Cats Don’t Carpool: The Leadership Blog Series
Herding Cats, Managing Chaos, and Leading with Less Hiss
They’re creative.
They’re passionate.
They have amazing ideas…
…and half-finished projects in four shared drives.
Meet the Free Spirit.
In the Cats Don’t Carpool universe, Free Spirits are those imaginative, enthusiastic team members who sparkle with possibility, but who sometimes treat deadlines like gentle suggestions rather than critical anchors.
They’re not flaky. They’re not lazy. They’re just wired differently, and if managed with care, they can be some of the most innovative, energizing contributors on your team.
So, how do you support a Free Spirit without micromanaging them, or letting timelines go up in glittery flames?
🎨 Understanding the Free Spirit Work Style
Free Spirits tend to:
- Follow inspiration over instruction
- Bounce between projects based on energy or mood
- Struggle with structure—but thrive with trust
- Need meaning and freedom more than rules and rigidity
When they’re “on,” they’re brilliant. When they’re not… things can stall. The key is to balance creative freedom with gentle accountability.
⏳ Why Deadlines Matter (Even to Free Spirits)
Deadlines provide:
- Clarity – What needs to happen, by when
- Rhythm – A sense of progress and pacing
- Boundaries – So creative overflow doesn’t derail deliverables
- Trust – From teammates who rely on their contributions
It’s not about being rigid. It’s about creating enough structure so that their brilliance can actually get to the finish line.
🧭 5 Ways to Help a Free Spirit Meet Deadlines
1. Co-create the timeline
Don’t just assign deadlines—build them together. This helps the Free Spirit feel ownership and reduces resistance.
🪶 Try this:
“What feels like a realistic window for this phase of the project? Let’s map that out together.”
2. Break big projects into creative sprints
Short, focused timeframes help keep momentum without overwhelming their nonlinear process.
🪶 Try this:
“Let’s aim for a rough draft by Friday, and then regroup Monday to see what direction feels strongest.”
3. Use visuals or trackers that spark joy
Think color-coded boards, sticky notes, or progress charts. Bonus points if they’re aesthetically pleasing or interactive.
🪶 Try this:
“I added your part to the visual tracker—want to pick your favorite icon to mark it ‘in progress’?”
4. Leave space for the idea wander—but gently reel it back
Acknowledge their process, then tie it back to the goal.
🪶 Try this:
“I love that idea—it might be great for Phase 2. For this version, let’s anchor it back to the current scope.”
5. Celebrate progress, not just perfection
Free Spirits thrive on encouragement. Acknowledge each milestone to keep the motivation flowing.
🪶 Try this:
“That draft isn’t just good—it’s got real spark. Let’s keep building from that momentum.”
🐈 Final Meows
Free Spirits aren’t the problem—they’re often the source of your team’s most magical breakthroughs. But creativity needs a container.
With the right mix of support, structure, and sparkle, you can help your Free Spirit teammates hit deadlines without dulling their shine.
This post is part of the ongoing series
🧶 Cats Don’t Carpool: The Leadership Blog Series – Herding Cats, Managing Chaos, and Leading with Less Hiss
Insights inspired by the book “Cats Don’t Carpool: They Come in Their Own Accord.”
📘 Pre-order the book for more practical (and purr-suasive) strategies for managing wildly different personalities on the same team:
👉 https://amzn.to/4kCSJ6B