A few big ones pop up over and over:

• Not making quarterly estimated payments.
  
  
• Mixing business and personal expenses.
  
  
• Missing legitimate deductions (like home office, mileage).
  
  
• Overstating deductions you can’t prove.
  
  
• Not filing or filing late, hoping it goes unnoticed.

These mistakes snowball fast because the IRS hits self-employed people with both income tax and self-employment tax — so every error hurts more.

They match your 1099s, bank deposits, and expense categories to what you filed. If your numbers don’t add up — or you “forget” a 1099 — you’ll usually get a CP2000 notice adjusting your return.

If you over-deducted something big, you may face an audit or penalty.

Self-employed people must pay taxes as they go. If you didn’t send in enough each quarter, you’ll owe underpayment penalties plus interest when you file.

But you can catch up with a clear payment plan — and sometimes lower next year’s penalties by adjusting how you pay in future quarters.

Yes. The IRS lets you file an amended return (Form 1040-X) for up to 3 years after the original due date.

If you forgot income, missed deductions, or found errors — fixing it yourself before the IRS notices often reduces penalties and shows good faith.

File anyway — then deal with the balance. The penalty for not filing is worse than not paying. Once filed, you can set up an Installment Agreement, explore penalty relief, or in hardship cases, negotiate an Offer in Compromise to settle for less.

Not automatically. Amending a return isn’t a red flag — messing up and ignoring it is. The IRS sees people fix honest mistakes all the time.

If you catch it early, file it right, and have the backup, you’re ahead of the game.

Good record-keeping and planning:

• Use a separate business bank account.
  
  
• Track income and expenses monthly.
  
  
• Work with a tax pro to plan quarterly payments.
  
  
• Use tools like Gusto for payroll if you switch to an S Corp.

Doing this upfront is way cheaper than fixing messes later.

Absolutely. I rebuild missing books, dig up old income records, fix missed deductions, file clean amendments, and negotiate with the IRS if needed.

DIY panic fixes often make things worse — so real help saves you headaches and money.