Radical Sabbatical Recap
I decided to take a year-long break, a sabbatical, to reset, re-center, and orient myself for the next decade. I wrote a piece about it at the start, and was actually quite surprised by the outpouring of responses it brought. Now, with 2022 done, I'm writing out the storyline and reflections of how it went and where my head was at during it. Here are lessons learned, adventures had, regrets, and unexpected plot twists. For me it's an important part of this exercise that I talk about the process, but I also hope it's informative or encouraging for those who may be facing similar life questions.
Here's a summary so you have a snapshot and know which sections you might want to jump to: sabbatical design and methods, travels, spiritual practice, romance, psychological health, therapy (including psychedelics), non-profit work and community organizing, applying to grad school, clarifying my mission and next moves.
Principles
Allotting a calendar year for this sabbatical, I wanted a set of guiding principles, thesis, or cheat-sheet to help in navigation. I was inspired by exercises I'd done in a workshop at the end of 2021 by the Brooklyn group Men at Work Healing (thank you to Rasu, Dahkil, Daoud, and Dashaun).
I worked with my accountability partner to document the why of the sabbatical:
live life to the fullest
find my next mountain to climb
Then named four pillars of activity:
service for good
spiritual training
study
contributing to the family business (sustainable building)
Other activities were travel, photography, Spanish, and working on my slightly but consistently high blood pressure. I also quickly found that, after ten years of business-building, I craved some time to rest, relax, and recover.
There were travels indeed!
I spent three weeks in Bolivia, staying in Santa Cruz, the village of Samaipata, and traveling to La Paz and Oruro for Carnaval (some photos below). I spent a few weeks in Los Angeles (Pasadena and Topanga), road-tripped with my dear friend Lina to Texas, fulfilling her wish to see Willie Nelson play. I lingered a week in Taylor, TX, then took a long solo drive back to LA in Lina's VW Eurovan, sleeping in national parks, visiting the bizarre wonder of Biosphere 2, and the airplane boneyard in the desert of Arizona what was once a secret CIA airbase during the Vietnam war. I spent a week in a Zen Monastery in the San Bernardino mountains and another at a monastery in Oregon (more on that). I stayed several weeks in Mexico (Sayulita and Mexico City). And a sojourn that wound from Vancouver down through the islands of the north pacific coast and to Seattle. At the end of the year my girlfriend and I took off for a three-week trot that started in Paris, dipped into Basel, drove across Poland for New Year's, saw Auschwitz and Birkenau for the first time, Tunisia (Tunis and Sousse), a stop in London, and then to Cancún for a very Bed Stuy destination wedding.
Here is a collection of photos from the year, mostly taken on 35mm and 120mm film: https://www.jacobhallgordon.com/photography/2022-in-photos
The plan was actually to be even more nomadic than this, but the kindling of an unexpected romance (aforementioned girlfriend) motivated me to stay close to Boston more than I'd anticipated.
I entered 2021 already in a legal (and ethical) battle with the corporate developer/landlord who owned the apartment building where I lived in Brooklyn. This escalated over the first quarter of the year as I became a holdover case (refusing to leave) and there were a string of court dates. Ultimately, they denied my lease renewal and I was forced to move out. The unfortunate drama, however, became a course in community organizing and neighborhood solidarity that I’m grateful for, and I was able to share proceeds of the eventual settlement with the community.
I documented the saga in an open letter here.
My plan was to stay in the Bed Stuy neighborhood I had grown so close to, expecting to move just to the other side of Bainbridge street. But when the owner of the brownstone apartment I was going to rent got last minute jitters about my sabbatical status and changed his mind, I took one long walk around the block and decided it was time to step into the nomadic unknown.
Almost exactly ten years after I first moved to New York City, I packed up a truck and drove to Boston where I put my things in storage, expecting only a brief layover at my parent's guest apartment en route to being a vagabond with a backpack of cameras. But almost immediately upon arriving, habitually opening a dating app, I encountered a woman I instantly had a different kind of feeling about, and a beautiful romance began. I'll speak more about this relationship as a major part of this year's story. First I'd like to describe how I designed the sabbatical itself.
Designing the time
The most consistent ritual of the year off was weekly check-ins with my accountability partner. Over dinner at a Mexican restaurant in DUMBO I asked my longtime friend, Wes Aull, if he would support me. I asked for an average of an hour-long conversation each week. We set up a shared document that I would populate with notes for each session. Wes would often begin each conversation with a visualization or breathing exercise to usher us into the space.
