. That is the power of the fractional model.
Frequently Asked Questions (FAQs)
1. Won’t I lose control by outsourcing my accounting?
No, this is the most common myth. You will gain control. Right now, you probably have a “black box” where you hope the numbers are right. A professional firm gives you a dashboard with 24/7 access to your data, plus weekly and monthly reports that are clear and accurate. You move from guessing to knowing.
2. What’s the difference between a Fractional Controller and a Fractional CFO?
It’s the same difference as in the full-time world. The Fractional Controller is focused on accuracy—closing the books, managing cash, and ensuring compliance. The Fractional CFO is focused on strategy—building 5-year models, managing investor relations, and guiding high-level decisions. Most firms (like us) bundle these services.
3. What if I already have a bookkeeper I like?
That’s a great setup! A fractional controller can be hired to supervise your existing bookkeeper. They’ll review their work, manage the month-end close, and add that crucial layer of oversight and accuracy that you’re missing.
The Bottom Line: Upgrade Your Expertise, Not Just Your Headcount
For 9 out of 10 SMBs in the $1M to $15M revenue range, the choice is clear.
Hiring a full-time controller is a massive, high-risk, six-figure investment in a single person.
Partnering with a fractional controller is a flexible, lower-cost, low-risk investment in a team of experts and a proven system.
You save 60-70% on cost, eliminate the “single point of failure” risk, and gain access to a level of talent and technology you could never afford in a single hire. It’s not just a cost-cutting move; it’s a strategic upgrade that turns your finance department from a liability into your sharpest competitive advantage.
Ready to See the Math for Your Business?
Stop guessing and start knowing. The team at Out of the Box Technology can provide a free, no-obligation analysis of your current accounting. We’ll show you the gaps and build a flat-fee proposal to provide you with a world-class, fractional accounting team.
Talk to An Advisor Today
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You open your QuickBooks P&L (Profit & Loss) statement. You’re looking for answers. You want to know, “Are we actually making money? Which services are profitable? Where are we over-spending?” Instead, you’re hit with a 10-page report that makes no sense. You have 40 different “Uncategorized Expense” line items. You have “Sales” as one giant…
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Along with the holiday rush and a final push for sales, “that” email has probably landed in your inbox. It’s from your accountant, and the subject line is something like, “Getting Ready for Tax Season.” For many small business owners, this email triggers a wave of anxiety. It’s the official start of the scramble—the hunt…
Claim your complimentary bookeeping assesment today
November 04, 2025
Top 10 Year-End Bookkeeping Questions Answered
Along with the holiday rush and a final push for sales, “that” email has probably landed in your inbox.
It’s from your accountant, and the subject line is something like, “Getting Ready for Tax Season.”
For many small business owners, this email triggers a wave of anxiety. It’s the official start of the scramble—the hunt for receipts, the confusion over reports, and the sinking feeling that your books are… well, a bit of a mess.
You’re not alone. At Out of the Box Technology, we’ve helped thousands of business owners navigate this exact process. We find that the same anxieties and questions come up every single year. The problem isn’t the work itself; it’s the uncertainty.
The good news is that clarity is the best cure for financial anxiety.
To help you move from chaos to confidence, we’ve compiled the 10 most-asked year-end bookkeeping questions we hear from business owners like you. Here are the expert, straightforward answers you need.
1. What’s the real deadline for my year-end bookkeeping?
This is the most common question, and the answer is a bit more complex than just “Tax Day.” There isn’t one deadline; there are three you need to know.
- Deadline 1: January 31, 2025. This is the first and most urgent deadline. It is the non-negotiable date for filing all employee W-2s and all contractor 1099-NEC forms with the government and sending copies to the recipients. Missing this can result in steep penalties.
- Deadline 2: Your CPA’s Deadline (e.g., March 1st). Your tax preparer needs time to do their job. They can’t just take your numbers on April 14th. Most CPAs will set a deadline (often in late February or early March) for receiving your “tax-ready” package. If you miss it, you’ll be filing an extension (and you’ll still have to pay your estimated taxes on time).
- Deadline 3: The Tax Filing Deadline (e.g., March 15 or April 15, 2025). This is the final date to file your business tax return. This date depends on your business structure (e.g., March 15 for S-Corps and Partnerships, April 15 for C-Corps and Sole Proprietorships).
