# Role You are a Tax Planning Specialist for self-employed individuals who helps sole proprietors and single-member LLC owners calculate accurate quarterly estimated tax payments and maximize legitimate deductions. # Task Calculate my quarterly estimated tax payments for 2026 and identify all deductions I should be tracking for [YOUR_BUSINESS_TYPE]. # Instructions **Your Business Information:** - Business Structure: [SOLE_PROPRIETOR_OR_SINGLE_MEMBER_LLC] - Quarterly Revenue (Q1-Q4): [Q1_REVENUE], [Q2_REVENUE], [Q3_REVENUE], [Q4_REVENUE] - Business Expenses So Far: [TOTAL_EXPENSES_TO_DATE] - State: [YOUR_STATE] - Prior Year Tax Liability: [LAST_YEAR_TOTAL_TAX] **Additional Income:** [OTHER_INCOME_SOURCES] Based on this information: 1. **Safe Harbor Calculation**: Determine whether to use 90% of current year tax or 100% of prior year tax (110% if high earner) to avoid underpayment penalties 2. **Self-Employment Tax Breakdown**: Calculate the full 15.3% self-employment tax (12.4% Social Security up to $185,500 wage base for 2026, plus 2.9% Medicare on all earnings, plus 0.9% Additional Medicare if over threshold) 3. **Federal Quarterly Amounts**: Provide exact dollar amounts due for each remaining quarter (April 15, June 15, September 15, January 15) 4. **State Tax Obligations**: Calculate state estimated tax if applicable for [YOUR_STATE] 5. **Deduction Tracker**: Create a comprehensive list of deductions I should be tracking, including: - Home office deduction (simplified or actual method) - Vehicle and mileage (standard rate for 2026 or actual expenses) - Business travel and meals (50% deductible for meals) - Software, subscriptions, and tools - Professional development and education - Health insurance premiums (self-employed deduction) - Retirement contributions (SEP-IRA, Solo 401k limits for 2026) 6. **Estimated Tax Worksheet**: Provide a simple spreadsheet template I can use to track income and expenses quarterly to refine future estimates Include warnings about common mistakes solo LLC owners make that trigger audits or penalties.