Wes offered wonderful feedback and questions, often more personal and intimate than I probably expected. I quickly appreciated doing this with someone who knows me well (we go back a dozen years), with whom I can be very open about emotions, finances, relationships, and fragile ideas still in the hatching, and many of our talks sounded more like therapy than career coaching.
At mid-year I scheduled us a longer check-in and prepared a slide deck that chronicled the first six months, made a plan for the next six, and articulated key themes in my thinking. I was surprised to see the Keynote grow to 100 slides (excerpts below).
As a general rule I tried to divide the year in divergent/convergent halves (a principle learned from the IDEO people). The first six months, divergent, were meant to be free and wandering, following what drew me in. The second half was meant to funnel down to a point where I'd have a clear arrow forward.
Scheduling with Wes was sometimes hard and it was definitely a lot to ask from a very busy friend. But even weeks when we missed our session I got great ballast from having someone on my side like this, knowing I'd be checking in again soon, and writing up summaries of the week even if we weren't able to meet.
slides from my mid-year deck
Methods
There are a number of methods I used and tried and maintained throughout the year.
Journaling
Each morning in bed I write a page in a notebook. I was inspired to do this by my friend Rodrigo Bellott on a retreat he led in Bolivia last year. The point is to write while the mind is open and tender, fill a page with whatever comes. Once done, I read the page from the morning before.
While this is a new habit for me, I've kept notebooks for a long time and I was pretty amazed to realize I have twenty years of paper journals.
I also journal on the computer throughout the day, in Workflowy, with an entry for each day. This year I did a lot of mind-mapping in Workflowy, as well as just keeping a running log of the day's thoughts and work. I also keep a timeline of each year with each month as a heading, and key events below them in columns. As someone with an often mushy sense of time this lets me see the arc of a year at a glance and track its seasons.
20 years of notebooks, starting with 2002 on the left.
80,000 Hours course
The organization 80,000 Hours tries to help people find the most impactful careers, and is an offshoot of the effective altruism world. The 80,000 Hours career course is quite in-depth and is meant to be done one module per week for several months with worksheets to fill in, etc. I did a lot of the course more or less as prescribed and found it informative and inspiring, though I wouldn't say it landed me into a precisely clear lane by the end. I'd say it was more helpful in imparting useful principles to consider along the way, such as: we over-estimate what we can do in a year and under-estimate what we can do in a decade, and the value of taking high-risk/high-reward bets on outsized positive impacts.
Study of decades
I found it edifying to look at my life in decades with themes. Inspired by the idea that we under-estimate what we can do in a decade, I enjoyed visually mapping out the decades of my life from now until age 100 (including backfilling previous decades based on what I was doing with my life then – NYC was a lot of work and hedonism). I'm now thinking of my 40's dedicated to positive impact, with more of an emphasis on cultivating and teaching wisdom in later decades.
My four lenses
I have a little system I use to approach work projects and other complex life stuff. It's four lenses that each offer a different logic and way of seeking paths forward:
Perspective/overview: the strategic view, bird's eye, where are we on the terrain and where are we trying to go. Tools: mind maps, Mural boards, timelines
Teamwork/leadership: the collaborative view. What happens when we work with others, listen, weave and splice ideas. How we guide others and/or take guidance from them. Tools: conversations, listening, questions, Asana, shared notes documents.
Doing the work: the productivity view. What it takes to get the labor done with fluidity and rhythm. What it looks like when you get down and grinding. Tools: pomodoro technique, do not disturb modes, sitting/standing/stretching/movement intervals.
Poking the universe: the X factor, the wheel of fortune. This fourth lens is an invitation to dabble in the unknown, take chances, and show up even if you can't know what will happen. One of the easiest ways to exercise this lens is to have open-ended conversations with people, and I was fairly intentional about making time with interesting people to just ask questions, listen, and share thoughts. Some were people I'd long known, others new acquaintances or introductions. Don't underestimate people's willingness to talk and what can come of it.
Meditation, yoga, exercise
I'll talk about meditation in more depth in the context of long-term practice and life path, but needless to say it held a key role in my daily routine. The simple meditation timer I've used for years (Enso) keeps track and connects to the iPhone's HealthKit, reporting that:
In 2022 I meditated for 216 sessions, an average of 39 minutes per day, for a total of 125 hours.
To this should be added sessions of guided meditation I did in the Waking Up app, and two weeks of meditation retreat (where I didn't use my own timer).
