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Your First Year Freelancing: A Tax Checklist

4 min readUpdated Feb 2026

Your First Year Freelancing: A Tax Checklist

New to 1099 life? Open the right accounts, set aside the right percentage, and you'll sail through your first filing instead of scrambling.

Going independent is exciting — and the tax side is more manageable than it looks if you set up a few habits early.

  • Open a separate business checking account
  • Set aside 25–30% of every payment for taxes
  • Save receipts digitally as you go, not at year-end
  • Mark the quarterly estimate dates on your calendar
  • Decide on a simple bookkeeping tool before income piles up

When to bring in a pro

The moment your income gets irregular, you take on a contractor, or you're unsure whether to form an LLC — that's the point a short consult pays for itself many times over.

Want this dialed in for your exact situation?

A 20-minute consult turns a general guide into a specific plan.

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