Jeff Carreira: First of all, Jay, thank you for this chance to speak with you about your book The Gate of Tears. When I read the book, I found it resonated very deeply with me and I am very excited to speak with you about it. To begin our conversation, I wonder if you would say a little bit about what the spiritual path has to offer to the spiritual aspirant, especially in these unusual times.

Jay Michaelson: I actually started writing the book during some of my early meditation retreats where a lot of sadness and loneliness was coming up for me. That wasn't necessarily unusual, but what was new was the developing relationship I had with the sadness. It started with the kind of standard mindfulness realization that it's possible to just be with those feelings rather than be consumed by them. In mindfulness practice, you are aware of feeling emotions – positive, negative, whatever – and you learn from them by seeing how they arise, develop, and how they pass away. As I did that basic mindfulness practice, over and over again, on those feelings of sadness, loneliness, grief, and loss that were arising, I started to see my relationship to them transform. I began to see that there was something incredibly beautiful about these mind-states and there was a lot of presence in them. My resistance to the sadness and the negative emotion yielded to a sense of spaciousness around them. That recognition of spaciousness and openness around negative experiences was the genesis of the book. It felt like I'd stumbled onto something important that I hadn't read in other books. It was certainly a big turning point in my own life and in my relationship to sadness, loss, and grief.

I started the book about 15 years ago and I found it to be a confusing project because of my complex relationship to those emotions. Eventually, I put the book down; actually, I put it away for almost 10 years. And I then reopened the book when my mother was ill with cancer, and I started rereading the book as a reader rather than as the writer. I found that what was in there was still really powerful for me, and I could apply what I had written about ten years prior to what I was going through in the face of my mother’s illness, and that's when the book came together.

The last thing I will say is that there are three ways of relating to sadness explored in the book. First, is the discovery that it's possible to have a different relationship with loss, grief or sadness. Second, that these mind states can actually lead to all kinds of artistic insight and production. And third, there's a way in which the Gate of Tears can open into a profound alchemical transformation from negative emotion to a kind of nondual awakening.

Jeff Carreira: As I already said, when I read the book, I resonated deeply with what you were saying, even though I would say that sadness has not played such a big role in my journey. I would say fear and insecurity were a bigger part of my experience, but the insights you share seem to apply to any negative emotion that we are challenged with. And the realization that can result is a recognition that, underneath our unpleasant states, we can discover a spaciousness – which is not an ordinary sense of happiness – but a deep sense of contentment that is always present even in the midst of challenging emotions. My spiritual work was coming more out of the Hindu tradition than the Buddhist mindfulness practice, and in that tradition that sense of spaciousness is called satchitananda: It's the underlying blissfulness of being that is the ground of everything else that arises. One thing I'm personally curious to ask you about is the subtle distinction between the more conventional experience of happiness and this deep underlying contentment. Can you explain how you see this distinction?

Jay Michaelson: I'll meet your Hinduism and raise you some Buddhism. The Buddha said that nirvana was the happiness that does not depend on conditions. And that's been a phrase that helps me. When there's happiness that depends on some condition that is great, but that’s normal happiness, not the unconditional happiness of nirvana.

Theravada Buddhism, which is where mindfulness practice comes from, tends to be more neutral in flavor than the Hindu tradition which contains more ananda (joy). I think the added juiciness of ananda creates a slippery slope that can lead to confusion with ordinary states of happiness. In the end, I think the difference between conditioned happiness and unconditioned happiness is pretty clear. For instance, it feels obscene, maybe even disgusting, for me to think of being happy in a hospital, but the joy of satchitananda is there too. That unconditioned joy can be juicy and rich, but it can also be a very thin, almost transparent joy. That joy is there in a hospital room, on a battlefield, and in a prison. In comparison to the louder conditioned emotions of those places, the unconditioned joy is very subtle indeed, but it's still there.

Jeff Carreira: Sometimes I think about this distinction in terms of the joy of life; the fact that it’s a joy just to be alive, to have been born. And there is a gratitude we can feel just for being here in spite of all the negative things that occur.

Jay Michaelson: Yeah, I like that. Ken Wilber has the phrase; the simple feeling of being. I often use the word “transparent,” meaning it's just a very subtle thin sense or perception. Certainly for me, at least over the last nine months, there's been a lot of unhappy times, and so just checking in over and over again with that sort of background awareness of contentment has been very helpful precisely because it doesn't depend on me feeling good.

