Want to know someone’s (or more importantly, your own!) personality pattern? Watch them on holiday.
When structure drops away, patterns show themselves—how we rest, control, avoid, pursue, organise, or disappear. Personality becomes especially visible when nothing needs to be achieved and no one is watching.
If you’re familiar with the Enneagram, you’ll recognise these as nine common patterns. If not, read them simply as familiar ways humans organise themselves when routine falls away.
Here’s a light, imperfect guide to how these patterns often show up on holiday.
The Improver
Has opinions about how the holiday should be done. Researches in advance. Notices inefficiencies. Relaxes only once everything feels “right.”
Tell: Corrects the Airbnb host in their head (or reorganises the kitchen).
The Helper
Makes sure everyone’s okay before checking in with themselves. Organises meals. Packs extras. Feels most relaxed when needed.
Tell: Says, “I’m fine,” while doing everything.
The Achiever
Turns rest into a project. Best beaches, best photos, best use of time. Holiday becomes something to optimise—or document.
Tell: Still checking email “just quickly.”
The Romantic
Feels the longing underneath the beauty. Wants the holiday to mean something. May feel disappointed if the feeling doesn’t match the fantasy.
Tell: Says, “It’s nice… but something’s missing.”
The Observer
Needs space from togetherness. Enjoys quiet, books, walks, museums. Energy is carefully rationed.
Tell: Disappears for a few hours and comes back restored.
The Loyalist
Tracks logistics, safety, and backup plans. Asks questions. Anticipates what could go wrong. Relaxes once risks feel managed.
Tell: Knows where the nearest pharmacy is.
The Enthusiast
Chases options, freedom, and pleasure. Doesn’t want to miss out—or slow down. Avoids boredom and heavier feelings.
Tell: Already planning the next stop before arriving.
The Challenger
Takes charge when things feel chaotic. Protects the group. Pushes through obstacles. May struggle with slowing down or showing vulnerability.
Tell: Says, “It’s fine, we’ll sort it,” and does.
The Peacemaker
Goes along with the plan. Doesn’t want to rock the boat. May genuinely forget what they want entirely.
Tell: Says, “I’m easy,” and genuinely means it—sometimes losing track of their own preferences.
When You Notice the Pattern
So you’ve spotted yourself in one of these. Now what?
If you catch yourself thinking, “Ah, there I go again,” pause there.
Often the next thing that appears is another part—the one that wants to fix, judge, improve, or make the pattern wrong. See if you can notice that part too, without letting it take over.
Once you’ve noticed the pattern from a place of compassion, most of the work is already done.
Something may soften. You might even start smiling—or laughing—at how familiar the move is. “Of course. There you are.”
That friendliness matters more than changing anything.
Gentle Experiments
From there, the holiday can become a low-stakes laboratory—not for self-improvement, but for gentle experimentation.
You might try:
If you usually plan—leave something unplanned.
If you usually take care of everyone—let yourself receive.
If you usually disappear—stay a little longer.
If you usually push—pause.
If you usually avoid—turn just slightly toward.
Not forcing or fixing or trying to do it “right.”
And if nothing changes at all, that’s okay too.
Being able to see yourself with kindness, especially when structure falls away is already a form of rest.
Presence over perfection.
For more reflections like this, insights, and interesting experiments, you can subscribe at nineways.substack.com.
Holidays reveal the great divide between the haves and the have-nots. And there are ways we find ourselves on both sides. But the fact that you’re reading this likely means you’re more in the haves category.
Somehow, though, we don’t register it. I speak for myself—I don’t register it.
The Poverty Tours
I grew up with parents who kept stressing we should count our blessings. When we were younger, my father tried to drill into us how lucky we were. He would drive us into poorer areas to expose us to what poverty looked like.
I’m not sure how effective it was. If anything, it drove home the point that I did not want to look like them. He lit the fear of poverty and loss in me like never before.
But looking back now, I see what I couldn’t then: in any of those scenarios, I could have been that person. I lucked out with the parents and situation I got. But to truly stand in someone else’s shoes, you have to take it all—the genetics, the upbringing, everything that led them to where they are.
