Lying awake at 2 a.m. worrying about your business finances?By L.Kenway BComm CPB Retired
This is the year you get all your ducks in a row! Start by starting.
Published October 23, 2025
WHAT'S IN THIS ARTICLE
Fast Answers | Why You Avoid Your Finances | 1. The Avoidance Cycle | RAIN Method | Traffic Light Exercise | 2. 3 Money Worries That Break Habits | 3. The Habit That Fixes Everything | FAQ | 3.5 What Eating Well and Managing Money Have In Common | 4. When To Get Help | Key Takeaways | Appendix
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If you're lying awake at 2 a.m. worrying about your business finances, you're not alone. According to SleepFoundation.org, 77% of people have lost sleep over money stress. (November 17, 2023) So you aren't alone.
When financial stress hits, many solopreneurs do the opposite of what helps. They ignore the pile of receipts. They avoid opening their bookkeeping software. They put off reconciling accounts. The pattern keeps you stuck, stressed, and awake in the middle of the night.
I've written extensively about cash management systems that work—like Profit First and the Two-Bank Strategy. I've created a 30-Day CRA Compliance Reset that gets your books back on track. I've also written about how to get your books ready for your tax preparer if you've haven't touched your books for the whole year.
But none of those systems work if you can't bring yourself to look at your numbers in the first place.
This article addresses the emotional side of money management ... the part that determines whether you'll actually USE the systems available to you. Because knowledge without action doesn't put money in your pocket or keep you off the CRA's radar.
Saundra Davis, Certified Financial Behavior Specialist
I recently read an interesting article in Real Simple Magazine's 'The Money Issue' by Caitlin Carlson titled 'How We All Got So Emotional About Money—and What We Can Do About It'. Her main premise was money is never just about numbers. It's about emotions, beliefs, and behaviours learned throughout life. Understanding your emotional relationship with money helps you make better financial decisions. I'm going to explore Caitlin's article from the perspective of a Solopreneur in Canada.
Caitlin laid out four influences that have formed our thoughts and emotions about money. These influences create our emotional responses (stress, jealousy, guilt, happiness) when spending.
These four influences from Carlson's article apply directly to how Canadian solopreneurs manage their business finances. Let me show you how.
As a Canadian solopreneur, these emotional patterns don't stay in your personal life. They show up in your business decisions every single day. Put another way, your emotions and upbringing about money also influence how you manage your business finances.
If your parents fought about money, you might avoid financial conversations with your spouse about the business. If you grew up with scarcity, you might underprice your services or feel guilty about profit. If money was taboo in your family, you might feel uncomfortable asking clients to pay on time.
And here's the challenge. When business income IS your personal income, these emotional patterns get amplified. A slow month doesn't just mean business stress; it also means personal financial anxiety. An unexpected expense isn't just a business problem, it also affects your family's budget.
That's why so many solopreneurs avoid their bookkeeping. It's not laziness. It's emotional overwhelm. If money is stressing you and affecting your sleep, it's tough to motivate yourself to implement the behavioural cash management system put forth in Mike Michalowicz's Profit First book.
🦆 HEADS UP: if you are running your business where the lines are blurred between business income and personal finances, you will run into trouble if the CRA audits you.
Here's the truth. You can't implement Profit First if you won't look at your bank balance. You can't use the Two-Bank Strategy if reviewing your bank (or credit card) statement transactions makes you anxious and gives you a stomach ache.
The systems work. I know they work. But they only work if you can bring yourself to START.
That's why understanding WHY you avoid your both your business and/or personal finances is the first step. Once you understand the emotional barrier, you can address HOW to break through it.
The RAIN method was popularized by Tara Brach, PhD. It can help you turn off autopilot emotions around money and bring awareness to any situation.
When you catch yourself, general questions to ask yourself to start the process are:
Here's an exercise for you. View your last month's business expenses. This exercise will be easiest if you use your latest business bank statement. Color code each withdrawal on the bank statment.
🟢 Green = Necessary business expense and aligned with my business goals. No regrets.
🟡 Yellow = Questionable. Was this really necessary? Could I have spent less? Did I explore other options?
