Tax-Ready All Year

STEP 1 — LEARN THE BUSINESS Ask: "What kind of business do you run? And how do you handle taxes right now — do you have an accountant? Do you make quarterly estimated payments? Do you have a sense of which expenses are deductible?" Wait for their answer. Use it to personalize everything that follows. STEP 2 — SET UP TAX CATEGORIES Their month-end expense categories are a starting point, but tax categories may be different. Walk them through extending the categories to include tax-relevant groupings. Have them tell Claude: "Look at my month-end expense categories and help me set up tax-ready categories. I need to track: [their deductible expenses — e.g., home office, mileage, software, meals, contractor payments, supplies, insurance, professional development]. Map each expense to the right Schedule C category." Explain: Claude doesn't replace their accountant — it just makes sure expenses are tagged correctly all year so there's no scramble in April. STEP 3 — TRACK DEDUCTIBLE EXPENSES Have them tell Claude: "When you categorize expenses in my month-end report, also flag which ones are tax-deductible and which Schedule C category they fall under. Keep a running total of deductions by category." Walk through an example: that software subscription is a business expense (Schedule C, Line 18). That lunch with a client is 50% deductible (meals). That mileage to a job site is deductible at the current IRS rate. STEP 4 — SET UP QUARTERLY ESTIMATES Have them tell Claude: "Based on my income and deductions so far this year, estimate my quarterly tax payment. Use [their tax rate or ask their accountant]. Remind me 2 weeks before each quarterly deadline: April 15, June 15, September 15, January 15." Explain: quarterly estimates prevent the massive April bill. Claude calculates them from real numbers, not guesses. STEP 5 — TRACK 1099 CONTRACTORS If they pay contractors, have them tell Claude: "Track my 1099 contractors. For each contractor, record: Name, Total Paid This Year, and whether I have their W-9 on file. At year-end, flag anyone I paid over $600 who needs a 1099." Walk them through adding their current contractors and year-to-date payments. STEP 6 — GENERATE QUARTERLY TAX REPORT Have them tell Claude: "When I say 'run tax prep' or 'quarterly tax report', produce a report with: total income YTD, total deductions by category, estimated tax liability, quarterly payment status (paid/due), 1099 contractor summary, and anything my accountant needs to know. Format it so I can forward it directly." Test it together and adjust the format. STEP 7 — SAVE AS A SKILL Have them tell Claude: "Save this as a skill called 'tax-prep'. When I say 'run tax prep' or 'quarterly tax report', run this full workflow." Explain: quarterly — not annually — is how you stay tax-ready. Run it at the end of each quarter. Forward the report to your accountant. No surprises. STEP 8 — POINT FORWARD Tell them what they've built: year-round tax tracking, quarterly estimated payments, deduction categorization, 1099 contractor tracking, and accountant-ready quarterly reports. Mention related guides: - "Month-End in 20 Minutes" (https://tsidai.com/guides/month-end) — the foundation this builds on - "Know What You Owe" (https://tsidai.com/guides/vendor-scorecard) — track vendor payments that may be deductible - "Business Planner" (https://tsidai.com/guides/business-planner) — tax planning fits into your broader financial picture If they get stuck, suggest booking a Tsidai starter session at https://cal.com/tsidai/starter-session.