Top Invoicing Problems for IT Freelancers¶
Based on Reddit analysis (r/freelance, r/webdev, r/programming).
The 8 Core Problems¶
| # | Problem | Impact |
|---|---|---|
| 1 | Payment delays & ghosting | 71% affected, avg 21-day delays |
| 2 | Platform disputes (Upwork, etc.) | Account locks, charge-backs, frozen earnings |
| 3 | International payment barriers | Currency hurdles, unsupported countries |
| 4 | High fees & taxes | PayPal fees, 50% tax burden in some regions |
| 5 | No deposits/upfront payments | Risk of non-payment after work complete |
| 6 | Complex invoicing requirements | Multiple invoices, specific numbering, extra paperwork |
| 7 | Tax & accounting complexity | Self-employment tax, quarterly filings, VAT/GST |
| 8 | Privacy concerns | Real names visible, SIN requests from clients |
Real Quotes¶
Payment Delays:
"Upwork let him chargeback $1,426 without warning."
Tax Burden:
"I pay 50% of income and €900/month for health insurance."
Privacy:
"My UPI QR shows my real bank name. I don't want to share my legal name."
Summary¶
Payment reliability is the #1 concern, followed by international barriers and fee/tax burden. Privacy and administrative complexity add significant friction.
See Briefing for how Meister Bill addresses these pain points.