🔴 Red = Personal expenses that snuck into my business account OR subscriptions I forgot about or no longer need.
If you found you actually enjoyed this exercise (or found it surprisingly revealing), you are ready to dig deeper. Learn how to self diagnose your business health at bookkeeping-essentials.com. Just so you know, when you start exploring possibilities and options around how you are spending in your business, it's fun for most entrepreneurs. Why? Most entrepreneurs are creative people and end up leaning into the process once they get started.
Before we go further ... this article isn't about diagnosing mental health issues or replacing therapy. If money stress is severely affecting your sleep, health, or relationships, please talk to a healthcare professional.
What this article DOES address is the normal-but-unhelpful avoidance patterns that keep smart business owners from maintaining their books. The kind of avoidance that's frustrating, not clinical.
Alec Quaid, Certified Financial Planner
Let's be clear, the following points aren't cash management problems. They're emotional barriers that PREVENT you from developing and USING a good cash management system in your business.
Jump to >> Worry #1 Worry #2 | Worry #3
How bad is it really? You can't create a debt payoff plan without knowing your actual numbers.TransUnion reported in February 2025 that the average Canadian carries a credit card balance of about $4,681 in 2024. For solopreneurs, that number is likely higher because business and personal expenses often blur together and the tariff trade tensions that began at the start of 2025 created uncertainty and exacerbated problematic cash flow issues.
For a Canadian solopreneur, business debt often includes one or more of the following:
And here's what makes it worse: When you are avoiding your bookkeeping, you don't actually know how much you owe. The uncertainty is often scarier than the reality.
🦆 The Bookkeeping Habit Connection: You can't create a debt payoff plan without knowing your actual numbers. This is where your bookkeeping habit saves you.
Here's the beauty of the Profit First cash management system. Even if you are behind in your bookkeeping (remember you are going for consistency not perfection so no judgment), you still know your real financial position. Your cash buckets act like an unofficial version of your books. Not quite audit-ready but it helps you keep the doors open. You can see what's available for debt payments, what's allocated for taxes, whether you need to reign in your operating expenses, and what's truly profit ... just by looking at your various bank balances (buckets).
No more 9 p.m. panic wondering 'how bad is it really?'. Your bank account balances tell you the truth.
But here's what makes it even better: When you DO catch up your bookkeeping, you'll see the complete picture. Where the money came from, where it went, and what patterns you need to change. (It's called your cash rhythm.) That's where it creates a space so you can create a real debt elimination plan.
Implementing Profit First in your business helps you manage debt while building profit. Mike loves to talk about not falling for the survival trap where you build your business on debt instead of profit.
With 2025's tariff uncertainty that won't be going away if you are not CUSMA compliant, knowing your numbers isn't optional—it's survival. You need to figure out:
My article on how tariffs impact Canadian small business walks you through the early warning signs to watch for.
Once you have a handle on your business debt (or if it's manageable), start building your personal buffer. My article on TFSA benefits for small business owners shows you how to create financial breathing room separate from your business volatility. Because when your personal finances feel stable, business stress doesn't hit as hard.
Grab some refreshment before you settle in for Money Mondays and Treasury Thursdays!In the same Real Simple Magazine issue, I came across another helpful article by Anna-Louise Jackson: 'Losing Sleep Over Money? Here's What Financial Planners Want You to Do First'. The article offers really great advice on how to approach your finances if you are feeling overwhelmed and frozen about what to do about it. She interviewed Elana Feinsmith, a certified financial therapist (yes apparently it is a thing!) and a certified financial planner.
Ms. Feinsmith offers this calming mantra: "Envision what it would feel like in the future once you've accomplished your goals. That can calm the nervous system."
When you're lying awake at 3 a.m. worrying about money, this technique actually works. Instead of spiraling into worst-case scenarios, picture yourself six months from now with organized books, a clear financial picture, and a debt repayment plan you're actually following.
So where to start?
You can't create a payoff plan if you don't know what you're dealing with. Set up a simple 'money date' with yourself. (In my 30-Day Admin Reset, I call these dates Money Mondays.)
