An Early History of The Service Guild

in the eighth grade, for some reason i can’t really explain, except *gestures broadly at reincarnation and my vow*, i got a very peculiar idea in my head. i thought i should form a kind of secret society.

i’d started doing chorus in fifth grade and kept at it through high school and into my freshman year of college at St. John’s. throughout the years, i auditioned for various extra choruses that were for more serious singers with more skill and dedication, who wanted to sing more often, with harder music. i’d love to go back and ask myself why i did this, because it’s actually not obvious to me now. i’m guessing that i felt a sense of belonging and community in chorus, and that the competition of applying for these more elite choruses spoke to a mostly-dormant sense of ambition.

that year, i befriended G and J, two younger chorus members. that was what gave me the idea.

i thought we should have a secret society, with one boy in chorus from each grade. they would appoint a new sixth grade boy each year when the years changed and the eighth grade boy went on to high school. in this way, they could form a brotherhood and pass on a kind of secret knowledge. (what exactly this secret knowledge was was not entirely clear to me, but it felt Important that we do so, that we be able to. it pleased me, aesthetically, spiritually.)

i had this whole idea that we would place a ledger of the members of our Order within the pages of a specific, obscure book in the middle school library, secreted away in an appointed page number—hidden from those who would never find it, never check out the book.

the other boys were baffled. they had no such ambitions or predilections. we didn’t successfully form that order, nor did they pass on our Ways and Rituals to a new boy in successive years.

looking back on it now, this story reveals an early, awkward, immature manifestation of some of my deepest gifts: a light-hearted playfulness and unorthodox creativity, a devotion to friendship, a longing for community, a reverence for structures and systems and organizations, a desire to create things that persist, a calling to lead.

this essay is an early written-oral history of The Service Guild, written in late 2024 from my perspective as Guildmaster. i’ll start by sharing several latent influences before it actually formed, like the above story, and then proceed to relate some of what’s transpired in the nearly thousand days since it began, as of this writing.

i trained at the Monastic Academy in two stints, from January 2015 to April 2017, and from July 2018 to March 2021. they were a bit like tours of duty. in retrospect, it was important and valuable that i had a stretch of a year or so between my training periods. i had the opportunity to stretch my legs, to explore a bunch of different ideas and ways of being in the world, and to appreciate the training more for what it was. 

in that year or so between training periods, i did a number of different work projects in a variety of contexts. i taught a weekly meditation class at a local yoga studio. i did some meditation coaching online. i worked for Brightmind, a meditation app start-up cofounded by one of my friends. i did a lot of tweeting, and blogging, and diving deep into rabbit holes that i was interested in for reasons i couldn’t quite explain. 

in December 2017, i took the fourth cohort of Tiago Forte’s Building a Second Brain course. i’d read David Allen’s Getting Things Done when i was… 13? and this took all of the productivity principles and practices i’d internalized for over a decade into the 21st century, especially with respect to note-taking.

i made several long-term connections during that course, including James Stuber, who i later made the Digital Productivity Coach with, and Ben Mosior, who was the course manager for the course. 

i started talking to Ben quite a bit, asking him lots and lots of questions, learning about how he saw things and how he went about his projects and work in the world. Ben kindly, patiently, clearly answered all of my questions—the more questions he answered, the more questions i had. and my increasing expertise led him to help me get hired in a variety of work contexts he was working in, including by Tiago at Forte Labs for a time.

in time, i learned that a lot of what i was interested in learning about from Ben could usefully be described as “strategy.” i’ve found it useful to see strategy as a natural outgrowth of productivity. productivity is about one’s own agency in the world—strategy is where ur own agency meets that of others’, where u learn to coordinate with (or compete against) other individuals and groups for the highest possible benefit.

this growing interest led me to do a deep dive into military and business strategy, including Wardley Mapping, Cynefin, the Logical Thinking Processes, Boyd’s OODA Loop and Maneuver Warfare, Daoist Strategy, and more. i must have read thousands of blog posts and many many tens of books on strategy-related topics during that time, between 2017 and 2021. i’ve since digested much of what i learned from Ben and the worlds he exposed me to into blog posts—see, for example, Strategy 101 or The Strategic Theory of John Boyd. 

i found the tools i was learning immediately useful, in all of the work contexts i was in. later on, i found them useful at the monastery—even if my perspectives and methods were unorthodox in that context. that is actually part of what made them so useful: they were unexpected. one of the best compliments i’ve ever gotten was from my friend Michael Ashcroft, who described me as “a Buddhist who understands OODA Loops.”

strategic ideas and thinking helped me establish a monastic training center in a vibrant social context when we were trying to create a new branch of our monastery in the San Francisco Bay Area; they helped me to raise tens of thousands of dollars for our Zendo construction project in Vermont; they helped me in countless ways as Assistant Director at MAPLE when I returned to Vermont. 

