Press Pause: Season 3, Episode 3
I’ve been wrestling with a question lately: Is Apple Notes actually the greatest notes app of all time?
My Journey Through Note-Taking Apps
There was a time when I used Apple Notes extensively, then left because of its lack of features. Here’s how I got back.
The Obsidian Era (2020-ish)
Around 2020, I read Building a Second Brain by Tiago Forte. That’s when Obsidian and note-linking caught my eye.
What pulled me in:
The graph view (though many now consider it just a meme)
Bi-directional linking capabilities
Markdown files stored locally
The reality:
I didn’t really care much about owning my own data at that point and markdown storage wasn’t the biggest driver for switching.
I spent tons of time manipulating Obsidian with plugins and Dataview to get it working how I wanted but iCloud syncing was slow.
I built up 700-800 notes in Obsidian over the years. I still use it to back up my Apple Notes.
Coming Back to Apple Notes
When Apple Notes added note-linking, I started thinking: Why am I not just using the first-party app that’s on all my devices?
The Forever Notes Framework (which came out after I migrated back) really helped. It showed me that Apple Notes could effectively do what Obsidian did:
Hubs and maps of content
Linked notes for making connections
Focus on learning, not just saving information
I’ve been using Apple Notes solidly for about 3 years now, since I started YouTube in June 2023.
The AI Integration Gap
The Biggest Downside
Here’s my main frustration with Apple Notes right now:
If I want AI help with writing or fleshing out an idea, I’m copying and pasting data into a different application.
What Notion AI offers:
All context built in
“Mega prompts” for specific workflows (titles, thumbnails, scripts)
Access to past examples and frameworks
Hope for the Future
I’m really hoping Apple nails the new Gemini integration with Apple Notes.
I want contextual awareness across my notes. The ability to point AI to specific folders or notes and personal assistant-level help identifying connections.
What I’m NOT looking for:
AI to do my thinking for me
Auto-generated scripts to read word-for-word
Replacement of my personal experiences and voice
What I AM looking for:
Reminders of ideas I’ve forgotten
Connections between stagnant notes
Prompts like “You already wrote about this” or “Here’s a relevant highlight from your Readwise”Subscribe now
The Free vs. Paid App Dilemma
I’ve been on a kick lately about paid subscriptions. Boy, do they add up.
My Evolution with Paid Apps
Early days (iPhone 6S Plus):
I was happy to pay $2-5 for apps and I had no problem supporting developers.
Now: I added up all my costs (more details coming soon) and I was shocked by the number.
The Notion Problem
Downsides of Notion:
It’s a paid tool
Online-only app
Not end-to-end encrypted
Focused on enterprise features now
The enterprise shift:
There’s always people on Reddit saying Notion’s become really bloated. It’s gotten slow (though they’ve worked on speed recently).
The issue: These companies have to constantly add features to bring in customers. When most revenue comes from enterprise, you get enterprise
features that solo users don’t need.
The Evernote Warning
We don’t really own anything anymore. Following the Evernote path shows us that companies can make decisions unfavorable to users.
People got locked into Evernote after 10+ years of use:
Still ridiculously expensive
Users with 10,000-15,000 notes feel trapped
They’re paying forever because migration is too painful
Data Ownership and Markdown
I’ve been thinking about the possibility of ownership. Is it even possible today, or just an illusion?
The Obsidian Advantage
What Obsidian does really well:
Access to all your files
Just a bunch of markdown files on your computer
Can self-host on your own server
Can sync via iCloud
About Markdown:
It’s 22 years old (I had to Google this)
At its core, it’s just plain text
Computers from 22 years ago can read plain text files
If you want your notes readable 20 years in the future, Markdown is a good bet
The Apple Subscription Concern
I feel like I’m going to be stuck paying Apple $50/month for the rest of my life:
Fitness
News
Apple One Premium plan
iCloud storage
Another monthly recurring cost that never ends.
The Creator Studio Question
Apple just released the Creator Studio subscription for:
Final Cut Pro
Logic Pro
Pages, Numbers, Keynote (with advanced features)
These apps stagnated because there was no revenue KPI tied to them. Now they’re subscription-based.
My conflict:
I’ve been vocal about wanting to pay for Apple Notes development.
But do I actually need that?
Apps like Bear Notes are only $30/year, but you’re still paying money to access your data.
The valid counterpoint: “Bill, you’re praising Apple Notes, but you have to buy Apple devices and be in the Apple ecosystem to use it.”
That’s true.
Recent Apple News
QAI Acquisition
Apple’s second-biggest acquisition:
$2 billion for AI startup QAI
Technology focused on audio content
For context: Beats was $3 billion
Shows Apple is getting serious about AI
Gemini Integration Updates
Coming in iOS 27 (Fall 2026):
Full chatbot experience (like Gemini or ChatGPT)
I did the betas last year, might do them again
Should be my upgrade year: 16 Pro to 18 Pro
This could be the year of AI for Apple.
The Anthropic Fumble
Mark Gurman reported on the Gemini deal:
It’s multi-year but not exclusive
Apple can still work with other AI companies
Anthropic reportedly wanted too much money
Apple said “screw you guys” and went to Google
My thoughts on this:
I’ve been a big fan of Claude
Anthropic’s mission and values aligned better with my preferences than OpenAI
But they apparently fumbled a huge opportunity
At some point, AI companies will need to become profitable
Did we just witness the downfall of Anthropic?
Shared Features Coming Up
I’ve finally started using Apple Notes’ shared features for this podcast. I’ll be collaborating with guests starting next episode.
What I’ll be evaluating:
Comparison to Craft and Notion for shared documents
What I like and don’t like
First impressions of the collaboration tools
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Where to find me:
Thanks for reading. Until next time, later!
P.S. If you wanted to see the full episode here it is!