You mentioned that fear and anxiety were a bigger part of your path and that was never true for me until this year. But in March and in April, I experienced periods of anxiety more intense than I ever have before. I found the fear and anxiety hard to work with because the energy was humming and buzzing and I couldn't get quiet, whereas with sadness I find I can always get very quiet. So, it was interesting to experience the difference.

Jeff Carreira: As the book progresses, you start with the discovery of the contentment that's independent of any circumstance. And then, in the second part, you speak about how these negative emotions can be rich with creative inspiration. Unpleasant experiences can be very fruitful in terms of the insight and the inspiration they offer. Can you say a little about your experience of this?

Jay Michaelson: I'm very aware that there can be a spiritual move that rejects or denigrates the messiness of life. But I think you and I have this in common; we both love to be engaged with the world. We want spiritual freedom and active engagement. I think there’s something terrible about rejecting the world and that is where I feel the devotional practices of say Hinduism, or of the Jewish aspect of my practice, can help. The Jewish tradition has a strong preference for living in the world. And I definitely wanted that to be part of the book. I wanted to counteract any potential tendency to flatten out or disconnect from life, but instead, to embrace all of life. To feel those unpleasant feelings and see what they give birth to, because they give birth to so much creativity, human flourishing and compassion. Perhaps there would be more authentic justice in the world if we could all feel our pain more honestly. Imagine that in the context of America right now. There are tens of millions of people who have been in pain for the last 10 or 20 years, feeling that society has left them behind and there's no place for them. But instead of feeling that pain, they've just papered it over with anger and prejudices, and it's become more comfortable to sit with all that than to feel the pain beneath it. Imagine if it were possible to really be in the pain rather than try to paper it over.

I may be the only person to mention Taylor Swift in your magazine, but her two albums this year are born of the loneliness and isolation that many of us have experienced. She’s really done incredible work on these albums as a singer/songwriter. Her songs are born out of her own experience of pain and then shared to ease the pain of so many others. Millions and millions of people can have that shared communion and connection through her art. That's incredibly powerful. And that is what art born of pain can do.

Jeff Carreira: That’s beautiful. I am also very interested in the creativity that emerges out of our spiritual work because I believe that deep awakening can occur as a result of what we create from the depths of our being. Now, I want to turn to the last part of your book where you've described how the sadness of the Gate of Tears becomes a path to awakening. Can you speak with us about the Gate of Tears as a path to awakening?

Jay Michaelson: I recently read something written by the English philosopher Bertrand Russell. He was saying that, as you get older and closer to death, you begin to care more about things that are wider than yourself because your life is coming to an end. He speculated that, when our lives do end, we will all see that the things we care about most then are things that will continue after we’re gone. I found that beautiful and it is similar to the awakening that can happen around our unpleasant feelings. We have all these difficult feelings, and so many challenging things are happening; people get sick, the rain is falling, the pumpkins are rotting, bad things keep happening. It can all get so loud and the only real relief we can find is in that place where the chattering inner voices just kind of quiet down a little. The key to finding that inner peace is to find a way to just allow the difficult experiences to be what they are. That’s the key. It doesn't really matter what the difficult experiences are. The key is always letting go into what is.

I waited until the third part of the book to talk about all the mystical stuff so people could stop reading if they just wanted the secular part. I use the word God in the third part and I knew that I would lose some people. But that's the entry point to satchitananda, Nirvana or the is-ness that's pointed to by the Hebrew word for God. I don’t see God as the anthropomorphic deity of the Bible; I see God as the source of the remarkable joy that exists right with the sadness, at the same time as the sadness. It is such a surprise to discover that they can coexist like two notes of a chord played on a piano or a guitar. You can actually experience both at exactly the same time. That's not what I was taught growing up. I was taught to banish sadness and strive to be happy all the time. Nothing makes me sadder than that. The idea of being forced to be happy just makes me sad.

Right now, I am doing a lot of work around the idea of 10% happier from the book by Dan Harris. What I love about that work is that it is not an all-or-nothing approach. Being 10% happier sets the bar somewhere realistic. And what I see so liberating about this approach to practice is that it means that having some tough times doesn't put us back at zero again. It’s not all-or-nothing that way. And, for me, this is one of the nice features of the Jewish contemplative path being a non-renunciate path lived in the world; it deals with the reality that we all go up and down. In that tradition, there is a mystical experience where angels run back and forth over and over again and this becomes a metaphor for spiritual practice. The point is to be able to go back and forth more quickly, because we all fall back at times. And that is my experience and I suspect it is yours.

