Independent work, without the folklore
Choose the decision in front of you. Each guide is built around an operating move, a worked example or tool, and sources that can be checked when rules change.
Pick your desk
P1 · 16 guides
Structure, EIN, 1099 reality, estimated taxes, bookkeeping, licenses, retirement.
Open this desk →P2 · 9 guides
Contracts, deposits, invoices, late-payment escalation, demand letters, small claims.
Open this desk →P3 · 4 guides
Health coverage, liability insurance, COIs, and disability planning.
Open this desk →P4 · 7 guides
Rates, pricing models, proposals, lead sources, outreach, and discovery calls.
Open this desk →P5 · 6 guides
Cards and ACH, chargebacks, scope creep, subcontractors, and clean exits.
Open this desk →Common starting points
These are not “best of” posts. They are high-leverage operating decisions where a wrong assumption can affect cash flow, taxes, scope, or risk.
P1 · Just went independent
Compare sole proprietorship, LLC, and S-corp decisions separately: liability, state costs, payroll, reasonable compensation, and break-even math for a one-person business.
P4 · Finding and closing clients
Set a freelance rate from required annual revenue and realistic billable capacity, then account for taxes, expenses, unpaid work, market evidence, and realized project margins.
P2 · Trying to get paid
Build a freelance contract around scope, acceptance, deposits, due dates, suspension, IP timing, revision limits, change orders, termination, liability, and governing law.
P2 · Trying to get paid
Create invoices that clear AP quickly with the right legal customer, due date, PO reference, itemized scope, payment methods, reminders, and clean reconciliation.
P3 · Covering yourself and the business
Compare Marketplace coverage, premium tax credits, spouse plans, COBRA, HSA-compatible options, and the self-employed health-insurance deduction by annual cost.
P5 · Handling payments and disputes
Respond to a freelance chargeback by identifying the reason and deadline, preserving the right evidence, and submitting a concise packet tied to the cardholder's claim.
IRS, DOL, HealthCare.gov, courts, state revenue agencies, and regulators lead where rules can change.
Examples show mechanics; planning ranges are labeled as ranges rather than laws or universal benchmarks.
Disputes and payment guides build the record before recommending a demand, court filing, or chargeback response.