Episode 4: When is the Right Time to Hire a Bookkeeper for Your Creative Business?

3/18/2025

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If your books are a mess, tax season sends you into a panic, and you’re spending way too much time figuring out your numbers—it might be time to hire a bookkeeper.

🎧 Listen to the Episode:

What I Yapped About:

Still doing your own bookkeeping? That’s great—until it’s not. Here are some clear signs it’s time to bring in a pro:

  • Your books are chaos. Multiple accounts, payment processors, and receipts everywhere? You’re losing track, and it’s only getting worse.
  • Mistakes are creeping in. Misclassified transactions, missing expenses, or numbers that don’t add up—these errors can cost you big time.
  • You’re wasting time. If bookkeeping is eating up hours you should be using to grow your business (or, you know, enjoy your life), it’s time to offload it.

So why is hiring a bookkeeper a smart move?

  • Smarter growth – A bookkeeper helps you plan for expansion, not just react to financial chaos.
  • Better financial clarity – You’ll make informed decisions instead of scrambling to figure out where your money went.
  • Less tax season stress – No more frantic searches for receipts when everything is properly categorized.

Your Next Step

A bookkeeper isn’t just a financial necessity—they’re a strategic partner in your business. If your books are holding you back, it’s time to let go and level up.

🎧 Listen to the full episode now, or if you can’t listen check out the transcript below.

Read the Transcript

 Hello, fellow dreamers and doers. You’re listening to the creative mind smart money podcast. I’m Samantha Eck, your host, ready to eliminate the path to financial clarity and success. Today, we’re discipling the signs and strategies for when to hire a bookkeeper. So sharpen your pencils and let’s chart the course through this essential financial decision.

If you’ve been listening to the past three episodes, you know, I’ve been talking about how you can do everything by yourself. But maybe finally reached the point where your asking yourself, Samantha. I need help. I need somebody else to take over my books because I just don’t have the time to do them. And that’s totally okay. It’s what I’m here for. So let’s talk about the signs of when you need to hire a bookkeeper, the benefits when is the perfect time choosing the right person and just implementing them into your workflow. So let’s dive right in.

There are some really key indicators that signal when you’re ready for a bookkeeper. As your business grows. So does the volume and complexity of your transactions? If you add in different payment processors, the more streams of income you have, the more credit cards, bank accounts investments, anything like that, that you have adds to the complexity of your bookkeeping? If you’re tracking your sales, expenses, and that feels like it’s just a labyrinth with no clear exit, it’s a really strong sign that you need a bookkeeper. You feel so overwhelmed every time you look at your books that you’re like, I don’t know how to do this I don’t know when I’m going to find the time to do this. That is really a clear indicator that you’re ready for someone to help you take over your books.

If you’re finding a lot of errors and inconsistencies, such as misclassified transactions, inconsistent entries that skew your outlook on your finances and can also lead to really big tax complications. That’s another sign that you’re ready for a bookkeeper, because a bookkeeper ensures accuracy and consistency across all of your financial records. So if you’re seeing just a bunch of inconsistencies, that’s when you’re ready and, you know, okay I’ve been doing something that just doesn’t make sense I need someone else to come and take over this.

The last and biggest reason when you know that you’re ready for a bookkeeper is time. If your financial tasks are consuming a substantial portion of your Workday, it leaves less time for you to be creative or for you to focus on strategic growth. That means it’s time to delegate to someone else, to have a bookkeeper come in and take over that part of your business. Outsourcing does not signify a sign of weakness. It’s actually a giant sign of strength. It shows that you are ready to focus on areas where your time is better and more well spent. So you don’t want to take the time to deal with the bookkeeping or handle something that you can hand off to someone else. It’s really about making sure that your focusing on what matters to you. If you’re in the middle of summer and what matters to you is going to a park with your children. Then you should have the ability to go to the park with your children. And if bookkeeping is something that is eating up a significant portion of your time. That’s when you really know. That you just need somebody else to come in and take that right off your plate.

So now you’re asking yourself, well, what are really the advantages of having a bookkeeper? Why is it a worthy investment for my business. A bookkeeper helps maintain a continuous clear view of your financial status. Which allows you to make more informed decisions quickly and efficiently. If you’re looking at your books on a very regular basis, that means that you have more financial control. You’ll be able to identify if maybe someone has hacked your credit card and, they’re spending money that you didn’t know about that, you know, What decisions do you want to make in the future. When you’re looking at your books so often you’re really aware of what’s going on in your business and how you can grow.

With all the changing tax regulations, having a bookkeeper ensures that your business remains compliant, minimizing the risk of penalties and fines. While bookkeepers themselves don’t necessarily handle taxes we’re knowledgeable enough about the thoughts and processes behind taxes that our goal is to give you the most deductions, even though your tax preparer is probably going to find you more. So we want to categorize things appropriately so that we make your tax preparers job even easier.

Bookkeepers also play a crucial role in budgeting and financial forecasting, which are essential for sustaining and scaling your businesses. They really help you understand the financial impact of past decisions. And predict future financial health. Budgeting is something that can help you just wrap your head around how much money you need to have in certain aspects of your business. So that you’re not overshooting and forecasting really helps you to project where your business could be in the future. Now, forecasting is something that is very volatile so it’s never accurate, but it allows you to get an idea and a grasp of where you want your business to be.