Jeff Carreira: Absolutely. And I often say to people that how much time you spend in nirvana is not a good measure of your awakening, because that's probably largely circumstantial anyway. But how quickly you can return when you fall out of it is a much better measure of attainment.

Jay Michaelson: The Tibetan model of small moments, many times, as opposed to going on a retreat and having a few great days of expanded mind. And look, those are great. And I’d give my eye teeth for a few days of expanded mind right now. That sounds really great, but, as a new father, that's not where my karma is leading me right now. The idea of having small moments, many times a day or many times an hour, without any expectation that it will necessarily last. The ability to kind of drop in over and over again into that kind of moment of open mind is almost always accessible. Steady-state enlightenment is for people who are living as monks or nuns, and marinating in those expanded states.

Jeff Carreira: I lived in a spiritual community for two decades and had opportunities to experience numerous sustained states of awakening. Then, after about 10 years of intensive practice, I hit yet another bad time and I realized that the bad state of mind hadn't changed at all. I was crushed because I really thought for years that, if I practiced hard enough, for enough hours a day, that it would change that, but it didn’t. The insecurity, the fear, the sense of unworthiness, it was all the same.

Sometime later, I had a realization that fundamentally changed things for me. I realized that it doesn't really matter if I'm in that higher state. What matters is knowing that it exists, that that it is possible, and always remembering that – no matter how I happen to feel. I can equate that to more theological ideas about knowing that God exists. What hit me so hard was the recognition that that higher possibility doesn't just exist when I experience it. It’s like knowing that the sun still exists warming the planet even on the stormiest day.

When you see it that way, you realize that states of consciousness come and go. They always arise in tune with what is needed in the moment, and nondual satchitananda bliss is not the appropriate consciousness for every moment. The appropriate consciousness for the loss of a loved one is grief and some kind of superficial happiness is not appropriate to that moment so it doesn’t arise. If we had the chance to go on retreat, the spaciousness would occur because it would be appropriate to that circumstance. So, you start to realize that the fact that our experience fluctuates isn't a problem. It's just part of the natural way life works.

Jay Michaelson: It's nice to think about that and it also gets us out of a certain narcissism. You can leave room so someone else can go have that experience. Otherwise, we only feel OK if we are having that experience. It becomes something for me to own. That’s spiritual materialism. Instead, I'm OK regardless of whether I can have that experience or someone else is having it right now. I always like to think about people on a retreat somewhere, and I find it comforting that some people are ardently practicing all their different traditions right now. That makes it less about me and remedying my psychological issues.

Jeff Carreira: Yes, and isn't there a Jewish idea about a smaller group of people that are holding something spiritually for everyone?

Jay Michaelson: Yes, there's a legend that there are 36 righteous people hidden somewhere on the planet. They aren’t famous. They’re people you might meet every day on the street, but you wouldn't know that they're one of the 36. There's something lovely about that. It's very comforting. It's a positive conspiracy theory.

Jeff Carreira: Exactly. And I like to think that I may not be on retreat resting in eternal bliss every day, but somebody is somewhere and that's holding the gate open. So, when it's my turn to be on retreat, the door will be open because someone held it for me.

Now, I would like to ask one final question and give you a chance to talk to people in the context of this challenging year that we're coming to the end of. What kind of advice or words of wisdom would you offer people who are having a challenging time right now?

Jay Michaelson: This year makes me grateful that I wrote a book called The Gate of Tears, because there is a lot of suffering right now and it's very real. And I'm glad the book has different avenues because there's different medicine for different people. For example, if someone has anxiety and they really just need a way to relax, there are ways to do that with regulated breathing and other techniques that help. You won't necessarily get wiser and it might not lead to lasting change, but right now, when pain is so acute, it might be exactly what people need. The main thing I want to share is wishing people good discernment among the different paths that are available. It might be possible to work with some of the fear and anxiety, or the grief and loss in some of the ways that we have been discussing here, but sometimes it's just too much and it’s not possible to be with it right now.

When we talk about learning to let things be as they are, we also have to discern when that is appropriate and when we just need to reach for an antidote. And this is sometimes the right move even if we know it is not ultimately the way to liberation and awakening. Sometimes, we just need to get a little bit of peace. And then, hopefully, there will be some room for some of the more valuable work that really can lead to awakening. I almost feel that, between us speaking now in the middle of December, and whenever someone will read it in January or February, things may have gotten much worse before they get better in six months' time or so. But that's still a long time. I'd be full of it if I said I wasn't a bit fearful for what this winter might hold here in the northeastern part of the United States. But that fear is OK too, it's part of the divine and part of human nature. It's also possible to sit with that.