The Expert Answer: Your “real” deadline is January 31st. You must have your books clean enough by then to accurately identify all 1099 contractor payments. Your goal should be to have your entire year-end close completed by this date, allowing all of February for a calm, strategic review with your accountant.
2. What’s the difference between “closing the books” and “filing my taxes”?
This is a critical distinction that trips up many owners.
Think of it this way: Your bookkeeper is the builder, and your tax preparer is the building inspector.
- Closing the Books: This is the building process. It’s the work you (or your bookkeeping team) do inside your accounting system to ensure everything is 100% accurate for the fiscal year. This includes reconciling all bank accounts, categorizing all expenses, posting depreciation, verifying loan balances, and finalizing your reports. The final product is a set of “locked,” accurate financial statements.
- Filing Your Taxes: This is the inspection. Your tax preparer takes your finished financial statements and uses them to fill out the complex forms required by the IRS.
Why It Matters: Your tax preparer’s job is not to do your bookkeeping. They assume the numbers you give them are correct. If you hand your CPA a messy, unreconciled set of books (a half-built house), they will either:
- File an inaccurate return that could put you at risk.
- Refuse to file and send you away.
- Charge you an enormous hourly fee to do the “clean-up” work themselves—a job they are overqualified and too expensive for.
Action Step: Your goal is to hand your CPA a “tax-ready package” based on a closed set of books. This is the entire purpose of our Accounting Clean-Up Services. We are the “builders” who make sure your foundation is perfect before the inspector arrives.
3. The 1099 question: Who gets one, what’s the form, and when?
This is, without a doubt, the single greatest source of year-end panic.
The Short Answer: You must send a Form 1099-NEC (Non-Employee Compensation) to any unincorporated contractor, freelancer, or individual (including LLCs) to whom you paid $600 or more for services during the year.
Let’s break that down:
- Who gets one?
- YES: Your independent marketing consultant, the cleaning service (if it’s an LLC, not a corporation), your freelance designer, and your lawyer (legal fees are a special case and always get a 1099).
- NO: Employees (they get a W-2), and corporations (e.g., “S-Corps” or “C-Corps”).
- How do I know if they’re a corporation? You ask them! Before you ever pay a new vendor, you should have them fill out a Form W-9. This form is your “golden ticket.” On it, they check a box telling you their exact legal structure (e.g., “Sole Proprietor,” “LLC,” “S-Corp”). If they are not an S-Corp or C-Corp, you need to track their payments for 1099 purposes.
- What’s the deadline? January 31st. This is a hard deadline to both the IRS and the contractor.
- What if I paid them via credit card or PayPal? This is a key exception. If you paid a contractor via a “third-party payment network” (like PayPal, Stripe, Venmo, or a credit card), you do not send them a 1099. The payment processor is responsible for that. You only file for payments made by cash, check, or direct bank transfer.
4. How do I handle expenses I paid for with my personal card?
This is the “co-mingling” problem, and it’s the #1 mistake we see.
The Wrong Way: You buy a new business laptop on your personal Amazon account. In your accounting, you create a “bill” from Amazon and mark it as “paid” from your personal account. This is a messy, complex nightmare.
The Right Way (The “Owner’s Contribution”):
- Stop doing it! The first rule of business is a separate bank account.
- But if you did… You need to record it as an Owner’s Contribution. Your business “owes” you that money back.
- You create the expense in your books (e.g., “$1,500 for Computer Equipment”).
- Instead of showing it paid from the business bank account, you categorize the “payment” to a special equity account, typically called “Owner’s Contribution” or “Shareholder Loan.”
This action tells the Balance Sheet that the business acquired an asset (the computer) and the owner’s equity in the business went up by $1,500 (because you invested your personal cash).
The opposite is also true: When you pay yourself, it’s not a “salary” (unless you’re on payroll) and it’s not an “expense.” It’s an Owner’s Draw, which reduces your equity.
5. Do I really have to count my inventory?
Yes. 100%. If you sell a physical product, you are required by the IRS to perform a physical inventory count at year-s end.
Why It Matters: This isn’t just busy work. Your inventory count is directly tied to your Cost of Goods Sold (COGS), which is one of the single biggest expenses on your P&L.