I’m one of those who doesn’t believe people want to suffer. Sometimes we just don’t know another way.
Pema Chödrön says this best:
“True compassion does not come from wanting to help out those less fortunate than ourselves but from realizing our kinship with all beings.”
The Comparative Trap
Where I’m going with this is: I didn’t really take my parents seriously. It’s not like they said “look how lucky you are” and all of a sudden I woke up to the great luck of my life.
Actually, it invoked the opposite. I looked around at my peers and, relative to them, I often felt a whole lot less lucky. They so often seemed to have what I didn’t. We grow up in this comparative world, measuring ourselves against the people around us.
But the eagle-eye view, that 20,000-foot perspective, shows an entirely different story: we lucked out on many fronts.
One: that we got born at all. As much as this life can be suffering, the miracle of it is astounding.
Two: that we had enough love and support that we find ourselves in the 1% of people who have enough shelter and food to sustain themselves.
So what I needed to hear and learn way back then was that both can be true. Relative to the people around me, I’m having a certain kind of experience that leads me to feel a certain way about what I have and don’t have. Some of that is good—it might light a fire under my ass to get going or inspire me in whatever ways.
But without that 20,000-foot view, I can’t really receive the miracle that so much of my survival I don’t need to worry about. That’s historically almost an anomaly. We have always had to worry and fear.
Maybe that’s the hard thing to let in: no matter how imperfect your life is and how much more you want, already you are actually there. This is, as they say, as good as it may get. And there’s a whole lot of good we could probably take in.
But that needs us to slow down on filling holes. And breaks and holidays are the times we try to fill them most. It needs to look like something.
But what if you made the main aim of your break just to let yourself be as you are? That may mean you don’t feel as happy as you’d like on some days. That doesn’t mean we need to go plaster it up with whatever quick and sure fixes are out there.
What if you just let yourself be as you are, and make that a curious fascination?
Handrail #1: Contraction and Expansion
Peter Levine, the trauma healing pioneer, uses a simple demonstration with a Slinky to show how the nervous system works. When we’re stressed, the Slinky contracts—tight, compressed, stuck. When we’re regulated, it expands—loose, flowing, free.
What we really want during holidays is that feeling of expansion: relief, letting go, space.
But as Peter points out so well, as soon as we slow down or when we get time, that’s when the contraction becomes more evident. And we don’t want to go there, so we avoid it. We use all kinds of strategies to keep those feelings at bay. But all that does is strengthen the contraction.
The secret—and this is the first handrail for the holidays I want to give—is that every time we touch a contraction and let it in for a while, it will lead to an expansion.
Just the way the body works. And then expansion leads to contraction. If we resist this less, we have the feeling we were always hoping the holiday would give us: space and an ever-growing expansion that can be further enhanced by placing ourselves in natural environments.
Here’s a practice for this:
Come back into your body
Breathe
Let the breath out slowly
Shake a little if it helps
Bring sound—hum, sigh, an “ahh,” or whatever wants to come through
Then shake some more
Notice what wants to contract, and let it
Stay with it, breathing
Feel what begins to soften and expand
Handrail #2: Boredom as Medicine
Make your goal to soften. To do nothing. And I mean nothing.
Sit there. Twirl your fingers. Think, What now?
That uncomfortable “what now” is often the doorway. We call it boredom, and it has a bad reputation. But what if boredom is not a problem to solve, but a gateway into a different mode of being?
When we stop filling every second, something else begins to move.
You might turn on music and actually listen. You might look outside and rest with the trees, or the rain. Life begins participating with you again.
A small note of kindness to yourself: any pleasant feeling you find will pass. Expect that. Let it be okay. When tension returns—and it will—you might notice yourself thinking, But I’m on holiday, I should be relaxed.
That’s the moment to step back and say:
It’s okay. It takes time to adjust.
My intention is to rest.
I can learn calm again, slowly.
Imagine a holiday you don’t need to escape from. One where rest and discomfort are both allowed. Where you can be peaceful and uneasy in the same body.
