6-MONTH LIVE MEDITATION TRAINING

Meditation and the Dark Night of the Soul

When the path gets difficult, a map matters.

A six-month live training exploring five of the difficult stages of insight through the 4 R’s: Recoil, Resistance, Resignation, and Renewal.

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Begins May 2, 2027 live online training

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6 months live teaching, practice, and integration

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5 stages of insight framed through the Progress of Insight

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$347 for the full six-month training

FIVE STAGES OF INSIGHT

The classical territory we’ll be working with.

This training focuses on five specific stages within the Progress of Insight. Rather than treating them as abstract doctrine, we’ll explore how they are actually experienced, how they tend to shape perception and behavior, and how to work with them skillfully in practice and in life.

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INSIGHT STAGE OF DISSOLUTION

When solidity begins to loosen.

Experience can become less cohesive and less dependable. What once felt stable may begin to break apart, fade, or lose its familiar sense of continuity.

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INSIGHT STAGE OF FEAR

When uncertainty becomes impossible to ignore.

As familiar structures lose their reliability, fear can arise. The practice begins to reveal how strongly the mind depends on predictability, control, and a stable sense of ground.

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INSIGHT STAGE OF MISERY

When the cost of clinging becomes more visible.

What was previously tolerable may begin to feel more burdensome. The meditator sees more clearly how grasping, resistance, and identification contribute to dissatisfaction.

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INSIGHT STAGE OF DISPASSION

When familiar attractions begin to lose their pull.

The mind can become less interested in the usual strategies of distraction, gratification, and control. This can feel flat or disorienting, but it can also mark an important shift in relationship.

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INSIGHT STAGE OF WISH FOR LIBERATION

When the desire to move beyond the old pattern becomes unmistakable.

The wish for freedom becomes more explicit. The practitioner can feel both the limits of old ways of relating and a growing impulse toward release, change, and a different way of meeting experience.

A MAP FOR ORIENTATION

These stages are not a checklist and they are not a diagnosis. They are a way of recognizing patterns that can appear as insight deepens and learning how to respond with greater understanding.

THE 4 R’S

Four movements through difficult territory.

The classical stages can be precise, but they can also feel technical or difficult to remember. I teach this territory through a simpler framework: Recoil, Resistance, Resignation, and Renewal.

RECOIL

When experience contracts away from what is being revealed.

The instinct to pull back

As familiar stability begins to loosen, the first response is often instinctive. The mind recoils from uncertainty, discomfort, loss of control, or the sense that something fundamental is changing.

The work begins by noticing that contraction clearly without immediately obeying it or turning it into a problem.

Can the recoil itself become something we learn to meet?

RESISTANCE

When the mind starts fighting what is happening.

The struggle for control

Recoil can harden into resistance. We try to fix the experience, regain control, return to an earlier state, or push away what the practice is making increasingly difficult to ignore.

Resistance is not a failure of practice. It becomes part of the practice when we can see how the struggle itself intensifies suffering.

What changes when resistance is seen rather than simply enacted?

RESIGNATION

When the struggle begins to exhaust itself.

The beginning of surrender

At some point, the familiar strategies of control stop working in the same way. The effort to force experience into a preferred shape begins to lose momentum.

Resignation here does not mean giving up. It means beginning to release the demand that experience conform to what we want it to be.

What feels like defeat can become the beginning of surrender.

RENEWAL

When space opens for a different relationship to experience.

The emergence of new possibility

As resistance softens, something new can become possible. Renewal is not simply a return to how things were before, but the emergence of greater freedom, flexibility, and willingness.

The movement is not back to the old ground, but toward a different way of standing in relationship to what is here.

What becomes possible when the old strategies finally loosen?

A PRACTICAL FRAMEWORK

The 4 R’s are not a replacement for the classical map. They are a way of making the territory easier to recognize, remember, and work with as it unfolds in meditation and in life.

THE 6-MONTH JOURNEY

Six months. Five stages. One unfolding process.

Each month builds on the territory that came before, giving enough time for teaching, meditation, investigation, questions, and integration.