at MAPLE, one thing we talked a lot about was trustworthiness, and what a trustworthy leader actually was. Soryu spoke about wisdom, love, and power. we were training in each of these qualities, and developing mutually supportive feedback loops between them. 

at one point, there was an idea to have different “teams”: a wisdom team, a love team, and a power team. U could be on multiple teams—and even theoretically all three—but U would have to pass some kind of baseline to become eligible, and there would be various responsibilities associated with each team.

i loved this idea. i’d recently been obsessively reading and re-reading the Ender’s Game series, which contains an abundance of strategic ideas in narrative form, and was inspired by the teams that Ender encountered at Battle School, which worked very similarly. 

at the time, i wanted to be on the wisdom team. i wanted to break through. i wanted to taste classical enlightenment. i think that was very much a head-idea, though, a head-idea of what i was supposed to do, what i was supposed to want—rather than a heart-calling or a soul-directive. 

they never did organize things in terms of those three teams at MAPLE, although for several years they had two programs, the Phoenix and Dragon programs (this has since been dismantled, if i understand correctly). but the idea stayed with me.

i left MAPLE in 2021. i had my goodbye ceremony in March—i flew back from OAK in San Francisco for just a few days to have at MAPLE in Vermont. i remember so vividly this one memory of crossing paths with Soryu, perhaps on the day i was leaving. 

he was going into the building, and i was going out, or the other way around. he asked about me leaving, and where i was going physically (Boston, with my parents). and he said, with a twinkle and a glint in his eyes, a mischievous smirk on his face: “i look forward to seeing how you serve the world!”

on the outside, i nodded and smiled politely. but on the inside, i remember having the strongest reaction to that. i remember feeling, thinking the equivalent of “fuck fuck fuck, i don’t want to serve the world, i just want to get the heck out of here and be with my family and figure out what’s next and be comfortable.”

it reminds me that when I first started training at MAPLE, then CML—the Center for Mindful Learning, still its legal name—was a meditation teacher training, for teaching mindfulness in schools. i thought something similar: “i’m not really interested in teaching meditation, but i do want to practice it, so i’ll do this.” 

teaching meditation has become an important part of my life’s work, as has service. the universe has its own plans for us. we can speak up about what we want, we can kick and scream all we want, but it is best to notice and accept the course that we are on, to flow with the stream of the Dao instead of fighting it.

as it turned out, one of the very first ways i started to serve the world after leaving the monastery was by teaching loving-kindness meditation. i wanted to have some basis for continuing my practice, some consistent structure in my life in a period of chaos and change. i also wanted to be practicing loving-kindness meditation in particular. on my long solitary retreat in 2020, i’d stopped doing mettā regularly and noticed i was the worse for it; that mettā kept me sane and happy. i wanted to make sure i was doing at least some mettā regularly. 

however, when i looked for weekly loving-kindness meditation groups, i couldn’t find much. so i decided to start my own group. the very first Saturday Night Mettā was held on Clubhouse, an audio chat social media program which was very popular at the time but has since faded into obscurity. the second one was held on Zoom, and i’ve been holding them nearly every Saturday since. 

it was a season of sharing about mettā and the brahmavihārās, and i enjoyed it. i’d taught many different techniques and approaches in a variety of contexts over the years, and i had always enjoyed sharing mettā as a technique—and i’d consistently received positive feedback about how i taught it, about how happy it made people. it seemed like a simple, fundamentally good technique. 

that focus on sharing mettā with the world blossomed in a number of ways, including hosting my very first mettā dance party (online, with the Stoa), and making my first two music videos. 

one thing i loved about teaching mettā at the time was how simple and unobjectionable it was. simple, because the technique is really rather straightforward (in Shinzen’s Basic or Unified Mindfulness System: See Good and/or Hear Good → Feel Good). unobjectionable, because who was going to argue about me teaching mettā, or find it to be a dangerous technique?

i was very conflict avoidant, and still somewhat averse to teaching in a proper sense after my time training and later teaching at MAPLE–feeling i had not very much to share, no realization to offer, no deep dharma to share. 

i’ve since become less conflict avoidant, and also more in honest connection with the truths and wisdom that i do have to share. i’ve also become aware of the many valid objections one actually might make to focusing overmuch on the path of the heart.

that summer, in August of 2021, i had a conversation with Dinesh Raju that would change my life. i’d had him on my podcast a month or two before, and i had followed up to ask to speak privately to discuss my service projects. 

i told Dinesh about my different projects, and shared my understanding at the time of what i was doing.

just taking the time to reflect on what i was doing, and how i understood it, and to share that with him, was already so helpful. 