Dissatisfaction often shows up here too. The ego rarely feels fully satisfied, even in beautiful places. Notice how often people look strangely miserable on holiday. We keep ourselves busy to avoid that edge.
Sometimes space itself is disorienting. Now I have time to be with myself—and I didn’t know it felt like this.
If that happens, breathe rhythmically. Sit on a balcony. Listen. Let a different story tell itself.
My Own Medicine
I’m going to take a great leap into boredom myself. It’s one of the things I struggle with most and, ironically, find most of my medicine in.
For someone like me who has spent most of his life feeling left behind and doing whatever he could to catch up, boredom is the antidote to false progress.
But who would have thought that boredom itself held clues into what real forward momentum looks like?
The catch is you have to let go of the need to move forward and actually just let yourself feel lost or disoriented for a moment. Boredom invites the great “I don’t know” moment, which is the polar opposite of where the mind wants to be. We want the known, the certain, the predictable.
Boredom can be, if we let it, a course correction. Because let’s face it: some of the stuff we do looks and feels serious but doesn’t move us in the ways we think. But it feels like direction. We’re pretending to be in control, filling the space with activity that keeps us from touching what’s actually here.
The Invitation
Thank you for being here this year.
May your holidays include rest, boredom, breath—and a little less striving.
May you touch the contraction and let it expand.
May you remember your kinship with all beings.
And may you receive, even for a moment, the miracle that you’re already here.
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As we arrive together, we also arrive at the end of a year that, for many of us, has held loss, transition, and deep reminders of the fragility and miracle of being alive. We also recognize the wider world we live within: the heartbreak of wars, environmental loss, and the difficulty our species has in evolving wisely.
There is so much we cannot control. And still, where we do have power, we choose to use it to water the possibility of peace, goodness, and a future worth inheriting.
This is why, each December, we gather around the theme of Remember.
Not to deny the agony of life, but to balance it by consciously collecting the good—the beauty, the meaning, the glimpses of magic that strengthen our capacity to live well and contribute well.
We invite you to remember in order to honour life—your life, your thread, the colours and steps of your journey this year.
The Practice of Sankofa
This first step is to hold an intention of opening to the past. As Sankofa teaches us, we turn back not with a critical eye, but with compassion and awareness. We watch this character we each are—following the thread of their story as they made their way through this year.
Sankofa is the magical bird that turns back to retrieve what was left behind. It reminds us that healing often comes from revisiting the past, not to get stuck there, but to gather the lessons, the wisdom, and the pieces of ourselves we abandoned along the way.
For many of us, myself included, turning back can feel uncomfortable. There’s a natural reluctance to face what we’ve avoided. It can feel daunting to revisit old memories or meet the difficult places again.
But when we turn toward the past with presence, something begins to move. The energy that has been frozen, unspoken, or forgotten starts to release. What was stuck becomes usable again—strength, clarity, compassion, insight. It comes back into our lives as fuel.
At the same time, we consciously gather the good. Sankofa is not only about tending to the wounds; it is also about honouring what supported us this year—the joys, connections, moments of courage, unexpected gifts, tiny victories. These are part of your story too, and they deserve to be named.
Gathering Memories
Imagine yourself as a collector of small treasures.
You might gather memories by:
Noticing what returns to you throughout the day
Paying attention to dreams and daydreams, which often carry forgotten messages
Letting your senses guide you—smells, songs, photographs, textures
Listening to what warms your body when you recall it
These are gentle ways of remembering who you’ve been, and who you’re becoming.
Remembering Your Song
Credo Mutwa, the renowned South African storyteller and traditional knowledge-keeper, tells a story of a people who once knew powerful songs that connected them to their purpose and their place in the world. Over time—through fear, shame, and silence—they forgot their songs. And with that forgetting came a loss of confidence, clarity, and direction.
But the important part of the story is that the songs were never lost. They were only forgotten.
They lived inside the people, waiting to be heard again.
As you gather memories, listen for your song—your deeper thread, your inner voice, the sound of your own life speaking back to you. It may come through a dream, through a memory that resurfaces, through a moment of gratitude, or in the quiet.
