1-TO-1 MEDITATION COACHING

Get clear about what your practice is asking of you now.

Private meditation coaching for experienced practitioners who want focused guidance around a question, challenge, transition, or area of uncertainty in their practice.

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30-minute sessions private one-to-one guidance with Miles

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Practice-specific work with what is actually happening

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$100 single session for focused guidance

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5-session package available for a short arc of continuity

WHEN A PRIVATE SESSION IS USEFUL

Sometimes practice needs a second set of eyes.

A private session can be useful when something in your meditation feels unclear, repetitive, unusually intense, or difficult to interpret on your own.

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You’ve reached a plateau

Your practice is consistent, but something feels flat, repetitive, or no longer as alive as it once did.

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You’re unsure how to work with a difficult pattern

Restlessness, doubt, striving, avoidance, emotional intensity, or another recurring pattern keeps showing up and you are not sure how to meet it skillfully.

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You’ve had a strong or unusual experience

Something significant has happened in meditation and you want help understanding it without either dismissing it or making too much of it.

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You’re not sure what to practice next

You have learned from different teachers, techniques, or traditions and want help discerning what is most useful now.

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Insight is not translating into daily life

You understand something clearly on the cushion, but relationships, emotional patterns, identity, or ordinary stress still seem untouched.

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You want experienced perspective

You may simply want to talk through where your practice is, what you are noticing, and whether your current direction makes sense.

You do not need to be in crisis or have an extraordinary meditation experience to benefit from guidance. Sometimes a small adjustment in understanding or direction is enough to change the quality of practice.

WHAT WE CAN WORK WITH

Bring the practice question that is actually alive.

There is no fixed curriculum for a private session. We work with the territory that is most relevant to your practice now, and use the time to clarify what you are seeing, what may be getting in the way, and what might support the next step.

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Practice direction

Clarifying what to emphasize, what to simplify, and where your current practice may need more continuity or a different approach.

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Plateaus, striving, and resistance

Looking at where practice feels stuck, effortful, dull, overly driven, or repeatedly pulled into avoidance.

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Insight and meditative experiences

Making sense of shifts in perception, unusual experiences, strong openings, or changes in how practice is unfolding.

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Identity and self-structure

Exploring how identification, self-image, roles, and habitual ways of organizing experience show up in meditation and beyond it.

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Emotion and shadow material

Working with emotional intensity, recurring reactions, disowned material, and the places where psychological patterns and meditation begin to overlap.

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Relationships and conflict

Looking at how practice expresses itself in intimacy, boundaries, reactivity, communication, and the way you meet difficult people or situations.

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Discipline and surrender

Finding a workable balance between structure and openness, commitment and flexibility, effort and letting go.

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Integration into daily life

Bringing insight off the cushion and into work, family, decision-making, emotional life, and the ordinary pressures of being human.

The session does not need to cover everything. One clear question, pattern, or area of uncertainty is often enough to make the conversation useful.

HOW THE SESSION WORKS

Focused guidance around what is most relevant now.

You bring the question, challenge, experience, or area of uncertainty that feels most alive. We use the session to look closely at what is happening, clarify the territory, and identify what may support the next step.

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BEFORE THE SESSION

Bring one clear area of focus.

You do not need to prepare an extensive history of your meditation practice. Arrive with the question, pattern, experience, or uncertainty you most want to explore.

One real question is usually more useful than trying to cover everything at once.

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DURING THE SESSION

We look closely at what is actually happening.

We’ll clarify the context of your practice, explore what you are noticing, identify patterns or assumptions that may be shaping the situation, and consider practical ways of working with it.

The conversation follows your practice rather than forcing it into a predetermined method.

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BEFORE WE FINISH

We clarify the next step.

The aim is to leave with greater clarity about what you are seeing and something concrete to work with in meditation or daily life.

Sometimes the next step is a practice adjustment. Sometimes it is simply seeing the situation differently.

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AFTER THE SESSION

Take it back into practice.

Give the conversation time to work. Return to your practice, test what we explored, and notice what changes when you approach the territory with greater clarity.

A single session may be enough. If the territory would benefit from continuity, the 5-session package gives us room to work with it over time.

FOCUSED COACHING, NOT LONG-TERM MENTORSHIP

The single session and 5-session package are designed for focused guidance. If you want sustained mentorship, regular contact, and a deeper year-long practice container, the Meditation Apprenticeship is the better fit.

Explore the Meditation Apprenticeship
Miles Kessler

ABOUT MILES

Meditation guidance grounded in long practice.

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

My training is rooted in the Burmese Mahasi Vipassana tradition, including direct training with Sayadaw U Pandita and Vivekananda. Over the years, that foundation has been complemented by embodiment, psychological work, relational practice, Aikido, and Integral approaches to human development.

In private coaching, I am less interested in giving you another system to follow than in helping you see more clearly what is happening in your actual practice.

That may mean clarifying technique, putting an experience into context, noticing where effort has become striving, exploring a psychological pattern that is entering meditation, or simply helping you discern the next appropriate step.

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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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Mahasi Vipassana trained in the Burmese insight tradition

More About Miles

IS THIS THE RIGHT FIT?