Speaking of which, I'd like to give a very honorable mention to the Waking Up app, which I've been using intermittently for about two years now. It is both a self-contained introductory course in meditation and a library of guided courses, talks, and conversations from some of the leading teachers, mostly Buddhist, but includes tracks like stoicism and The Headless Way. I think it's inexcusable that Sam Harris hasn't included content from more women teachers (there is no shortage in the world), but what's in there is of high quality. I think it's $100 a year, but you can always request a free subscription if price is a deterrent.
Then there's yoga. While I take my meditation super seriously, I take my yoga easy breezy and cheesy, baby! Since turning to yoga in quarantine desperation in 2020, I've become a dedicated living room practitioner, taking in the best of what YouTube offers for free in 25 minute bites, ideally with fuzzy dogs present in the frame. And I've felt these relatively timid doses of yoga change my body in wonderful ways: relieving me of a low-level hum of soreness and discomfort I thought was permanent, and convincing me this is how you stay supple and agile into old age.
But on deeper levels, I'm also convinced that the movements taught in yoga have psychological healing properties that go far beyond flexibility and moments of calm. It makes me think of what I've read about Bessel van der Kolk's PTSD work with combat and assault survivors using gentle yoga to process trauma. It has also opened me to the great power of breath. And I've definitely seen synergistic benefits pairing yoga followed by meditation.
Thank you, Yoga with Adrienne and Yoga with Tim (and Benji and Ollie, the token fuzz pups)
About exercise I'll only say that I've recently loved punctuating long desk-work sessions (30-45 minute pomodoros) with five-minute exercise breaks, often including vigorous kettlebell moves. This method keeps my energy levels going much better, and research suggests it may be surprisingly good for you. A study of 25,000 people recently published in Nature Medicine found:
"Those who engaged in one or two-minute bursts of exercise roughly three times a day... showed a nearly 50 percent reduction in cardiovascular mortality risk and a roughly 40 percent reduction in the risk of dying from cancer as well as all causes of mortality, compared with those who did no vigorous spurts of fitness." (NY Times)
But no mention of sex??
Anyway, I even made my own workout timer: a Spotify playlist of songs that are all five minutes long:
Five day foci
I don't have a formal name for this practice, and I haven't documented it other than telling friends about it conversationally. 2022 is the second year I've used a little system I devised that invokes a mental focal point that is assigned to each of the five weekdays. You could think of it as a mindfulness exercise, and its meant to gently nudge my thoughts in directions in which I want to grow, each one meant to build on the last over the course of the week.
2022's regimen was:
Monday – mindfulness, open awareness
Tuesday – saying yes, leaning in, acceptance, curiosity
Wednesday – loving kindness, compassion
Thursday – critical thinking, deconstruction, cause and effect
Friday – generosity, giving, non-clinging, patience
I haven't quite formalized a set for 2023, but currently my draft is:
The Earth Mother, the chorus of humanity (inspired by hearing the call the prayer in Tunisia), breath, asking questions, and the warm and undefended heart.
I'm curious if this practice is of interest to others or if you do anything similar. I picture people choosing their own five for the year, or every three months, or whatever feels right. I'll likely write about this practice more elsewhere.
Spiritual practice
With each year I find myself more and more dedicated to the contemplative way. The teachings of Zen Buddhism and meditation were central elements this year, and I see myself on a lifelong project of examined existence and spiritual unfolding. This was a strong year of practice, self-excavation, learning, and the first time I was exposed to the beautiful tradition of Metta, lovingkindness meditation (see my book report).
I sat in meditation daily and was able to spend a week at two different Zen monasteries in the US. The first was Yokoji Zen Mountain Center, a temple and retreat center in the San Bernardino Mountains of Southern California. Back in 2007 I stayed there six weeks, two of those in silent intensive (sesshin). Yokoji was founded by Japanese Zen priest Taizan Maezumi as the satellite to the Zen Center of Los Angeles. It's a cluster of traditional Japanese buildings perched in a secluded ravine between mountains where wildfires and rattlesnakes guard the landscape. My week there was residency, so rather than the more demanding non-stop schedule of the formal retreat I was up a 4am for meditation, but the day had more flexibility and was not conducted in silence. Meditation totaled about three hours a day and included private meetings with the abbot, a British-born teacher Tenshin Roshi.
After meditation, services, and daily periods of working on the grounds I had a decent amount of time to myself. Aside from long jogs and walks in the stunning (but intimidating) landscape, I raided the monastery's little library and treated myself to a self-guided micro theology school, reading Native American myths, Islamic history, essays on perennialism, and stumbling into Stanislav Grof's book Beyond the Brain, a brain-bending treatise on the origins of mental maladies and a model of psychiatry based on the several thousand LSD sessions he conducted with his patients, mostly in his home country of Czechoslovakia.
