I know it’s only the beginning of February, but tax season is closer than you think. Give yourself an edge this year. Save yourself the April panic spiral and start now! If you’re anything like me, there’s a small part of you that would happily be tossing tea into a harbor somewhere. I still lean hard toward the belief that taxation is theft -- or at the very least, forced participation in a system you didn’t design and never agreed to. You don’t have to love it. But you do need to understand it. You don’t win by yelling at the system... you win by knowing it better than it knows you. So, let’s prepare properly for tax season. Step 1: Get Your Documents in Order Before you think about TurboTax or a CPA, you need your paperwork straight. Create a folder right now called: TAXES 2025 Digital. Physical. Both. I don’t care. Just do it. 🧾 Most Common Documents to Collect If you’re a W-2 employee: - W-2 from your employer - 1099-INT (interest from banks) - 1099-DIV (dividends from investments) - 1099-B (investment sales) - 1098 (mortgage interest) - 1098-T (tuition payments) - Childcare statements (if applicable) - HSA contributions (Form 5498-SA) - Retirement contributions (Traditional IRA receipts) - Property tax statements - Charitable donation receipts Overlooked items people forget: - Side gig income (Venmo, PayPal, Stripe 1099-K) - Bank bonuses - Gambling winnings - Jury duty pay - State tax refunds from last year - Marketplace health insurance Form 1095-A If it hit your bank account, assume the IRS might know. Step 2: If You’re an Entrepreneur, It’s a Different Ballgame If you’re 1099 or self-employed, welcome to the big leagues. You are responsible for: - Income tax - Self-employment tax (15.3%) - Quarterly estimated payments Before filing, have: - All 1099-NEC / 1099-K forms - Full income summary (Stripe, PayPal, Square, etc.) - Profit & Loss statement - Mileage log - Business receipts - Home office square footage - Health insurance premiums - Equipment purchases - Software subscriptions - Contractor payments (and 1099s you issued)