My friend L has been hanging out for months in a swamp of sad feelings. It all started, she tells me, a week after she broke up with a guy she’d been dating. She didn’t understand why the experience triggered such a reaction. It hadn’t been a serious relationship and she had even been the one to end it. “But now I’ve become obsessed with endings – all the things that haven’t worked out for me, all the sad stories I hear about other people. I can’t let go of this feeling of grief.”

L says that all she really wants to do is cry, watch sad movies, and cry some more. It’s as if she’s enjoying the blues. She says the sadness feels juicy, even delicious. It feels good to let herself grieve.

You might wonder why a person would want to hang out in their sad feelings. Most of us are trying to get ‘over ‘our sadness, or at least come up with other ways of engaging life. Yet if you’re at all romantic or nostalgic, if you’ve ever experienced the strange sweetness of missing a person or a place, or mourning love’s passing, if you’re a lover of Rumi and the other Sufi poets of longing, you’ve probably felt the depth and aliveness that sadness can engender. You might even notice , as L did, that it feels quite a lot like love.

In L’s case, there’s a good psychological explanation for her tendency to conflate sadness with love: She was the youngest child of busy parents who never showed up at softball games or choir recitals, and she grew up crying over broken promises and sad love songs. Nonetheless, L in her own way is discovering the truth that sadness can itself be a path.

“This sounds weird,” she told me, “but I feel as if all this grief is opening my heart. It feels painful, but it’s tender as well. I look at people on the street and I wonder if they don’t have a grief in their lives. Sometimes it’s as if my heart is about to spill over.”

Surfing Sadness
Sadness is a swampy emotion. Like a fugue with only minor chords, sadness tends to cycle round certain well-known melodies – the ache of self-pity with its narrative of victimization, the somber notes of despair, the dark tones of hopelessness. Left to feed on itself, sadness can turn into depression, and it unquestionably messes with your immune system.

Yet, paradoxically, there’s another face to sadness, a sweet secret core that opens like a hidden doorway into a state that ‘yes, ‘looks a lot like love. Just the way anger can be a doorway into strength, and desire the force behind creativity, sorrow can trigger soft-heartedness, humility, and other profound spiritual emotions.

All this jibes with a fundamental insight of the Tantric traditions: the understanding that the difficult feelings – terror, lust, anger as well as sadness – which act like poisons for the body and mind, can also be ladders to transcendence. Their power to drag you down can, if properly engaged, lift you beyond the ordinary way of seeing and being. Tantra regards everything that exists as being made of divine creative energy, a radically non-dual view that can help us recognize the hidden power that arises when we approach negative states constructively. As a famous Tantric aphorism goes, “That by which you fall is that by which you rise.”

Granted, this way of working with sadness isn’t easy. It’s a lot like surfing. To succeed at it, you need to attune yourself to the currents and swells. You need to be willing to suffer the occasional wipe-out. And you need to be clear about the quality of the surf – in other words, to know which level of sadness you’re engaging.

Trigger Unhappy
At one level, sadness is simply a natural emotion, the basic human response to any loss or deprivation. Ideally, you’d let it move through you, feeling it without holding on too tenaciously. However, simple sadness has a way of morphing into something more shadowy when, instead of letting go, you let it settle in, becoming part of a growing bundle of losses.. Often early childhood griefs, emotional whammies that at the time simply felt too overwhelming to be processed, get locked into the body, forming neuronal connections that get triggered with each new loss.

For someone like L, breaking up with her boyfriend is that sort of trigger. The present-time event activates her cache of childhood disappointments, so that what should be a passing sadness becomes a huge swell that threatens to swamp her. To complicate matters, L, like most of us, has a story she developed to make sense of (and, in that way, survive) those early losses.

It’s our stories as much as the losses themselves that perpetuate the sadness, even becoming self-fulfilling blueprints that shape our reactions to all future situations. My friend C, whose sick mother rarely touched or even spoke to him, grew up with the assumption, “No one is there for me.” Not surprisingly, he involves himself with friends, business partners and lovers who “prove” that assumption correct.

World of Sorrow
The good news is that the very recognition of the different layers of your personal sadness can open the door into what I like to call Transformative Sadness. Transformative sadness often begins with the realization that suffering and grief are universal, that they occur in everyone’s life. Knowing that, you can take a step out of identifying with sadness, and begin to work with it.