This week of no technology (phone and computer completely off), meditation, time with a teacher and other students, and my own reading and writing was one of the most restorative I've had, and served two of my sabbatical themes well: spiritual practice and academic study.
The second week I spent in retreat was in the fall at Great Vow Zen Monastery in the hills of Oregon. Great Vow was founded by one of Taizan Maezumi's early students, Jan Chozen Bays, and occupies a converted 1970s public elementary school amidst mossy pine forests. The place has been lovingly converted over the years into a serious Zen training center where a number of full-time monastics live and many students come and go (mostly from the Portland area). It still has the linoleum-floored cafeteria and a school gymnasium that is now filled with farming equipment and a dozen large marimba xylophones (that I never did get an explanation for).
This time it was sesshin: the traditional Zen format of intensive silent retreat. The twist was that it was this Zen master's yearly retreat dedicated to the Jizo Bodhisattva, a gender-shifting member of the Buddhist pantheon often revered as a protector of travelers, guardian of children (unborn, born, and passed away), and one who can retrieve people from the hell realms (also making Jizo the patron saint of firefighters in Japan). (you can read my summary of Chosen's book on Jizo in my book report)
The demanding schedule of meditation throughout the day, traditional regimented Oryoki meals, dharma talks, and afternoon work practice of silently picking fruit in the orchard and clearing brush, were infused with the traits of Jizo Bodhisattva, such as great compassion and unyielding optimism. And, a new experience for me, there were periods for making art when we worked in clay and painted stones and paper lanterns in honor of our Jizo-like nature. The retreat concluded with a lantern-lit procession through the temple's forest Jizo garden, where hundreds of child-like stone statues dwell in the moss and ferns commemorating lost loved ones, in particular children who had to leave too soon.
I also attended this retreat about one week after undergoing a round of psychedelics as part of ongoing work with a therapist. I'll have more to say about this in the next section, but I'd like to emphasize how well these two modalities complimented each other. We hear a lot about the importance of "integration" in the world of psychedelic therapies, and I can hardly think of a better way to dwell and reflect on the subtle shockwaves of an axis-shifting dive beyond consciousness. My therapist was supportive of the pairing, though it was not at his suggestion, and I didn't coordinate it explicitly with the monastery, but I won't be surprised to see these activities being talked about in the same sentences more frequently. This interview the psychedelics researcher and meditator Roland Griffiths touches on entheogenic/meditative synergy a fair bit.
I'm so grateful to Chozen Roshi, the abbot of the temple, for her radiantly compassionate encouragement and guidance throughout the retreat, and for leaving me with one of my year's most precious lessons: the strength to lay down my guard and face the world with a warm and undefended heart.
Mental/emotional health and therapy
The two biggest challenges to my psyche this year have been an ongoing family strife (that has left me feeling misunderstood and chronically angry), and my emotional turbulence in a new romantic relationship. I'll try to share insights about these themes, but I'll be be vague on details for the sake of privacy. I'll also give a fair bit of detail on the role of psychedelics as administered to me by a therapist. I do this because of the influence it has had on my mental wellbeing and interpersonal struggles, though the narrative should not be read as a tale of drugs quickly solving problems. A major reason I give detail of the therapy is because I believe these approaches should be destigmatized, de-criminalized, and probably used much more broadly for a considerable range of maladies, and to many people it's still a fairly foreign and probably scary topic.
Certainly the most unexpectedly joyful sun to rise in my life this year has been a new love. As things started to get serious and I was riding the early highs and lows, Wes asked me: "Jacob, is love going to be your teacher this year?" And yes, it's been one of the biggest.
It's been nine months since Inès and I met, and we've been calling it a relationship since the summer. It's a beautiful thing. I'm watching us do something I've never successfully done: dwelling in a romance that is tenderly emotional, ecstatically hot, emotionally mature, spirituality profound, while also being comfortingly domestic and cozy. But I have faced, and continue to face, considerable personal difficulties.
My relationship history is a curious picture: a ten year relationship spanning my 20s, then single for the better part of a decade, followed by a 1.5 year long-distance relationship that ended painfully against the backdrop of COVID 2020.
For years I was very dedicated to being single, often describing myself as oriented that way. But especially over the last year I had been facing some very unnerving psychological symptoms in my intimate/dating life, with disorienting emotional drops that left me wanting to remain unattached, even as I was growing more curious about greater intimacy.
As the new relationship started feeling serious, the dark waves rose up again. But this time the stakes seemed too high, and I needed help. I wasn't seeing a therapist at the time – the therapist I'd seen through COVID (who mediated the sibling therapy I wrote about in my 2020 recap) I had broken up with in a fair bit of frustration.