MONTH ONE

Activation of Dissolution

Insight Stage of Dissolution

We begin with the moment familiar solidity starts to loosen. Experience can feel less cohesive, less predictable, and harder to organize in the ways we are accustomed to.

The work is to recognize Dissolution clearly before rushing to interpret, resist, or fix what is happening.

What happens when the ground of experience begins to change?

MONTH TWO

Acceptance of Recoiling

Recoil

As uncertainty becomes harder to ignore, the mind often pulls back. Fear, vulnerability, contraction, and the search for safety begin to enter the foreground.

Rather than treating recoil as a mistake, we learn to recognize it as a natural response to changing experience.

Can recoil be met without immediately trying to escape it?

MONTH THREE

Working with Resistance

Resistance

Recoil can harden into struggle. We try to regain control, return to an earlier state, push away discomfort, or make the experience conform to what we think should be happening.

This month is about seeing resistance directly and learning how the struggle against experience can become part of the suffering itself.

What changes when resistance itself becomes the object of practice?

MONTH FOUR

Surrendering to Resignation

Resignation

Eventually, the strategies of control begin to exhaust themselves. What once worked no longer produces the same result, and the struggle itself becomes increasingly difficult to sustain.

We explore the difference between collapse and surrender, and how resignation can become an opening rather than a defeat.

What becomes possible when we stop demanding that experience be different?

MONTH FIVE

Making Space for Renewal

Renewal

As resistance softens, a different relationship to experience can begin to emerge. Renewal is not a return to the old ground, but the beginning of greater flexibility, openness, and freedom.

We explore how the wish for liberation can mature from wanting to escape experience into a deeper willingness to meet it differently.

What new possibility appears when the old strategies finally loosen?

MONTH SIX

Integrating the Dark Night of the Soul

Integration

In the final month, we bring the whole journey together: the five stages of insight, the 4 R’s, and the ways this territory can show up both in formal meditation and across the wider movement of life.

The emphasis shifts from understanding the map to integrating what the journey has revealed about change, resistance, surrender, and renewal.

How does the Dark Night become part of the path rather than merely something to survive?

HOW THE TRAINING WORKS

Six months of live teaching, practice, Sangha, and integration.

The training unfolds through a steady monthly rhythm of teaching, meditation practice, Sangha, Q&A, and weekly support between sessions. The aim is to give the material enough time to become lived practice.

LIVE MODULE SESSIONS

Two live teaching and practice sessions each month.

2× monthly · 90 minutes each

Each month includes two live module sessions with Miles, combining teaching, meditation practice, guided inquiry, and exploration of the stage or theme we are working with.

The core teaching rhythm of the six-month journey.

MONTHLY SANGHA

A dedicated space to practice together.

Monthly · 60 minutes

Each month includes a live Sangha meeting for shared meditation, reflection, and connection with others moving through the same training.

A place to stay connected to practice and community.

MONTHLY Q&A

Bring the questions that arise from actual practice.

Monthly · 60 minutes

Each month includes a dedicated Q&A session for clarification, practice guidance, and questions connected to the territory currently being explored.

Let the map meet the complexity of real experience.

WEEKLY PRACTICE VIDEOS

Keep the teaching alive between live sessions.

Weekly

Weekly practice videos help you stay connected to the current theme, bring the teaching back into meditation, and continue working with the material between live meetings.

Small, regular touchpoints that support continuity in practice.

INTEGRAL DOJO COMMUNITY

Stay connected throughout the training.

Ongoing

You’ll have access to the Integral Dojo Community throughout the six-month training for announcements, reflection, conversation, and connection between live sessions.

The live sessions are the anchors; community holds the space between them.

SIX-MONTH ARC

Enough time for the teaching to become practice.

Begins May 2, 2027

The training is intentionally spread across six months so there is space to encounter each stage, practice with it, return with questions, and notice how these movements show up both in meditation and in life.

Depth comes from returning to the territory, not consuming it quickly.

