The Easiest Way to Improve Your Business' Contracts: Dwell on the Pain
- Caleb Ellis

- Jul 29, 2025
- 1 min read
No one likes to dwell on the pain - but for creative businesses, painful client experiences can be one of the most valuable tools for improving your contracts.
When things go wrong in a project - whether it’s miscommunication, scope creep, late payments, or lack of credit - there’s usually a legal gap behind the scenes. And the best way to close those gaps is to make your contracts smarter.
Here’s a simple 3-step practice we recommend to all of our clients:
1. Think about your most difficult client or project.
Who comes to mind? What went wrong? Was it about timelines, revisions, deliverables, payment terms, or something else entirely?
2. Ask yourself: if you had to do it again, how would you change the contract?
Could clearer language have helped? Should there have been a stronger termination clause? Was there a missing payment milestone, IP clause, or scope definition?
3. After every project, refine your terms.
Each experience - especially the painful ones - is an opportunity to improve your standard agreement. That doesn’t just mean protecting yourself; it also builds confidence and clarity into your process moving forward.
Contracts don’t have to be static. In fact, the best ones evolve with you. A clear, tailored contract gives you the freedom to focus on your creative work - and the peace of mind to take on your next big opportunity without fear.
Need help strengthening your contracts? We’re here to help. Book a consultation: hello@outputlaw.com.
This is not legal advice.
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