In this second of a two part episode, Rev. Deborah Duguid-May interviews Brother Jacob, a transgender Anglican Benedictine monk, about his winding spiritual journey to monastic life and his experience at Holy Cross Monastery.
The interview was recorded in September of 2025. The two parts of this interview are the last content with Rev. Deborah that will be released on this podcast.
The interview is presented with minimal editing to retain the flow of the conversation.
Transcript
DDM [00:03]: Hello and welcome to The Priest and the Prof. I am your host, the Rev. Deborah Duguid-May.
MET [00:09]: And I’m Dr. M. Elizabeth Thorpe.
DDM [00:11]: This podcast is a product of Trinity Episcopal Church in Greece, New York. I’m an Episcopal priest of 26 years, and Elizabeth has been a rhetoric professor since 2010. And so join us as we explore the intersections of faith, community, politics, philosophy, and action.
CRT [00:38]: This is the second part of a two part interview with Brother Jacob at The Holy Cross Monestary in the Hudson Valley, New York. The interview was recorded in September of 2025. The two parts of this interview are the last content with Rev. Deborah that will be released on this podcast. The interview is presented with minimal editing to retain the flow of the conversation.
DDM [01:02]: What have been some other surprises that you’ve discovered in monastic life? I’m sure there’s been many, but just what comes to mind?
BRJ [01:12]: I, I think, I think I’ve surprised myself more than anything.
BRJ [01:17]: My, my favorite story is of my first week of silence. Um, every two or three months we have a week of si- it’s, it’s actually only five days.
BRJ [01:28]: Contemplative days. Um, and when I, when I first entered the monastery, I’m– I mean, you know, entering a monastery is a big deal, right?
BRJ [01:36]: Like, there were a few things I knew here and there that I would struggle with, right?
BRJ [01:41]: But silence was the only thing that truly scared me. I had never even spent a day in silence. I was not at all sure that I would survive a whole week, right?
DDM [01:55]: I mean, we live in a world that’s just constantly bombarded by news. You’ve always got a radio on or a TV on or, you know? Right.
BRJ [02:02]: Right. Yeah. Yeah. So I, I, I was terrified. I, and I’m, I’m not even sure what I thought exactly would happen.
BRJ [02:11]: I just didn’t want to spend that much time alone with myself,
BRJ [02:18]: As the first– as my first contemplative days drew nearer, our formator was a huge support, um, and I had conversations with other brothers about it, how to occupy myself, and taking comfort in their stories of struggling in the silence.
BRJ [02:38]: I had a plan of what to do, and that was, like, extra prayer, study, work, leisure. These are the backbones of, uh, uh, or the backbone of Benedictine life.
BRJ [02:51]: Um, so the first day came, and it, and it, it went okay.
BRJ [02:59]: Th-there were moments that I struggled, and so, like I was told to, I took them to prayer, then the moment passed.
BRJ [03:08]: And, and I went, “Oh, well, that wasn’t so bad.”
BRJ [03:14]: Like, I, I survived. Um, this is the funny part of the story. That, that night after my first day of silence, I actually woke myself up talking in my sleep.
DDM [03:30]: That’s hilarious.
BRJ [03:32]: I don’t even remember what I was dreaming about, but I just needed to vocalize apparently. And then, you know, the rest of the week just went and it, you know, it, it got easier, and I realized that I would survive and it, it wasn’t horrible.
BRJ [03:49]: Right? And I could even see how maybe I would enjoy it one day. And now I do. And, um, actually this year, uh, I’ve had to miss contemplative, contempo- contemplative days twice in a row because I was away.
BRJ [04:03]: And so, and actually today begins the first set since then. I’ve been craving it for months. So that’s, that was a big surprise.