The point is to just start. That's often the hardest part.
Gather everything:
Write it all down. Yes, seeing it all together might be uncomfortable. But the anticipation is always worse than the reality. Now you know what you are dealing with.
Use one of the Canadian banks' loan calculators or debt consolidation calculator to play with the numbers:
This isn't about committing to anything yet. It's about seeing what's possible.
Choose one of two payoff methods. Which one you choose depends on your personal style. Both are good but for different reasons.
Snowball method pays the debt with smallest balance first.
Avalanche method pays the highest interest rate debt first.
🦆 The best strategy is the one you'll actually stick with.
Now that you know what you need to pay, where will that money come from?
This is where you look at your spending. Get your latest business bank statement (and personal bank statement if expenses are mixed). Do the Traffic Light Expense Review that I introduced earlier in this article if you didn't do it when I first mentioned it.
🟢 Green = Necessary business expense, aligned with my business goals, no regrets
🟡 Yellow = Questionable. Was this really necessary? Could I have spent less? Can I explore other options?
🔴 Red = Personal expenses that snuck into business account OR subscriptions I forgot about
🦆 The Bookkeeping Habit Connection: Look for the pattern. Where is your money going to things that don't help you achieve your goals? This is literally what categorizing expenses does. When you review your books regularly, you see patterns.
Here's the hard truth. If you're a solopreneur drowning in debt, you probably need to look at personal spending too because your business and personal finances are likely intertwined.
With tariff uncertainty making everything more expensive, cutting unnecessary spending isn't optional. It's S U R V I V A L.
My article on asking the right questions before you spend money can help you make better decisions going forward.
You can't save what you can't see!Most financial advice talks about personal retirement. But as a solopreneur, you need a business emergency fund FIRST. Especially now, with tariff uncertainty.
In my TFSA Benefits For Small Business Owners article, I showed you how to build financial stability for your personal finances separate from the volatilities of your business profits ... or lack thereof. Let's look at how to do the same thing for your business.
In my article, A Simple Cash Management System For The Self-Employed In Canada, I walk you through a streamlined version of the Profit First method. Here's the broad overview of putting your cash on autopilot:
🦆 The Bookkeeping Habit Connection: You can't save what you can't see. When your books are current, you know your true profit not just your bank balance.
Here's why this matters. If you're using just one business bank account for everything, your bank balance lies. It includes money you owe for GST/HST, upcoming bills, and that big annual insurance payment coming up. You think you have $10,000, but $8,500 is already spoken for.
This is exactly why the Profit First system works so well. Each bank account has a specific purpose:
When your bookkeeping is current AND you're using Profit First, you have complete clarity. You know what you can afford to save because the money is already separated.
Even $50/week transferred to your Profit account (covers emergency fund or future growth or your owner's bonus) adds up to $2,600/year. Start small. Build momentum.
🦆 Your goal: Three months of operating expenses saved.
Why? Because when (not if) something unexpected happens (tariff impacts, supplier issues, slow season, equipment breakdown) you have breathing room. You can make good decisions instead of panic decisions.
Once your debt is paid off, route 50% of that payment to your business emergency fund. (In my cash management system, I call this your Future Growth account.)
This isn't pessimism. It's preparation. And in 2025's uncertain economy, it's S U R V I V A L.
Now you understand the three emotional barriers that keep you from managing your money. You've seen yourself in at least one (maybe all three) of these patterns. So what do you actually DO about it? That's what the next section is about ... the one habit that changes everything.
Bookkeeping-Essentials.ca
No. No. No. There's a huge difference between flexible and just plain wrong.
What I'm referring to here are your habits and system for recordkeeping and cash management ... they work best when you're consistent. It's like going to the gym. You don't abandon your exercise routine because you had a busy week and couldn't go. The next week, you get right back at it.
Let's look at some 'habits' that work and those that don't:
✅ GREEN LIGHT 'Imperfection' (Flexible but totally fine)
❌ RED LIGHT 'Imperfection' (Wrong and may hurt you)
🦆The standard: Your books need to be accurate enough to make good decisions and survive an audit. They don't need to be colour-coded perfection, but they can't be fiction. Remember: garbage in, garbage out. You need good, accurate information to make informed business decisions.
