Where to Start with the Enneagram: Books, Podcasts and Resources I Recommend

Samantha Mackay

If you’re new to the Enneagram, one of the hardest parts isn’t necessarily learning about the nine types.

It’s choosing where to start.

There are hundreds of Enneagram books, podcasts, videos and online resources. Some focus on personality descriptions, others on relationships, leadership, spirituality or personal growth.

And different Enneagram teachers approach the system in quite different ways.

So where do you begin?

I’ve put together a collection of books and resources I recommend, from accessible introductions to more advanced explorations of the 27 subtypes, emotional development and inner transformation.

You don’t need to work through everything in order. Start with what interests you, learn about all nine types, and follow your curiosity from there.

If you’re new to the Enneagram

The Enneagram Guide to Waking Up — Beatrice Chestnut and Uranio Paes

This is the book I recommend most often to people who are new to the Enneagram.

When it was published in 2022, I was studying with Beatrice and Uranio, and I wasn’t convinced we needed another introductory Enneagram book.

But I was pleasantly surprised.

It’s accessible without being simplistic, psychological without being clinical, and spiritual without losing its grounding in everyday life.

What I particularly appreciate is how it introduces each type as a whole personality structure, exploring its motivations, emotional patterns, struggles and potential for growth.

Rather than reducing people to a collection of traits, it helps us understand the internal experience of each type.

And that’s important when we’re first learning the Enneagram, because it’s all too easy to identify with a few familiar behaviours and assume we’ve found our type.

Enneagram in Real Life — Stephanie Barron Hall

Another accessible starting point, particularly if you want to understand how the Enneagram applies to your everyday experiences.

Stephanie takes a practical approach to understanding personality patterns and working with them in real life.

If you’re someone who likes concrete examples and wants to start applying what you’re learning, this is another option worth exploring.

If you want to apply the Enneagram to a particular area of life

Once you’ve developed a basic understanding of the nine types, you might want to explore how personality influences an area of life that’s particularly important to you.

Here are a few books I’d recommend.

Work and leadership: The 9 Types of Leadership — Beatrice Chestnut

Don’t be put off by the word leadership.

This book is useful well beyond formal leadership roles.

It explores how the nine personality patterns influence communication, relationships, conflict and the way we navigate working with other people.

I’d particularly recommend it if you’re interested in understanding your patterns at work, whether you’re leading a team, running a business or trying to change the way you work.

Stress and burnout: Shock Point — Chad Prevost

Shock Point: The Enneagram in Burnout and Stress explores how our personality patterns interact with stress and burnout.

I particularly appreciate resources that go beyond identifying personality traits and help us understand how our familiar strategies contribute to the problems we’re experiencing.

This is worth exploring if you’re interested in the Enneagram’s application to stress, recovery and creating a more sustainable life.

Relationships and intimacy: The Enneagram, Relationships, and Intimacy — David Daniels and Suzanne Dion

Our closest relationships have a remarkable ability to bring our unconscious patterns to the surface.

This book explores how the different Enneagram types navigate intimacy, connection and the challenges that arise between people.

I’m currently reading it and appreciating the depth it brings to understanding how our patterns influence our relationships.

Creativity: Paint by Numbers: Art and the Enneagram — Ann Gadd

Creativity isn’t limited to artists, writers or musicians. We all express creativity in different ways, and our personality influences how we approach the creative process.

Ann Gadd brings together her experience as an artist and Enneagram teacher to explore creativity through the lens of the nine types.

An interesting choice if you’re curious about creative expression, creative blocks or how your personality shapes what you make.

If you’re ready to explore the Enneagram more deeply

The Complete Enneagram — Beatrice Chestnut

If you’ve learned about the nine types and want to understand why people of the same type can look so different, this is where I’d head next.

Beatrice explores the 27 Enneagram subtypes, showing how the three instincts interact with each of the nine core types.

I place considerable importance on understanding subtype because it helps us recognise the particular defensive strategies we’re working with.

That precision becomes especially valuable when we want to use the Enneagram for deeper healing, growth and transformation.

You can also explore the 27 subtypes on my website.

The Enneagram of Passions and Virtues — Sandra Maitri

For those interested in the deeper psychological and spiritual dimensions of the Enneagram, I’d recommend Sandra Maitri.

This book explores the nine passions, the habitual emotional patterns associated with each type, and the virtues that become more accessible as we loosen our identification with personality.

It’s a book for people who want to move beyond recognising their patterns and explore what transformation might actually involve.

Prefer listening? Try these podcasts and interviews

Sometimes listening to people describe their experiences helps us understand the Enneagram in ways that books can’t.

It’s also a useful way to challenge the mental pictures we’ve created of the nine types.

Enneagram 2.0 — Beatrice Chestnut and Uranio Paes

One of my favourite Enneagram podcasts, and a valuable resource whether you’re a beginner or have been studying for years.

Beatrice and Uranio explore topics ranging from the nine types and subtypes to instincts, relationships, emotional development and spiritual growth.

Their conversations bring depth and nuance to the Enneagram, while keeping the focus on how we can use it for our own development.

Listen to Enneagram 2.0.

Enneagram subtype panels — The Art of Growth

One of the most useful ways to deepen your understanding of the Enneagram is to listen to people describe their own experiences.

The Art of Growth, hosted by Joel Hubbard and Jim Zartman, began as a panel-based Enneagram podcast and includes conversations with people of different types and subtypes.

I particularly value panels because they help us hear how similar underlying patterns can be expressed in very different ways.

Explore The Art of Growth podcast.

Creativity and the Enneagram — my YouTube interview series

I began this series because I was curious about something.

Enneagram descriptions often emphasise creativity in Fours and Sevens, but what does creativity actually look like for the other types?

I started interviewing people from different types and subtypes about how they experience and express creativity.

Some talked about painting, writing or music. Others described creativity through problem-solving, business, teaching or designing experiences.

The conversations explore how our personality can both support and inhibit creative expression, and how creativity can become part of our healing and growth.

Creativity and the Enneagram YouTube playlist

A final thought on learning the Enneagram

No Enneagram book, podcast or teacher has the whole picture.

Each brings a particular perspective, shaped by their training, experience and understanding of the system.

And while I have my preferred teachers and approaches, I think it’s valuable to remain curious and keep testing what we learn against our own experience.

We can spend years reading about the Enneagram and still hold an incomplete picture of a particular type.

Sometimes a conversation with someone who expresses their type differently can challenge an assumption we’ve held for years.

So don’t feel you need to rush towards identifying your type, or read every book before you can begin using the Enneagram.

Learn about all nine types, stay curious about your own patterns, and remember that finding your type is the beginning of the journey, not the destination.

The real value of the Enneagram comes when we start applying what we’ve learned to the way we live, work and relate to others.