Payment Milestones: How to Get Paid On Time (Every Time)

Cash flow kills more freelance businesses than bad clients.

The Problem with "Net 30"

Most freelancers invoice like this:

1. Do all the work
2. Send invoice
3. Wait 30-60 days
4. Chase payment
5. Repeat

This is backwards. You're financing your client's project with your time and money.

The Professional Approach: Payment Milestones

Break every project into payment milestones tied to deliverables. Get paid as you work, not after.

4 Proven Milestone Structures

1. Simple (2 Milestones)

Best for: Small projects under $5K

• 50% upfront (project kickoff)
• 50% on delivery (final files)

Why it works: Low admin overhead. Client commitment is clear. You're never more than 50% exposed.

2. Standard (3 Milestones)

Best for: Most projects ($5K-$20K)

• 40% upfront (project kickoff)
• 30% mid-project (first deliverable review)
• 30% on delivery (final handoff)

Why it works: Balanced cash flow. Built-in checkpoints catch scope creep early. Client stays engaged.

3. Enterprise (4 Milestones)

Best for: Large projects ($20K+)

• 25% upfront (discovery & deposit)
• 25% phase 1 (first major deliverable)
• 25% phase 2 (second major deliverable)
• 25% final (handoff & training)

Why it works: De-risks large projects. Keeps cash flowing. Easy to pause if client ghosts.

4. Retainer (Monthly)

Best for: Ongoing work (maintenance, support, content)

• 100% upfront (first day of each month)
• Covers X hours of work
• Unused hours roll over (with cap)

Why it works: Predictable income. Client gets priority access. No invoice chasing.

How to Present Milestones

Don't apologize. Don't negotiate. Present it as standard practice:

"For a project of this scope, we structure payment in 3 milestones:

• 40% upfront to secure your spot and begin discovery
• 30% at mid-project review (after you approve Phase 1)
• 30% on final delivery

This keeps the project moving smoothly and ensures we're aligned at each stage."

Frame it as a benefit to the client, not a protection for you.

Red Flags (Walk Away)

If a client says:

• "We only pay on completion"
• "Net 60 is our standard policy"
• "We'll pay you after we get paid"
• "Can we do Net 90?"

Walk away. These clients will drain your time and energy.

The Upfront Deposit Rule

Never start work without at least 25% upfront.

This filters out:

• Tire kickers
• Budget shoppers
• Payment ghosters
• Scope creepers

If they won't commit money, they won't commit time or feedback either.

Tools That Help

• Contracts: Include milestone schedule in your SOW
• Invoicing: Send invoices 7 days before milestone due date
• Automation: Use tools like FreshBooks or HoneyBook to auto-send reminders
• Quotes: Use FreelanceQuote to calculate totals and generate milestone breakdowns

The Bottom Line

Payment milestones aren't negotiable. They're standard business practice.

If you're still invoicing Net 30 after project completion, you're running a charity, not a business.

Calculate your next quote with built-in milestones → FreelanceQuote Calculator