DDM [04:13]: That’s interesting
BRJ [04:16]: Um, I, I have another short story to tell, but do… I don’t know if we want to include it or if that’s enough
DDM [04:26]: Yeah, no, I’d be interested to hear. Yeah. We don’t get to speak to a monk very often,
BRJ [04:33]: Okay. Um, so one thing that surprised me about monastic life, which then led to another surprise about myself, is how our natural God-given gifts and desires are, are really encouraged and allowed to grow here. Uh, well, I mean, I think I had a feeling that’s how monastic life was supposed to be, you know? But, but to actually experience it really is surp- um, for me, it was surprising.
BRJ [05:05]: Um, ’cause, you know, like other groups outside monasteries tend to focus on, on what does the group need, and how do you fit into it? How can you meet our needs?
BRJ [05:18]: But here it’s what does the community need, and what do you need, and how can we fulfill both of these needs at the same
DDM [05:26]: Oh, that’s beautiful.
BRJ [05:28]: right? Yeah. And so like in that process, hidden gifts and desires come ali- come alive.
BRJ [05:34]: I, um, I experienced that in becoming the assistant groundskeeper, which has been a true blessing. Um, I was still a postulant in my first six months here, and we needed someone to take over the compost system, and not like I have never been a gardener. I barely managed to keep three houseplants alive before joining, right?
BRJ [05:56]: I had no idea what I was doing. But I’m an animal lover, and we don’t have animals here.
BRJ [06:03]: I want something to care for, to nurture, and it won’t be a cat, I’ll settle for worms.
DDM [06:10]: Oh my gosh.
BRJ [06:13]: So I volunteered to take over the compost, right? And, and like happily thinking that that would be the extent of it, right?
BRJ [06:19]: Like, I’ll just do the compost. I don’t want the ground, you know? But of course, my desire grew from there. And now I’m in the garden every day, right? And in the spring, you and, and our friend Petra are coming to the monastery to lead a gardening retreat with me. I would never have seen that coming.
DDM [06:36]: I’m looking forward to that.
BRJ [06:39]: Yeah. I, it’s gonna be a blast
DDM [06:41]: So it’s so interesting because, you know, we’re speaking about compost and worms, which are things that people don’t generally think about in relationship to monastic life. Um, which, which is a reminder for us, you know? But, but I am interested very specifically in this whole journey, where is God in all of this?
DDM [07:00]: I mean, I know you’ve, you’ve mentioned it, you know, a number of times, but I’m just kind of interested in specifically.
BRJ [07:07]: Yeah. I mean, I see God so much more than I ever did before. I see God in people and places I never would’ve thought to look in- including on the compost pile.
BRJ [07:21]: A- a- and this is, uh, this is just the beginning of the journey. Um, so the, the first year and a half at Holy Cross are, are spent in initial formation.
BRJ [07:35]: It’s mostly about learning what it means to be a monk and how to live in community, right? Um, uh, around the end of that time, I went back and read my spiritual autobiography, and I was shocked to see how much I’d grown and changed in less than two years
DDM [07:57]: It’s interesting, yeah
BRJ [07:59]: And now that I’m a junior professor, this stage in– of formation is more about the individual spiritual life.
BRJ [08:09]: So our studies go deeper and, and we really work to let them sink in and surrender to conversion of life. We, um, we study the Bible. The Psalms are very important. The writings of the mystics, theology,
DDM [08:24]: It’s interesting, sorry, it’s interesting that you begin with, with exploring community and only after that then move on to the individual. That I find is fascinating.
BRJ [08:35]: Yeah. Well, I mean, uh, it, uh,
DDM [08:38]: Of course, it’s all woven together.
BRJ [08:42]: There’s… The, yeah, it’s a matter of emphasis,
DDM [08:45]: Mm, mm, mm.
BRJ [08:47]: but yeah, I mean, uh, uh, because, because community life is, is so essential, so vital to religious life. Yeah. Yeah.
DDM [08:59]: always
BRJ [09:00]: Yeah. You got it. Yeah.