Giving Voice to What Wants to Speak
Putting pen to paper, naming the year, the lessons, the losses, the learnings—builds strength, clarity, and inner coherence. And while it may feel like a hard thing to do, in another way there’s nothing simpler than giving voice to what already wants to be spoken inside you.
Reflections for Week One
To start us off, here are five guiding questions for the next few days. Use any medium you like: writing, painting, collage, movement, altar, or simple quiet reflection.
#1 — What have I received this year? Nothing is too small. Let yourself acknowledge what came into your life—support, experiences, insights, relationships, moments of grace.
#2 — What have I offered, done, or created? Honour your efforts, seen and unseen. Even attempts that didn’t “work” are part of the path. Celebrate what you stood behind with your heart, hands, presence, or work.
#3 — What have I let go of? What have you released—by choice or by life’s insistence? Acknowledge the endings, the fallen leaves, the skins shed. Honour the grief or relief that came with them.
#4 — What have I learned? Name the teachings of this year. What wisdom has settled in you that you want to carry forward?
#5 — How have I grown? Where is your edge of evolution? What small shifts, new understandings, or deep changes are shaping you?
Ways to Recollect Your Year
Different people remember in different ways. Choose the methods that feel natural and enjoyable for you:
1. Morning Pages
A practice from Julia Cameron’s The Artist’s Way. Three pages of stream-of-consciousness writing in the morning. No editing, no analysing. Just letting the year spill out.
2. A Sketch Journal
Sometimes what the heart knows can’t be written. Use drawings, symbols, colours, maps, timelines—anything that helps the memory speak.
3. Collage
Collect images from magazines, printouts, old photos, or screenshots. Create a visual mosaic of your year: moments, themes, emotions, dreams.
4. Objects & Stones
Gather meaningful objects—stones from walks, ticket stubs, shells, pieces of fabric, small items that hold memory. Lay them out on a table as a map of your year. Notice what stories emerge.
5. Dream Notes
Keep paper next to your bed and jot down dreams. Dreams often carry memory, insight, and forgotten parts of the year that want to be honoured.
Practical Notes:
Work with these questions at your own pace over the next few days
There’s no “right” way to respond—let your intuition guide you
It’s that time of year again when we find ourselves nearing the end of a full cycle around the sun.
As a teacher of mine says: “December arrives with her bag of paradoxes: joy and grief, victory and defeat, beauty and difficulty all tangled together.” This is the season of remembering, not as a dusty archive of “what happened,” but as a living practice of honouring what was, so that it can ripen into fuel for what wants to come.
It’s also a time when we start to think about next year. As we approach the new year’s moment, it is a transition we cross never to return again. This year we are in—2025—takes its place in the library of the past. And as we continue to move into the future, things of this year that felt so important and urgent begin to fade as new priorities take their place.
The Problem with New Year’s Resolutions
The challenge in this great arc between past, present, and imagined future is that we live in a culture intensely future-focused. Exhibit A: the tradition of New Year’s resolutions — “This year I’m going to be better!”
And yet, we so often repeat the same patterns. Because willpower isn’t enough. Motivation isn’t enough. Good intentions aren’t enough.
The Real Condition for Change
There is only one real condition for change from my perspective: seeing.
We have to be willing to see ourselves clearly. Awareness itself contains all the ingredients for the changes we are looking for. It’s unusual to think about it this way, that we don’t have to try so hard to change. In fact, the trying often gets in the way. Every year we witness people making bold resolutions, keeping them up for a while, and then falling back even harder into the old ways.
But what if the issue isn’t the resolution? What if the issue is our relationship to the old ways?
Take an extreme example: someone whose old way is drinking too much decides to stop. It’s probably an intelligent idea. But it also reveals one of our human blind spots — the belief that we can simply decide to change and that will be enough.
The decision isn’t the problem. The how is.
How to Change
How do we change? How do we dream a future that actually fills and guides us?
We are dreamers by nature. Every night we drift into that mysterious inner landscape of imagination that feels utterly real. To dream deeply is to be in communion with something larger than ourselves. And the dreams that most fulfill us are always, in some way, in service to life.
