Setting up a 'Personal Learning OS'

I have spent way too much time trialling different tools and platforms to find a good balance of how to ingest, manage, recall and enjoy interesting content. A few people have asked how I have set things up, so after a lot of trial and error, here is where I have landed (so far).

Basic Set-up

I use Instapaper and Kindle as my primary reading tools. Everything on the web worth remembering I save to Instapaper and I do almost all my reading on Kindle. I use Castro for podcasts.

I highlight passages extensively, trying to focus on only the most salient and essential parts that I want to be able to reference in the future or remember. Over time I have begun to highlight less and less from each source, being a bit more judicious in an effort to increase the signal to noise ratio of these reference passages.

Both Kindle and Instapaper highlights can be synced through the amazing aggregator platform Readwise. I have Readwise set-up to email me daily with a collection of highlights from all of the books and articles I have ever read. (You can fine-tune the settings to increase or decrease the frequency for each book or article)

This set up gives you a light form of ‘spaced repetition’ learning which I find incredibly helpful in retaining information. It’s also surprising how much things I forget over time. The daily reminders help keep it at the forefront of the mind and I enjoy the serendipity of discovering passages that would have completely been lost in the ether.

Of course, all of this only matters if you find good source material to begin with. For me, the best conduit is Twitter, which I work constantly on curating and pruning to ensure a steady stream of interesting things. If edited properly, Twitter can be an incredible tool for collecting information across a wide spectrum of perspectives and viewpoints. It takes work to maintain, but it is endlessly powerful if you stick with it. (I also block a lot of terms that I don’t want to be distracted by. Politicians, news events, the TV show of the moment etc. I love pop culture, but I try and keep Twitter as pure as possible and get that ‘fix’ elsewhere)

Lately, I have also gotten into deep reading into certain “non-book” sources that catch my eye. For me, this was reading all of Howard Mark’s memos and working my way through all 24 years of Berkshire Hathaway’s annual reports. In this incredible essay, Peter Kauffman read through the entirety of Discover magazine’s cover stories to learn how the top scientists were thinking about their field.

For long-form reading, I like to read many books concurrently. I just find it easier to pick up certain types of book at different times. Meatier reads require more focus and attention, while some books I can read anywhere, so I like to have a bunch of books on the go at one time.

For podcasts, I use Castro because you can prioritize and favourite episodes, and most importantly, save excerpts of podcasts and share or save those snippets. It’s also a joy to use.

Additional Tips

  1. Batch read your Instapaper queue. Most things are not time sensitive, and you are better off reading when you are away from distractions and have time to digest. This is also a helpful curation tool, because after a few days you might find certain articles just don’t look as interesting. I usually do this in the morning.
  2. Read all books on Kindle. It took me a while to adjust to this, but I have now fully converted because of the ability to highlight key passages for retrieval later.
  3. Be sure to install Instapaper on all devices and edit your Share Sheets If you are an iOS user, you can edit your Share Sheet settings to make sure the Instapaper is in the in the “Top 5” items. I prefer Instapaper over Pocket because of its highlighting ability and syncing with Readwise.
  4. Categorize your Instapaper for easy reference If I read a particularly great article, I add it to a defined folder in Instapaper for reference later. This can be really helpful when someone is looking for information on a topic (ie Marketplaces). I just send all the links directly from the folder.
  5. User the Search in Instapaper and Kindle Highlights You can search both platforms for keywords and search terms. This can be hugely helpful when trying to dig up a key concept or idea.
  6. Prune your sources Don’t be afraid to unfollow people or unsubscribe from that podcast. Be your own editor — the content stream is too big and the good stuff can get lost in the algorithms. Filter aggressively.

A step further…

This won’t be of any interest for some of you, so read on at your own peril.

After getting hooked on Readwise emails, I decided to utilize
Anki to act as a secondary tool to better retain specific quotes, ideas and concepts that I want to really know well. Anki is essentially a digital flashcard system, where you can test your knowledge by creating custom cards and reviewing them.

When I hear or read something interesting, I create a card in Anki and review them every few days. I have the app on my home screen and use “found time” to do a quick review. I was skeptical if this would work over the long term (or if I would stick with it) but I have found it to be really addicting and a powerful tool.

After diving into the Building a Second Brain system a year ago, I still use a modified form of Tiago’s system for Evernote to capture broader business concepts and reference information I categorize key concepts (ie things like Anecdotes, Product Pricing, etc). When I read something that has significant ‘evergreen” value, I add it to the Evernote Note on the topic so it is indexable and easy to find if I need it.

Hope this helps, would love to know your system and how it changed over time.