DDM [09:06]: that there is that impression that, that monks are simply, you know, sort of on their own reading scripture, praying, that sort of individual journey, you know, and deeply spiritual people, you know?
BRJ [09:21]: Yeah. Yeah, I mean, uh, well, it, it is tr- it is true to some extent, right? Like, and, and some of us are like super intellectual, constantly reading and, and heavy philosophy and stuff. But like I d- before entering, I didn’t have any theological training or experience, right? Like, I’m only now learning the basics and like different ways of reading the Bible.
DDM [09:48]: Right
BRJ [09:49]: And like I’m, I’m just… You know, we, we all participate in these theological philosophical classes, discussions, but, um, I’m much more comfortable shoveling worm poop.
DDM [10:02]: Right
BRJ [10:03]: know? Like we all have to hang, but, you know, we, we, we do it differently
DDM [10:07]: Right, right, right I think that’s liberating for people to hear, you know, because I do think that often in, in our mindset we think that monks and nuns are, almost have this super spiritual direct line to God, you know? But when I’m listening to your journey, it’s, it’s so much more about discovery rather than already necessarily having the answers, you know?
BRJ [10:34]: Yeah. And I mean, well, it probably is true that like we pray more often than the average person outside a monastery, but that doesn’t mean that God hears me more than you or any of your congregants or even a random atheist walking down the street,
BRJ [10:48]: Right, Like,
DDM [10:49]: right. Yeah. What are some of the things that you love most about your particular community?
BRJ [10:56]: Oh, I love this question, Deborah.
BRJ [11:00]: Um, number one, top of my list is worshiping with these guys. We are in church five times a day together, so it helps that I like it.
DDM [11:14]: Yeah.
BRJ [11:17]: But I just, I, I love the way we do church and, and share responsibilities around it and just show up in our human frailty, right? Like, no matter what kind of day we’re having,
BRJ [11:34]: Um, I love how diverse we are. I– Our, our gifts and interests are all over the place. We have brothers from all over the world.
BRJ [11:47]: Our socioeconomic backgrounds run the gamut. We, we represent four generations. Our sexualities are diverse. Our abilities are diverse. Our levels and area of education are diverse. I mean, we, we check a lot of DEI boxes.
DDM [12:07]: I hope you’re not getting funding from the state, but sorry, carry on.
BRJ [12:14]: it do- it makes for a willy, a really well-rounded community,
DDM [12:18]: It does. It does. It’s beautiful.
BRJ [12:20]: cool thing is that, is that even with all of these differences, we manage to love each other and accompany each other, and we build intimacy, right, with each other on our journeys to building intimacy with our creator. And that’s, that, I mean, that’s what monastic life is all about,
DDM [12:38]: And that’s such an example, I think, to us in our world for those listeners, um, you know, who, who are aware of what’s happening in the USA. You know, just what you’re describing of how diverse you are, you know, the difference, and, and yet how you, you manage to love each other, you know, and, and build intimacy with each other.
DDM [12:58]: It’s a, it’s a real model for what would be wonderful if we could be achieving more in our own communities.
BRJ [13:07]: Well, and, um, we’re not perfect, right?
DDM [13:11]: sure
BRJ [13:12]: we practice love because it’s, it’s hard sometimes, right? And sometimes we truly screw it up because we’re human, right?
BRJ [13:22]: And, and then we do our best to be honest with ourselves and with each other, and then we try again,
BRJ [13:28]: right?
DDM [13:29]: So when you’re talking about DEI, I have a question. So why can’t girls then join your particular order?
BRJ [13:38]: Yeah. Yeah, we don’t check all the DEI boxes
DDM [13:41]: I know, I’m thinking for instance, like given the fact that you’ve taken vows of celibacy, you know, why can communities, religious communities not be beyond gender? You know. Now, on the other hand, when I say that, I also am aware that for female-based communities, those have sometimes been very redemptive spaces for women to be in a, in a space beyond patriarchy and outside of patriarchy.