Just know this. For every receipt you don't chase down, you're losing a tax deduction ... which means you're paying more income tax.
Learn more >> 13 Non-Deductible Business Expenses: Form T2125 For the Sole Proprietor in Canada
Now you understand the three emotional barriers that keep you from managing your money. You've probably recognized yourself in at least one (maybe all three) of these patterns.
So what do you actually DO about it?
Here's what I've learned after years of working with solopreneurs. The anticipation is always worse than the reality.
Yes, your books might be behind. Yes, you might owe money. Yes, you might need to make changes.
But once you KNOW, you can DO something about it.
The Problem with 'Just Start Somewhere'? You've probably heard advice like 'just pick one thing and start'. But which thing? File receipts? Categorize expenses? Update mileage logs? Reconcile accounts?
When you're overwhelmed, even choosing where to start creates paralysis. That's why I created the 30-Day CRA Compliance Reset.
Why a System Beats Random Habits?
The Reset isn't about doing everything perfectly. It's about building a sustainable routine that:
It's designed specifically for solopreneurs who are behind, overwhelmed, or avoiding their bookkeeping.
What Does The 30-Day Reset Gives You? A clear path from 'I don't know where to start' to 'I have a routine that works'.
The 5-step process you will be creating.You'll learn:
Each week builds on the last. By Day 30, you'll have:
🦆 Here's the key: The Reset gets you CURRENT and keeps you current going forward. If you have months (or years) of backwork, you'll tackle that separately—a little bit each week—while maintaining your new routine.
You're not trying to fix everything in 30 days. You're building the habit that prevents future chaos.
You've done the emotional work in this article:
✅ You understand why you avoid. (RAIN method)
✅ You've faced your debt reality. (if applicable)
✅ You've reviewed your expenses. (Traffic Light method)
Before you dive into the 30-Day Reset, get your cash organized.
The Reset works best when your money is already flowing in an organized way. Otherwise, you're just tracking chaos.
🦆 Your next step: Set up a Simple Cash Management System. This puts your cash on autopilot with separate accounts and automatic allocations. Once your cash is organized, then you're ready for the 30-Day Reset to get your bookkeeping current and build your maintenance routine.
S T A R T H E R E.
If you're ready to break the avoidance cycle, start with doing the emotional work outlined in this article. It addresses all three emotional barriers we talked about:
N E X T,
S T A R T S M A L L E R begin with ...
These tiny steps break the avoidance cycle. Once you can look at your money without panic, you're ready for bigger systems.
🦆 Remember Consistency beats perfection.
You don't need perfect books. You need books you actually maintain. You need to know your numbers. You need to stop avoiding. This doesn't give you free license to categorize expenses intentionally!
The systems are here when you're ready:
Take the next right step. That's all.
Here are answers to common questions about managing your business cash:
I'm behind and overwhelmed. Where do I start?
If you are wanting to get your ducks in a row, start with week 1 of the 30 day reset. Week 1's goal is to create one place where all your business paperwork lands, and build the habit of actually using it. You're not fixing everything. You're building momentum.
If it's tax time and you're scrambling: I show you how to get your paperwork organized quickly for your tax preparer when you didn't touch your books all year.
How do I stop mixing personal and business spending?
Short answer: pay yourself a regular amount to cover your non-discretionary personal expenses.
Now let's look at what's really happening. You're pouring everything into the business because you want it to succeed. Taking a 'paycheque' feels like you're taking money away from the business. So you don't pay yourself officially ... until reality bears its ugly head and you have a personal bill comes due ... so you have to dip.
But here's the truth. If your business can't support you, it's not a business; it's an expensive hobby.
You deserve, yes deserve, to be paid for the work you do. Your business exists to support your life, not the other way around.
The fix isn't restriction. It's intention.
Pay yourself first, automatically, twice a month. Not what's 'left over' (there's never anything left over). A set amount that covers your basic needs, transferred before you pay other bills.
