I still remember the moment I found the original UK version, The Secret Dreamworld of a Shopaholic, in a London library during one of my first trips to Europe. When they brought it to the U.S., they renamed it Confessions of a Shopaholic, fitting, because yes, I totally identified with Becky. Too many confessions to make!

Becky is a financial journalist who’s thousands of pounds in debt due to her shopping addiction. She admits to knowing very little about personal finance and racks up reckless spending on designer homeware, clothes, and beauty products, rationalizing every purchase as an “investment” or an “absolute necessity”. Sound familiar?

While Becky’s choices are personal, the mindset isn’t far off from what I see in business owners who justify personal expenses as business deductions. The thrill of shopping, the internal justifications, the dramatic receipts, been there, lived that.

These days, I’m living only my Advisor era. Still making confessions, just with spreadsheets instead of shopping bags. Let’s just say that I’ve seen things. Things that keep me up at night and I don’t mean horror movies. I mean financial statements.

As a Fractional CFO, I get invited into the most sacred space of a business: THE BOOKS. While I approach every engagement with professionalism, strategy, and zero judgment, I’ll admit, sometimes I raise an eyebrow.

Most business owners aren’t trying to be reckless. They just don’t know what they don’t know. And when you’re focused on selling, serving, or simply staying afloat, the financial side can easily fall behind.

But those books? They tell a story. Sometimes it’s a love story, sometimes a horror story, and sometimes, a comedy of errors. And as a CFO, I read that story to figure out what happens next. Not to fix the past, but to build the future.

Now, my very own Confessions of a CFO.

1. “This Chart of Accounts, bless it” It’s the blueprint of your financial house, and in many businesses, it’s chaos. When I open a chart of accounts and see ten variations of the same accounts, random names, or no clear structure, I know we’ve got work to do. If your categories are vague or duplicated, you’re not getting accurate reports. And if leadership can’t read the reports? The business suffers.
2. “The Uniform Account… Oh, Really?”

I once opened a client’s P&L and saw a Uniform Expense account with a number that made me blink twice. The funny thing? This business didn’t even provide uniforms to employees. When I dug deeper, it was full of branded pens, fancy clothes and, I kid you not, a luxury handbag. “But I’m the CEO”, they said, “I need to look good.” Listen, I’m all for representing your brand with style, but, that Louis Vuitton tote isn’t a deductible operating expense. That’s a personal style choice, not a tax strategy, and it’s definitely misleading when trying to create a future plan and manage cash flow.

3. “Planes, Trains, and Other Travel Expenses” Travel can be a real business investment, but it can also become a catch-all for things that have nothing to do with business. I’ve seen entire family vacations tucked into the travel category with no business purpose documented. One client even listed concert tickets as part of a “networking event”. If you’re not clearly tying the expense to revenue, or at least to business development, that is not a business expense.
4. “Let’s Talk About Meals and Entertainment” Ah, the infamous lunch meetings. I’ve seen everything from daily coffee runs to birthday brunches for family members logged under Meals and Entertainment. If you’re going to use this category, make sure you’re following the rules, and track who was there and what was discussed. If the receipt says ‘happy hour’ but the notes say ‘strategic planning,’ there is a problem.
5. “The Mysterious Miscellaneous” This one’s my favorite and my biggest headache. The infamous Miscellaneous Expense account. If your P&L has a number over a few hundred dollars in this category, and especially if it’s a few thousand, we need to talk. What is it? Why can’t it be properly categorized? Miscellaneous is a red flag. It tells me no one is paying attention to the details, and maybe that’s where the money is leaking.

Cafecito Takeaways: Spot It. Clean It. Lead On.

Do not kid yourself. Pay yourself whatever is needed for your lifestyle (and of course, that the business can support), and stop using the business accounts to fund your personal life or apply “tax strategies” that cross the line into illegality.

• Your chart of accounts is not a formality—it’s a strategic tool. If it’s a mess, your decisions will be too.
• That “uniform” line item? Better make sure it’s not secretly your wardrobe budget.
• Travel and meals can be deductible—but only if they’re real business expenses, not personal perks.
• The miscellaneous account should be tiny and rare, not your financial junk drawer.
• If you’re justifying personal expenses through the business, you’re not strategizing—you’re risking.

When you don’t have clean books, you can’t make clear decisions. You’re navigating almost recklessly, guessing instead of making inform decisions. Financial leadership doesn’t come from perfect bookkeeping, it comes from using that information to drive strategy, growth, and smart risk.

So, are your books confession-worthy? Grab your cafecito and review your last P&L. What story is it really telling you? Let’s chart the path forward, strategically, powerfully, and with purpose.