Freelance Debt Collector

Freelancers lose ~$6,000/year on average to slow or missing payments, and the reason is rarely the client's bank account — it's that chasing money feels awkward, so reminders happen late, sound either apologetic or radioactive, and stop entirely at exactly the moment escalation should start. Professional collections is a sequence, not a mood: predictable dates, escalating formality, fees that compound, and a paper trail a court can read. This skill runs that sequence.

When to Use

• An invoice is unpaid at due date (or about to be) — start the ladder at step 0, not step 4
• Several invoices outstanding across clients: aging report to see where the real risk is concentrated
• 30+ days late: is small claims realistic? (amount vs local cap, filing fee vs recovery, evidence completeness)
• Client keeps promising "Friday": acknowledgment documentation and the decision point at day 45
• Active project for a client who owes on earlier phases: stop-work notice that pauses without cancelling

Don't use for: clients in bankruptcy (stop — automatic stay applies; file a proof of claim instead); suspected fraud (different playbook); wage claims (labor board, not small claims); amounts large enough to need a real collections attorney.

The Method

1. status — aging buckets (current / 1-30 / 31-60 / 61-90 / 90+), total exposure, >60-day at-risk line. Run weekly; that's the whole monitoring cost.
2. ladders — per invoice: current ladder step + tone, accrued late fees (simple or compound, from day 8), total with fees, and the DATED next step. The dates matter: an escalation that arrives on a predictable cadence reads as process; random escalations read as anger.
3. smallclaims — claim amount (+fees) vs jurisdiction cap for all 50 US states (+UK/DE/ON reference), net recovery after filing fee, the 6-item evidence checklist, and the formal demand letter.
4. stopwork — the suspension notice: pause, don't cancel; resume condition stated; licensing of delivered work tied to payment terms.

INV='[{"client":"Acme Corp","no":"INV-1042","due":"2026-08-01","amount":4200},
{"client":"Beta LLC","no":"INV-1051","due":"2026-09-15","amount":1850}]'

python3 scripts/late_invoice_nudge.py --invoices "$INV" --today 2026-10-17 status
python3 scripts/late_invoice_nudge.py --invoices "$INV" --today 2026-10-17 ladders
python3 scripts/late_invoice_nudge.py --invoices "$INV" --today 2026-10-17 \
    smallclaims --jurisdiction TX --fee 46
python3 scripts/late_invoice_nudge.py --invoices "$INV" stopwork

The Ladder (what the steps mean)

The two fatal behaviors this cadence prevents: skipping steps (client escalates the relationship conflict because you exploded at day 40) and stalling at reminder #3 forever (the invoice ages out of collectability — most small-claims judges respect a diligent trail, and debt buyers pay pennies for stale paper).

Late-Fee Math

Default 10%/yr monthly-compound from day 8 (configurable --rate, --mode simple|compound). Two rules that keep fees enforceable:

1. Fees must be in the contract (or statutory — e.g., UK Late Payment of Commercial Debts Act: 8% + fixed sums £40-100).
2. Invoices and letters must SHOW the fee accrual — retroactive fee bombs at day 60 read as bad faith and get struck.

Common Pitfalls

1. Waiting to start. The ladder starts 3 days BEFORE due. Early professional contact is the strongest single predictor of on-time payment.
2. Apologizing or threatening. Neither. The drafts are deliberately neutral-process: dates, amounts, next step.
3. No log of sent reminders. The trail IS the small-claims case (and the deterrent). Log date/step/channel for every send.
4. Continuing work on a late account. Every hour after due date is unsecured credit you're extending. Use stopwork at ~2 weeks late.
5. Skipping the demand letter. Many jurisdictions require a formal demand before filing; it also converts "dispute" into "acknowledged debt" when they reply.
6. Small claims for the wrong amounts. Over cap → civil court (lawyer economics change); under ~2× filing fee → collection letters only. The smallclaims command shows net recovery so this is a number, not a vibe.
7. Shutting up after payment. Send the receipt + thanks, and note the client's payment behavior for next engagement's terms (deposit %, shorter net).

Verification Checklist

• Every open invoice has: current step, last-send date, next-send date
• Late fees shown in writing before being charged
• Stop-work decision made consciously at 14d (either paused or explicitly extended)
• Day-45 decision recorded: collections / court / write-off
• Evidence checklist complete BEFORE filing (contract, invoice, delivery proof, acceptance, reminder trail, acknowledgment)
• Payment terms for future work adjusted per client payment history

References

• references/collections-playbook.md — psychology and scripts per step, contract clauses that make collection mechanical (fees, venue, suspension, kill-fee), collections-agency economics, write-off/tax notes, and preventing recurrence via terms.