Dinesh emphasized the work I was doing to spread loving-kindness meditation in the world. he asked a piercing question: why not just focus on that? why not become the best loving-kindness meditation teacher in the world?

this was a very good question—a natural one given what i’d shared with him—but that plan didn’t sit well with me. i knew that focusing exclusively on spreading loving-kindness meditation—as important as it was and is for me—would be leaving something important behind in my work in the world, and wouldn’t feel fulfilling for me. but i couldn’t articulate why—not on that call, and not in the days or weeks to come.

i had to really sit with Dinesh’s question, letting it itch, letting it nag at me, asking myself it again and again: what was my life’s work, if not just spreading love in the world? what else was there? why would i, for example, also write a blog, or record a podcast? how did the other projects i was doing, which didn’t relate to spreading loving-kindness, which i enjoyed, and found fulfilling for me and beneficial for others—how did those fit in?

in November of 2021, i realized that “following my curiosity” described a large chunk of my projects, including my blog and podcast. i wasn’t just spreading love in the world—i was also following my curiosity. i remember that my body relaxed, as if i had found an object i’d misplaced. 

despite the felt sense of clarity and relief associated with that discovery, i still felt i hadn’t completely answered the question. something was still missing. 

i believe the seed of what is now called The Service Guild began when i met Mary Bajorek on April 5, 2022. my friend Eric Chisholm, who had been on my podcast, had recently started dating Mary, and wanted me to meet her. Mary was interested in going on podcasts—maybe it would make sense for Mary to go on my podcast? i was open to it, and trusted his recommendation, but wanted to meet Mary first to get to know her and to understand her a little better. it’s a lot easier to have a good podcast conversation when you already have some context about someone!

in that call, a number of things became clear:

first, i really liked Mary, and i definitely wanted her to come on my podcast.

second, i realized in conversation with Mary that there was a third piece of my work, beyond spreading love and following my curiosity. i call this aspect of my work “empowerment”: empowering others to find and live their vow.

thirdly, i wanted to work with Mary! i said, “no pressure, but i could see us working together for thirty or forty years.” i realized this was a big ask, and i had no expectations about how she would respond—we’d just met, after all—but Mary responded with a big, clear, “yes!” and we’ve worked together since, for more than two years now—and we still hope to work together for many years and decades.

Dinesh’s question helped me to clarify my understanding of my life’s work. spreading the technique of loving-kindness meditation and the brahmavihārās—spreading love in the world—is a meaningful, and important part of my work in the world, but it is not all that i feel called to do. when i met Mary, the third and final piece fell into place. i want to spread love, follow my curiosity, and empower others. i see these three efforts as complementary and mutually supportive.

that summer, i began speaking to Mary about these three areas with a playful metaphor: “it’s as if there’s a company, Tasshin Inc., and it has three departments: Love, Curiosity, and Empowerment.”

Mary took that metaphor very seriously, and we began to run with it. i put her in charge of the Empowerment Department (as the C.E.O, the Chief Empowerment Officer), and sought out people in similar roles for the other two departments.

i guess it just intuitively made sense to me to have a lead collaborator for each of the themes i felt called to work on—someone who felt called in the same direction, who could hold all of the relevant context with me, who could make decisions and work alongside me. over time, we’ve evolved to see these roles more as co-leads or co-parents, rather than leads or startup co-founders.

with a lead in place, we could build a team, decide on a vision, establish goals and projects—execute on our shared intent. ideally, we could create mutually supportive feedback loops between each of these “departments.”

gradually, core teams formed for each of the three departments. i drew on a number of existing collaborative relationships, and began seeking new collaborators for specific roles. 

in December 2022, after our first private loving-kindness retreat in the summer and running our first in-person mettā dance party as a team, i shared a very special, magickal evening with Zev Benjamin and Bee Eye in a small wood cabin in Black Mountain, North Carolina where we agreed to found the Love Department, to have a go at trying it together for a year. 

in September of 2023, i felt called to change the organization to the name “The Service Guild.” i wanted the organization to be less about me, and more about service; less about being a company or a start-up or even a non-profit, and more about being a crew, a team of heroes and friends.

i was also so excited that, in November of 2023, i learned about the “.fun” top level domain, and could purchase the serviceguild.fun domain. if there was a single, beautiful, resonant word, that meant “the intimacy of fun and service,” then we would call it THAT Guild. but in the absence of that word, and given that we are a global, distributed, extremely online crew, the name “serviceguild.fun” felt like an apt name for our online home.

it’s interesting to me, looking back now, that both MAPLE and we at the Service Guild changed their name from the original name to something else, as they came more closely into alignment and connection with its innermost spiritual intention, its collective vow. 

in this calendar year, 2024, much of the larger work of the Guild has been to clarify what it means that we are a guild, and what The Service Guild in particular is, how it operates.

on one call in January, Anansi asked me, “what is the spirit of The Service Guild? what is that entity? how does that entity, the we, The Service Guild do magick? what is the will of the collective entity known as The Service Guild? what would it mean to contact that?”

i channeled what is now the stuff that’s on the front page of the guild website: 

We do not want to be a company, we do not want to be a nonprofit, we do not want to be in government. We want to do something different, because the affordances that have been made available to us are insufficient for what’s in front of us, for our future—not only for the external world and what it needs, but for our souls, and what is being asked of us spiritually.