The formula for COGS is: Beginning Inventory + Purchases - Ending Inventory = COGS
If your “Ending Inventory” number is a guess, your entire COGS number is a guess. And if your COGS is a guess, your entire Net Profit is a guess.
Example:
- You think you have $20,000 in inventory left.
- You actually have $10,000 in inventory (due to theft, damage, or miscounting).
- By overstating your inventory, you are understating your COGS by $10,000.
- This means you are overstating your profit by $10,000.
- Result: You will pay taxes on $10,000 of “phantom profit” that you never actually earned.
Action Step: Schedule your physical inventory count. Count everything. Then, give this final number to your bookkeeper or accountant so they can make an adjusting journal entry to make the Balance Sheet match reality.
6. My books are a mess. How “clean” do they need to be for my CPA?
This is the “shame” question, and it’s the one that keeps business owners up at night.
The Expert Answer: Your books need to be “audit-ready.”
This doesn’t mean “perfect.” It means provable. “Audit-ready” means:
- Every single transaction (in and out) is categorized—no “Uncategorized” or “Miscellaneous” junk drawers.
- Every single bank, credit card, and loan account has been reconciled for all 12 months. This means your books exactly match the bank statements.
- There is a receipt or source document for all major purchases.
- Your Balance Sheet is accurate. (Your loan balances are correct, your inventory is right, etc.)
A SCORE.org survey found that 40% of small business owners spend 80+ hours per year on bookkeeping tasks. If your books are a mess, that 80 hours can easily become 200 hours of stressful, year-end work.
This is precisely why our Monthly Outsourced Bookkeeping exists. Our clients don’t have a year-end scramble. They have a “year-end review” because the work is already done, reconciled, and proven, every single month.
7. What reports does my accountant actually need?
You’re worried about handing over a 200-page document. Your accountant just wants the “Big 3” and one master list.
Here is the perfect “Tax-Ready Package” to send your CPA:
- The Profit & Loss (P&L): Your income and expenses for the year. This shows if you made a profit.
- The Balance Sheet: Your assets, liabilities, and equity on December 31st. This shows your financial health.
- The Statement of Cash Flows: This explains why your cash balance changed, even if your P&L showed a profit.
- The General Ledger (or Trial Balance): This is the “master” report. It’s a list of every single transaction, by account, that adds up to the final numbers on the P&L and Balance Sheet. This is what your CPA will use to dig in and find details.
Pro-Tip: Run a “P&L vs. Last Year” comparison for yourself. Look for any huge jumps or drops (e.g., “Why did ‘Repairs’ go up 200%?”). Be ready to explain these big changes to your CPA. This is the kind of high-level analysis a Fractional Controller would prepare for you.
8. Cash vs. Accrual: Which one am I, and does it matter?
This concept is simpler than it sounds, and yes, it matters immensely for your taxes.
- Cash Basis: You record revenue when you receive the cash. You record an expense when you pay the bill.
- Accrual Basis: You record revenue when you earn it (e.g., when you send the invoice). You record an expense when you incur it (e.g., when you receive the bill).
Example: You do a $10,000 project for a client. You finish the work and send the invoice on December 20, 2024. The client pays you on January 10, 2025.
- On a Cash Basis, that $10,000 is 2025 revenue.
- On an Accrual Basis, that $10,000 is 2024 revenue.
Why It Matters: You must be consistent. Your CPA has likely already chosen a method for you on your past tax returns. You can’t just switch back and forth. This is a technical decision that has massive implications for your tax bill.
Action Step: Ask your CPA, “Am I filing my taxes on a cash or accrual basis?” Their answer will determine how you finalize your year-end reports.
9. What’s the difference between a W-2 and a 1099, really?
This question is about worker classification, and it’s one of the IRS’s favorite audit triggers. Misclassifying an employee as a contractor can lead to crushing penalties, including back payroll taxes.
- W-2 (Employee): You control how, when, and where they work. You provide the tools. You give them a regular wage and benefits. You withhold and pay their payroll taxes.
- 1099 (Contractor): They are a business. They control how, when, and where they work. They use their own tools. They send you invoices. You pay their invoices just like any other vendor. You do not withhold taxes.
