A little over a year ago, as our second pregnancy was coming into its final stages, I realized that my current process for working and tracking my thoughts and general note-taking was not going to survive two children under 2.5 years of age. Candidly, I was ready to declare process bankruptcy well before a second kid was on the horizon.
I started looking at frameworks, systems, tools, and all the above to try to think about how to build a more robust way to track my notes.
The main substrate I went with was Forever✱Notes -- a pattern for organizing and using Apple Notes (though you can replicate it with any other tool that supports cross-note linking and tags like Obsidian, Evernote, or others) with a few niceties around building the initial framework and using a special character, the Heavy Asterisk, as an anchor point for search and indexing.
However, over the past year -- literally 365 days at the time of writing this draft -- I've been loosely extending this system with a number of tools and techniques. Before I get too deep into the broad use case and the deep dive, I'll list all the tools that go into my note-taking process, which has since expanded into building a broader "second brain."
The tool list (may include referral links)
As I mentioned at the top, our family was expanding from one small child to two. Looking back, when our first kid arrived, I didn't plan how to adjust my work style and operating cadence to the changing family dynamic. I was wildly caught off guard -- a topic of a different post. Building on past experiences, I conducted a thorough review of the nuances in my work and personal life that would need to evolve as we welcomed a second little one into the family.
Previously, I was a huge believer in exclusively handwritten notes in a well-organized notebook. Specifically, a LEUCHTTURM1917 notebook with square-grid pages. Beauty. Simplicity. Amazing materials. The perfect notebook for me. At the end of every day, I would rewrite each of my notes into a cleaner format, summarizing them. At the end of each week, I would perform the same collation and convert it to a digital format (slides for async review with managers). Then, at the end of the month, I could take the collated digital weekly notes and very quickly build a high-level summary cross-referencing these items against larger quarterly and annual projects to assess how I was doing.
It worked well before my family obligations reduced my idle time. Given my current focus constraints, I can't consistently set aside 45+ minutes a day to summarize handwritten notes and produce weekly and monthly summaries.
Enter Apple Notes. I know going too hard into one ecosystem has its risks and trade-offs, but I've been in the Apple hardware and iMessage ecosystems for a very long time. The appeal of software that "just worked" across my computer, my phone, an iPad, and anything else I needed, including the ability to share notes with family within the ecosystem, was interesting. However, random one-off notes in tools like Apple Notes, Evernote, or others have never really been my jam. I need a structure. I do really well with chronology, hence my love of notebooks that are by design linear. In many ways, Apple Notes is underpowered and offers fewer formatting features than other options. I encounter these limits regularly, but working within these constraints for a year has enforced consistency and discipline that are important for building habits. That might be me spinning the best of an annoying situation, but limitations have upsides sometimes.
Enter Forever✱Notes. I won't break down the broader aspects of the framework here. Their website is elegant, simple, and straightforward, and if it resonates within the first five to ten minutes of browsing, you're going to love it. If it doesn't, move on. But a few of the things that really stood out to me that became anchors of my organization system are:
The key theme here is flexibility, extensibility, and adaptability. Calling Forever✱Notes a "framework" is a bit of a misnomer in that it's so loosely structured that everyone's implementation is going to look different, and that's the beauty of it. It's a framework in the programming sense of the term.
Anyway, I stood it up, and I started using it while on paternity leave. It worked. It was easy. It required minimal maintenance and did everything I needed it to.
You know a new system is working when you start finding ways to extend, improve, and do more with it, rather than feeling an urge to completely blow it all away. That happened with this process pretty quickly, which was exciting.
As I mentioned at the start, I'd already been using Grammarly for quite some time, based on recommendations from past bosses and mentors. I've always considered myself a competent writer, and I've been proud of my communication for a long time, but Grammarly catches things I miss, and as I've gotten more distracted and busier, it catches more mistakes. It's simply the spell-checker that should always exist on Mac (or your OS of choice). Grammarly works out of the box with Apple Notes on Mac, so that was an immediate augmentation win.
The next challenge was the inability to type while wearing a small sleeping baby. Neither of my kids were able to sleep well on their own as newborns. I often wore a chest carrier for extended periods of the day while walking around to soothe them as my wife got some rest.
Typing anything for an extended period with your thumbs on a phone keyboard is terrible for me, mentally and physically. So I started experimenting with Siri's voice-to-text. However, Siri leaves a lot to be desired, and I found myself correcting it more often than not. It's gotten a little bit better over the past year, but it still leaves a lot to be desired. That's probably on my list of the biggest unforced errors that Apple has ever made.
