Should I Hire a Bookkeeper? 5 Signs Your Business Is Ready
Panic Googles: “How do I know if I need a bookkeeper?”
If you’re reading this, you’ve probably asked yourself this question more than once… maybe while staring at a pile of receipts at 11pm. Maybe during tax season when you realized you have no clue what you made last year. Or maybe right after you spent 3 hours trying to reconcile your bank account while you would’ve rather rewatched Schitt’s Creek for the 7th time.
The reality check you need is that you’re not behind on your bookkeeping because you’re irresponsible or bad at business. You’re behind because the systems we’re defaulted into are super flawed and don’t care about you time. It’s no wonder your bookkeeping spreadsheet feels overwhelming. You’ve got a comfort show to watch and this task is sending your nervous system into flight response. That’s not a character flaw, that’s biology. Ugh, science.
So let’s chat about whether hiring a small business bookkeeper is the right move for you right now. Not because I think you need a bookkeeper (you might, you might not), but because Schitt’s Creek is waiting, so let’s solve this for once and for all!
Sign #1: You have no idea if you’re actually profitable
You’re making sales. Money is coming in. But when someone asks you if you’re profitable, you freeze.
Maybe you think you are?
Probably?
You made $23K last quarter but you also spent some amount of that… on things?
And your bank balance isn’t $0, so surely that’s a good sign, right?
That freeze might look like indecision, but it’s your nervous system protecting you from information that feels threatening. Working with a bookkeeper, especially if they are trauma-informed, can help you build more supportive pathways to access your numbers.
This is incredibly common. Research from the Canadian Federation of Independent Business (CFIB) shows that around 60% of Canadian small business owners say accounting and bookkeeping throw them off, leading to (often) costly errors.
Needless to say, it’s a relatable struggle.
When you don’t know your actual numbers, you can’t make informed decisions about your business. You can’t know if that website refresh you’re dying to do is actually affordable. You can’t plan for slow seasons. And you can’t confidently price your services because you don’t know what they actually cost you to run.
Working with a bookkeeper can give you the clarity and confidence you need to make those judgment calls. Instead of “I think I’m profitable…?” you get to say “I brought in 23K this quarter, and 57% of that was profit!” Whether you’re a therapist in private practice, a wellness practitioner, or really any service provider, this kind of visibility is vital for sustainable growth.
Sign #2: Tax season triggers either a fight, flight or freeze response
Most people think tax time stress is about math. It’s not. It’s about transparency. If you’ve been avoiding your numbers all year, tax season is the moment you’re forced to be seen. For many service providers, that feeling of being 'found out' or 'exposed' triggers a deep survival response. Working with a bookkeeper provides support and reduces the isolation of facing financial obligations alone.
According to BDC research, cash flow issues contribute to 21.5% of Canadian small business failures in their first year. When you’re managing your own bookkeeping, it’s easy to let things slip. You’ve got a million other things to do, and it’s easy to forget that bookkeeping is a thing you need until the urgency of tax season hits. The CRA expects accurate records, and falling behind can mean penalties, missed deductions, and a whole lot of extra stress. Ew, pass.
When your bookkeeping is organized and up-to-date, tax season stops feeling like a crisis you need to manage. What if instead of scrambling to reconstruct a year's worth of transactions, you already had everything you needed? Your bookkeeper can coordinate with your tax preparer to make sure you’re not missing out on any deductions, and not overstating your income… aka paying more taxes than you should.
Sign #3: You’re spending hours on tasks that you don’t vibe with
Let’s do some math.
I know, I know. Hear me out.
Service-based business owners can spend upwards of 5+ hours per month on bookkeeping tasks when managing their own books.
That’s 60+ hours a year.
Maybe you’re truly interested in bookkeeping and that feels like time well spent. Honestly, same.
But if you’re like most of the therapists and wellness practitioners I work with, those hours feel like a massive energy drain that you’d rather put toward client care, business development, or getting back to Schitt’s Creek.
It’s not about whether you’re “too good” or “too busy” for bookkeeping. We’re talking about whether it’s the best use of your limited time and capacity… they’re finite resources after all. When you hire a bookkeeper, you’re making a strategic decision about where your energy goes.
Ready to buy your time back? Let’s chat about building a bookkeeping system that actually works for you.
Sign #4: Your books are “caught up” only right before your accountant needs them
You know the pattern…
Your bookkeeping gets neglected for months, then there’s a panicked catch up session when your accountant starts asking for your numbers for tax filing.
This isn’t procrastination.
This is often a freeze response to a system that feels punitive. This is sometimes a sign of perfectionism. But your books don’t need to be “perfect”, they just need to be done. Sometimes good enough is good enough. The financial systems we exist in thrive on shame as a motivator, which literally does not work when your nervous system is already overloaded.
The CFIB reports that 38% of Canadian businesses struggle with poor financial health. This can often be linked back to inadequate (read: unsupportive) financial management systems. When your books are current, you can make decisions based on real data, not guesswork. Professional bookkeeping services don’t just keep you compliant, they actively support business growth by giving you the information you need when you need it.
Sign #5: You’re making financial decisions based on your bank balance
If your go-to money decision making strategy is to check your bank balance, hoping there’s enough money in there, we need to talk.
Like yesterday.
Your bank balance doesn’t tell you:
What you owe in upcoming expenses
How much you’ve already allocated to taxes
Whether that deposit is revenue or a refund
If you can actually afford that business investment
What your profit margin really is
Constant financial uncertainty and invisibility like this keeps your nervous system in a low-grade state of alarm. Working with a bookkeeper gives you real financial visibility. You get to make decisions based on actual data: revenue, expenses, profit margins, cash flow projections. You know where you stand, financially speaking.
If any of these signs feel familiar, let’s chat about what nervous system aware bookkeeping could look like for your business.
The Bottom Line
You wouldn’t expect your bookkeeper to run their own therapy sessions, would you?
You also wouldn’t expect them to cut their own hair or fix their own car. So why should you be expected to be an expert in everything your business needs?
When you work with someone who understands how nervous systems respond to financial stress (like me!), who builds choice and flexibility into their services (me again!), and who treats the heaviness you feel around your finances as a resource issue rather than a character flaw (hello!), bookkeeping stops being something you avoid and starts becoming something that actually supports you.
Your business deserves accurate books. You deserve to know where you stand financially. And you absolutely deserve a system that doesn’t require you to be someone you’re not.
And yeah, you'll finally get to watch Schitt's Creek without that nagging feeling that you're forgetting something important.
Book a Discovery Call and let’s figure out what kind of support would actually support you.
Still not sure if you need a bookkeeper?
If you're reading this thinking "okay, some of these resonate, but I'm still not sure if outsourcing my bookkeeping is the right call," I get it. That's why I created a quick quiz to help you figure out where you stand.
Take the 2-minute bookkeeping quiz and get a personalized recommendation based on your current situation. No pressure, just clarity on what kind of support would actually help you right now.