So the real question for the dreamer in us, the one longing for a more honest, grounded, or sober life is:
How do we move with the dream in a real and embodied way?
And here comes the part many of us resist.
The Practice of Composting the Year
The Akan people of Ghana express the art of remembering through the symbol Sankofa, a bird walking forward while turning back to retrieve an egg. Its teaching is simple and profound:
“Go back and fetch what you left behind.”
In this worldview, the past isn’t something to escape. It’s a living source of guidance. Nothing is wasted, every experience contains nutrients if we’re willing to look.
Sankofa is mythic composting:
Feet in the present
Body moving forward
Awareness turning back to gather what’s useful
It’s not nostalgia. It’s integration.
We must look backward and make it a practice. Not clinging to what was, but composting it. The triumphs, the failures, the awkward moments and the shining ones—all of it belongs. When we bring it into the circle of our awareness, memory transforms. It becomes medicine instead of baggage.
This is not indulgence. It’s evolution.
So we reflect on the kinds of people we have been. See ourselves with compassion and clarity, with a little distance.
Watch this character go about their year. What stood out for them? What was difficult? What did they do with the difficult? To see the ways that they persevered and got through hard things. The fact that we’re still here is a testament to our strength.
We acknowledge the times that we fell down. The ways that we got up again. What is it that we learned this year about who we are and what truly matters to us?
What will we take with us next? Think like we might have left parts of us behind that had important things to tell. Now is a good time to remember, to make a space for the field of past and allow the memories to surface.
The Invitation
If this practice interests you, there are two ways to engage:
Join the Sankofa Writing Journey – We Go Further Together A guided group experience where we reflect on the year through writing and ceremony. All sessions are online via Zoom. Three meet-ups: 10th – 22nd December. Find all the details on my website here or on Facebook.
Solo Reflection – If you prefer the recollection project on your own, here are some prompts to guide you:
What stood out this year? What moments feel most alive when you think back?
What was difficult? How did you meet those difficulties?
What parts of yourself did you discover or rediscover?
What do you want to acknowledge about your journey—both the falling down and the getting back up?
What wisdom from this year do you want to carry forward?
What are you ready to leave behind?
You might follow the morning pages ritual, you can read more on that here.
Set aside time. Light a candle. Write with honesty and compassion. Let the memories surface without judgment. This is how we change our relationship with the old ways—not by forcing them out, but by seeing them clearly and choosing how we carry forward. The meaning that we give these experiences, or finding the stories to tell that acknowledge the past and also give us strength to meet the future.
The dreamer in you knows what wants to emerge. Give yourself the gift of looking back, so you can move forward with clarity and truth.
A friend of mine once tried an experiment: for three months, she decided to be 100% honest with everyone. No filters. No polite fictions. Just raw truth. She lost most of her relationships.
It turns out we’re not built for complete transparency. The social fabric depends on a little pretending. Belonging, evolutionarily speaking, kept us alive
But where’s the line? When does performance stop serving connection and start working against it?
The Phoney Layer
Fritz Perls, the unusual therapist who founded Gestalt therapy, used to say his task wasn’t to fix you but to bring something out of you, the way a sculptor coaxes form from stone. What is there in you that wants to come out?’ he would ask
Sitting with Fritz wasn’t easy. He met people where they were and gave them back what they brought to him—unfiltered. He saw the psyche as a series of layers, and the first one we meet in ourselves is what he called the phoney layer.
If you were sitting with him and he sensed you were in that layer, he would call it out immediately. “Do you know you’re doing that?” he might ask. “Do you realise you’re acting?”
People would often get defensive. Some would break through. All of them would have to face what they were hiding.
That was the giveaway. In the phoney layer, you’re not being real. You’re saying what you think someone wants to hear, trying to make an impression or avoid being seen a certain way. You’re managing the room instead of being in it.
Perls saw these pretences as the first barrier to self-actualisation.
Why We Need the Mask
We learn to perform early. Psychologists document the “social smile” appearing within months of birth; we’re trained to manage others’ feelings before we can walk. We smile when we don’t feel like it, cry when it serves us, present a version of ourselves that will keep us safe and accepted.