I'd been searching for a better mobile voice dictation tool for quite a long time, and it may have been through an episode of Lenny's Podcast that I heard about Wispr Flow. Wispr Flow is the integrated voice dictation tool that you've always wanted. It started as a desktop tool for coding by voice, but when they released a mobile option a few weeks into this note program, I tried to get access as quickly as possible to test it. Once I tried it, it was immediately apparent how much better it was than Siri.
On desktop, you have mapped hot keys to quickly toggle a mic or flip a mic switch for longer conversations. On iOS, it functions like an installed keyboard, so you can use it in all the apps on your phone.
Most importantly, it's called Wispr Flow because you don't need to speak loudly; you can literally whisper into the mic, and it's still accurate.
While on paternity leave, I was able to walk while keeping my son asleep and dictate long passages (blogs, ideas, plans, shopping lists) into note files within the Forever✱Notes framework. I could then go back to those notes on an iPad or my desktop later, use Grammarly to clean up some of my initial thoughts, and then make my final edits to bring them to fruition.
This was the tool stack for quite a long time. At least three-fourths of the year was really this, just really good capture tools, really good organizational structure, good clean-up tools, and freeing me to do the final editing and thinking, ie: the fun parts.
I want to be really clear here that I don't put literally everything, every conversation, or every item into this stack of tools.
There are many components that touch a lot of information in this workflow. Generally, anything related to one-on-ones or sensitive issues, I don't put into this system from a best-practices standpoint. This is where good old-fashioned pen and paper still shines, and I use pen and paper every single day.
It's still the best way for me to think things through concretely. And if I'm on a call with others, I don't want to be switching between apps and typing. I would rather have a screen fully focused on the people that I'm speaking with, or my attention fully focused on the people in the room, which is really the point of all of this. I want to be as present and effective as possible with the people I am with in a given moment.
I'll then go back and digest those paper notes and put them into this tracking system in a way that keeps the information as hygienic as possible.
A mouse in a note-taking system? What the heck is going on here? This was a real unintentional win, but it's become a big part of how I use this system. Logitech makes great peripherals, and I've been wanting to upgrade my mouse for a while, so I got the MX Master mouse. This mouse has different click wheels, forward and back buttons, an app switcher, and typical features you would see in a productivity mouse. It has a haptic "app menu" action button that can be configured to perform different actions across different software. When I got it, I thought it would be interesting to do more with video editing software or use Zoom. In reality, the off-the-shelf functionality hasn't been super useful, so I just haven't used it for anything.
However, Wispr Flow produced some content about remapping this specific mouse's action button to be a dictation toggle. I'll link to how that works here. But what it means is that when I'm working on a desktop, I can very quickly switch on voice-to-text in a way I really couldn't before. This means I can very quickly add comments to docs I'm reviewing, rattle off quick replies to Slack messages, or walk through my thinking while note-taking, all more easily than before. It's a very nice friction reducer, and I want to call out that. This whole workflow is software and hardware.
Now that I've been back at work for several months after paternity leave, I actually do much less long dictation and more of these quick little one- or two-sentence comments to get the ball rolling. Then I'll take over with typing.
Adding the mouse example above didn't noticeably change how I used this note-taking system. It's just an easier way to tap into it, more of an incremental approach than anything. Though still a delightful win. About a month or two ago, I uncovered something in the way that our various business tools work that did feel like it was the next evolution and turning this broader framework into more of an "AI-streamlined second brain", if you will.
It really started with just a jokey icebreaker our leadership team did at an offsite, which I heard about later. Somebody said that you could go ask Slackbot what your animal avatar is based on your Slack activity (or your Pokémon avatar, or your Drag Race avatar, or your sandwich avatar). It's a fun, silly little icebreaker, and we are a Slack-heavy company, so there's a lot of data to work from.
I got "border collie" because: I'm doing many projects in parallel, try to be positive, and work hard to move things forward. It is legitimately a fun thing to do with your co-workers to see what they get and how accurate it is. It's just that sometimes these silly little things can make your day -- try it!
When I was reviewing the summary, I realized that Slackbot could pull in DMs, files, shared channel activity, and app notifications -- really anything that pushes into the tool. And a LOT pushes in -- Google Calendar, JIRA, Salesforce, Google Drive, GitHub. So many integrations.
That's when I started asking Slackbot to give me weekly summaries of my week, activities in the context of broader goals, and action items based on the data that it has. That's been super helpful. I'm asking other tools to do this too, though they rarely have as comprehensive a picture of my workweek as something like Slack does, with all the adjacent applications integrated.