An influential novel by the great 19th century German writer Johannes Goethe, ‘The Sorrows of Young Werther ‘, told the story of a student whose sadness seemed to arise without a personal cause. Goethe referred to this sadness as ‘weltsmerz ‘, literally, world-sorrow – an almost transcendent feeling of pain for the state of the world. Goethe’s story struck such a chord that it inspired a fashion for melancholy behavior and even a rash of teen suicides in Germany.

Nonetheless, Goethe was hinting at something about the nature of reality. He seems to have understood that when you face your own sadness, feel your way into the core of it, you’ll realize that sadness is not just personal. On some level, all sadness is ‘The ‘ Sadness, the non-personal human sadness you feel when you recognize that ‘nothing ‘ lasts, that plans and dreams rarely turn out as expected, and that the world is filled with apparent injustice. Looked at from that point of view, transformational sadness is the ‘felt ‘ experience of Buddha’s first noble truth: There is suffering.

For centuries, yogis, mystics and meditatators skillful or lucky enough to confront their bedrock suffering with some degree of awareness, have found it to be a catalyst for profound spiritual growth. The 20th century spiritual master, Chogyam Trungpa, when asked what he did when facing great stress or discomfort said, “I try to stay in it as long as I can.” [FC: The Way of Failure, p 14] Trungpa (whose own life included exile from his homeland, serious physical disabilities, and alcoholism) was not suggesting that you wallow in or cultivate suffering. He was describing a Tantric practice for dealing with strong negative experience by being present with it, and ultimately, by working with it as energy.

Notice how radically different is this approach from your ordinary response to sadness. If you’re like most of us, you deal with sorrow – or any form of suffering – by finding some strategy for avoiding it. Even a dedicated yogi has moments when psychological pain drives her to eat comfort food, have a drink, dive into a novel or a TV program, or bury himself in work. At a healthier, more sophisticated level, you might use an endorphin-releasing approach like aerobic exercise, breath work, yoga, or even meditation to bypass sadness. Or you might take refuge in psychological or spiritual understanding, telling yourself, “I guess this is supposed to teach me compassion.”

This is not to deny the enormous value of practices that increase your wellbeing, nor is it an argument for getting mired in sadness. But it’s true that sadness only begins to reveal its transformational power when you’re willing to step away from even the most spiritually correct avoidance strategies, and turn towards the sadness as an immediate present experience, ‘while dropping any ideas, thoughts, associations, or stories you might want to make up about it ‘.

Facing Sadness
You begin by simply sitting with the sadness, and letting yourself feel it. You notice where it is in the body. You breathe into that part of the body, letting the feeling be there. You stay with it for a while. Insights might come up, information about yourself. When that happens, note them, and come back to the immediate experience.

This kind of inner work takes a degree of courage and willingness. It isn’t easy to face into feelings of hurt and grief, especially because most of us identify, or merge with these feelings. Even when you know better, you have a natural tendency to believe that you ‘are ‘ your feelings.

If you’re going to work with sad feelings without getting swamped, its important to have a practice that lets you experience that there is something behind or beyond the “me” that identifies with emotions. That wider sense of being is often called the witness. Another way of describing it is as the non-verbal “I am” – the felt sense of awareness that can be present with those feelings without judging, justifying them, or blaming.

For most of us, the encounter with pure awareness happens most easily in meditation. The more you can anchor yourself in the part of you that is larger than the sadness, the more easily you can process the emotions that come up.

Often as you work with sadness in this way, you’ll become aware of another layer of Transformative Sadness – a sorrow at your own stuckness. Spiritual psychologist John Welwood calls this “purifying sadness,” or soul sadness, a direct recognition, he says, of “the price we have paid for remaining stuck in our narrow patterns while turning away from our larger nature.” (FACT CHECKER: P. 32 The Psychology of Awakening by John Welwood)

This purifying sadness is one of the most powerful of all incentives to transformation – especially if you can resist the urge to beat yourself up for not being better, more awake, or more compassionate. When you allow yourself to feel purifying sadness, you also open to your own longing to awaken, your wish to live with integrity, to drop your persona and truly find out who you are as a free, fully alive being.

A Crisis of Love
A few years ago, I was privileged to watch a student, Bea, go through this process. As so often happens, it began with a crisis of love. She had been married for ten years to a man who was also her partner in business. One day, he called her from an out of town trip to say that he had been in love with another woman for some time, and had decided that he wanted a divorce. Bea was, of course, stunned by this betrayal, blindsided by anger, fear of the future, and most of all, intense grief.

