Financial guides & checklists

Cross-topic checklists for the specific moments in a freelance business that touch taxes, banking, and benefits all at once.

The new freelancer's first 90 days: financial checklist

Most of the financial groundwork for freelancing needs to happen in the first three months, before habits (and bad habits) set in. This is the checklist we'd hand a friend who just left a full-time job to freelance — check items off as you go.

Open a dedicated business bank account (see Best Business Bank Accounts)
Decide your business structure — sole prop is the default, but check LLC vs S-Corp
Set up a simple bookkeeping system (see Bookkeeping Basics)
Estimate your first quarterly tax payment using the Tax Calculator
Research health insurance options if you lost an employer plan (see Health Insurance Options)
Build a baseline budget around your lowest expected month (see Budgeting on Irregular Income)
Open or confirm access to a retirement account (see SEP IRA vs Solo 401(k))
Start a running list of deductible expenses (see the Tax Deduction Checklist)