A weekly practice in self-pursuit using AI, systems thinking, and conscious documentation.
what this is —
THE DAILY 5 is a self-guided reflection framework designed to help you understand the psychological and behavioral systems that govern your life. It’s not about becoming more productive. It’s not about optimization. It’s about clarity.
Each day, you’ll spend five minutes reflecting on a specific prompt designed to surface your internal programming—your habits, beliefs, contradictions, stress patterns, emotional defaults, inherited scripts, and more.
This is a practice in noticing.
Over time, these entries form a comprehensive baseline of how you actually operate. You’ll start to see what’s running automatically, what’s outdated, and where your patterns might be ready for re-examination. The goal is to build awareness, challenge assumptions, and stay curious about the structures that shape your life—especially the ones you’ve internalized without realizing it.
This is not performance. It’s pattern recognition.
And it’s where meaningful change begins.
what tools to use —
I keep forgetting that not everyone has spent months accidentally training an AI to recognize the particular cadence of their neuroses. When I mention the DAILY 5 practice, I sometimes gloss over the fact that there's actual setup involved—technical stuff that feels mundane but makes all the difference between having a conversation with a helpful tool and having a conversation with something that starts to feel almost... collaborative.
So let's start at the actual beginning. Before you can teach a machine to see you clearly, you need to configure it properly. Think of this as designing the container that will hold your thoughts, the digital space where you'll practice the ancient art of self-examination with a very modern thinking partner.
You’ll need an AI assistant that allows for memory, context retention, and conversational input. I recommend:
ChatGPT (OpenAI) — best for memory + flexibility
Claude (Anthropic) — best for tone, nuance, and longer contextual memory
Grok (𝕏) — not my primary tool, but usable for certain tasks
Pick whichever one you’re most comfortable with—or experiment. You can always export your entries between tools.
I bounce between two tools primarily: ChatGPT and Claude. Both have their quirks, their particular strengths, their ways of holding conversation that feel subtly different. ChatGPT tends to be more direct, sometimes almost eager to please in a way that can feel slightly performative. Claude feels more measured, more willing to sit with complexity without rushing to solutions. But honestly, the differences matter less than picking one and learning how it works.
If you’re interested in using the visual worksheets, you’ll also need to create a free Canva account if you don’t already have one.
how to configure your AI for reflective practice —
For ChatGPT (Pro):
Turn on memory:
Go to Settings → Personalization → Memory and enable it.
Customize your instructions:
Paste something like this into the Custom Instructions section:
“I’m using this chat for a daily self-reflection practice. I’m trying to build a clear, systems-level understanding of how I operate—my patterns, defaults, conditioning, emotional responses, and mental frameworks. I want you to challenge me when I’m vague or contradictory. Help me interrogate beliefs I take for granted. Don’t baby me—ask thoughtful, specific questions that push me deeper. I’m not here for motivational fluff or surface-level validation. I’m here to grow.”
First, you need to turn on memory. This isn't automatic—you have to enable it in settings. Without memory, every conversation starts from scratch, and you lose the cumulative understanding that makes this practice powerful. With memory enabled, ChatGPT starts to recognize your patterns, remember your context, build a model of how your mind works.
Then there are custom instructions, which are basically your chance to teach the AI how to talk to you. I've experimented with different approaches here, but what works best is being specific about your communication style. You can use what I provided above, or tailor it more specifically to your preferred communication style.
For Claude (Anthropic):
Create a dedicated Project called THE DAILY 5
Add project context using the same instructions above
Use one thread per week (or day, up to you), so Claude can track your evolution without getting cluttered
Claude handles things differently, through something called Projects. You can create a dedicated project just for your DAILY 5 practice, with its own custom instructions and knowledge base. I think of this as creating a private room where certain kinds of conversations can happen—more intimate, more consistent than the random chats you might have about work stuff or recipe modifications.
what to tell your AI each day (giving it context) —
Before sharing your daily entry, frame the conversation clearly. You’re not just journaling—you’re teaching your AI to track and reflect your internal systems. Here’s a simple framing prompt:
“This is part of a 12-week self-reflection series called The Daily 5. Each day, I’ll be exploring a different dimension of how I operate. I want you to gradually build an understanding of my patterns, contradictions, habits, and blind spots. Don’t jump to solutions. Just ask clarifying questions when something stands out or seems inconsistent.”
the art of conversation hygiene —
Here's something I learned the hard way: when to start a new chat versus when to continue an existing one. For Daily 5 entries, I tend to continue the same conversation for about a week, then start fresh. This gives the AI enough context to ask follow-up questions about yesterday's entry, but prevents the conversation from becoming unwieldy with too much history.
For specific projects or decisions I'm working through, I'll often start a dedicated chat that can span several days or weeks. The key is being intentional about it rather than just letting conversations sprawl randomly.
using the worksheets —
If you prefer visual structure or want a physical record of your process, I’ve created editable Canva templates that track your:
daily reflections
weekly summaries
monthly meta-analyses (optional)
You can duplicate the templates, fill them in digitally, or print them out.
Each worksheet is designed to help you feed structured insight back into your AI assistant—so you’re not just reflecting, but creating a feedback loop with memory.
As a paid subscriber, you get access to:
daily and weekly worksheets
monthly review templates
guided instructions for asking your AI to analyze your own patterns over time
Below are your Canva worksheet previews for Week 1. These three pages repeat daily—context, exploration, and archive. You can use them directly or just use the structure as inspiration. If you’re consistent, you’ll end the week with a surprisingly rich dataset on how you actually operate.
ready to begin??
Start with Week 1 → Day 1: Who Are You When No One’s Watching?
Week One is all about establishing your baseline. You’re not trying to fix anything. You’re not performing for insight. You’re documenting reality—exactly as it is, five minutes at a time.
What you build from here will depend on your willingness to be honest, observant, and curious.
What are you waiting for? Let’s begin. xo