Finding a new therapist always feels absurdly blind and haphazard and I was daunted. Fortunately a call to a friend in the Bolivian healing world yielded an introduction to a guy in Vancouver. "If he'll take you, he's the guy you want."
The therapist and I had an encouraging first conversation and he explained his approach. Trained in Gabor Maté's method of Compassionate Inquiry, he does talk sessions and also works with a range of mind-altering plants and compounds.
We began with weekly hour-long sessions on Zoom, going broadly through the major themes in my life, but looking for where I did and didn't feel emotionally safe, secure, and sufficient in my upbringing. We knew we were building toward the option of doing sessions with psychedelics, and would occasionally discuss which substances might be best suited.
The therapist is not a certified therapist in the conventional Western sense. From what I understand, he's gone through Gabor's Compassionate Inquiry training, a year-long certification that is meant to be an add-on to a more formal degree. (Also, Gabor is an MD, not a psychotherapist, and his co-leader in the certification is a naturopath and kundalini yogi, not a Western-style therapist.)
The therapist's greatest credential is the extensive number of ayahuasca and other ceremonies he has both assisted and imbibed in over many years. I was immediately moved by his tenderness, gentle directness, and wise manner, and our sessions were insightful, caring, and occasionally would move me into uncommon states of mind (one session was emotionally draining such that as soon as it ended I tipped over on the couch and fell instantly asleep).
About three months into our work I had a date to visit him on the west coast for a session of medicine. I took him up on his suggestion of working with three substances in sequence: MDMA (ecstasy), psilocybin (dried mushrooms), and 5-MeO-DMT (a synthetic version of the DMT-based substance that is traditionally extracted from venomous toads). All in considerably high doses. The logic of this combination was that the empathogenic MDMA would create a forgiving emotional cushion as well as physical embodiment, the mushrooms would stimulate insight and introspection, and rounds of DMT at the end would create the opportunity for a crescendo of surrender.
It was quite a day.
“Breath work session in progress
Loud expressions are expected
All is well 🙂”
The sequence of events was made up of an in-person visit the evening before to discuss the plan, the intentions, and to arrange an altar that included photos of loved ones I'd brought. Then a full day of session starting the next morning. Then there would be an integration session a few days later. We've been doing monthly sessions since.
I won't give much in the way of details about the psychedelic experience itself here (though I'm happy to do so in private conversations) but I'll say that it was predominantly an exercise in physical embodiment and breathing. The therapist and his husband, who is an emergency room nurse, held space for me throughout the day, administering the substances along with a regimen of vitamins and antioxidants (meant mostly to mitigate neurotoxicity). They offered chanting, drumming, pleasant aromas, and took handwritten notes throughout, which they later provided to me.
It was an exercise in endurance – and not easy. It's a special kind of endurance I've come to know, made of surrender and release, not bracing and clutching. "Breathe, trust, let go."
I would call it revelatory, but not in the form of visions, visitations, or neon messages from the universe. And I sure wasn't chatty: my therapist described me as one of the least verbal clients he's had.
Three months later, what have been the effects? That's not easy to say. It was definitely one of the most memorable and meaningful events of my year, and one I'll recall with awe for many years to come, I'm sure. It also brought me into harmony with my therapist in a way that has made our sessions stronger since.
My best assessment at this point is that the effect has been a subtle softening of my anxieties (in relationship and life in general), a gentle unification of my mind and body by way of the breath, and an energizing tailwind to my spiritual practice (in the long days of the meditation retreat that followed, my mind whispered: breathe, trust, let go). I also suspect that it has helped me navigate a particularly hard family issue that's been stewing for a number of years and arousing difficult negative emotions. There was some hopeful progress made this fall, and I'm inclined to credit the medicine with helping me connect to insight, compassion, and oneness.
After a day to recover I left Vancouver for more travels. I spent the night at an intentional community and farm, stayed the weekend with my high school girlfriend, her husband, and two daughters on one of the Pacific Northwest's pine-covered islands (reconnecting with her was a fascinating reflection on who I was as a teenager), stayed with another two-decade friend in Seattle, and finally landed at the Zen monastery in the faded old school for a week of rigorous silence.
It's amazing that at age 42, with no notorious traumas in my past and with considerable time already dedicated to therapy and self work, I'm still dredging, decoding, and massaging the scar tissue and short circuits in my psyche. And there still seems so much more to do. But this doesn't upset me. This is the work of becoming ourselves. We humans are both tough as nails and delicate as flowers. We can live through a meteor strike, but even life's bruises and abrasions can hobble us over time. This is especially true in a society that so often takes advantage of our wounds to get what it wants from us.