DDM [14:05]: So I know there’s definitely, you know, an argument for same-gendered, um, communities, especially like for female-based communities. But I’m just interested. Yeah.
BRJ [14:16]: Yeah, I do– I, I mean, it’s a great question, and honestly, like one I really struggle with. Um, I, I, I think the simple answer of why we continue to be gender separated is, is tradition, right? And like you said, in, in old days, we were gender separated because of celibacy, right? Like, but, um, the claim I’m about to make, I don’t know if any official numbers exist, but like judging by what my eyes tell me and anecdotes I’ve heard, the population of queer people is much more dense in religious orders than in the general population, right?
BRJ [14:57]: So like celibacy is not necessarily the basis of a valid argument to maintain gender separation anymore, right?
DDM [15:08]: Right
BRJ [15:09]: Um, now there are a handful of mixed gender communities out there. Or I, I’ve heard of both Anglican and Catholics, uh, order, um, communities doing that. But, but most, as we know, uh, enforce the gender binary.
BRJ [15:25]: So in my struggle to understand and feel at home in this strict gender system, I have found a few factors that add up to a, a more substantive argument for continuing this tradition, okay?
DDM [15:41]: Oh, interesting. Okay.
BRJ [15:42]: not that I’m arguing that it should be continued, but that there is, there is what I would call a valid argument for it, okay?
BRJ [15:51]: So l- I’m gonna preface it by saying I am about to make some sweeping generalizations that are clearly not true for everyone, okay?
DDM [16:00]: Sure, sure
BRJ [16:02]: But while, um, individual experiences of, of gender are quite varied, we still live in a culture that treats sex and gender as binary, and we cannot escape the reality that men and women and girls and boys are, are treated differently and have very different expectations laid out for them from a very early age, right?
BRJ [16:26]: So having lived on both sides of that divide, right?
BRJ [16:32]: See gender as a spectrum, not a binary. There is a big divide between the way I was treated when I had breasts and the way people treat me now that I have a beard,
DDM [16:42]: That must be so fascinating to actually know the different ways people treat in your own body. You know, I mean, I can only think and see with my eyes how I’m treated versus somebody else, whereas you’ve experienced that in your own body. I mean, that’s fascinating.
BRJ [16:58]: It’s, it’s a wild shift to experience, yeah. Um, so, so I’ve spent a lot of time exploring and playing in the gray area or m- the lavender area, right? Like between pink and blue. I, I’m quite comfortable there, and I’m sure some of our listeners are
BRJ [17:17]: So while I’m about to make some binary gender remarks, it’s not to deny or offend those of us who, who revel in this middle space, but to acknowledge the effects that our highly gendered society has on us.
BRJ [17:34]: Okay,
DDM [17:35]: Okay, I hear you.
BRJ [17:36]: Okay. So in general, boys are encouraged to express anger, and girls are encouraged to express a wider range of emotions. Like I said, it’s not, it’s not true for every child, right, but the vast majority.
BRJ [17:52]: Uh, boys are encouraged to be more analytical and girls to be more feeling, right? And this has, uh, uh, an impact on our psychological health and makeup o- of men and women, right?
BRJ [18:05]: Another thing, um, Sister Lynn said, um, at that formation retreat, which resonates with my experience, is that our psychological development and spiritual growth cannot be separated. It’s one journey.
BRJ [18:22]: So the way we process and express our emotions is like directly related to the way we live our spiritualities.
BRJ [18:31]: And, in religious life, the way we live our spiritualities guides everything, right? Okay. So this is the, the basis for the first factor here. Okay? Let’s call this the psychological spiritual factor of this gender argument.
BRJ [18:51]: Okay. Th- this, this factor gets amplified. Um, it’s, it’s probably gonna sound a little controversial, so hang, hang with me for a minute, okay?
