Frequently Asked Questions
Real answers to the bookkeeping questions I get asked all the time. If yours isn't here, just reach out. I'm always happy to talk.
Bookkeeping Basics
What exactly is bookkeeping?
In simple terms, I keep track of all the money flowing in and out of your business. That means logging every transaction in QuickBooks Online, making sure your bank accounts match your records, and pulling together reports so you can see exactly how your business is doing financially.
What will you actually do for my business?
I handle the financial record-keeping that eats up your evenings and weekends. Specifically, I sort and categorize every transaction, match up your bank and credit card statements with QuickBooks Online, keep tabs on what customers owe you and what you owe vendors, and deliver your Profit & Loss and Balance Sheet each month so you always know where things stand.
What's the difference between a bookkeeper and an accountant?
I keep your day-to-day financial records organized and accurate in QuickBooks Online. Your CPA or accountant takes those clean records and handles tax filings, tax strategy, and bigger-picture financial advice. Think of it this way: I build the foundation, and your accountant builds the house on top of it.
What core principles guide good bookkeeping?
It comes down to three things: get it right, keep it consistent, and don't let it pile up. Every transaction needs to land in the correct category, be recorded the same way each time, and get entered before it becomes a mystery. When those three things happen, your financial reports actually mean something.
What is double-entry bookkeeping?
It's an accounting system where every transaction touches two accounts. One gets a debit and the other gets a credit. This is what keeps everything balanced and makes it possible to spot errors. The good news is QuickBooks Online handles this automatically behind the scenes, so you don't need to think about it.
Can you explain debits and credits in plain English?
Every transaction has two sides. Debits add to your asset and expense accounts, while credits add to your liability, equity, and revenue accounts. They always have to balance out. I know it sounds backwards at first, but that's completely normal, and it's honestly one of the main reasons people hire a bookkeeper.
Why should I care about the balance sheet equation?
The balance sheet equation (Assets = Liabilities + Equity) is basically a health check for your books. If those numbers don't add up, something's wrong somewhere in your records. It's one of the first things I look at, and regular reconciliations are how I make sure it stays balanced.
Should my business use cash basis or accrual basis?
With cash basis, you record income when you actually receive payment and expenses when you write the check. Accrual basis records them when they're earned or owed, even if the money hasn't moved yet. Most of my clients start on cash basis because it's simpler. If your business is growing and you need a clearer picture of what's really happening financially, I can help you decide if switching to accrual makes sense.
Getting Started
I'm brand new to bookkeeping, where do I even start?
First things first: get a separate bank account for your business if you don't already have one. Then set up QuickBooks Online, connect your bank feeds, and build out a chart of accounts that fits your business. That said, most of my clients come to me specifically because they don't want to figure all this out alone, and that's exactly what I'm here for.
Do I really need bookkeeping software, or can I use spreadsheets?
Spreadsheets technically work, but they're slow, error-prone, and don't scale well. QuickBooks Online pulls in your bank transactions automatically, handles the math, and generates reports in seconds. For the cost of the subscription, the time and headaches you save are absolutely worth it.
Which bookkeeping software do you recommend?
I work exclusively in QuickBooks Online and I recommend it for virtually every business I work with. It's cloud-based so we can both access it anytime, it connects with your bank and hundreds of other apps, and it makes collaboration between you, me, and your CPA seamless. As a certified ProAdvisor, I know the platform deeply and can help you get real value from it.
How frequently should my books be updated?
Monthly is the minimum, and that's when I reconcile everything and close the books. If your business has a high volume of transactions, weekly check-ins can be helpful. The worst thing you can do is let months go by without touching your books, because small issues turn into big messes fast.
What's the best way to keep my books accurate?
Keep your business and personal spending completely separate, save your receipts, and make sure someone is reconciling your accounts every single month. That's really what it comes down to. When you work with me, I handle the reconciliation and categorization piece, and I catch the things that are easy to miss when you're busy running a business.
What bookkeeping mistakes do you see most often?
The biggest ones I run into: using one bank account for business and personal expenses, letting months go by without reconciling, categorizing things inconsistently (or just guessing), and ignoring the books until tax season. Every one of these creates problems that snowball. Monthly bookkeeping with someone who knows what they're doing prevents all of it.
