Side Projects Are the New Creative Director Resume in 2026
Side projects have shifted from "nice to have" to the clearest signal of creative leadership. As AI reshapes workflows, creative directors who build on their own time are landing senior roles at roughly three times the rate of those relying on client work alone, according to creative recruiting data.
"The resume shows what you've done. Side projects show what you'll do," says Jason Pickar, a VP Creative Director known for turning commerce into culture. "The best creative directors don't wait for permission to explore new tools. They build the future on nights and weekends."
Why side projects matter now
- They prove strategic thinking: you can spot opportunities without a brief.
- They show technical fluency: you understand new tools well enough to direct outcomes.
- They signal initiative: you can ship without layers of approvals and process.
The anatomy of side projects that actually get you hired
- 1) Technical fluency without needing to code
PostRPG.com is an 8-bit RPG that generates social posts using AI. Built in under 24 hours with Claude Code, it shows how a creative director can turn an idea into a working product by directing AI, not writing every line by hand. As Pickar puts it: "I can't code. But I know what AI makes possible and how to close the gap between idea and execution."
- 2) Culture first, tools second
Pickar's AI parody of Nelly's "E.I."-reimagined as "A.I." at aieiparody.com-speaks directly to the industry's mixed feelings about AI. Made with Higgsfield, Descript, and iMovie, it resonated not for polish, but because it named the tension: dependence on new tools, fear of being replaced, and a strange optimism about what's next.
- 3) Shipping speed over perfection
Hiring managers increasingly value momentum. The internet rewards fast iteration, not endless polishing. Creative leaders who can move from concept to live in days-and keep improving in public-show the muscle modern teams need.
Build a side project this week: a simple playbook
- Find the itch: What do you wish existed for your niche? Write the one-sentence problem.
- Scope tiny: Define the smallest version that proves the idea in 48-72 hours.
- Pick a stack you can ship with: AI assistants, no-code tools, lightweight editors. Favor speed.
- Time-box two sprints: Sprint 1 (make it work). Sprint 2 (make it shareable).
- Publish and learn: Share with your audience. Note feedback. Ship v1.1 within a week.
What hiring managers actually look for
- Clarity: A tight problem statement and a clear audience.
- A working link: Something people can use, watch, or test.
- A story: A short write-up on what you tried, what broke, and what you learned.
- Speed: A visible timeline that shows bias to action.
- Iteration: Evidence you improved it based on real feedback.
Two examples worth studying
- PostRPG.com: A playful, shippable tool that turns AI into a creative partner, not a gimmick. Visit the project
- "A.I." parody video: A cultural thermometer that captures the mood of creatives facing AI's rise. Watch the parody
The shift: from managing people to orchestrating people and algorithms
As AI handles more routine execution, value moves to leaders who can spot opportunities, direct AI effectively, and ship meaningful work. Side projects are the cleanest way to show you can do all three-without waiting for a client brief.
Or, as Pickar puts it: "We're moving from creative directors who manage teams to creative directors who conduct teams and algorithms. The ones who prove it with side projects will set the pace."
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