BRJ [19:02]: So having lived about half my life now with estrogen as the dominant sex hormone and then testosterone as dominant, and admittedly, I, I have no empirical evidence for this, okay? This is my lived experience.
DDM [19:16]: Okay
BRJ [19:17]: I believe there is a biological element that contributes to the difference between the way men and women experience emotions.
DDM [19:27]: Interesting. Okay
BRJ [19:28]: When I started taking testosterone, I was seriously shocked to, to watch my thoughts and emotional reactions change, right? Like, I, I really did begin to view things more analytically and less emotionally.
BRJ [19:47]: And when I had emotions, anger was right up front in a way that I had never experienced before
DDM [19:54]: I’ve heard this from, from other friends of mine.
BRJ [19:57]: Yeah. Yeah. So, so this is not to say that, like, my empathy or capacity for emotional processing or, or expression changed, or that my intelligence changed, right? But my first thoughts and reaction to a stimulus tended more toward logic or anger than they had before, right? So that’s my personal ex-experience, and apparently others as well, right?
BRJ [20:25]: Like, and, and, and recognizing this has helped me make sense of our gendered society,
DDM [20:32]: Right, right
BRJ [20:34]: So because it seems to me that, that our, our hormones affect our emotions and, and, and psychological makeup, they in turn then affect our spiritual lives,
DDM [20:45]: Interesting.
BRJ [20:47]: So the psychological spiritual factor is enhanced and becomes the, the, the psychological biological spiritual factor,
BRJ [20:57]: right?
BRJ [20:57]: Like, all of these things are working together and affecting people differently depending on where they fall in these, like, multiple spectrums, right?
DDM [21:06]: right.
BRJ [21:10]: So, okay, now that’s one complex bit of it. Then un- like you said, another part is simply patriarchy,
BRJ [21:20]: Um, now I have heard that cultures exist in which women hold the power and men are subordinate to them,
BRJ [21:29]: but they’re like so rare and obscure that I couldn’t tell you w- like what they’re called or even on what continents they exist, right? So this means that no matter where we come from, no matter what governing or caste system or biases we carry from our past, the vast majority of us carry an embodied experience of men being dominant and women being subordinate,
DDM [21:59]: very true. Yeah. Very true.
BRJ [22:03]: The Rule of St. Benedict and many other religious rules make it clear that, that we are to make great efforts to level the playing ground when people enter,
BRJ [22:14]: And introducing gender diversity brings an entirely new and complex bias to tackle, right? It’s not to say that it can’t be done or that it’s not worth the effort, just that it is a significant reality that would need to be faced and reckoned with in a mixed-gender community,
DDM [22:40]: I mean, I’m thinking of, you know, those unequal power relationships and sexual violence and, you know, the vulnerability. Yeah, I hear you. Mm-hmm.
BRJ [22:53]: Um, and, and then there’s the community life factor.
BRJ [22:59]: So, um, religious community is, is like being married to a whole group of people, okay?
DDM [23:09]: Polygamy at its best.
BRJ [23:11]: Yeah.
DDM [23:13]: All right.
BRJ [23:13]: polygamy. No. Uh, I’m a little anxious about using those words,
DDM [23:19]: I’m sorry. I’m sorry.
BRJ [23:22]: Um, but, well, I mean, maintaining a marriage with one person is hard enough,
BRJ [23:28]: right?
BRJ [23:28]: Like, it’s why half of marriages fail.
DDM [23:31]: Right
BRJ [23:32]: So imagine being married to 20 people, right? When, when you consider all the diversity we touched on earlier that we have, like the race, culture, background, et cetera, community life gets very complicated and messy very quickly,
BRJ [23:47]: right?
BRJ [23:49]: And navigating and negotiating how we live and, and minister to the broader community together
BRJ [23:58]: while honoring each other’s needs and perspectives is a lot of work,
BRJ [24:05]: So, so given, given these factors, the, the psychological, biological, spiritual factor, the, the patriarchy factor, and community life,
BRJ [24:19]: from a gender-separated monastery or convent to a mixed-gender one requires great intentionality and awareness and constant work on both the individual and communal levels, right?