Deeper into youth work, mental health, violence prevention, and anti-racism
Stepping out of the workforce this year gave me time to put more into a new Brooklyn non-profit I've been volunteering with. The B.R.O. Experience does social-emotional mentorship with young men of color in Brooklyn's most marginalized communities. You've surely seen things I've been posting about B.R.O. this year. I was able to get very close with the founder, Barry Cooper, who is a remarkable educator, a Bed Stuy native who has spent a decade working with black children, teens, and fathers, including bringing his coaching into the gang units of Rikers Island.
I first was attracted to this work while looking for ways to support black lives and strengthen my neighborhood in the face of COVID shockwaves, gentrification, predatory real estate dealings, and rising gun violence. I approached Barry, asking if I could volunteer, and we soon found that many of the skills I'd built at Artiphon translated well to a fledgling non-profit. I became part of a small volunteer development team that has supported Barry and the board in areas across the org.
In 2022 I expanded the website, published a series of video interviews with Barry and five of the young men he's worked with, compiled our theory of change, sent many an email newsletter, lovingly nagged everyone about how to use Asana, and took about a thousand photos. In the second half of the year we got more serious about raising institutional funding and grant writing. We applied to The David Prize (Barry was a semi-finalist) and compiled a large pipeline of grants (educating myself on non-profit management and grant-writing in the process), submitting about a dozen LOI's and applications.
I'm joyous to say that we were able to end the year with a great victory. After being declined for a city-sponsored anti-violence grant, we were approached by one of the foundations that funded it. Barry and I wrote the application at their request, and in December, the day before our holiday housewarming of the new B.R.O. community center in Bed Stuy, we were awarded a $200,000 grant from The Pinkerton Foundation, one of NYC's most respected philanthropies.
I'm learning such an enormous amount by participating in this work. I'm learning for the first time how non-profits work, how money flows to them, and so much about what it means to work on social justice, racial justice, violence prevention, and youth support in a black-led organization.
It has also opened my eyes to the availability of opportunities that go beyond short-term volunteerism and chipping in here and there. Many of us have specialized talents and resources that can be highly valuable to mission-driven organizations and causes (but that they often can't justify paying for), and it would be wonderful to see more of this type of collaboration happening.
Advising reVillager
Throughout the year I also met weekly with the team at reVillager, where I've been serving as a pro-bono advisor. reVillager is a digital communication platform designed to build non-exploitative connectivity and harmony for intentional communities, both digital and in-person. Picture Facebook Groups plus Slack with conflict resolution tools built in.
One of the things I've enjoyed most about working with the founders is that they're all living their values in such weird and wonderful ways: Sante codes the app via StarLink while migrating around the continent with a tribe of van life nomads, Jasper lives on an intentional community on Vancouver Island where he and his neighbors grow their food, Warren is phoning in from the eco healing retreat center he runs in the Andean highlands, and Nick is an active member of the men's circle community. I've also never met a team who is so committed to NOT continuing the Facebook/Instagram tradition of exploiting the hopes and fears of their users. So much so that they're considering building reVillager as a non-profit.
A search engine for meditation retreats?
I’ve probably done a dozen silent meditation retreats over the years, and each time I’m simply amazed by the tremendously deep power of these experiences. I sincerely believe that if more of us were investing the time and willpower to look deeply within, guided by wise and caring teachers, it would have measurable positive effects on our society and future.
This summer, as I was drifting from Texas back toward the southwest, I wanted nothing more than to spend a week in some dusty monastery. “Surely, in 2022, there is some lovely website that will show me what I can sign up for in this part of the world.”
**rolls up sleeves and pulls up search engine** Curious… nothing?
Indeed, despite a large and growing number of retreat centers around the country and world, there is no central repository. For a time I became quite fixated on what a solution would look like. I started a Google Map and a spreadsheet of centers and the retreats they offer (linked below), and when I posed the idea to my circle of friends the response was super strong. Yes, many people are curious to do some form of meditation immersion, but that world remains opaque and scattered.
The cocktail napkin business plan I sketched was:
a nonprofit that aggregates all the upcoming meditation retreats and presents them in a search engine, calendar, and map
if you need guidance, the site has a recommendation service, where you fill out a form and a human provides you with suggestions and advice on what might be the best fit
it has features like: enter a date range and a geography (“summer break, southeastern US”) and you’ll get email notifications of upcoming retreats
Sorta AirBnb for meditation retreats, but I do think it should ideally be a non-profit. These centers are technically religious non-profits we’re talking about for the most part, and I’d be very concerned about the long-term role of a for-profit company doing this match-making. Though I remain open-minded about what business model is best. Perhaps simply community crowdsourced?
