As a child, I loved the game of chess. My dad had a little jar with odds and ends in it, including a little plastic White Knight. I fell in love with that piece, and became so curious about what the game of chess entailed. I loved knights and swords, kings and castles, and any game about them must surely be a very good game indeed.
I learned the game as soon as possible. At first, like most children and beginners, I was not very good. My dad could beat me readily. But I loved the game even when I lost, and I persevered.
I read books about chess obsessively, and took notes about what I learned. My early ideas about chess were very naive, based on ideas of symmetry. I created fantastical opening sequences based on worshipping this unstrategic ideal.
Later, I began to gain a rudimentary command of tactics and strategy, as well as an honest assessment of the mistakes I was prone to making. I began to beat my Dad, much to his consternation. I moved on to more challenging opponentsāother twelve year old boys and girls.
These days, many years of obsession and blitz later, I am good enough at chess to know I am not very good. I will probably never be a grandmaster or world champion, as I once dreamed. I do not feel particularly sad about this; my ambitions have only grown, in both size and scope.
But chess remains a very beautiful game to me, and a compelling and suggestive metaphor in my mind.
To play chess, U must have a specific set of pieces, arranged in a specific order. U can use different pieces, but then that’s a different game (checkers). U can put the pieces in a different order, but then that’s also a different game (Chess960).
Each of those pieces must move in specific ways to play a legal game, and coordinate elegantly to play a victorious game. Within these constraints, there are thousands upon thousands of possibilities.
To my mind, a good collaborative project is a bit like chess in this way. There is a small finite number of players, with clear roles, who coordinate together in precise ways to do something beautiful together.
Unlike chess, U can have different sets of pieces (team members) to accomplish different goals or projects. And importantly, collaborative projects don’t necessarily need to be competing against someone else, although they certainly can be.
Take the film Oceanās Eleven, for example. In order to pull off an enormous heistāstealing $150 million from three Las Vegas casinosāDanny Ocean recruits a team with ten other thieves, each playing distinct roles: a fixer, a financier, a surveillance tech, an explosives expert, mechanics, a pickpocket, multiple con men, and an acrobat. The whole operation hinges on all eleven specialists working together seamlessly, carefully orchestrated through a master plan, assisted with a knack for improvisation, and a generous extra helping of luck.
I’ve done many tens and hundreds of collaborative, fun service projects over the years. I hope to do many hundreds and thousands more before I die, of increasing complexity, scale, benefit, and joy. The organization I am creating, The Service Guild, is essentially infrastructure for coordinating with trusted and beloved collaborators, in the direction of coherent, beneficial themes (Love, Curiosity, and Empowerment).
Over time, I’ve started to develop a taste or intuition for what combinations of what kinds of people will coordinate effectively on which kinds of projects.
I have been taking notes on these patterns and combinations for some time, and have started developing theories and best practices for this kind of coordination.
In this post, I will share a typology of types of roles I’ve noticed over the years, as well as notes about their strengths and uses.
I call these Quest Classes. In Dungeons & Dragons (D&D) and other roleplaying games, a “class” represents the primary profession or vocation of a character, determining the character’s abilities, skills, and role in a partyālike Wizard or Thief, Monk or Cleric. And in the Empowerment Department, we sometimes refer to fun service projects as Quests.
Quest Classes, then, are like a set of player classes available in a roleplaying game, or a manual of chess pieces, but for collaborative projects rather than battle. This is just my own personal typology of collaborators, that I repeatedly find useful in my projects.
Unlike chess, these roles aren’t unalterable. But I hope they provide a language for coordination that will be useful for planning and reflection, that will make more projects possible in the world, for greater benefit and joy.
Quest Classes
- Vision Lead: Collaborative projects work best if there is one person who is the head / source of the project. They hold the vision, know the purpose, hold all the context. If push comes to shove, itās their call.
- Ops: On complicated, long-term, multi-step projects, U are very likely going to want someone to manage logistics, to weigh tradeoffs, to manage the complicated state, and help make tricky decisions.
- Project Manager: On larger projects, with multiple stakeholders, it may be useful to have someone distinct from both the Vision Lead and the Ops person to coordinate people, manage the intersection of the peopleās needs and the project operations.
- Creatives: Often, U will want one or more experts in specific mediums, with an artistic flair. Some Creatives Iāve worked with: visual artists, animators, vocalist, music producers.
- Tech: A similar, but potentially distinct, roleāan expert in a technical medium (e.g. a Sound Tech at a dance party). They also have a creative, artistic sense, but often there are established best practices, correct ways of doing things that they know well.
- Support: In a similar way, thereās often one or more people who are not holding the vision or managing operations, but are beasts at executing on the tasks that need to be done.
- Marketing/Sales/Fundraising: Depending on how a project is funded, it can be useful to have dedicated marketing, sales, or fundraising leads.
- Mentor/Advisor: For complex or novel projects, it can be helpful to have one or more general mentors or domain-specific advisors.
Project Breakdowns
Here are some major projects I participated in, broken down in terms of the roles or Quest Classes that were needed to execute those projects.
Animated MettÄ Music Video [2021-2022]: I made an animated music video, with the help of a whole team. I played the role of Vision Lead/Producer, Fundraising Lead, and also Talent (dancing and running for the film). To pull off the project, I collaborated with two Creatives (Music and Animation), a Tech (Film), and a couple of Marketing people to help me distribute the final project.
Private Loving-Kindness Retreat [2022, 2023, 2025]: The Love Department has held several small, private loving-kindness retreats over the years. When we started, we just had three roles: a Lead (me), an Ops role, and a Venue Contact. For our second year, we added a Kitchen Manager. This year, weāre planning to host our third in this series, with the help of a whole host of support roles. Here is a simplified, abbreviated list of roles for the event:
Conference [2025]: For my Empowerment work, I am currently helping to plan a conference that we hope will take place in Fall 2025. If we pull it off, this will be one of the largest projects Iāve participated in to date. Here are all the roles we are planning around:
- Vision Lead
- Chief of Staff (Ops)
- Experience Coordinator
- Event Coordinator (Ops)
- Attendee Services Manager (Ops)
- Marketing and Communications Lead
- Sponsorship Coordinator
- Finance and Budget Manager
- Technology Coordinator
- Workshop Coach
- Facilitators
Conclusion
Small teams with a clear intent, shared purpose, clear division of roles and responsibilities, strong relationships can coordinate incredibly effectively. The whole can be greater than the sum of the parts, resulting in an outsized impact.
By viewing ur collaborative projects in terms of their constituent roles, developing a familiarity with what kinds of recurring roles are useful, and how they compose into functional projects, U will expand ur capacity to plan and execute successful collaborations. Over time, ur service project throughput will expand, alongside the scope and complexity of projects U can reasonably take on and deliver.