Working with a Bookkeeper
My CPA handles my taxes. Do I still need a bookkeeper?
Absolutely. Your CPA needs clean, organized records to do their job well. If they're spending hours sorting through a year of uncategorized transactions, you're paying CPA rates for data entry, and that gets expensive fast. I keep your books current all year so your CPA can focus on what they do best: taxes and strategy.
Can you do what my CPA does?
No, and I'm upfront about that. I don't file taxes, give tax advice, or do audits. What I do is make sure your financial records are accurate and organized so your CPA doesn't have to start from scratch every spring. I work directly with your CPA or tax preparer to make sure the handoff is smooth.
Is it better to hire an individual bookkeeper or a big firm?
With a solo bookkeeper like me, you always work with the same person, someone who actually knows your business, remembers your questions from last month, and cares about getting it right. A larger firm might have more people on staff, but you often lose that personal connection. With Pretty Smart Bookkeeping, you get real expertise with a personal touch.
Do I need a bookkeeper in my area, or can we work remotely?
Location doesn't matter at all. Everything I do happens in QuickBooks Online and over Zoom, so it works the same whether you're here in Excelsior or on the other side of the country. I have clients around the Lake Minnetonka area that I see in person sometimes, and plenty of clients in other states that I've never met face-to-face. The quality of work is identical.
How much does bookkeeping cost?
It depends on how many transactions you have and how complex your books are. My plans start at $250/month and go up from there, with no long-term contracts locking you in. Check out my pricing page for the full breakdown of what's included at each level.
Why should I pay someone else to do my bookkeeping?
Because the hours you spend wrestling with QuickBooks are hours you're not spending on your actual business. Outsourcing your books to someone who does this every day means fewer errors, less stress, and real financial reports you can use to make smart decisions, all without hiring a full-time employee.
QuickBooks
Should I use QuickBooks Online or the Desktop version?
QuickBooks Online, hands down. It's cloud-based so you can access it from anywhere, it updates automatically, and it connects with your bank feeds and tons of other tools. Plus, Intuit is winding down the Desktop version, so Online is where everything is headed. I work exclusively in QBO and I wouldn't go back.
What does QuickBooks Online actually do for my business?
It pulls in your bank and credit card transactions automatically, lets me set up rules to categorize recurring expenses, generates financial reports with a few clicks, and tracks your invoices and bills in one place. Basically, it's the central hub where all your financial data lives, and when it's set up properly, it makes bookkeeping dramatically more efficient.
Should I set up QuickBooks Online myself, or have you do it?
You can try it yourself, but a lot of the problems I fix for new clients started with a DIY setup. Getting the chart of accounts right, entering correct opening balances, and connecting bank feeds properly makes a huge difference down the road. As a certified QuickBooks Online ProAdvisor, I set things up correctly from the start so you don't end up paying to fix it later.
Which QuickBooks reports should I actually look at?
Your Profit & Loss statement and Balance Sheet are the two must-reads every month. The P&L shows whether you're making or losing money, and the Balance Sheet shows your overall financial position. Depending on your business, I might also pull cash flow statements, AR aging reports, or AP summaries. Basically, whatever helps you understand what's happening with your money.
How do you help me get more value from QuickBooks?
I set up automation rules so recurring transactions categorize themselves, customize your chart of accounts to match how your business actually works, build reports that give you useful insights (not just data dumps), and keep everything clean so the numbers you see are numbers you can trust. My goal is to make QuickBooks work for you, not the other way around.
Why should I use a Certified QuickBooks ProAdvisor?
Because QuickBooks is only as good as the person setting it up. A lot of the cleanup work I do comes from businesses that had someone “who knows QuickBooks” handle their books, but knowing how to enter transactions isn't the same as knowing how to structure your chart of accounts, automate bank rules, or generate reports that actually tell you something useful.
Think of it like hiring a mechanic who's factory-certified by the manufacturer. A Certified QuickBooks ProAdvisor has passed Intuit's own training and certification exams. It's not just a title, it means I know QuickBooks at an expert level. Here's what that means for you:
- Faster problem-solving. I've seen hundreds of QBO setups. I can spot issues and fix them quickly instead of guessing.
- Correct setup from day one. Chart of accounts, bank feeds, automations. I configure things the right way so you're not paying to fix mistakes later.