I’m still passionate about this idea; I just don’t know if I’m the person to do it. If it speaks to you, either in terms of work, financial support, etc., let me know. One way or another, definitely should happen.
And in the meantime, if you yourself are interested in such an adventure in consciousness and compassion, I’m happy to advise however I can.
Study
One of the pillars of my sabbatical year was study. I read a lot and I learned a lot and I don't regret any of the books or rabbit holes I went down. I do have some regret that I hadn't been more systematic and directed with my studies, though. Toward the end of the year I started taking an interest in Nietzsche and Heidegger (not sure exactly why) and found myself wishing I'd taken on one of their major texts.
The books I read circled around the topics of contemplative spirituality, race/racism (with an eye for youth issues, poverty, and violence), psychology, and psychedelics. My yearly book report summarizes each: https://www.jacobhallgordon.com/writing/book-report2022
I studied Spanish, with hopes of gaining some decent conversational abilities. I used Duolingo daily and met with a tutor for an hour a week for the first half of the year. I did make progress (as evidenced during three trips to Spanish-speaking countries) but I'm confronting how hard of a climb it is in the early intermediate levels. There are moments when the words come smoothly, and others when listening to native speakers sounds like an incomprehensible blur. I'll continue my study, but it's hard to estimate my rate of progress at this point.
Grant writing became an area of study in itself. I blasted through Non-Profit Management for Dummies and Grant-writing for Dummies (laugh if you wish), read blogs and watched videos, and scoured the websites of innumerable charitable foundations. This was all learning I was putting immediately to work at The B.R.O. Experience, and by the end of the year I was submitting LOI's and applications on a weekly basis (most of which we're still waiting to hear back on).
As for what's next on the study docket: I'm actively gathering texts on Christianity (realizing I'm woefully uneducated on the history of the religion), and I'm getting deeper into the world of existential risk calculation, cause prioritization, and impact assessment, which will all be part of my upcoming chapters.
What comes next?
Time to get back in the game. I feel rested, inspired, and more thoughtful and collected than I've felt in a long time. If this decade of my career is about positive impact in the world, what's the plan?
When I asked myself to write a simple life manifesto, this is what came out:
Do as much good as I can on the issues that matter most
Cultivate and transmit wisdom
Be a regular person
I like it. Let's define…
Doing the most good
This is one I've been thinking a lot about. My work has always related to this value in some way. I was an environmental journalist because I care about the environment. I helped build Artiphon because I believe creativity is one of the great things in life and it should be more accessible. I support The B.R.O. Experience because I believe in social-emotional education as a strong way to fight inequity.
I've also been trying to learn more about how to think critically and prioritize the big issues in the world. "Doing good" can't be a generic field of concern – we should be looking hard at what issues are of greatest consequence and what makes the biggest impacts on them. Thinkers from the Effective Altruism movement have given me a lot to work with here. I feel the gravity of risks facing life on earth that are existential in scale. Environmental collapse, engineered and natural pandemics, war, and uncontrolled artificial intelligence are all capable of blowing out the flame of humanity, or reducing it to a tragic sputter. We also face immense challenges and injustices in global health, poverty, human rights, and democracy. Each person is very much entitled to their views on what matters most, but each of us should take the time to study, observe, and decide (at least in each era of their lives) what they prioritize.
As for me, I'm still learning, but three areas stand out.
Climate and ecosystem stability. We've been too slow to act on too many environmental issues, but there is still time to avoid the worst outcomes. We need a global economy that is de-carbonizing and getting atmospheric CO2 levels back to safe levels. We need to value and preserve natural habitats that are home to biodiversity and essential metabolic functions. And so much is at stake, with climate and ecosystem disruptions having cascading, destabilizing effects, including over a billion climate refugees predicted by 2050.
Artificial intelligence. AI is already transforming the world, and will introduce the potential for massive new threats. I'm actually quite optimistic about what a thriving future can look like, with abundance, justice, and beauty for ten billion people and beyond. And AI will be a big part of what gets us there. But it will also grow into an unprecedented force that can be weaponized by humans with bad motives, or it can take on a bad agenda of its own. Getting wise about how we design, contain, and regulate AI is one of the great existential questions of the century.
