Hello there, I’m starting my Obsidian journey… Actually, I have been deliberating since at least 2022 but I’m finally convinced that this is a good investment so I’ll be giving at least 2 weeks and probably 3 months experimentation (I’ll try daily connecting/prioritizing of thoughts). Any who… want to hear from you: What are the things you regret doing/learning (if unlearning is harder than learning, it makes sense to be cautious about what you learn!)… and also, what are the things you wish you have done or grasped earlier?
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I regret that I knew about Obsidian since its first releases, but joined only later.
Using Obsidian is a journey, because you work in function of personal knowledge management, this means Obsidian is just a tool and not the end goal in itself.
Also, there are no shortcuts, because only through failing you learn to improve what you really need vs what appeals you at first.
Also, you can use pkm to deal with your experience in very different ways, depending your profession and interests. Are you a “gardener” or “architect”, how do you treat your notes ?
Important to
- start with the basics, this would be to learn markdown.
- Second, to organize meaning with default tools, by studying other people’s vaults similar to your research and interests.
- Third, to expand with plugins, to refine your experience.
- Forth, a willingness to deepen pkm, this are the best “news” you can absorb to move forward.
Important guides are books about pkm. Example
It seems to me, often we like to collect data, but don’t work with data, but that’s crucial and our knowledge work:
- create projects,
- refine main information, use links to highlight important, branching references
- try to delete as much notes as possible to keep the best. Like in math: summarizing what matters
- put quick notes in a daily note,
- use properties to give your notes meaning
Take it easy and don’t try to force a perfect system to organize your vault unless you have already workflows you want to implement.
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I’d say take it easy, make it as simple as possible, and make it work for YOU.
Create a note. Start writing in it. Consider each line in a note as it’s own thing. Add some bullet points. Use tab to add indentations to structure your thoughts. Add some # Headings to add even more structure. Once you got something content, consider turning the heading into its [[own note]]. Add a #tag to your note. Repeat. But hey, that’s just how my brain works. See what works for you. But most of all: use it, instead of thinking how to use it. See what works for you. Make it work for you. Think what else you’d need, see if there are some plugins that do that. Have fun with it and consider it a tool, an extension of your brain. Check out how other’s do it, but don’t try to force your brain into someone else’s system. Do your thing to your own benefit
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my biggest mistake was not following my own rules and restrictions. i would change so many things impulsively. i would create new properties and tags whenever i wanted to. i would put some notes into folders for no particular reason.
doing this creates chaos very fast. you don’t even want to look at your vault. it’s like looking at a website designed by someone who hates their job.
and i solved this problem unintentionally. i created a templater script for my quick notes, which asks for “content”, “(note) type” and “subject”. i could only enter a single value for each property. i used this template very frequently. being limited to 3 properties was a little bit counter-productive, but my main problem was being too impulsive and it really helped me.
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I regret not having access to AI when I was setting up Obsidian. For example, the following Copilot prompt was especially helpful to improved my setup:
“Recommend an Obsidian taxonomy for me based on the book The Organized Mind by Daniel Levitin. Use properties to maximize the power of the Bases plugin.”
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1. Why I Switched from Evernote to Obsidian
I’m new to Obsidian too. I switched because I watched how others do knowledge management and realized Obsidian is better suited for the AI era—plus all files are stored locally, not in the cloud.
2. What I Regret Doing
I spent too much time talking with AI about design details instead of just starting to write a journal. After two weeks of using Obsidian, those details (like how to configure Templater) answered themselves.
I also wasted a lot of time downloading multiple local LLMs. To learn Obsidian, you just need to get one working first.
3. What I Did Right
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Watched different YouTubers introduce Obsidian and quickly grasped its essence: connections.
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Moved only about 20 active notes into Obsidian to learn the basics while using it.
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Kept asking myself “Why do I need knowledge management?” This step is crucial. The tool is just a tool; the core is my own goal: to express, share, and better see myself—essentially to externalize and train my second brain.
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Realized that Obsidian + flomo + Apple Keychain are enough to achieve my goal. So I decided to make “iterating my knowledge management with Obsidian” my first real AI project.
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Started designing a workflow and set small goals (see below).
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Saved each iteration version, which later automatically became a navigation guide for how to use this system with AI.
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My current Knowledge Management V3 is a personal system based on Obsidian, with five folders (
clippings,copilot,Archive-Past,Create-Present,Connect-Future) and five tags (#core,#archive,#active,#daily,#copilot-conversation). Core principles: MOC‑driven “map‑territory” separation, AI assistance, low decision cost, high scalability. Goals: store, create, connect—let the system drive action and help me see myself.
My five small milestones:
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Journal → AI reflection
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Reading notes → script generation
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Dashboard to see “orphan notes”
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Daily AI nudge (optional)
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Full workflow flywheel
Each takes 1‑2 hours to complete, and checking them off feels great.
4. What I Wish I Had Done Sooner
If I could start over, I’d tell myself:
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Write 10 journal entries first, then use Templater to auto‑fill dates. Needs emerge from using, not from tutorials.
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Start with one AI plugin, use an online API to get one small loop working (e.g., journal reflection), then think about local models. Otherwise you’ll get stuck in environment setup.
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Ask myself once a week: “Why am I doing this?” This question matters more than any plugin config—the end goal of knowledge management isn’t the tool, it’s seeing yourself.
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hello! I’m also new here and there answers people are posting here are wonderful! thanks 
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