The phoney layer isn’t a personal failure. It’s a survival strategy. A cultural requirement.
How often do we ask “How are you?” but hope the answer is “fine”? The phoney layer has become the norm. The culture rewards positivity and punishes vulnerability. Being too real, too honest, too soon can make others uncomfortable or push them away entirely.
So what’s the cost?
When life energy is spent on performance rather than presence, something real in us gets buried. We start to forget we can drop the act. We lose touch with what actually wants to come out.
When Realness Backfires
There was a woman in one of my university classes who taught me a lesson. She brought herself so fully and vulnerably—that it became hard to watch.
She would start with “I must be honest…” and then offer something raw and unfiltered. Once, in a group discussion about family dynamics, she shared intimate details about her mothers mental illness and how it made her feel unlovable. The room went silent. You could feel people pulling back. Some subtly rolled their eyes. Her honesty was pure, but it wasn’t attuned to what the group could hold.
Later she learned to hold back a little, to read the field, to sense what the space could carry. She still brought depth, but with discernment. Authenticity without awareness isn’t strength; it’s vulnerability without protection.
As an Enneagram Four, I understand her impulse. Authenticity feels sacred to me. But I’ve also learned its shadow: oversharing, offering truth where it isn’t yet safe to be received. There’s a difference between being real and being reckless.
I’ve made this mistake more times than I can count, bringing my full self to rooms that weren’t ready, thinking honesty was always the answer.
I had a good friend who was upbeat and playful. She wanted lightness, fun, easy connection. But I kept trying to push her deeper, into more sincere relating, more vulnerability, more “realness.” I really believed this was a good impulse. But instead, my authenticity ended up pushing her away.
What I needed to do was attune to her. To meet her where she was, not where I thought she should be.
One of my biggest learnings over the years has been surprisingly odd: getting better at being in superficial conversations and spaces. I had so much resistance to it. Who would have thought I could develop that skill, or that it could actually be fun?
Sometimes the deepest act of connection is allowing things to stay light.
The Middle Path
The writer Carlos Castaneda called this dynamic “controlled folly”—a kind of conscious play within the performance. You recognise the mask, but you wear it with awareness. You act, knowing you’re acting. It’s not naivety; it’s wisdom.
In societies where sincerity can cost you belonging or power, controlled folly is a kind of self-protection. You choose when to reveal and when to conceal. You learn to read the field.
This isn’t the same as the phoney layer. The phoney layer is unconscious—you’ve forgotten you’re performing. Controlled folly is conscious—you know exactly what you’re doing and why.
Noticing the Act
So what do we do with this phoney layer and the performing parts of us?
We don’t shame it. We thank it. It helped us belong, survive, navigate unsafe spaces. But we can also begin to see it. To recognise when we’re in performance mode.
You can feel it in your body. There’s a tightness, a holding. Your breath gets shallow. You’re monitoring yourself, calculating responses. You’re not quite there.
The question isn’t “Am I being authentic enough?” but “Do I know when I’m performing?”
That awareness changes everything. Once you can see the mask, you can choose when to wear it and when to let it slip.
The Practice
Think of it as a spectrum.
On one end: fake, inauthentic, insincere. On the other: real, authentic, true.
Where do you find yourself most of the time?
Here’s what one notch closer to real might look like:
When someone asks “How are you?” saying “I’m tired” instead of automatic “fine”
Admitting “I need to think about that” instead of immediate agreement
Sharing your actual opinion instead of mirroring theirs
Saying “I’m not comfortable with this” when something feels off
Small moves. Nothing dramatic. Just slightly more true.
The invitation isn’t to strip away all masks; it’s to know when they’re on and to choose when to take them off. To move one notch closer to the real without losing the grace that keeps you connected.
Maybe that’s what Perls was getting at: not a demand for raw honesty at all costs, but an invitation to notice the act and ask—
What’s underneath that wants to come out?
Maybe the real work of authenticity isn’t tearing masks off, but learning which ones still let us breathe.