This isn't taking from your business. This IS your business working for you.
Here are two ways to start:
Option 1: How to Pay Yourself as a Business Owner — Set up regular transfers today.
Option 2: Simple Cash Management System — Automate your entire cash flow (owner's pay, taxes, profit, expenses) so paying yourself becomes non-negotiable.
When you pay yourself first, you stop operating from scarcity. You make better business decisions because you're not in survival mode. And you finally know your business's true operating costs because your pay is included (even if it is not a deductible expense).
Bottom line: You can't build a sustainable business on unpaid labor ... even if that labor is yours.
What's the fastest way to lower my money stress this week?
Short answer: Implement the Profit First cash management system so your money runs on autopilot.
A few hours of setup, then you can see your cash flow (taxes set aside, profit allocated, bills covered) just by logging into your bank. Clarity kills anxiety.
Why does this works? You're taking action instead of worrying. Once setup, the system makes decisions for you based on your targets (no more "should I spend this?"). And you'll immediately know where you stand financially every time you login and check your bank balances.
Do you want to understand why you were stressed in the first place? Read about [the three money worries that break habits] and [the avoidance cycle]. But the system works whether you understand the psychology or not.
Know your bank balance right now ... not what you think it is, what it actually is. Then set up the so you can see your cash flow (taxes set aside, profit allocated, bills covered) just by logging into your bank. Clarity kills anxiety.
The plate method for nutrition. The bucket method for business finances. Same principle: organized diversity creates health.Why are we talking about food in a bookkeeping article (and why it matters)?
I recently read a January 2, 2025 article from ZOE, a nutrition science company, titled "How to eat in 2025: 7 science-backed tips." [https://zoe.com/learn/how-to-eat-in-2025] As I read through the recommendations from Professors Tim Spector and Sarah Berry, I kept thinking: 'This is exactly what solopreneurs need to hear about their finances.'
Stay with me here.
Because poor diet and erratic routines can worsen stress and sleep—two things that make it harder to face your numbers. These quick comparisons borrow the food guidance from ZOE’s research and translate it into simple money habits you can start this week.
Why? Because both food and finances trigger the same avoidance behaviors:
Plus, you probably know ... when you're stressed about money, you're probably not eating well either. And when you're not eating well, your brain doesn't have the energy to tackle financial decisions. So this is actually a two-for-one: better nutrition supports better financial management.
Important: This is general information, not medical advice.
Let's look at the 7 parallels:
Just as ultra-processed foods blur the structure of real food, mixed business/personal finances blur your true financial picture. The food plate keeps categories clear ... your bank accounts
should separate income, expenses, and taxes.
The food plate shows vegetables, fruits, proteins, and grains—each feeding different body systems. Your 6 bank accounts (Income, Tax, Profit, Owner's Pay, Operating, GST) each serve different business functions.
Both require:
✅ Consistency over perfection → Small, regular actions beat extreme measures.
✅ Mindfulness → Awareness of what, when, and why you consume.
✅ Systems reduce decision fatigue → Automation and establishing boundaries.
✅ Diversity with purpose → Multiple accounts (or plant-based foods) serving specific functions.
✅ Focus on the real problem → Cash flow (fiber), not just debt (protein).
And here's the bonus ...
When you eat well, your brain has the energy to make better financial decisions. When your finances are organized, you sleep better and stress less which helps you make better food choices.
It's all connected.
Alec Quaid, Certified Financial Planner
Sometimes the emotional barriers are too high to tackle alone. Or the financial situation is too complex. Or you simply need expert guidance.
That's not weakness. That's wisdom. Here's when to reach out and who can help.
If you're experiencing any of these, it's time to talk to a non-profit credit counsellor:
All of these organizations offer reputable Canadian debt counselling services. With the exception of FCAC, these non-profit credit counselling services have free initial consultations:
What these organizations can help you do:
🦆 Important: Avoid for-profit 'debt settlement' companies that charge high upfront fees and make unrealistic promises. Stick with accredited non-profit counsellors.
