Enneagram Five

19/03/2025

The Five Trap

02/03/2025

For six months, I sat on my first podcast episode, convinced I wasn’t ready to release it.

I waited. I refined. I over-prepared.

Then I finally put it out, and it took off *despite* my hesitation.

Here’s what I learned about taking action as a Five 👇

Fives love to be prepared. It’s how we feel safe. But sometimes, preparation is just a sophisticated way to *stall*.

We tell ourselves we’re gathering information, refining our plan, ensuring success.

But what we’re really doing? Avoiding uncertainty.

The biggest reason we don’t take action is the illusion of readiness.

We believe that if we don’t feel 100% prepared, we aren’t capable.

But in reality, confidence isn’t something you have before you act, it’s something you build *by* acting.

Research backs this up. Studies show that action-oriented individuals develop more confidence over time, while overthinkers tend to reinforce self-doubt.

The longer we hesitate, the more impossible action feels.

I used to believe that more knowledge would make me feel ready. But no matter how much I learned, I still hesitated.

That’s because knowledge doesn’t create readiness, *experience* does.

So how do you break the cycle?

Yesterday’s newsletter breaks it all down—how to stop waiting and start moving forward *without* feeling reckless.

📩 Read it at the link in the comments.

28/02/2025

I waited too long to start—don’t make my mistake.

For months, I told myself I wasn’t “ready” yet. More prep, more research, more refining. But when I finally took action? It worked *despite* my overthinking.

Tomorrow’s newsletter breaks down how to stop waiting & start moving as an Enneagram Five.

Subscribe at the link in the comments.

23/02/2025

Have you ever felt disconnected from life—without really knowing why?

I spent years trying to think my way through life. It didn’t work.

Yesterday’s newsletter breaks down the 𝗵𝗶𝗱𝗱𝗲𝗻 𝗰𝗼𝘀𝘁 of over-relying on thought. Recap 👇

As Fives, we trust our minds more than anything.

Thinking gives us clarity. It makes us feel safe. It’s how we navigate the world.

But when thinking becomes our 𝘰𝘯𝘭𝘺 way of engaging, something happens: we start 𝘸𝘢𝘵𝘤𝘩𝘪𝘯𝘨 life instead of 𝘭𝘪𝘷𝘪𝘯𝘨 it.

We tell ourselves we’re preparing:

📌 If I just read one more book, I’ll feel ready.

📌 If I analyze this conversation, I’ll know what to say next time.

📌 If I plan more, I can avoid mistakes.

In reality, we’re not preparing—we’re 𝘱𝘰𝘴𝘵𝘱𝘰𝘯𝘪𝘯𝘨. At some point, knowledge stops being a tool for growth and starts becoming a shield. It protects us from uncertainty, failure, and discomfort.

But it also keeps us 𝘴𝘵𝘶𝘤𝘬.

The cost of thinking your way through life? 𝗗𝗶𝘀𝗰𝗼𝗻𝗻𝗲𝗰𝘁𝗶𝗼𝗻.

The paradox of being a Five: We want deep understanding. But the deepest understanding doesn’t come from 𝘵𝘩𝘪𝘯𝘬𝘪𝘯𝘨 𝘮𝘰𝘳𝘦—it comes from 𝘴𝘵𝘦𝘱𝘱𝘪𝘯𝘨 𝘪𝘯𝘵𝘰 𝘵𝘩𝘦 𝘶𝘯𝘬𝘯𝘰𝘸𝘯. And that’s terrifying.

Which is why most advice fails us...

The solution isn’t to "stop thinking." Thinking isn’t the problem—it’s the 𝗶𝗺𝗯𝗮𝗹𝗮𝗻𝗰𝗲.

What if instead of retreating into thought, you used it to 𝗲𝗻𝗵𝗮𝗻𝗰𝗲 experience, not escape from it?

That’s what this week’s newsletter explores. Read it at the link in the comments 🔽

21/02/2025

I spent years trying to think my way through life. It didn’t work.

But when I finally stopped just thinking—and started engaging—everything changed.

How do you do that as an Enneagram Five? That’s tomorrow’s newsletter.

Make sure you’re on the list! (link in comments)

16/02/2025

Enneagram Fives don’t just get lost in thought—we retreat into our minds.

Not because we love thinking (though we do), but because it feels safer than engaging with the outside world. But when does this retreat stop helping and start hurting? Let's dig in...

As Fives, our minds are our safe place.

Thinking is familiar. It feels productive. It feels like us.

But when we over-rely on retreating into thought, we run into a problem: We start using thinking as a shield to avoid things that feel uncomfortable.

Here are 5 common reasons we retreat into our minds:

💭 Emotional Avoidance – Thinking feels safer than feeling.
🧠 Intellectual Identity – We define ourselves by our intellect.
🌍 Sensory Overload – The world can be too much, so we retreat.
😨 Fear of Inadequacy – We avoid real-world challenges to stay “safe.”
🛑 Vulnerability – Deep engagement requires openness, which feels risky.

The problem isn’t that we retreat. It’s that we don’t always know why we’re doing it. And when we retreat on autopilot, our sanctuary starts feeling more like a cage.

Yesterday's newsletter breaks down why we get stuck in our heads and what’s really driving our retreat.

🔽 Link in comments to read the full issue 🔽

14/02/2025

Why do we retreat into our heads, even when it makes life harder?

We tell ourselves it’s for clarity, control, or “recharging.” But more often, it’s a habit of retreating from discomfort, uncertainty, or connection.

Tomorrow’s newsletter breaks it down—and what to do about it.

Sign up here:

Insights and strategies for navigating life as an Enneagram Five, delivered to your inbox for free every Saturday.

25/07/2024

These are the steps for developing your intuition as a Type 5:

• Accept the value of intuition
• Limit information overload
• Make time for reflection
• Tune into your body
• Journal regularly

Follow these, and you’ll become more intuitive.

18/07/2024

These are the steps foster deeper friendships as a Type 5:

• Accept the importance of friendships
• Initiate and maintain contact
• Be consistent and reliable
• Practice active listening
• Open up gradually

Follow these, and you’ll make friends for life.

11/07/2024

Here are the steps for effective energy renewal as a Type 5:

• Identify what does & doesn’t energize you
• Engage in mindfulness practices
• Seek social connections
• Pursue creative outlets
• Prioritize sleep & rest

Follow these, and you’ll refill your personal energy tank.

04/07/2024

These are the steps to emotional expression as a Type 5:

• Accept the importance of emotions
• Increase emotional awareness
• Expand emotional vocabulary
• Address fears and barriers
• Start small, be patient

Follow these, and you’ll learn to express your emotions.

24/06/2024

Myth: Fives don’t enjoy socializing

Reality: We Fives can enjoy socializing immensely, especially when it involves meaningful conversations or revolves around our areas of interest.

We simply prefer depth over breadth in our social engagements.