Happiness, insight, and wisdom. As the world develops more complex systems, societies, technologies, and problems, I think it very important to prioritize ways of being that lead toward contentment, gratitude, awe, and peace that glows inward and outward. Humanity's ability to act like fools (on a good day) and maniacs (on a bad day) is one of our great threats. Insight and wisdom are the antidotes to delusion. They denude us of our illusions that we're islands unto ourselves, and germinate inward peace and outward kindness. I see signs that civilization is pursuing paths to wisdom that are practical (practicable), flexible, and free from dangerous dogmas. I'm excited to see what can be done on the frontiers of consciousness as we take on the ever-more-complex future.
Cultivate and transmit wisdom
This is a more personal heading, certainly. But I don't think seeking deeper meaning in life should be something we keep only in private life or private conversations. With each year that goes by I find myself more concerned with living in an awakened way, in close relationship with the panorama of life and death. My main pathways for this project of awakening are meditation, Buddhist philosophy, psychoactive plant medicines and compounds, and breath/movement, and therapy. This was also the year that I foresaw myself moving into a role as a teacher of wisdom along the way. I'm not there yet, not in a formal capacity, but the time will come.
Be a regular person
This last one kind of just popped out. I looked at it quizzically, but quickly nodded. Yes, it's advice I need right now. I've come to learn that I have a dark side of narcissism. The egotistical stories I tell myself are insistent, seductive, and continue to cause me no shortage of anxiety. Especially if I want to orient my life around doing good and becoming wise, humbleness is one of the most important foundations for both. Be a regular person is a reminder to not take things so seriously all the time. To not think I'm going to be the one who saves the world or is always the coolest person in the room. Relax, Jacob. You don't need to be so special. You're enough just as you are.
So... do good, get wise, be humble.
Environmental Business School?
Over the course of 2022 I on-and-off pondered additional schooling, but I've long been skeptical. I come from a family of PhDs, but after my undergrad I made a pretty strong resolution to get out there and learn by doing. But here, in my early 40s, I began contemplating what I might want to go back to school to study. Philosophy, psychology, history, economics? I was looking most closely at programs in non-profit management when accountability-buddy-Wes suggested I see what my alma mater, Bard, was up to.
And yes indeed, for about a decade Bard has been running graduate programs in environmental policy, education, and business. Their MBA is one of the few in the world built from the start with environmentalism at its center. I was surprised to find myself intrigued right away, and after considerable research I applied.
I'm pleased to say that this week I was accepted to the program (thank you Artiphon founder Mike Butera and B.R.O. Experience founder Barry Cooper for the letters of recommendation). I haven't given my response yet, and I have some other programs to try out for, but I've come to think of an MBA as a very fitting move. A sustainability-focused MBA, ideally, will:
solidify and strengthen business skills, especially the ones I was able to avoid over the past ten years (budgeting and finance among the key ones)
expand my knowledge of non-profit management, making me a better worker, advisor, and board member
expose me to the deeper workings of philanthropy and charitable foundations
let me dive further into the field of emerging beneficial technologies (from renewables to distributed finance) for the sake of working in new ventures as well as investing in them
refine my skills in leadership, especially with a focus on diversity, equity, and inclusion
and let's be honest: gain a better command of my own financial life
Ideally I can combine my experience in environmental media, my twelve years in startups/consumer tech, and my recent work in non-profits and community organizing to be a meaningful part of powerful solutions to gnarly problems.
As for what kind of shape that work takes, I don't know that yet. I'm starting a survey of the field of technologies, movements, companies, and organizations that are bringing new approaches to bear. This will either lead me to joining an existing organization or launching something new. If you're reading this, you'll pretty soon be seeing an email from me as I start re-introducing myself to the professional sphere.
Closing thoughts
What a fascinating and beautiful year. I unexpectedly lost my apartment but it landed me in Boston where I fell in love. I boxed with my chaotic mind but it pushed me to inner explorations that brought me more to life. I lived off my savings but was able to help a fledgling non-profit raise its first big grant. I didn't make it to a monastery in Asia but I trained in seclusion with wise and caring teachers. I wasn't able to work on the family business as I'd hoped but I was able to spend more time with family than I expected, including being in Boston for the birth of my first niece.
I hope I never lost sight of what a massive privilege it is to stop the clock for a year like this. I tried to stay grateful and attentive every day to what an uncommon luxury I was enjoying. I do believe it was time well spent. And I could see myself doing something like this each decade, as I reflect and summon in a new chapter of the book of Jacob.
I hope that what I've learned and how I've grown this year will be of service to the people around me and the world at large, making me a better contributor to this earthly drama we all share.