Those outputs, after some heavy sanitization, have become a building block for my weekly summaries, so I am not starting from scratch every Friday, which is super helpful given my limited focus time.
This is also where MCP comes in. If you're reading this post and you've gotten this far, I'm going to assume you know what MCP is and what it can do. If not: it's a way for systems to interact with each other in a structured manner.
Claude (my preferred LLM tool at the moment, though I use several) has a great MCP integration to Apple Notes via Claude Cowork. So, every week or month, I can ask the system questions similar to the ones I'd ask Slackbot in the example above. "Summarize broad themes, activities, and action items in the context of ongoing projects." Also, since I put personal journals into these notes, it can do the same thing for home projects or family goals.
Most importantly, because of the Forever✱Notes framework (to loop it all back to the original source), the MCP scan can very quickly and efficiently comb through the daily notes and provide more useful summaries than if they were truly free-form gibberish.
From this point forward, the notetaking process evolved into more than "notes" -- it's taken the shape of a structured information corpus, with notes as the primary use case. I realize that sounds deeply uncanny and too much like the tech echo chamber, and there might be a better way to describe the shift. But it's definitely different from a mindset perspective.
Now that I have tools that summarize and analyze the content that goes into the notes corpus, I'm putting more stuff into it. Obviously, this is again a call for common sense and sanitization. That is still deeply, deeply important here, but now that machines are reviewing some of this content (and not just me, the human), I can add more context to these notes for future analysis. I still will write hand notes and put top-level submarine bullets for my own review and reading. If there are deep contextual nuances or details that emerge in Zoom transcripts/summarizations or other communications that are important to include in these reviews, I'll put them in the body or in the corpus for later analysis.
For now, the system works, and I've been using it consistently for a year with incremental evolutions. Week in, week out, it doesn't seem like much changes, but after a year of using this, it's gone from a note-taking process to a borderline second brain, with all the augmentation and information it entails. That frees me up to think more about the future, do more planning, conduct smarter analysis, and use more concrete information when making decisions and working on strategic projects.
I can't predict where this will be in another year, but it's fun to work on this machinery over time.
Some quick thoughts on things that I've reviewed and not implemented (or implemented very slowly):
It seems like all my friends are using Obsidian or switching from Apple Notes to it. It's extremely cool, and I think if I were starting from scratch, I would give it an honest try. But I want to move slowly and thoughtfully with something as big as a platform migration. Plus, I would have to pay for a lot of features I get for free with Apple Notes, namely multi-device sync. I will continue to watch Obsidian, and I may move, but I'm not planning to migrate for novelty alone.
Collections and Hubs are just fancy names for nested linked lists within the framework. I avoided using these heavily at the start because it's so easy to over-engineer complexity within a note-taking framework. There are a few things I'd probably explore a bit more in the coming year, specifically around professional segmentation from personal notes, though I do this lightly with just a really long home note. I'd also do this to break out larger and ongoing projects, but it's too easy to add unnecessary complexity with a note-taking framework, and moving slower is better here.
Tagging within notes took me a long time to get right, and I finally have a system that fits my mind well. The hang-ups are almost always around naming conventions.
The plus about notetaking tagging systems and the search tools within Apple Notes is that I can search for specific text in the past to attach new notes, and I can alter tags all at once when I come up with new naming conventions.
The list I walked through earlier feels like a lot, but each one was thoughtfully and intentionally integrated in after deep consideration. And almost none of them were preplanned decisions for the future. It was more about quickly spotting a potential winning addition, then thinking it through slowly. So I can't predict which tools or add-ons might be included in the future. If it continued in its current form, it would still be valuable. Candidly, if the original implementation from 365 days ago was the only implementation that would be valuable -- it didn't need "more stuff" to be good.
The system is good for me and probably no one else.
I mean that in a slightly tongue-in-cheek way, but these days it feels like everyone wants to whole-cloth implement another person's process for building and doing things. I don't think that's the right mindset at all. I think all of us are unique and contain multitudes, and need a wide set of tools and techniques to help our own brains and bodies be their best selves.
I wrote an extensive breakdown of my thinking and exploration because the mindset behind building this ecosystem is worth documenting. If that can help anybody else do the introspection and evaluation of which tools are useful for improving their own lives, that's great!
If you do think this would be useful and you'd like to chat more, I love talking about craft and work styles and all of these wonky, somewhat dorky things, so please reach out.
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