Her morning meditation – normally a refuge from stress – turned into a kind of caldron of multi-layered grieving. Because her thoughts felt so punishingly intense, she would focus on the part of her body where the emotion felt most acute.

In each meditation, she would find herself remembering and reliving another layer of her grief. Of course, her husband was just the tip of the iceberg. She had a backpack of sadness: memories of lost lovers, of feeling hurt by friends in high school, of an overwhelming feeling of abandonment that seemed to have no origin. As time went on, she saw that she had been living out an inner blueprint of loss, that her identity was based on a sense of herself as a person who was not allowed to be loved and happy.

The sadness that arose from this was so sharp and intense that it was like being cut with a knife. Yet as she sat with it, she began to feel her way into the core of it, as if she were experiencing the very heart of sadness. One morning, she found herself feeling the grief of orphaned children in war zones, men and women who’d lost their families. She began sobbing – but this time her tears were not just for herself, but also for the wrenching poignancy of human life.

At that point, she said, her heart seemed to open outward, as if it were the doorway into a huge sky, and a feeling of overwhelming tenderness moved through her. She said that it felt as if an ancient wall within her heart had cracked open, and she was sitting inside a field of heart-breaking compassionate love.

Bea’s willingness to stay with her sadness – sitting through the layers of blame, anger, self-pity – had let her move into the profound empathic compassion that is its heart. She was experiencing divine sadness, the feeling that some mystics have called “God’s grief for humanity.” Paradoxically, that sadness was also filled with a pulsation that Bea recognized as absolute ecstasy.

That event was also her personal turning point. A few days later, Bea got up from meditation with a clear recognition about her next step in life. Her grief had been processed, and though it didn’t disappear overnight, it was manageable. What I noticed about her was that her personality had deepened. Her conversation and her personal practice had taken on a more resonant, soulful quality. Her willingness to work with the sadness had cooked her, seasoned her. When I spend time with her these days, I’m impressed at how freely she is able to allow emotions to come and go, without identifying or getting stuck in them.

Because, after all, sadness – even transformative or purifying sadness – is not a place in which to make your home. It’s a station you move through on your way to living with a fully open heart. When you learn the art of letting sadness move you into the heart, what you find there is not sadness but softness, not suffering but peace. The other face of sadness is something that looks an awful lot like, well, love.

Practice: Working with Heartbreak
Feelings of acute sadness can offer a powerful doorway into the open heart. The next time you feel loss or sorrow, try this practice for connecting yourself with Transformative Sorrow.

1) Begin by fully feeling your sadness. Notice all the qualities of that feeling. Perhaps there’s a sense of heaviness associated with it. Perhaps you feel tears rising. Now, become aware of the sensations in your body associated with the sadness. Feel the sensations as fully as you are able. Breathe with them. Let go of the story – the content of the memory.

2) Now, let your attention drop into the heart area. Sense that you are breathing in and out through the heart.

3) Bring the energetic sensation of sadness into the heart area.

4) Simultaneously, become aware of a field of space, or a sky, stretching out behind you. Imagine that this sky has a color – perhaps golden, or deep blue.

5) Begin to breathe the feeling of sadness in through your heart, and into the field of sky behind you. Then breathe out, imagining that you are breathing out the sky, with its color, through the feeling in your heart and out into the room. Continue to do this for a while.

6) Next, think of others who might be suffering sad feelings. You will find images coming up quite spontaneously – people who have lost loved ones, people who have failed at something important, people you know, people in the news.

7) Breathe in with the sense that you are taking these people’s sadness in, letting it ‘pass ‘ ‘through ‘ your heart (not remain in your heart), and dissolve into the beautiful sky behind you.

Exhale, breathing the color and spaciousness of the sky back into the people who are sad.

It’s important here to breathe the sadness ‘through ‘ the heart and into the sky, and to breathe sky back through the heart and into the sad images you have drawn in. You’re not holding the sadness in your heart, but rather, using the heart as a portal to let the sadness dissolve into the spaciousness of sky.

8) Pay attention to the inner states that arise as a result of this practice. There may be an awareness of your intimate connection with all others, or a sense of the impersonal nature of sadness. For me, this practice will almost always dissolve the sad feeling, or let it morph into a kind of tenderness or compassion. As you practice this over time, you may notice that it does arouse feelings of true compassion, love for yourself and others, and a recognition of your own soft heart.