When should I send an invoice?

Send your invoice the moment the work (or a defined milestone) is done — and for ongoing relationships, send on a steady, predictable schedule. The rule of thumb is simple: the sooner an invoice lands in your client’s inbox, the sooner it gets paid. Waiting “until you have a few to send together” almost always costs you cash flow.

The three good moments to send

Most freelance and studio work fits one of these timing patterns. Pick the one that matches the job in front of you.

• On completion. Finished a logo, a website, an edit, a one-off project? Invoice the same day you deliver. The work is fresh in everyone’s mind and the client is happiest right after they receive something good.
• At a milestone. For bigger engagements, bill in stages — discovery done, design approved, launch shipped. Each milestone is a natural checkpoint to send an invoice (or apply a deposit you already collected) so you’re never carrying weeks of unpaid work.
• On a schedule. Retainers, ongoing support, and monthly engagements should bill on the same day every month. Predictability is good for you and reassuring for your client.

Tip: If you collected a deposit on the original estimate, you don’t have to wait until the very end to see money. The deposit covers your early effort, and the final invoice settles the balance when you deliver.

Don’t start from a blank invoice

In most cases the fastest, most accurate invoice is one you don’t type from scratch. If your client already approved an estimate in the portal, convert it — the line items, tax, and any deposit carry straight over.

1. Open the approved estimate from Estimates in the left sidebar.
2. Click Convert and choose to create an invoice (you can also spin up a project at the same time).
3. Review the carried-over lines, confirm your payment terms, and send.

The client gets an invoice with a Pay button and can pay by card straight into your own Stripe account. No re-keying, no math, no delay.

For ongoing work, let it send itself

If you’re billing the same amount on the same cadence — a retainer, a hosting plan, a monthly coaching package — set up a recurring invoice instead of remembering to do it by hand. Fee-Lion generates and sends each cycle automatically, so “when should I send?” answers itself every month.

• Create the recurring schedule once and let it run.
• Turn on auto-pay so enrolled clients are charged the moment the invoice issues.
• Use Settings → Preferences to set your default payment terms so every invoice goes out with a clear due date.

A word on timing and terms

Sending fast is only half of getting paid fast — the due date on the invoice matters too. Your payment terms (due on receipt, net 7, net 14, and so on) set the clock, and you can pick a sensible default once in Settings → Preferences. Shorter terms paired with same-day sending is the combination that keeps your cash flowing. If an invoice slips past its due date, you can always send a reminder rather than letting it drift.

What’s next

• Convert an approved estimate to an invoice
• Create a recurring invoice
• Set your default payment terms
• Send a payment reminder for a late invoice