The Test: The IRS’s test is all about control. If you treat someone like an employee (e.g., you set their hours, you give them a company laptop, you manage their day-to-day tasks), you must pay them as an employee. You cannot just call them a contractor to avoid payroll taxes.
Action Step: Review your 1099 vendors. Is there anyone on that list who acts like an employee? If so, you need to have a serious conversation with your CPA or HR consultant before you file.
10. Can I just do this myself?
This is the ultimate question: “Do I spend my time or my money?”
The Expert Answer: You can do your own year-end bookkeeping, just as you can change your own car’s oil.
The real questions are:
- Do you have the 20, 40, or 80+ hours it will take to do it right?
- Do you know what to look for? Will you catch the miscategorized expense that’s costing you $1,000 in taxes?
- Do you know how to reconcile a complex loan or an owner’s contribution?
- What is your time worth? If you spend 40 hours on bookkeeping, that’s 40 hours you didn’t spend on sales, marketing, or serving your clients. If your billable rate is $150/hour, you just spent **$6,000 worth of your own time** to save a few hundred dollars on bookkeeping.
You’re a visionary entrepreneur. You’re a master of your craft. You are probably not an expert bookkeeper. And that’s okay.
A clean year-end isn’t a chore; it’s the foundation for a profitable new year. It’s the data you need to make smart, strategic decisions. Don’t let the most important financial task of the year be done by a stressed, overworked, non-expert (you).
Still Have Questions? (Advanced FAQs)
Q1: What’s the single biggest year-end mistake small businesses make? Hands down, co-mingling funds (see question #4). It’s the fastest way to make your books an indecipherable mess and lose all legal protection from your LLC. The second biggest is failing to reconcile bank accounts, which means the data in your reports is built on a foundation of sand.
Q2: What’s the difference between a “soft close” and a “hard close”? A “soft close” is what we do for our monthly bookkeeping clients—we reconcile the month, review reports, and lock that period. A “hard close” is the year-end. It includes posting final adjusting entries (like depreciation) and formally “locking” the fiscal year in the software so no one can accidentally change 2024’s data in the middle of 2025.
Q3: Help! I just found a big mistake from last year. What do I do? Do not “just fix it” in the current year. This will make both years’ reports inaccurate. You must contact your tax preparer. The “correct” way to fix it is often by making a “Retained Earnings” adjustment, and your CPA may need to file an amended tax return for the prior year.
Your 2026 Starts With a Clean 2025
Don’t let another January be lost to financial chaos. These questions are a start, but the answer isn’t just “knowledge”—it’s action.
If you read through this list and felt more overwhelmed than relieved, that’s a sign. It’s a sign that it’s time to delegate. It’s a sign that it’s time to let the experts handle the books, so you can get back to building the business.
Let us take this entire, stressful checklist off your plate.
Talk to An Advisor Today
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Claim your complimentary bookeeping assesment today
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You open your QuickBooks P&L (Profit & Loss) statement. You’re looking for answers. You want to know, “Are we actually making money? Which services are profitable? Where are we over-spending?” Instead, you’re hit with a 10-page report that makes no sense. You have 40 different “Uncategorized Expense” line items. You have “Sales” as one giant…
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It’s the paradox that haunts most small business owners. You look at your Profit & Loss statement. It’s a good month! You’re showing a healthy profit. You feel a moment of relief. Then you look at your bank account. The number staring back at you is nowhere near the profit on your P&L. You have…
Claim your complimentary bookeeping assesment today
Talk to An Advisor Today
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It’s 10:00 PM on a Tuesday. You just finished a 12-hour workday. Before you can finally close your laptop, you pull up your bank account. You feel that familiar, sinking knot in your stomach. You just landed a huge $50,000 project. Your P&L statement says you’re “profitable.” So why is your bank balance just $12,000…
You open your QuickBooks P&L (Profit & Loss) statement. You’re looking for answers. You want to know, “Are we actually making money? Which services are profitable? Where are we over-spending?” Instead, you’re hit with a 10-page report that makes no sense. You have 40 different “Uncategorized Expense” line items. You have “Sales” as one giant…
Your business has hit an inflection point. It’s a place of uncomfortable, chaotic success. You’ve grown beyond what your part-time bookkeeper (or worse, your own late-night QuickBooks sessions) can handle. The “financials” you get are a month late, you don’t fully trust them, and you’re making million-dollar decisions by “feel.” You know you have a…
