From Apple Notes to Obsidian

Building a Learning System That Lasts

I’m finally doing it. I’m documenting my personal development projects with some assistance from AI. School may be behind me, but the desire to keep learning isn’t. Now, it’s about finding and utilizing the tools that will aid in continual growth.

Enter: Obsidian

I recently learned about Obsidian from a friend who sent my husband and I one of those “Learn Obsidian in 15 Minutes” YouTube tutorials. It was…overwhelming, to say the least. And yet, that overwhelm led to curiosity. I wanted to figure out how this markdown-based “second brain” could actually fit into my life.

To cut through the noise, I asked Claude for a blank-slate assessment: What is Obsidian actually for? The answer was both inspiring and paralyzing. Knowledge management, fiction writing, project management, recipe collections, D&D campaigns, legal research—the list seemed endless. I fixated on the book notes feature (a nudge to restart my reading habit beyond the occasional fiction novel binge), but I also saw potential for research and study workflows that go beyond my current Apple Notes setup.

The Real Challenge: Understanding vs. Memorizing

Here’s the truth: I’ve been a “repetition learner” my whole life. Drill, memorize, repeat. It works for tests, but the knowledge rarely sticks in a way I can use. What I’m hoping Obsidian offers isn’t just better organization, but a structural shift toward understanding. The linked notes, the visual graph of connections, the atomic nature of the ideas—I’m hoping these features force me to process information deeply rather than simply store it.

I already know this transition won’t be seamless. I’m comfortable with Apple Notes. It’s accessible and it’s familiar. Moving to Obsidian means stretching my brain around new workflows, new syntax, and the paradox of choice that comes with 1,500+ plugins. So, what’ll be my strategy? Start embarrassingly small. I’ll run it locally first (skipping the sync subscription until I’m committed), pick one low-stakes use case, and resist the urge to build a perfect system on day one.

AI as a Thinking Partner, Not a Crutch

Where does AI fit in? It definitely won’t be a replacement for the work, but it’ll act as a guide through the confusion. When I’m stuck on a feature or can’t visualize how to execute a specific workflow, I’ll use Claude to troubleshoot. The key is resisting the temptation to let AI do the learning for me. Frankly, my attention span is beginning to resemble that of a goldfish, which is why I want to rebuild the discipline of sitting with complexity—reading, internalizing, and then acting.

I’m also using the VoicePal app to record my thoughts and capture the raw, stream-of-consciousness reflections, which I will then share in this newsletter.

Systems Over Motivation

Motivation is fleeting, but discipline is more likely to result in consistency. So, I’m building systems I can maintain when the initial excitement fades. That means regular check-ins, documented milestones, and permission to be human when the “limitless capabilities” of Obsidian feel more intimidating than exciting.

I’ll be sharing updates as I install, poke around, and inevitably break things. If you’re also trying to build a learning system that prioritizes depth over speed, I’d love to hear how you’re doing it.