INCLUDED IN THE TRAINING

12 live module sessions · 6 Sangha meetings · 6 live Q&A sessions · weekly practice videos · Integral Dojo Community access · six months of guided progression

IS THIS THE RIGHT FIT?

You don’t need to be in a “Dark Night” to benefit from this training.

This training is open to all practitioners who want a clearer understanding of the difficult stages of insight and a more grounded way to relate to them in meditation and in life.

THIS TRAINING MAY BE A GOOD FIT IF

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You want to understand the dukkha stages of insight more clearly, whether or not you are currently experiencing them.

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You have encountered difficult, confusing, or destabilizing territory in meditation and want a more reliable framework for understanding it.

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You are interested in how the Progress of Insight relates not only to formal meditation, but to broader patterns of change in life.

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You want to learn how Recoil, Resistance, Resignation, and Renewal can help make difficult contemplative territory easier to recognize and work with.

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You value live teaching, practice, Sangha, and the opportunity to ask questions as the material unfolds.

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You want to approach these stages with curiosity and discernment rather than treating the map as a rigid sequence or identity.

THIS MAY NOT BE THE RIGHT CONTAINER IF

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You are looking for a way to diagnose every difficult emotional experience as a stage of insight.

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You want a rigid formula that tells you exactly where you are on the path or what should happen next.

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You are primarily looking for psychotherapy, crisis intervention, or treatment for a mental health condition.

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You want to use the language of the Dark Night to bypass psychological, relational, or practical issues that may need to be addressed directly.

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You are looking only for information and are not interested in bringing the material into meditation practice and lived experience.

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You are not willing to hold the map lightly and distinguish between contemplative insight, ordinary life difficulty, and psychological distress.

AN IMPORTANT DISTINCTION

This training is contemplative education and meditation practice. It is not psychotherapy, mental health treatment, or crisis support. Not every difficult period in meditation or life should be interpreted through the Dark Night framework.

Miles Kessler

ABOUT MILES

Teaching the map from decades of practice.

I’ve spent more than 25 years practicing and teaching meditation, with more than 25,000 hours of formal meditation practice.

My primary meditation training is rooted in the Burmese Mahasi Vipassana tradition, including direct training with Sayadaw U Pandita and Vivekananda. The Progress of Insight has been an important part of that training and of the way I understand the development of contemplative practice.

Over the years, I’ve become especially interested in the stages that practitioners often find difficult to understand: the places where meditation stops feeling straightforward, familiar strategies no longer work, and practice begins to challenge how we relate to control, uncertainty, identity, and change.

My approach is to hold the classical map seriously without turning it into a rigid formula. The map can help us recognize territory, but the real work is learning how to meet what is actually happening with greater clarity, discernment, and freedom.

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25+ years teaching and practicing meditation
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25,000+ hours of formal meditation practice
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3 years total in intensive silent meditation retreat
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Mahasi Vipassana trained in the Burmese insight tradition
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Progress of Insight grounded in the classical map and its practical application

The purpose of a map is not to tell you what your experience should be. It is to help you recognize the territory clearly enough to practice well within it.

More About Miles

WHAT PRACTITIONERS SAY

Deep teaching. Lived practice. A strong container.

Miles’s approach combines the depth of traditional meditation practice with clear teaching, direct experience, and a learning community that supports practice over time.

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“Miles offers a clearly structured, rich, and deep learning experience. In all my years of studying, I never had such an excellent combination of learning and practice.”

Annette Rolig

Bowen Therapist, Aikido & Meditation Teacher · Germany

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“I am lucky to have found a teacher like Miles who models how to walk the talk with an emphasis on shadow work and ethics. My own sitting practice has blossomed under his guidance.”

Michael James Miller

LCSW-BACS

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“Miles teaches in an open, probing fashion that invites his students to not only learn, but to question, search, challenge and grow.”

Rich Sims

RSME, RSMT, CTP

The aim is not simply to learn another meditation map. It is to understand the territory deeply enough that the teaching can become part of how you practice and how you meet your life.

JOIN THE TRAINING

Meditation and the Dark Night of the Soul

A six-month live training for understanding and working with the difficult stages of insight through the Progress of Insight and the 4 R’s.

