How up-to-date are your books right now?
Updated weekly (or more)
Updated monthly
Updated quarterly / only when I “have to”
Updated when I need to file taxes and I have trouble meeting tax deadlines.
When you look at your bank balance, do you actually know what’s available to spend?
Yes - my balance matches my reality
Mostly, but I occasionally get surprised
No - I’m guessing and hoping
I’ve had overdrafts or “oops” moments
What happens to receipts and documentation?
I upload/store them consistently in a digital format
I save some, lose some
They live in my car/purse/shoebox/email chaos
Receipts? What receipts?
Do you know your profit (not revenue) for last month?
Yes, I can tell you right now
I could find it pretty quickly
I have no idea
Profit?… is that what’s left in the bank?
How confident are you that your bookkeeping is accurate and is capturing all applicable tax deductions?
Confident - my transactions are categorized correctly, reconciled, and I’m capturing all (or nearly all) deductions.
Somewhat - I think it’s mostly right, but I worry I’m missing deductions or miscategorizing things.
Not confident - I’m guessing, behind, or I know deductions are being missed.
Not attempted - I'm behind by multiple years.
If your CPA asked for clean financials today, how stressed would you be?
Not stressed - I could send them quickly
Mildly stressed - might take a little cleanup
Very stressed - would take weeks/months
Panic - I’d avoid the email
Do you use your bookkeeping to make decisions?
Yes - pricing, spending, taxes, cash flow planning
Sometimes - mostly for tax time
Rarely - I don’t trust the numbers
No - I run the business off my bank balance
If nothing changes and you keep doing bookkeeping the same way for the next 3 months, what’s most likely to happen?
I’ll be fine - my system works and my books will stay clean
I’ll get by - but I’ll probably feel stressed or fall behind
I’ll keep operating without clear numbers, which makes it harder to price confidently, plan hires, or grow.
It’ll become a problem - scrambling, unsure of numbers, tax-time chaos
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