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.