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BEGINS

May 2, 2027

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LENGTH

6 months

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FORMAT

Live online training

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COMMUNITY

Integral Dojo Community included

CHOOSE YOUR PAYMENT OPTION

PAY IN FULL

$347

One payment

Join for $347

PAYMENT PLAN

$122

3 monthly payments

Choose Payment Plan

BOTH OPTIONS INCLUDE

  • 12 live module sessions
  • 6 monthly Sangha meetings
  • 6 monthly Q&A sessions
  • Weekly practice videos
  • Integral Dojo Community access
  • Six months of guided progression and integration

The Dark Night is not something to romanticize or fear. It is territory to understand, practice with, and learn how to navigate well.

FREQUENTLY ASKED QUESTIONS

A few things you may want to know.

This is a six-month live meditation training focused on understanding and practicing with difficult stages of insight. Here are the practical details and a few important distinctions.

01 Do I need advanced meditation experience to join?

No. The training is open to all practitioners who are interested in understanding the difficult stages of insight more clearly.

You do not need to believe that you are currently going through a “Dark Night,” and you do not need to have identified yourself with any particular stage of the Progress of Insight.

02 When does the training begin and how long does it run?

The training begins on May 2, 2027 and unfolds over six months.

The extended format gives us time to explore the stages gradually, bring them into meditation practice, return with questions, and integrate the material into everyday life.

03 What is the live meeting schedule?

Each month includes:

  • Two 90-minute live teaching and practice sessions
  • One 60-minute Sangha meeting
  • One 60-minute live Q&A session

Across the full six months, that means 12 live module sessions, 6 Sangha meetings, and 6 dedicated Q&A sessions.

04 What are the Weekly Practice Videos?

Weekly Practice Videos help you stay connected to the current teaching between live sessions.

They are designed to bring the month’s material back into your meditation practice and support continuity as the six-month journey unfolds.

05 What exactly do you mean by the “Dark Night of the Soul”?

In this training, the phrase refers to difficult territory described within the Buddhist Progress of Insight, including stages such as Dissolution, Fear, Misery, Dispassion, and the Wish for Liberation.

The phrase is not used as a blanket explanation for every difficult emotional or psychological experience. The purpose of the map is orientation and discernment—not diagnosis.

06 How do the 4 R’s relate to the classical stages of insight?

The 4 R’s—Recoil, Resistance, Resignation, and Renewal—are a simpler framework Miles uses to make difficult contemplative territory easier to recognize, remember, and work with.

They do not replace the classical Progress of Insight map. Instead, they provide a practical way of understanding some of the movements that can occur as difficult territory unfolds in meditation and life.

07 How is this different from the Progress of Insight course?

Progress of Insight is a self-paced workshop and lecture series that explores the broader classical map of insight.

Meditation and the Dark Night of the Soul is a six-month live training focused specifically on the more difficult stages of that territory and how we can work with them through meditation, inquiry, Sangha, and ongoing practice.

08 Is this therapy or mental health treatment?

No. This training is contemplative education and meditation practice. It is not psychotherapy, mental health treatment, diagnosis, or crisis support.

Difficult meditation experiences and psychological distress can sometimes overlap, which makes discernment important. If you are experiencing severe or ongoing psychological distress, appropriate professional support may be needed alongside—or instead of—a meditation training.

09 Will I have access to the Integral Dojo Community?

Yes. Integral Dojo Community access is included throughout the six-month training.

It provides a place for announcements, reflection, conversation, and connection between the live sessions.

10 What is the investment?

The full six-month training is $347.

The next cycle begins on May 2, 2027.

READY TO GO DEEPER?

Learn to navigate difficult territory with greater clarity.

Join Meditation and the Dark Night of the Soul, a six-month live training in the difficult stages of insight, beginning May 2, 2027.

6 months Live online Begins May 2, 2027

PAY IN FULL

$347

One payment

Join for $347

PAYMENT PLAN

$122

3 monthly payments

Choose Payment Plan

Study the map. Practice with the territory. Learn how to meet it well.