(And What To Do About It)

Remember when you first started your business? Your financial "system" might have been as simple as a spreadsheet and checking your bank balance. And back then, that probably worked just fine!
But as your business grows and evolves, the financial systems that once served you well can start to feel like trying to fit into your favourite jeans from high school – uncomfortable, restrictive, and not designed for who you are now.
The Emotional Cost of Outgrowing Your Financial Systems
Before we dive into the signs, let's talk about something many business owners experience but few discuss openly: the emotional toll of financial confusion.
When your business outgrows your financial systems, it often doesn't announce itself with a clear sign. Instead, it shows up as:
- That knot in your stomach when you think about your books
- The late-night worry about whether you're actually profitable
- The embarrassment of not having clear answers for your accountant
- The dread of making business decisions without clear financial data
If any of these feelings sound familiar, please know you're not alone. Most successful businesses go through this growing pain – it's actually a sign you're doing something right!
5 Tell-Tale Signs You've Outgrown Your Current Financial System
1. Your bookkeeping takes more than a few hours each month
What it looks like: You're spending evenings and weekends catching up on bookkeeping tasks, reconciling accounts, or trying to make sense of your numbers.
Why it happens: As your business grows, you have more transactions, more complexity, and more financial data to manage. What once took an hour now takes five or six.
Real impact: Every hour spent on bookkeeping is an hour not spent on growing your business or enjoying your life. That's a real cost that doesn't show up on your profit and loss statement.
2. You have multiple income streams or payment methods
What it looks like: Money comes into your business through different channels – maybe you have online sales, in-person services, recurring subscriptions, or multiple product lines.
Why it matters: Each income stream might have different profit margins, expenses, and growth patterns. Without proper tracking, you can't tell which parts of your business are most profitable.
Real impact: You might be focusing your time and energy on the least profitable parts of your business simply because you can't see the difference clearly.
3. You're not confident in your tax situation
What it looks like: Tax time brings anxiety, you're never quite sure if you're setting aside enough for taxes, or you've been surprised by a tax bill in the past.
Why it happens: As your business grows, your tax situation becomes more complex. Deductions, estimated payments, and tax planning opportunities all require more sophisticated tracking.
Real impact: Without proper tax planning, many business owners either overpay taxes (losing money they could keep) or underpay (creating stressful surprises later).
4. You can't quickly answer basic questions about your business finances
What it looks like: Someone asks "How much profit did you make last month?" or "What's your most profitable service?" and you don't have a clear answer.
Why it matters: These fundamental questions should be easy to answer with the right systems in place. If they're not, your financial visibility is compromised.
Real impact: Without clear financial visibility, you're essentially making business decisions blindfolded – hoping for the best rather than basing decisions on actual data.
5. You've had at least one "where did all the money go?" moment
What it looks like: Your bank account showed a healthy balance, but suddenly you're struggling to cover expenses or tax payments.
Why it happens: Without proper systems to track profitability, set aside money for taxes, and distinguish between revenue and actual profit, it's easy to spend money that isn't actually available for spending.
Real impact: These cash flow surprises create enormous stress and can force you to make rushed decisions about your business.
What To Do If You've Outgrown Your Financial System
If you recognized your business in any of the signs above, here are some simple next steps:
1. Start with a financial clarity check-in
Take 15 minutes to ask yourself these questions:
- Do I know exactly how profitable my business was last month?
- Can I quickly see which services or products are most profitable?
- Do I feel confident about my tax situation?
- Do I spend more than 3-4 hours monthly on bookkeeping tasks?
- Do I have financial clarity or financial anxiety?
Your honest answers will tell you a lot about whether your current system is serving you well.
2. Consider separating your accounts
One of the simplest improvements is creating separate bank accounts for different purposes:
- An income account where all revenue lands first
- A tax savings account (for setting aside tax payments)
- An operating expense account
- A profit account (even if you start with just 1%)
This separation creates immediate clarity about your true financial position.
3. Explore bookkeeping systems designed for your current business size
The financial systems that work for a solo startup are different from those that serve a growing business with multiple revenue streams. Research options that match where your business is now, not where it started.
4. Get a professional perspective
Sometimes an outside perspective can see things we can't. Consider booking a session with a bookkeeper who specializes in businesses at your stage. They can help you identify specific improvements that would make the biggest difference for your unique situation.
5. Remember: This is a good problem to have!
Outgrowing your financial systems means your business is evolving and growing. While it can feel stressful in the moment, it's actually a positive sign that you're moving in the right direction!
One Quick Win You Can Implement Today
Here's something you can do in the next 10 minutes that might give you immediate clarity:
Make a list of your top 3 services or products, and for each one write down:
- What you charge
- Your direct costs to deliver it (including time)
- The approximate profit margin
Even this simple exercise often reveals insights about where to focus your energy for the best financial returns.