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Transcript

Your Notes App Is Failing You

Acquired Taste, Episode 3 — Notes, Obsidian, and LLM context

Your Notes App Has No Idea What It Is Anymore

What is a note?

Not a rhetorical question. Because if you look at your note-taking app right now, you’ll realize it can’t answer that question either.

Is it a journal? A file manager? A task list? A team wiki? A context layer for your AI?

The apps don’t know anymore.

In Episode 3 of Acquired Taste, we tear down the current state of note-taking apps and what it means for your workflow when your notes need to serve a new reader: your AI.


Notes Were Never the End of the Journey

Notes started as throwaway thought, like a digital sticky note. Something to capture before it slipped away, then toss.

Then Evernote showed up with a different pitch: put everything in here. We’ll remember it all. The logo was an elephant! Never forget.

We took that literally. Notes became life management systems. Meeting notes, medical records, recipes, tax returns, half-finished ideas, all in one place.

The problem was that Evernote thought its job was done once the note was inside. The information went in, and didn’t really go anywhere from there. Engagement was the metric, not the real job to be done.

But notes have always had a life beyond capture. The apps just stopped the journey there.


Three Ways Your Notes App Is Failing You

1. Data sovereignty

Do you own the data? When did you last actually trust these services with your personal information?

Google had enormous user trust 15 years ago. Evernote too. That trust eroded slowly, then all at once. Pricing changes, acquisitions, terms updates. Nobody reads the terms. But everyone notices when the rules change.

Putting your health records, financial notes, and personal journal into a cloud service means trusting they won’t change on you. That trust isn’t what it used to be.

2. Passive-aggressive data portability

Every one of these apps will tell you: you can export your data.

They’re not wrong. But exporting from Evernote or Google isn’t getting your data back. It’s getting a fossil of it. The metadata is stripped, the format is proprietary, and whatever you get back is basically unusable without a ton of manual cleanup.

Here’s your data. Good luck.

3. Your notes are useless as LLM context

This is the one that snuck up on everyone.

Notes used to matter because you would retrieve them. Now they also need to work as context for your AI. And almost nothing captured over the past decade is formatted for that.

Most of what’s in there is vague bullet points and half-finished thoughts. If you tried to dump your Evernote into Claude today, you’d spend more time curating than thinking.

The notebook is becoming the database of you. Most people’s databases are a mess.


The Product Teardown

Evernote — struggling to find its relevance

Evernote built something genuinely new. Then it spent a decade losing the thread.

At some point it added a calendar, a scratch pad that’s somehow different from a note, tasks, spaces. The product just kept accumulating surface area without a clear reason why.

There is no point of view in this product. It doesn’t know who it’s for. That’s not a design problem. It’s a strategy problem that became a design problem.

It’s software that is struggling to maintain its relevance. The core function: to get a note in, retrieve it later, act on it, got buried under a decade of feature creep.

Notion — a PhD in library sciences required

Notion was the legitimate heir to Evernote for a lot of people. It’s more powerful, more flexible, and honestly better-looking.

The problem: that flexibility has no opinion. Notion doesn’t tell you how to use it. That’s fine if you’re a librarian. It’s exhausting if you just want to capture an idea.

Every person using Notion eventually builds a system, forgets how they built it, and starts over. The power users love it. Everyone else gets lost.

At enterprise scale, it works. But even then you need a Notion administrator. That’s not a note-taking app, it an intranet.

And from an LLM perspective: there’s an MCP now, which is cool. But you’re still in the lock-in problem. If you ever need to leave, good luck getting your data out in a format that works anywhere.

The lowest friction wins. Always. David tried to migrate from Notion, couldn’t copy/paste a spreadsheet out of it, and ended up recreating it in Google Drive. The app with worse features won because it was easier.

Obsidian — just files

Obsidian is different in one fundamental way: it’s a text editor sitting on top of markdown files.

Your vault is a folder on your machine. Every note is a markdown file you can open in TextEdit, VS Code, Cursor, whatever you’re using that week. There’s no database underneath it, no proprietary format, nothing tying you to the app itself.

That sounds like a limitation, but it’s actually the strength.

Because they’re files, any AI tool can read them. Because they’re local, you control what gets shared. Because they’re markdown, they move cleanly between systems.

The tradeoff is real. Obsidian requires intentionality. There’s no frictionless “just dump it in” mode. The setup cost is real for non-developers.

But that friction is the right kind. Notes captured in Obsidian tend to be more structured, more useful as context, because the tool doesn’t let you be lazy about it.

The architecture became a superpower. Obsidian didn’t plan that. It just stayed simple while everyone else got complicated.


The Design Lessons

Jakob’s Law explains why people stay on bad tools.

Users prefer interfaces that work like the ones they already know. Evernote felt like a notes app, so people stayed. Notion felt like a more powerful Evernote, so people migrated.

The switching cost isn’t just migration. It’s the cognitive cost of relearning. Any tool that wants to replace Obsidian for mainstream users needs to feel familiar enough to feel safe.

The Doherty Threshold is why Apple Notes survives everything.

It opens in under 400ms. That’s it. That’s the whole product. Fast capture is the core UX contract for a notes app. If it makes you wait, you lose the thought. Speed isn’t a feature. For capture tools, it’s the product.

Friction as a feature is the Obsidian story in one sentence.

The apps that made it easiest to get notes in made it hardest to get value out. The app that requires structure at capture time gives you something actually useful later. The right amount of friction, in the right place, for the right reason.


What Comes Next

Notes were always a collaboration problem.

It started as a problem between you and your future self, then grew into a team coordination problem, and now it’s a problem between you and your AI.

None of the current tools are designed for that third collaboration. Evernote and Notion are trying to bring AI inside their walls. That’s the wrong move. Your notes represent you, and that context should move freely, not stay trapped in one platform.

Andrej Karpathy has been talking about LLM wikis: structured knowledge bases designed to feed AI context efficiently. That’s probably where this ends up. Obsidian is closest today, but it’s not productized for most people.

And paper? Paper isn’t going anywhere.

Write it down, take a photo, and let the AI handle the filing. In a world where everything feeds into a machine, having a space that doesn’t might be the most valuable thing you own.

About Us

Design Language is a newsletter for all product builders (PMs, Engineers, Founders, etc) who want to improve their design literacy, hone their sense of tase, and improve their craft when building products.

Jeremy Belcher is a 15 year product and design veteran. He has designed UX/UI for products used by tens of millions for brands like Google, Salesforce, Saturday Night Live, DirecTV, BMW, Emirates, Visa and in the past several years has focused on new enterprise workflow products. He runs the product studio Robot Heart, which designs, builds, and validates 0 → 1 B2B workflow tools for teams and founders.

David Issa is a digital strategy and product design leader with over 15 years of experience guiding companies through transformation. He has helped scale products and teams across healthcare, fintech, and enterprise software, translating complex systems into human-centered experiences. David runs a strategic design practice focused on aligning purpose, architecture, and execution—bridging design, AI, and organizational strategy to help teams build with clarity and intent.

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