Even if debt isn't your issue, you might need professional help to get your books current or create a financial plan:
Start with your most pressing need. The right professional can break the overwhelm into manageable steps.
For detailed information on when to hire each professional, what they do, costs, and red/green flags to watch for, see Appendix: Choosing the Right Financial Professional.
If you're losing sleep over your business finances, reach out:
• A bookkeeper can help you get current
• An accountant can help you plan and strategize
• A financial planner can help you see the bigger picture
• A credit counsellor can offer solutions for overwhelming debt
The right professional can break the overwhelm into manageable steps. Sometimes just knowing you have expert support is enough to break the avoidance cycle.
If you're losing sleep, talk to someone. A bookkeeper can help you get current. An accountant can help you plan. A financial planner can help you see the bigger picture. A debt counsellor can offer you solutions for your current circumstances ... and may even not require bankruptcy.
The good news? Financial stress thrives in the dark and what you are imagining is always worse than the reality.
Yes, your books might be behind. Yes, you might owe money. But once you KNOW, you can DO something about it. The systems are here. The help is available. Start small, build one habit, and take the next right step.
Your future self (and your sleep) will thank you.
Even if debt isn't your issue, you might need professional help to get your books current or create a financial plan. Here's when it makes sense to get other professional help:
Certified Professional Bookkeeper (CPB - https://cpbcan.ca/career-centre/find-a-bookkeeper.html)
When to hire:
• Your books are months (or years) behind
• You don't have time to maintain bookkeeping yourself
• You need someone to set up your systems properly
• Tax season is approaching and you're not ready
What they do:
• Catch up backlogged bookkeeping
• Set up accounting software correctly
• Establish systems you can maintain
• Process transactions accurately for CRA compliance
Cost: Varies. My preference is work with a bookkeeper who does not charge by the hour but prices the project and includes extras like sharing their insights into what they see and what you could perhaps do differently. I especially like bookkeepers who give a minimum of 3 pricing packages so you can pick what services you want. Backwork may require an hourly rate for a variety of reasons - sometimes it's a hornet's nest once you get started!
Chartered Professional Accountant (CPA)
When to hire:
• Tax planning and strategy questions
• Deciding on business structure (sole proprietor vs. corporation)
• CRA audit or payment arrangement issues
• Year-end financial statement preparation
• Complex financial decisions
What they do:
• Prepare and file tax returns
• Provide strategic tax advice
• Represent you with CRA if needed
• Analyze financial statements and advise on business decisions
Cost: Varies widely; many offer small business packages
Note: Some CPA firms are currently advertising bankruptcy filing services if your situation has reached that point in this economic tariff environment. I would note you want to hire a CPA licensed for public practice ... not a CPA employed in the private sector and does consulting on the side.
Certified Financial Planner (CFP - https://www.fpcanada.ca/planner-directory)
When to hire:
• You want a whole plan that integrates business and personal finances
• Retirement planning as a solopreneur
• Investment strategy questions
• Insurance needs assessment
• Exit strategy from your business
What they do:
• Create comprehensive financial plans
• Help you see the big picture beyond day-to-day operations
• Plan for retirement when you don't have a company pension
• Balance business reinvestment with personal financial security
Important: Look for CFPs who specifically understand solopreneur finances, not just corporate employees with benefits packages.
Tax Lawyer - see 'Is Voluntary Disclosure The Right Move'.
How to Choose the Right Professional
Start with your most pressing need:
• Books are a mess → Bookkeeper
• Tax questions or CRA issues → Accountant
• Overwhelming debt → Credit counsellor
• Want to plan for the future → Financial planner
• Emotional overwhelm about money → Consider all of the above but getting your ducks in order one at a time
Red flags to watch for:
• Guarantees specific financial results
• Pressure to buy products before understanding your situation
• Won't explain things in plain language
• Makes you feel stupid for asking questions
• High-pressure sales tactics
Green flags to look for:
• Asks about your goals and concerns first
• Explains fees clearly upfront
• Willing to collaborate with your other professionals (bookkeeper + accountant working together)
• Makes you feel capable, not dependent
• Answers questions patiently
• Has experience with solopreneurs specifically