It’s the paradox that haunts most small business owners. You look at your Profit & Loss statement. It’s a good month! You’re showing a healthy profit. You feel a moment of relief. Then you look at your bank account. The number staring back at you is nowhere near the profit on your P&L. You have…
Claim your complimentary bookeeping assesment today
Talk to An Advisor Today
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It’s 10:00 PM on a Tuesday. You just finished a 12-hour workday. Before you can finally close your laptop, you pull up your bank account. You feel that familiar, sinking knot in your stomach. You just landed a huge $50,000 project. Your P&L statement says you’re “profitable.” So why is your bank balance just $12,000…
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Your business has hit an inflection point. It’s a place of uncomfortable, chaotic success. You’ve grown beyond what your part-time bookkeeper (or worse, your own late-night QuickBooks sessions) can handle. The “financials” you get are a month late, you don’t fully trust them, and you’re making million-dollar decisions by “feel.” You know you have a…
It’s the paradox that haunts most small business owners. You look at your Profit & Loss statement. It’s a good month! You’re showing a healthy profit. You feel a moment of relief. Then you look at your bank account. The number staring back at you is nowhere near the profit on your P&L. You have…
Claim your complimentary bookeeping assesment today
Talk to An Advisor Today
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It’s 10:00 PM on a Tuesday. You just finished a 12-hour workday. Before you can finally close your laptop, you pull up your bank account. You feel that familiar, sinking knot in your stomach. You just landed a huge $50,000 project. Your P&L statement says you’re “profitable.” So why is your bank balance just $12,000…
You open your QuickBooks P&L (Profit & Loss) statement. You’re looking for answers. You want to know, “Are we actually making money? Which services are profitable? Where are we over-spending?” Instead, you’re hit with a 10-page report that makes no sense. You have 40 different “Uncategorized Expense” line items. You have “Sales” as one giant…
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Claim your complimentary bookeeping assesment today
Talk to An Advisor Today
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It’s 10:00 PM on a Tuesday. You just finished a 12-hour workday. Before you can finally close your laptop, you pull up your bank account. You feel that familiar, sinking knot in your stomach. You just landed a huge $50,000 project. Your P&L statement says you’re “profitable.” So why is your bank balance just $12,000…
You open your QuickBooks P&L (Profit & Loss) statement. You’re looking for answers. You want to know, “Are we actually making money? Which services are profitable? Where are we over-spending?” Instead, you’re hit with a 10-page report that makes no sense. You have 40 different “Uncategorized Expense” line items. You have “Sales” as one giant…
Your business has hit an inflection point. It’s a place of uncomfortable, chaotic success. You’ve grown beyond what your part-time bookkeeper (or worse, your own late-night QuickBooks sessions) can handle. The “financials” you get are a month late, you don’t fully trust them, and you’re making million-dollar decisions by “feel.” You know you have a…
It’s the paradox that haunts most small business owners. You look at your Profit & Loss statement. It’s a good month! You’re showing a healthy profit. You feel a moment of relief. Then you look at your bank account. The number staring back at you is nowhere near the profit on your P&L. You have…
Claim your complimentary bookeeping assesment today
Talk to An Advisor Today
You might also like these articles
It’s 10:00 PM on a Tuesday. You just finished a 12-hour workday. Before you can finally close your laptop, you pull up your bank account. You feel that familiar, sinking knot in your stomach. You just landed a huge $50,000 project. Your P&L statement says you’re “profitable.” So why is your bank balance just $12,000…
You open your QuickBooks P&L (Profit & Loss) statement. You’re looking for answers. You want to know, “Are we actually making money? Which services are profitable? Where are we over-spending?” Instead, you’re hit with a 10-page report that makes no sense. You have 40 different “Uncategorized Expense” line items. You have “Sales” as one giant…
Your business has hit an inflection point. It’s a place of uncomfortable, chaotic success. You’ve grown beyond what your part-time bookkeeper (or worse, your own late-night QuickBooks sessions) can handle. The “financials” you get are a month late, you don’t fully trust them, and you’re making million-dollar decisions by “feel.” You know you have a…
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