The Problem With Finding a Good Bookkeeper
If you've ever posted in a Facebook group asking for a bookkeeper recommendation, you already know what comes next is a gamble. Some bookkeepers are great, while others leave you with a stack of confusing reports, unanswered emails, and more financial anxiety than you started with.
For service-based business owners—especially those running solo or with a small team—handing over your books is a big deal. Your business is your baby. You've put long days, sleepless nights, and a lot of yourself into building it. The last thing you need is a bookkeeper who makes you feel like you’re more in the dark than before you hired them.
So… what should you actually look for? This post is built around a real client story of a CMO-turned-marketing-consultant who worked with two bookkeepers before finding the right fit. Her experience is a roadmap for what to avoid, what to expect, and what becomes possible when bookkeeping is done right.
Mallory’s Story: A Tale of Two Bookkeepers
"I worked with two other bookkeepers before I found Elli, and both left me feeling completely in the dark.”
My client Mallory, is a former CMO who made the leap into running her own marketing consulting practice. She knows strategy inside and out. She helps other businesses make smart decisions every single day.
But when it came to her own finances? She was flying blind.
She hired her first bookkeeper hoping to finally get clarity. Instead, she got generic reports that were hard to read. And when she asked questions, the answers were even harder to understand. The bookkeeper wasn't responsive and clarification never really came.
She tried again, hiring a second bookkeeper. This time, the books were never even kept current. She found herself constantly nagging for information, never sure if her numbers were up to date, unable to get a clear picture of where her business finances stood.
By the time we connected, she was ready to throw in the towel and go back to DIYing her books. She told me that after two bad experiences, she wondered if her expectations for a bookkeeper were just too high.
They weren't. She just hadn't found the right one yet!
The Bookkeeping Solution She Needed
"Elli has gone above and beyond my expectations! She updates my books fast, has a super clear and easy process, and actually took the time to walk me through my first report so I knew what everything meant."
When I took over her books, they weren't a disaster. The numbers were being entered and the books were technically being completed. Sure the bookkeeping was being done, but the person providing the service wasn’t a fit.
Lack of communication, zero context, and no one available to answer simple questions (like: What subscriptions am I paying for right now? What made my advertising and marketing expense category so high this month?) is not a great recipe.
Those are questions you want (and need) answered by your bookkeeper. When your bookkeeper goes silent, you're left guessing—or worse—making business decisions without understanding the full picture.
One thing my clients will never say about me is that I don't respond. (They might actually say I respond too fast.) Being available, being clear, and making sure my clients actually understand what their numbers mean is one of my favorite parts of the job!
I don't take it lightly that people trust me with their books. Your business is your baby. You built it from the ground up, and good bookkeeping is fundamental to a strong business, not just something you should scramble to get organized at tax time.
What Good Communication With a Bookkeeper Actually Looks Like
When we started working together, I used a platform called Financial Cents to onboard her. She received detailed task lists with everything she needed to complete. Step-by-step instructions for granting me view-only access to her bank accounts, payment processors, CRMs, and payroll tools like Gusto.
No onboarding tasks lost in an email thread or confusion about what was needed or why.
I ask a lot of questions upfront and that's intentional. The more I understand about your business at the start, the less I need to ask each month, and the smoother everything runs over time.
The monthly rhythm with my bookkeeping clients looks like this:
During the first week of every month, I complete your books from the prior month. If anything needs clarification—like an Amazon charge that could literally be anything—I flag it and ask. I don't guess or don't skip over it. Getting the categorization right matters, especially come tax time. Once everything is confirmed and finalized, I send your reports!
And my clients know they have full email access to me at any time. No question is off limits, and no such thing as a dumb question when it comes to your own business finances.
For more, this explores exactly what the onboarding process looks like!
The Revenue-by-Offer Breakthrough
"For the first time, I know exactly how much I'm making from each of my offers, and I'm not constantly wondering if my books are right."
One of the first things we did together was set up her income categories so she could see exactly where her revenue was coming from by offer.
She had a vague idea, but she'd never taken the time to dig into the actual percentages. And when you're a marketing consultant running multiple offers—1:1 client work, digital products, maybe a course or group program—that information isn't just interesting, it's strategic.
Is the digital product she put so much time into actually generating profit once you factor in all the time and resources that went into creating it?
Would it make sense to pull back on 1:1 work and put more energy into a different income stream?
You can't answer those questions confidently without the actual numbers.
We also walked through her P&L, balance sheet, and statement of cash flows together, I didn’t just hand them over. She left that first report review with a deep understanding of what was in each category, how to read the reports, and what the numbers meant for her business.
She said for the first time, she knew exactly how much she was making from each of her offers. And she could use that information to make confident, informed decisions.
How Clean Books Help Your Business Beyond Tax Season
A lot of business owners think of bookkeeping as something they deal with once a year. Scrambling to get everything together before the tax deadline, or filing an extension because the books still aren't done.
But clean, current books do so much more than help you navigate tax season.
They mean no guessing what a transaction was for.
When I see an Amazon charge and don't have a receipt, I ask — because that transaction could be anything, and categorizing it correctly matters for your taxes and for understanding your actual expenses. When I see a Stripe deposit hit your bank account, I make sure I'm recording your actual income, not just the net deposit after fees. Those details add up.
They also mean your accountant has what they need at year end without a last-minute scramble.
Any contractor payments are tracked throughout the year, W-9s are collected as we go, and anything unusual gets flagged and communicated so nothing is a surprise.
Most importantly, clean books mean you can make decisions from a place of clarity, not anxiety.
You don't have to wonder if your numbers are right. You don't have to guess whether a new hire or investment makes sense. You have the information right there, and if you need something specific, you're one email away from getting it.
That's what Mallory meant when she said hiring me was one of the best moves she made for her business. It wasn't just about the bookkeeping, it was about the mental load that lifted when she stopped having to think about it all by herself.
Is It Time to Hire a Bookkeeper?
"Hiring Elli was one of the best moves I made for my business!"
If any of these sound familiar, it might be:
You don't want to do your own bookkeeping anymore
You keep telling yourself you'll catch up on the books next month (and have been saying that for a while)
Tax season is always chaotic because your books aren't done
You're filing extensions every year for the same reason
You need clean financials to apply for a loan—personal or business
You have no idea which of your offers is actually the most profitable
At Pothos Bookkeeping, I offer judgement-free bookkeeping services for service-based female business owners. My job is to keep your books clean so you can focus on what you do best, or spend your free time doing something you actually love.
If you're ready to stop guessing and start making business decisions with confidence,
…and let's talk about what working together could look like.