We rise to the challenge of meeting that occasion as friends first and foremost. We are friends and heroes, brothers and sisters, kings and queens, wizards and witches, sorcerers and sorceresses who are in relationship with one another and as a community, where there are webs of relationships being woven between the people.

From that basis of relationships of mutual love, trust, care, respect, we decide, we elect, voluntarily, as volunteers to choose to do service projects together that resonate for us as friends.

We may never make money from this, this may never be understood by anyone other than us, but we feel called to do this.

We feel this will be fun for us individually and collectively, and we feel this will be of benefit to the world and all beings. We give it as a gift out of a spirit of generosity.

That is our magick, that is our desire, that is our prayer.

over this year, i’ve decided to lean into the wisdom in that message: we are not a company, or a non-profit. we are a guild of friends. 

with that clarity, i began planning membership ceremonies to formalize Guild Membership, and to craft an oath that will form the basis of those ceremonies. we will hold these Ceremonies in the beginning of the new year, 2025. 

i am pleased that the final form the Oath has taken is a modular one—some parts are things that everyone in the Guild will say, some parts just members of a specific department will say, and there is one sentence (about one’s vow) that each individual alone will say.

this, for me, is an example of a kind of hegelian synthesis of individualism and collectivism, where an individual’s vow, personality, idiosyncrasies, desires, needs, boundaries, etc. are respected and held at the same time as a reverence for the overall collective well-being.

we’ve already accomplished so much, things that none of us in the Guild would have been able to do alone, certainly not as effectively or enjoyably.

and what’s to come? what lies ahead?

life has many adventures, those we dream up, that we plan and pray for—and those unexpected quests, which take us by surprise, which challenge us to face obstacles we might not otherwise choose, but will, in the end, take us to heights we might never have imagined.

to my mind, i can see our current bottleneck, and a series of bottleneck-dominoes that i expect will follow it:

• Guild Culture; shared understanding of our vision, values, best practices, etc.
• Staffing
• Organizational structures and infrastructure
• Funding
• Probably me needing an assistant
• Ability to take on new Leads—explicit externalized knowledge of how to start and run a Department, infrastructure, SOP’s
• Public knowledge of the Guild

i aspire that, one day, the Guild will be able to host new Departments, alongside the original three—that we could share our best practices with them, to help them form powerful teams and impactful fun service programs more swiftly and effectively—and that the mutually supportive feedback loops between the Departments would grow and strengthen.

while there are many possible departments, there are three departments i would especially love to see—which I will not create myself, but which I would love to help a dedicated person create as part of the Guild. i pray for an Art (Creativity) Department. i pray for an Earth Department. i pray for a Peace Department. 

the prospect of a Peace Department is particularly interesting to me, in that it is actually quite aligned with a vision of one of my heroes, Peace Pilgrim:

We can only change through example. Therefore, if I had the power to do so in this country I would set a very gentle, good example. I would establish a Peace Department in our government. It would have very useful work to do. It would research peaceful ways of resolving conflicts, war prevention measures and economic adjustments to peace. It would be established with some fanfare and we would ask every other nation to establish similar departments and come and work with us for peace. I think many nations would be willing to do so. Communications among the Peace Departments would be a step toward peace in our world.

as i imagine it now, a lead would need to be someone i know well; who i know to be a person of great integrity, wisdom, power and love; who i know has the capacity to realize their vision, and whose vision is aligned with the Guild’s, and proper to their vow; who has the skill to execute on that vision, and will do so for years and decades.

i imagine asking a Lead to tattoo an icon representing their Department’s theme on their body, as I have with my tattoos. no one will demand someone create a Department—but if U want to do that, U must be ready for it to be something U do for the rest of Ur life. put skin in the game.

i’m so proud of the things i’m doing with my collaborators, and i know and trust that we will go on to do even more service projects for the world, that are even more impactful. 

may the service guild flourish. may the love department flourish. may the curiosity department flourish. may the empowerment department flourish. may an art department arise. may an earth department arise. may a peace department arise. may our work bring us joy; may it have maximum deep benefit. may all beings be happy ❤️

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