Private coaching works best when there is already something real to work with.

You do not need to be an advanced meditator. But you should have enough experience with practice to bring a genuine question, challenge, pattern, or area of uncertainty into the session.

THIS MAY BE A GOOD FIT IF

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You already have a meditation practice and want experienced perspective on something specific.

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You are willing to look honestly at your practice rather than simply being told what technique to use.

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You are navigating a plateau, difficult pattern, strong experience, or change in the way meditation is unfolding.

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You want to clarify direction without committing to a long-term program.

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You are interested in the relationship between meditation, psychological patterns, embodiment, and daily life.

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You are open to having assumptions about your practice questioned when that would be useful.

THIS IS PROBABLY NOT THE RIGHT FIT IF

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You are completely new to meditation and primarily need basic instruction in how to begin.

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You are looking for a rigid prescription or guaranteed roadmap for what should happen next.

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You want someone to confirm a particular interpretation of a meditation experience rather than explore it openly.

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

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You want ongoing accountability, regular coaching, and a sustained mentoring relationship.

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You are mainly looking for more information rather than help working with your actual practice.

If what you need is sustained mentorship rather than a focused session, the Meditation Apprenticeship is designed for that longer arc.

Explore the Meditation Apprenticeship

COACHING OPTIONS

Choose the level of support that fits what you need now.

Book one focused session when you have a specific question or challenge. Choose the 5-session package when the territory would benefit from some continuity over time.

SINGLE SESSION

$100

One 30-minute private coaching session

For a focused question.

A good choice when you want experienced perspective on a specific practice question, challenge, experience, or decision about direction.

  • 30-minute private session with Miles
  • Focused on your current practice
  • Clarify one primary area of concern
  • Leave with a clearer next step
Book One Session

LOOKING FOR DEEPER CONTINUITY?

The 5-session package provides a short coaching arc. If what you want is sustained mentorship, regular guidance, group practice, and a deeper year-long container, explore the Meditation Apprenticeship.

Explore the Meditation Apprenticeship

FAQ

A few things to know before you book.

Private coaching is intentionally simple. These answers should help you decide whether a focused session or a short coaching package is the right next step.

Do I need to be an advanced meditator?

No. You do not need advanced retreat experience or mastery of a particular tradition. But you should have an existing meditation practice and enough experience to bring a real question, challenge, pattern, or area of uncertainty into the session.

What should I bring to the session?

Bring the issue that feels most alive. That might be a plateau, a recurring difficulty, a strong meditation experience, confusion about practice direction, or a question about how meditation is intersecting with your emotional, relational, or everyday life.

Do I need to prepare anything in advance?

No extensive preparation is required. It is helpful to spend a little time clarifying what you most want to explore so we can use the session well.

Should I book one session or the 5-session package?

Choose a single session when you have a focused question, challenge, experience, or decision about practice that you want perspective on. Choose the 5-session package when the territory is likely to benefit from continuity, follow-up, and adjustment over several conversations.

What is included in the 5-session package?

The package includes five 30-minute private meditation coaching sessions for $450. That is $90 per session, saving $50 compared with booking five individual sessions.

The sessions can be used to stay with one developing area of practice or to work with different questions as they emerge.

Will you tell me what meditation technique I should use?

Sometimes a practical adjustment in technique may be useful, but the session is not built around prescribing a single method. We look at the context of your practice and what seems most appropriate for the territory you are actually in.

Can we talk about unusual or intense meditation experiences?

Yes. A private session can be a useful place to put a strong or unfamiliar experience into context and explore how to relate to it without dismissing it or turning it too quickly into a fixed interpretation.

Is this therapy?

No. Meditation coaching is not psychotherapy, crisis support, or treatment for a mental health condition. Psychological and emotional material may arise in the context of meditation, but the focus of the session is your contemplative practice and how it is relating to your life.

What is the difference between coaching and the Meditation Apprenticeship?

Private coaching is designed for focused guidance. A single session may be enough, or the 5-session package can provide a short arc of continuity around a developing area of practice.

The Meditation Apprenticeship is different. It is a 12-month mentoring relationship designed for sustained guidance, regular contact, deeper integration, and continuity over time.

Explore the Meditation Apprenticeship
What if I am not sure which option is right for me?

If you have one clear question or simply want experienced perspective on where your practice is now, start with a single session. If you already know that the issue would benefit from follow-up and continuity, the 5-session package is the better fit.

PRIVATE MEDITATION COACHING

Bring the practice you actually have.

You do not need a dramatic problem or a perfectly formed question. If something in your meditation feels unclear, stuck, alive, or ready for a closer look, private coaching gives you a place to work with it directly.

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SINGLE SESSION

One focused conversation.

A 30-minute private session for a specific question, challenge, experience, or decision about your practice.

$100 one 30-minute session
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5-SESSION PACKAGE

A short arc of continuity.

Five 30-minute sessions for territory that would benefit from follow-up, adjustment, and reflection over time.

$450 $90/session · save $50

CHOOSE WHAT FITS

Start with the amount of support the practice actually needs. More is not necessarily better. The right container is the one that helps you see clearly and keep practicing.

Choose Your Coaching Option