- Access to ProAdvisor-only tools. Intuit gives ProAdvisors wholesale pricing on subscriptions, priority support lines, and advanced diagnostic tools that regular users don't get.
- Ongoing training. Certification requires annual recertification, so I stay current on every new feature and update Intuit rolls out.
- Direct line to Intuit. When something breaks or a feature changes, I have a support channel that skips the general queue.
Bottom line: it's the difference between someone who uses QuickBooks and someone who truly specializes in it. It's a real credential, not just a badge.
Services & Pricing
Can you help with sales tax tracking?
Yes! I set up sales tax in QuickBooks so it's tracked correctly on every transaction, and I make sure you have the reports you need when it's time to file. I don't file the actual sales tax returns (that's usually your CPA's territory), but I make sure the numbers are right and ready to go.
Do you handle payroll?
I don't run payroll directly, but I help with the setup and ongoing coordination. Whether you're using QuickBooks Payroll or another platform, I make sure it's configured correctly, keep an eye on compliance deadlines, and troubleshoot when something goes sideways. Check out my payroll support page for more details.
Who handles invoicing, me or you?
Totally up to you. Some of my clients like to send their own invoices because they want to control the timing and messaging, and I take care of tracking payments and following up on what's outstanding. Others hand off invoicing entirely and I manage the whole process. Either way works. We'll figure out what makes the most sense for how you run your business.
What does accounts receivable mean?
Accounts receivable (AR for short) is money that customers owe you for work you've already done or products you've already delivered. I track it in QuickBooks Online so you always know who owes you, how much, and how long it's been since you invoiced them. No more guessing or digging through emails.
What about accounts payable?
Accounts payable (AP) is the flip side: it's money you owe to your vendors and suppliers. I keep it organized so your bills get paid on time, you dodge late fees, and you maintain solid relationships with the people you rely on to run your business.
Will having a bookkeeper actually save me money?
In my experience, yes. I regularly spot duplicate charges, catch expenses filed in the wrong category (which can mean missed deductions), and flag subscriptions clients forgot they were paying for. On top of that, clean books mean your CPA spends less time sorting through your records, which means a smaller tax prep bill. Most clients end up saving more than what they pay me.
How does bookkeeping affect my taxes?
Everything I do with your books feeds directly into your tax return. When expenses are categorized correctly, you capture every deduction you're entitled to. When your records are accurate and organized, your CPA works faster, your tax bill is lower, and you sleep better knowing the IRS isn't going to have questions.
Can clean books help me plan and budget better?
One hundred percent. When your books are up to date, you can look at last month's numbers and actually learn from them: where the money went, what's coming in, and whether you can afford to hire, invest, or expand. You can't make smart financial decisions if you're guessing at your numbers. I give you the real ones.
Practical Tips
How am I supposed to keep up with bookkeeping on top of everything else?
That's the thing: most business owners can't, and there's no shame in that. You've got clients to serve, a team to manage, and a hundred other things pulling at you. Carving out time for bookkeeping every week is great in theory, but in practice, it's the first thing to fall off the list. That's exactly why hiring someone to handle it consistently is the smartest move you can make.
Is bookkeeping simpler for some businesses than others?
Generally, yes: fewer accounts, fewer transactions, and simpler structures make bookkeeping more straightforward. But that doesn't mean it matters less for smaller operations. Businesses with tighter margins need accurate numbers even more, since every dollar counts. The upside is that bookkeeping is more affordable and easier to get right when your operation is less complex.
What financial terms should I understand as a business owner?
Here are the ones that come up most: revenue (what you earn), expenses (what you spend), assets (what you own), liabilities (what you owe), equity (your ownership stake), AR (money owed to you), and AP (money you owe). But honestly, don't stress about memorizing jargon. Part of my job is translating all of this into language that actually makes sense to you.
Is it safe to have my bookkeeping done remotely?
Completely. QuickBooks Online uses bank-level encryption to protect your data, and I follow strict security practices on my end: secure logins, controlled access, and I never share your financial information with anyone. Honestly, remote bookkeeping through QBO is more secure than emailing spreadsheets back and forth, and a lot more convenient too.
Still Have a Question?
I'd love to hear from you. Book a free call and we can talk through whatever's on your mind: your books, your business, or just whether working together makes sense.