1. Unexpected Tax Bills - Receiving a tax bill that's much higher than expected.

• Why It Happens:
• Miscalculating quarterly taxes.
• Not setting aside enough for taxes throughout the year.
• How to Prepare:
• Regularly estimate your tax liability.
• Set aside a portion of your income for taxes each month.
• Work with an accountant to ensure you're paying the correct estimated taxes quarterly.

2. Tax Penalties for Misclassifying Workers - Penalties for treating employees as independent contractors.

• Why It Happens:
• Misunderstanding the difference between employees and contractors, or intentionally misclassifying to avoid taxes.
• How to Prepare:
• Learn the differences between contractors and employees.
• When in doubt, consult a tax professional to ensure proper classification.
• Use IRS guidelines to help clarify the classification rules.

3. Failure to File or Pay Penalties - Penalties that pile up when taxes aren't filed or paid on time.

• Why It Happens:
• Forgetting the filing deadline, not having the money to pay, or simply procrastinating.
• How to Prepare:
• Set reminders for important tax deadlines.
• File your taxes even if you can't pay the full amount—partial payments help reduce penalties.
• Work out a payment plan with the IRS if needed.

4. Audits & the Fear of Being Unprepared - The fear of receiving an audit notice and not having your records in order.

• Why It Happens:
• Incomplete records, claiming large deductions, or mistakes in your tax return can trigger an audit.
• How to Prepare:
• Keep organized and thorough financial records all year round.
• Double-check deductions to ensure they are accurate and justifiable.
• Don't panic if you're audited—respond promptly and provide the requested documentation.

LINKS:

Independent Contractor or Employee

Worker Classification 101