Getting naked with your numbers: A bookkeeper's truth about business fear and the habits that actually create financial clarity
Recently, I had a conversation with Hugh Carnahan about something that happens more often than you'd think in my bookkeeping practice. We talked about how easy it is for business owners to find themselves blindsided by tax obligations they didn't even know they had, simply because they weren't tracking their numbers properly.
This scenario perfectly captures something I see every single day: brilliant entrepreneurs running successful businesses who are absolutely terrified of their own numbers.
The five-gallon bucket revelation
Here's how most business owners operate: Imagine you're Bob, running Bob's Mowing. You've got one five-gallon bucket. All your money goes into that bucket—customer payments, reimbursements, everything. Then all your expenses come out of that same bucket: payroll, taxes, fuel, equipment repairs.
Bob's only financial strategy? Look in the bucket. If there's money, spend it. If there's not, panic.
This is exactly how most businesses run today, especially in the early days. It feels simple, but it's actually where most financial stress begins.
They'll obsess over metrics that excite them: how many calls they made, how many units they sold, how many followers they gained. But when it comes to understanding where their money actually goes? They're just hoping the bucket doesn't run dry.
Why we're all afraid (and why it's costing us)
After fifteen years of working with business owners, I've identified the real reasons behind this fear:
It's not about the math. It's about the shame.
Most entrepreneurs didn't start their business to become accountants. They had a vision, a passion, a service they wanted to provide. Then somewhere along the way, someone told them they needed to understand assets and liabilities, cash flow statements, and P&Ls.
The industry doesn't help. We bookkeepers and accountants often talk over your heads—not out of malice, but because these concepts are second nature to us. When you don't understand, you feel stupid. So you avoid the conversation entirely.
The only time you interact with your numbers is tax season.
And who wants to think about taxes? Your financial statements become this dreaded annual ritual instead of the powerful decision-making tools they're meant to be.
The post-it note genius
I once had a client who built commercial buildings, and everything—and I mean everything—was tracked on Post-it notes. When we started doing his bookkeeping, we discovered his Post-it note system was more accurate than our initial reports.
He'd call me and say, "It's wrong because my Post-it note says something different."
This man was brilliant. He'd figured out a system that worked for his brain, his workflow, and his reality. The lesson? There's no one-size-fits-all approach to managing your money. The best system is the one you'll actually use.
The bucket trap most businesses fall into
Many businesses fall into the same trap: all money goes into one big bucket (their checking account). All expenses come out of that same bucket. The only financial question they ask is, "Is there money in the bucket?"
This is like trying to run a household where your mortgage payment, grocery money, vacation fund, and emergency savings all live in the same envelope. You'd never know what you could actually afford to spend.
My personal confession
I need to be honest with you: I run a bookkeeping company, but for the first few years of most businesses, I don't recommend hiring a bookkeeper.
I know that sounds crazy coming from me, but here's the truth. You should put that money into marketing or growth until you can truly afford professional help.
What you should do instead is get intimate with your numbers yourself. Start simple:
Track what money comes in and what it's for
Track what money goes out and why
Use two bank accounts: one for money coming in, one for money going out
Never attach a credit card to your income account
The $14,000 mowing revelation
Hugh's story perfectly illustrates why this matters. When we organized his numbers, we discovered he'd spent $14,000 on mowing services plus $6,900 on fuel. That's over $20,000 just to cut grass.
Armed with this information, he made a business decision: hire an employee and buy electric mowers. Now he has that $14,000 back in his business plus a crew member for other tasks.
But here's the kicker. He never would have seen this opportunity if he hadn't gotten "naked" with his numbers.
The Amazon wake-up call
I can't tell you how many times I've shown business owners their Amazon spending, and they're shocked: "We spent THAT much on Amazon? I had no idea."
Amazon made it so easy to click and buy that many business owners don't realize they're bleeding money on supplies they could buy in bulk elsewhere, or items they don't actually need.
Your numbers tell stories. They reveal patterns. They show you where you're winning and where you're losing. But only if you're brave enough to look.
Start with fear, end with power
I understand the fear. I really do. Numbers can feel overwhelming, especially when you're already running a million miles an hour trying to grow your business.
But here's what I've learned after helping hundreds of businesses: the fear of looking at your numbers is always worse than the actual numbers themselves.
Even when the news is bad (like Hugh owing taxes to Missouri), knowledge gives you power. Once you know what you're dealing with, you can make a plan. You can take action. You can fix it.
Your 15-minute financial revolution
If you're ready to stop operating with just one bucket and start making informed decisions, here's where to start:
Open four bank accounts today:
Income (where all money flows in)
Profit (your reward for taking risks)
Taxes (so April never surprises you again)
Operating expenses (what you actually have to spend)
Set up automatic transfers so when money hits your income account, it immediately splits into the other accounts based on percentages you decide.
Start with something, even if it's just $10 in your profit account. Something magical happens when you begin that habit.
The truth about financial transparency
Getting honest with your numbers isn't about perfection. It's about facing reality so you can change it.
Your business deserves better than living paycheck to paycheck, crisis to crisis, hoping there's enough in the bucket to make it through another month.
You deserve to pay yourself. You deserve to know where your money is going. You deserve to make confident decisions based on facts, not fear.
The numbers are just waiting for you to look. And I promise, they're not as scary as you think.
🎧 Watch the full interview:
Hear even more real examples and strategies from my conversation with Hugh:
Ready to get honest with your numbers?
Start with our free Business Financial Health Check, your judgment-free first step toward financial clarity and confidence: Take the quiz here