BRJ [24:37]: And quite frankly, I can understand why a vowed religious of any gender would say, “You know what? That is a whole can of worms we are just not ready to open yet.”
DDM [24:48]: You know, honestly, when I asked you that question, why can’t girls join, I, I was expecting just some short, you know, s- quick answer. But honestly, this is the, I think about the most that I’ve actually really seriously thought about it as I’ve been listening to you, and I mean, a, a lot of what you’re saying makes sense, you know, which is very interesting.
DDM [25:05]: I’ve… Yeah. Thank you. Thank you for taking it seriously, that question.
BRJ [25:09]: Oh, I’ve– I’ve, oh, I don’t know that I would’ve survived here if, if I hadn’t been wrestling with it already, you know?
DDM [25:17]: right
BRJ [25:19]: I’m, uh, well, I mean, because I personally believe that more diversity is better, right? I would love to see our order move toward being mixed gender. And I totally understand, having wrestled with it, those who say that our life is complicated enough, and we already have enough to wrestle with,
BRJ [25:40]: And, and in wrestling with this, I see that gender-separated communities have their unique blessings too,
BRJ [25:48]: right? Like for me, being raised as a girl with a sister in a gender-separated conservative Christian culture
DDM [25:55]: That’s interesting. That’s interesting, that phrase. Yeah.
BRJ [25:59]: and then finding refuge in the lesbian community, I am more comfortable with women than I am with men,
BRJ [26:07]: I, have known what a unique blessing it is to be part of a loving and supportive community of women. And honestly, I wasn’t sure that living m- with men would work out for me, right?
BRJ [26:22]: but they obviously wouldn’t let me move into a convent looking like this, so I probably like, I had to give it a shot.
BRJ [26:30]: And there have been some difficult moments, right? But it’s because of those moments that I learned what it’s like to be part of a loving and supportive community of men.
BRJ [26:43]: And I mean, there, there have been some individual men in my life who have loved me in extraordinary ways.
BRJ [26:52]: to be part of a community of men,
BRJ [26:56]: it’s, it’s different, and it’s just really special.
BRJ [27:00]: It’s a true gift.
BRJ [27:03]: while I’m in favor of more gender diversity, I, I also recognize that gender separation brings its own unique gifts and graces.
DDM [27:13]: Oh, Brother Jacob, I feel like there’s so many more questions I would love to ask you, but we just don’t have time for today. And so to our listeners, if you have any questions that you would like to ask Brother Jacob about monastic life, about being transgender or transgender in monastic life, about spirituality, sexuality, community life, or anything else that you may be interested in asking, please write your questions to us at the end of this episode, and perhaps we can have Brother Jacob for a follow-up conversation to explore your questions.
DDM [27:48]: And so honestly, Jacob, thank you for your openness, your vulnerability, your honesty, and just being this authentic you in our world.
BRJ [27:58]: Oh, thank you, Deborah. Same. It has, it has been a blessing. And many thanks to, to Elizabeth and Carl.
DDM [28:06]: Oh, thank you so much. Have a beautiful day
BRJ [28:10]: Oh, you too. May the grace of our Lord Jesus Christ and the love of God and the fellowship of the Holy Spirit be with us all evermore.
DDM [28:17]: Amen
BRJ [28:17]: Amen
MET [28:22]: Thank you for listening to the Priest and the Prof. Find us at our website, priestandprof.org. If you have any questions or concerns, feel free to contact us at podcast at priestandprof.org. Make sure to subscribe, and if you feel led, please leave a donation at priestandprof.org slash donate. That will help cover the costs of this podcast and support the ministries of Trinity Episcopal Church. Thank you, and we hope you have enjoyed our time together today.
DDM [28:53]: Music by audionautix.
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