Nobody taught you quarterlies or what actually counts as a write-off. These posts are the short version, updated when the IRS changes the rules.
The hard part of leaving QuickBooks isn't the price, it's the year of history inside it. Here's how to move your transactions, vendors, and customers in an afternoon, sorted onto real Schedule C lines.
Send the wrong 1099 and the penalty starts at $60 a form and climbs to $660. Here's the decision tree for which one each payee gets.
The whole bookkeeping job is five steps and about 40 minutes a week. No journal entries, no March cram, and a Schedule C your CPA can file from.
The underpayment penalty runs 8% annualized, even if you pay your full balance on April 15. Two safe harbor rules shut it off. Here's how.
One wrong basis number on Form 8829 and you pay up to 25% recapture when you sell your home. The line-by-line walkthrough for sole props.
Simplified caps your home office deduction at $1,500. Actual can be triple that, but it claws some back when you sell. Here's how to pick.
TurboTax's interview hides seven traps that cost sole props deductions every January. Here's the annotated walkthrough, trap by trap.
Run your freelance income through the family joint account and business drops to under 30% of the transactions. That's 70% noise to sort every month. The fix is structural, not more tagging.
The vehicle deduction is the most-disallowed Schedule C item in audits, and it's almost never the driving that gets denied. It's the mileage log. Here's what the IRS actually requires.
Run your freelance income through a personal checking account and 70–90% of every month's transactions become noise you classify by hand. Here's the clean split.
Skip your quarterlies and the IRS charges 8% annualized, even if you pay your whole balance on April 15. Here's how to compute the four estimated tax payments and dodge the penalty.
Underpay your S-corp salary and a reclassification audit can cost $20K–$60K in back FICA, penalties, and interest. Here's how the IRS defines 'reasonable' and how to defend your number.
You don't need a paper receipt for every expense. Under $75, a card statement usually does it. But lodging always needs a receipt, and meals need names. Here's the actual rule.
At $100K profit, an S-corp election saves roughly $2,500–$3,000/yr after payroll and CPA fees. Below $60K, the friction eats it. Here's the break-even math.
Every dollar you don't deduct on Schedule C costs you a 25–35% bite in SE tax plus income tax. Here's every line, what counts, and the receipts the IRS expects for 2026 returns.
SE tax is 15.3% on top of income tax, and it blindsides most first-year sole props. Here's the exact Pub 334 formula: the 92.35% adjustment, the wage base, and the half you can deduct back.