Where insight becomes practice, and practice becomes change.

Once you’ve seen your patterns, it’s hard to unsee them.
These coaching sessions help you live into that awareness—not perfectly, but honestly.

Whether you’re coming back after a deep dive, or simply ready to work through what’s unfolding in real time, this is where we practise speaking truth, repairing rupture, setting boundaries, and learning how to stay with what matters.

1:1 Coaching

60 minutes | SGD 250
For the one learning to stop abandoning themselves.

This is a space to make sense of what you’re feeling and why. We’ll work with your real-life dynamics—relationships, patterns, triggers, and dreams—and practise more grounded, courageous ways of showing up.

No masks. No rushing. Just clear, wise conversation rooted in emotional presence and self-trust.

What we might explore:

• Self-worth and self-compassion

• Communication habits and how to shift them

• Learning to set boundaries that honour both you and the relationship

• Rewriting stories of self-sacrifice and silence

Recommended for:
Anyone seeking continued support after an Enneagram deep dive, or those feeling stuck in familiar pain and ready to try something new.

→ Book your 1:1 coaching session

1:2 Coaching

75 minutes | SGD 350
For two people working on love, not perfection.

This is an ongoing space to practise communication and connection in your relationship—whatever that looks like. We’ll work with real conflicts, misunderstandings, and stuck points, offering tools and dialogue that make the hard stuff more human.

This isn’t about fixing each other—it’s about learning how to meet each other better.

What’s included:

• Gottman Method-informed coaching

• Clinical tools (connection cards, conflict charts, dream-sharing frameworks)

• Space to slow down, listen better, and speak what’s true

Recommended for:
Couples, close friends, or family members who want to deepen trust, repair ruptures, and move from reactive patterns to more conscious connection.

Understand your blueprint. Speak honestly with intention. Build real connection.

So many of us move through life on autopilot—people-pleasing, avoiding conflict, wondering why we feel off-centre. The Enneagram gives language to what you’ve long felt but couldn’t quite name.

This isn’t a personality test. It’s a map back to yourself (or to your partner).

Whether you come alone or with someone you love, this is a guided process to understand who you are under the habits, how you’ve learnt to survive, and how to finally live and love with more awareness and direction.

There are two options — individual and couple profiling:

1:1 Enneagram Deep-Dive

90 minutes | SGD 375
For the person who’s ready to meet themselves with clarity and compassion.

This foundational session is designed to spark deep self-awareness. You’ll walk away with insight into your personal patterns—how you think, love, stress, defend, and connect—plus actionable ways to show up with more truth in your life and relationships.

You’ll receive:

• An 18-page accredited Enneagram report: your personal “instruction manual”

• A full debrief and coaching consultation to unpack what it means for your life

• A facilitated exploration into your values, strengths, trigger profile, developmental tasks for growth, etc.

• A customised connection plan with guidance on your ideal communication style (and blindspots!)—and how to grow from here

This is for you if you’re ready to start seeing all of yourself, and start aligning your life with what really matters to you.

1:2 Enneagram Deep-Dive & Connection

4 hours | SGD 830
For two people who want to understand each other—not just communicate better, but connect deeper.

Whether you’re romantic partners, siblings, parent and child, or lifelong friends—this extended session helps you uncover what makes each of you you, and how to better navigate your differences with respect, clarity and care.

This is connection work—real, relational understanding that gives you the tools and scripts to help you speak and hear each other differently.

You’ll receive:

• Two 18-page accredited Enneagram reports (your relationship instruction manuals)

• A full report debrief and 2:1 consultation to unpack communication and conflict patterns

• A facilitated exploration into both your values, strengths, trigger profile, developmental tasks for growth, etc.

• A front-row seat to witnessing your partner and what supports and weakens them

• A personalised connection plan for both of you, with practical tools to deepen your relationship and advance it to the next level

This is for any duo who wants to stop looping in the same arguments and start building a relationship where both people can feel fully themselves—and fully seen.

For spaces that want to grow in emotional fluency and relational depth.

I run workshops that centre on human connection—how we speak, listen, set boundaries, and build trust.

These are especially powerful in environments where people are craving more authenticity, clarity, and care in how they show up for themselves and one another.

Customised for your group, always rooted in presence.

For workshop and speaking engagement enquiries, please email hello@maisiecheong.com, or use the contact options at the bottom of the page. Thank you!

For events and communities that need a human bridge.

Whether you’re hosting a gathering, panel, or retreat—my work as a speaker is to bring insight, intimacy and warmth to your space.

I talk about self-worth, boundaries, emotional honesty, conflict transformation, and what it means to build a life where you’re fully showing up as yourself.

Let’s make the room feel a little more human, together.

For workshop and speaking engagement enquiries, please email hello@maisiecheong.com, or use the contact options at the bottom of the page. Thank you!