When is the perfect time to hire a bookkeeper. If you’re gearing up for growth, you’re launching a new product line. You’re expanding into new markets. Having a bookkeeper can make sure that your financials keep pace with all of your business ambitions. Usually a bookkeeper is someone that you want to hire really early on in your business, but it’s not always ideal for a lot of people, maybe they want to outsource something else first.

When your business evolves to include more complex financial activities like loans, leases, or sophisticated vendor contracts, someone who has more expertise in this areas can really help. Some of my clients are on Shopify and they don’t understand the amount of work that goes into recording Shopify transactions in a set of books. So once we’ve gotten into to their books, we realize how they’ve been recording things improperly from months on end. We now have to go back and fix that. So if it’s something that you just have no idea what you’re doing, that’s when that’s the perfect time to hire somebody.

Hiring a bookkeeper before tax season is really ideal. It’s proactive and allows me to straighten out any discrepancies and optimize your financials so that when it gets to tax season and we hand off your stuff to your tax pro, it makes your tax season a complete breeze. So the earlier you do it in the year, the better off you are.

Now you’re asking yourself, you’re like, okay, I know the benefits I know when to hire I know why, I need to hire, but how do I choose the right bookkeeper? Now this being my podcast, obviously I would recommend myself. But I’m not the best fit for everyone. And I know that, and I have a list of other bookkeepers that if I’m not the perfect fit, I refer other people to the reason being that there is no competition within my industry. I believe that it’s a strong mentality for community. Finance pros are very hard to find, especially really good ones. So when you find those, you want to stick with them and you want to have other people that you can refer out to them. So it’s always good for me to connect with other people so that I can have those connections.

So when you’re looking at a bookkeeper, you want to consider their specialization in relation to your industry. For example, if for me, I specialize in creatives. So I’m familiar with the e-commerce industry. I understand Stripe, PayPal, square, all those different types of platforms so that I can help those business owners better understand that type of information. Now , for example, I’m not very skilled in construction bookkeeping. I would never want to take on a client who is in construction because I wouldn’t be able to help them get to where they need to be.

You want to ensure that your bookkeeper is adept with the accounting software you’re using or better yet one who can recommend and implement a system that scales with your business needs. If you’re using fresh books and your bookkeeper can’t use fresh books, they might not be a good fit for you. But if you’re like, I’ll go with whatever accounting software you think will be best then obviously you want to find someone who can fit that.

Now since you’ll be closely involved with the working of your business. You want to ensure that they’re a cultural fit, that they understand your work ethic and the communication style should align with your company culture. So if someone who responds to you every four to five days, doesn’t work for the kind of communication that you’re looking for, they might not be a good fit and that’s really important.

A bookkeeper shouldn’t just be someone that you just hire, just because you’re looking for a bookkeeper. You really need to think about if they’re a fit for your business. And if you guys vibe really well, then that’s a really sure sign that you’re a perfect fit for each other.

Once you’ve hired a bookkeeper it’s time to integrate them into your business. Usually a bookkeeper will have a structured onboarding process that allows you to see their process and understand what’s going on and they’ll ask you for a lot of access to your financial documents and things like that. So you having that kind of already set up to know, Kay, I need to get this to them. I need to get this to them would be really helpful.

You want to be with someone who keeps you informed on a monthly basis. So I offer my clients monthly looms, where we talk about their financials. We go over their income statement, their balance sheet, their statement of cash flows, and really just dive into each one of those so that I can help them understand how to best grow their business. We also offer strategy meetings either every year semi-annual or quarter based on the package that you picked so that we can really dive into aligning your business more with your goals. And of course, with those meetings, you can invite other people. So if you wanted to invite your CPA, if you wanted to invite your business coach, just so that we’re all on the same page and we can help your business thrive the way it needs to thrive.

Now you also want to regularly review your bookkeeper’s performance. So if you’re noticing. That your bookkeeper has a lot of different issues. As compared to what your seeing that might be a red flag . So if you’re like, this is not where I asked you to categorize this. That might be a chance for you to be like , it might not be a good fit.

So let’s take a look at a couple of case studies. Just ideas of people that have hired a bookkeeper and how that helps them.

So for example, this boutique store utilize the bookkeeper’s forecast and financial analysis to secure funding for expansion and this strategic move increased their market reach and profitability.

Digital marketing freelancer use savings from reduced banking fees and improved interest rates. To reinvest in marketing efforts, yielding higher client engagement and increased project opportunities. They found these specifically because their bookkeeper showed them this on their financials every month and they were able to identify those areas for growth.

Remember a bookkeeper is personal to you. So when you’re interviewing bookkeepers, make sure they’re a good fit for you and your business. It won’t hurt someone’s feelings. If you say no. And it’s better off if they know that, they’re not a good fit for you and your business.

Listen to the other Four Foundation Episodes:


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meet your host

Hi, I'm Samantha—

The thing about financial advice is that it hits different when it comes from someone who's actually been in your shoes. As the host of Creative Minds, Smart Money, I don't just talk about finances – I share real strategies I've learned from running my own creative businesses and helping clients like you transform their financial chaos into clarity.

Want to know more about how I went from creative business owner to financial strategist for creative entrepreneurs?

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