The Misfit Playbook

About The Project

In 2013, I took on the challenge of managing a collaborative anthology book project with 12+ writers, multiple editors, and artists spread across different time zones. All of them had been attendees of Misfit Con and were volunteers working out of passion and enthusiasm rather than for paychecks. As the project lead and creative director, I built a comprehensive project management infrastructure: detailed timelines, role definitions, style guides, tracking systems, and coordination processes.

We successfully completed phase one, producing 12 polished essays that explored what it means to be a misfit. But when we moved into phase two, which involved collecting additional stories or "plays,” the project stalled. Despite having structure, systems, and genuine excitement, we couldn't maintain momentum. After months of effort, we reluctantly decided to end the project.

While working on this project, I learned that enthusiasm doesn’t always lead to successful execution, that having the right infrastructure can’t always solve the fundamental challenges of volunteer projects, and effective leadership without authority requires different skills than traditional project management. In addition to the systems and documentation I created for this project, I developed an 11-page action plan detailing every phase, role, and deadline, demonstrating my ability to organize complex creative work. Even though the project did not succeed, it provided me with invaluable insights into what it takes to manage a creative project effectively.

The Challenge

The project started at Misfit Con, a conference in North Dakota that brought together creative entrepreneurs and independent thinkers. Everyone left inspired and energized, writing prolifically. Someone in our Facebook group casually suggested we collaborate on a book together. Several of us were immediately intrigued.

But we faced significant challenges:

Nobody had managed a project like this before. We had writers scattered across the country, no budget, no publisher, and no clear model for structuring collaborative creative work among peers. We weren't a company with hierarchy—we were a group of equals working together to create something.

The concept itself was evolving. It wasn’t clear if we were creating an anthology, guidebook, or something else entirely. The concept was to write essays outlining the core misfit principles, along with concrete examples we called “plays” for applying them to your life and art. But it was challenging to define this vision clearly enough for 12+ people to write coherently toward it.

We were all volunteers. Everyone had day jobs, client work, and other projects. No one was getting paid. Success would depend entirely on people following through on commitments driven purely by passion and peer accountability.

The biggest challenge, though, was one I didn't fully appreciate at the start: How do you lead a creative collaboration when you have no formal authority? I couldn't fire anyone for missing deadlines. I couldn't offer raises for good work. I had to create systems that would make people want to participate and make it easy for them to follow through, while somehow maintaining quality and momentum.

My Approach

Building Project Infrastructure

I started by creating comprehensive documentation to give the project structure and clarity. I drafted an 11-page action plan outlining every phase of the project, from initial writing through artwork and website development, and eventually a Kickstarter campaign to fund printing.

The action plan defined clear roles and responsibilities:

• Vision Team (including me): Shape the book's direction and maintain consistency
• Manager: Oversee internal communication and deadlines
• Editors: Ensure quality and adherence to style guidelines
• Writers: Create the book's content (12 writers initially)
• Creative Director: Oversee visual elements
• Marketer: Handle external communications and website

I created a detailed style guide that explained what the Playbook was and how to write for it. This gave writers a framework while preserving their individual voices.

I established a phased timeline with specific deadlines:

• Phase One: Writing (July - December)
• Phase Two: Artwork and Website (January - February)
• Phase Three: Kickstarter and Printing (February - March)

Each phase had multiple milestones with clear deliverables and due dates. Nothing was vague, and everyone knew exactly what was expected and when.

Creating Management Systems

To track progress, I set up a Podio application where writers could suggest "plays," sign up to write them, and we could monitor who was working on what. This gave everyone visibility into the project's status and helped prevent duplication of effort.

I compiled a working draft of the book, which was over 11,000 words, so people could see how their contributions fit into the larger whole. This helped maintain alignment with the vision as the project evolved.

I coordinated regular check-ins and created video presentations to update the team on progress and next steps, while maintaining energy and momentum.

Managing the Creative Process

For phase one, I worked with editors (including my mother, Margaret E. Ward) to establish a multi-round editing process:

1. Writers submit initial drafts
2. Vision team provides guidance
3. Writers revise
4. Editors review for quality and style
5. Final revisions

This process worked well. By late 2014, we had 12 strong essays about misfit principles. The writing was good, people were proud of their work, and we had something tangible to build on.

Where It Broke Down

Phase two was supposed to expand the book by adding "plays,” but this is where we hit the wall.

Despite having solid systems in place, the plays proved difficult to produce, and we were not receiving enough submissions to fill an entire book. The momentum we'd built in phase one evaporated, and I found myself carrying an increasing burden as I tried to keep the project alive, while support from the team waned.

I realized the problem wasn't a lack of structure or unclear expectations. The problem was that enthusiasm and good intentions don't automatically translate into sustained execution, especially for volunteers juggling other priorities.

After months of diminishing returns, we made the difficult decision to end the project. We had created something valuable in phase one, but couldn't sustain the effort needed to complete the full vision.

What I Learned

Infrastructure is necessary but not sufficient. I built robust project management systems, including detailed plans, clear roles, tracking tools, and quality processes. These were essential and worked well when people were engaged. But they couldn't solve the fundamental problem of volunteer work: people are busy and may only have so much time to dedicate to unpaid labor.

Enthusiasm fades; systems sustain. The initial post-conference excitement got us through phase one. But when that emotional energy dissipated, we needed something else to maintain momentum, and pure structure wasn't enough. Successful volunteer projects need either very small teams, very short timelines, or some form of accountability beyond peer pressure.

Leadership without authority is a distinct skill. Managing employees or contractors is straightforward because you have financial leverage. Managing peers who are volunteering their time requires a different approach. You can't demand, you can only inspire, facilitate, and make participation as easy as possible. And sometimes that's not enough.

The gap between "would be cool" and "will actually do" is enormous. Many people expressed interest in the project. Some committed to roles. But far fewer actually delivered work consistently. This gap is the death of most collaborative creative projects. You need people who are not just excited about the idea but genuinely committed to doing the work, and willing to prioritize it when other things compete for their attention.

Clear roles don't guarantee people will fulfill them. Even though I carefully defined roles and had people commit to them, not everyone performed effectively in the roles they chose. That’s not necessarily their fault, they were volunteering after all, but this disconnect really hurt the project. In hindsight, I should have started small and scaled up only once I had truly reliable collaborators.

Sometimes the right decision is to stop. There's a point where persistence becomes stubbornness. After months of trying different approaches to revive momentum, I recognized we weren't going to finish the project as envisioned. Ending it was disappointing but honest, and it freed everyone from a commitment that had become more of a burden than a joy.

What Remains

The 12 essays we completed in phase one still exist, and I plan to share them on my website as a record of what we accomplished. While the full Misfit Playbook was never published, the first phase demonstrated that we could create quality collaborative content when conditions were right.

More importantly, the project helped me understand the challenges of structuring complex work, coordinating distributed teams, maintaining quality standards, and learning the limits of systems and documentation. The action plan I created for this project has informed how I approach project planning ever since, though now I'm more realistic about what structure can and can't accomplish when managing volunteers.

While The Misfit Playbook may not have become the book we envisioned, it taught me invaluable lessons about collaboration, leadership, and the gap between enthusiasm and execution.