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Creativity Runs on Systems: Caitlyn Wells of Upwell Strategies on Automating Without Killing the Vibe
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In this episode of The Sly Agencies Podcast, Andrew dives into an often-overlooked topic—how solid systems can actually fuel creativity—with systems strategist Caitlyn Wells of Upwell Strategies.
Caitlyn helps creative agencies streamline their operations through systems and automation without sacrificing individuality or spontaneity. If you've ever feared that organizing your work would kill your creative flow, this conversation will flip your thinking.
You’ll learn:
- Why systems don’t kill creativity—they support it
- How file organization and naming conventions can save hours a week
- The right way to use project management tools like ClickUp or Asana
- Why founders must lead by example for systems to stick
- How even simple automations (think: folder generation) can offload mental clutter
- The mindset shift required to actually embrace systems—and love them
This episode is loaded with tips for any creative entrepreneur feeling overwhelmed by operational chaos. If your “systems” are sticky notes and half-finished Google Docs, this one’s for you.
🔗 Show Notes:
Learn more about Caitlyn’s services: www.upwellstrategies.com
Follow Upwell on Instagram: @upwellstrategies
Connect with Caitlyn on LinkedIn: Caitlyn Wells on LinkedIn
Watch tutorials and tips on YouTube: Upwell Strategies YouTube Channel
✅ TL;DR Takeaways:
- You don’t have to choose between systems and creativity
- Simple tweaks (like better file naming) = major clarity
- Use tools you like — not just what’s popular
- Automate your way to freedom
Like what you heard? Hit that subscribe button so you don’t miss the next episode.
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