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Roxine’s 12 Favourite Questions

You have to keep a dozen of your favourite problems constantly present in your mind, although by and large they will lay in a dormant state. Every time you hear or red a new trick or a new result, test it against each of your twelve problems to see whether it helps. Every once in a while there will be a hit, and people will say, “How did he do it? He must be a genius!”
— Richard Feynmann

My brain has two modes: the conscious “frying pan” of my attention and the unconscious “slow cooker” of my subconscious.

Day-to-day, my attention is in frying pan mode. It’s sharply focused on what what I need to get done for the day. Banging out words. Checking off tasks.

But I’m also learning to let my subconscious stew creative problems in the back burner. I pay attention to what I pay attention to. I save resources, notes, and ideas for some future time. I let large, non-urgent projects sit idle for days, weeks, or months. I slowly adding resources and thoughts to them as they come, until the moment I’m ready to activate them. And put them on the frying pan.

This list of questions are the big-picture slow-cooker questions that have haunted me for years.

These questions let me focus on my values and my priorities. These questions categorize virtually everything that interests me. Having everything in one list lets me me prioritize and sequence projects, get an overview of the areas of my life, and remind myself of the topics that I deeply care about. It’s the litmus test to see if a project is something I really want to do or something I just feel obligated to do.

These questions let me go deep without forgetting the big picture. I might go deep into a rabbit hole. Or obsess about a new skill. Or take a course. This list makes sure I can focus deeply without forgetting the over-arching question I’m trying to answer.

These questions remind me to focus on solving problems. It’s easy for me to get into the mindset of “I’ll be happy if…” This list reminds me that no decision will ever be problem-free. Ultimately, this list reminds me that a free life isn’t about avoiding problems. That freedom is being able to pick which problems I want to have in life.

Here are my 12 favourite problems, in no particular order:

  1. What does it mean to be a Christian who has a tender heart and a theological backbone of steel?
  2. What does it mean to be “in the world, but not of the world”?
  3. How do I build a humane, people-first business empire, as Paul Jarvis and Dale Partridge call it? I want a business that blesses my employees and customers, a business that I would want to work for.
  4. What does it look like to master marketing in a way that prioritizes the receiver of the marketing messages, marketing that is based on fundamental principles, rather than time- and tech-sensitive strategies and tactics?
  5. What does agape love – to fully love someone – look like?
  6. Why can’t non-profit organizations — like churches — function more like profitable, for-purpose businesses?
  7. What does wealth look like/mean for me?
  8. How do I build wealth my way?
  9. What does it look like when I stop trying to please everyone and worrying about what other people think?
  10. What are the problems I want to solve and can best solve in the world?
  11. What would happen if I applied my experience in competitive swimming to ultimate frisbee?
  12. What does my best look like as an athlete?

How to publish a weekly newsletter in 4 hours or less (Building a Second Brain case study)

A quick conversation with other newsletter creators reveal that most of them spend about 5-8 hours on their weekly newsletters each week.

Thanks to Building a Second Brain, I’ve cut that time down to 4 pain-free hours maximum.

Here are a couple of notes on my process before we get into the walkthoughs:

I like to split each part up into different days. I tend to start my Monday newsletter on Friday mornings, Saturday mornings, or Sunday mornings. Specifically, curating and outlining are ideally done on Friday morning, and the actual writing done on Saturday morning or Monday morning.

My weekly newsletter is the culmination of my weekly review. I bake the curation process of my newsletter into my weekly review checklist. It’s a way for me to regularly practice going through the Building a Second Brain process:

  • When I curate, I progressively summarize the resources I might want to share.
  • When I write about the resources, I get into Level 4 and 5 of progressive summarization — sharing my thoughts and remixing them into my newsletter.
  • When I work on my newsletter, I practice slow-cooking, project planning, and project completion every week. I accelerate the feedback loop of my second brain system. I achieve unconscious competence in using my second brain faster.


Finally, like my previous Building a Second Brain post,the actual walkthroughs are in the videos. This article will just fill in the details.

Part 1: Headache-Free Curation (~30 min. - 1.5 hours)

Evernote is where 90% of my newsletter curation happens because that’s where most of my resources are stored. But some weeks, I capture tools or action items in my Things 3 project for that newsletter. So I make sure to check that, too.

A step that I didn’t show in the video is what I do after I put my notes outline together. Before I add them to the Markdown template, I progressively summarize notes I want to share. I read through each note in my outline, bold items that catch my eye, and highlight items that are already bolded to emphasize them even more.

By doing this step, I only progressively summarize the notes that I already find interesting. I don’t waste any time on notes that I wouldn’t even consider adding to my newsletter.

Instead of moving notes over to the newsletter project folder, I add a table of contents note. This way, the resource notes stay in their topical containers, and are more easily searchable and reusable for future projects.

Finally, when I paste the Markdown outline to Ulysses, I don’t stop the session there. I like to fix the links and make sure they’re all in Markdown formatting. Maybe write the first paragraph or a few points under each recommendation. This greases the wheels and makes it easier for me to just write in the next session.

Part 2: Pain-Free Writing and Editing (~2 hours)

It’s all downhill after the thorough setup in the first section. All the logic — my resources, links, quotes, and recommendations — are ready to be turned into language.

(Tip: I type “TK” for parts I need to fill in with photos or a link. Many writers and bloggers use “TK” to mark up document edits because it’s rare to find those two letters together. On ConvertKit, I do a search for all the “TK” bits in my writing, which usually mean to add a link or drag in a photo from Ulysses. Ironically “ConvertKit”, the name of my email service provider, is one of the few words that has it.)

I really like writing in Ulysses because it removes many of the barriers between writing and publishing:

  • Writing in Markdown means my fingers don’t have to leave my keyboard.
  • Copying the Markdown as HTML (without annoying spanstyles!) means I don’t need a render window. All my formatting appears in ConvertKit exactly how I visualized it in Ulysses.

After editing, I’m usually good to go and I hit “Publish”.

In-Depth: How to Edit Quickly (but Suprisingly Thoroughly)

This is how I’ve edited every academic essay, research paper, article, newsletter, and email for the past 5-8 years. Hat tip to Cal Newport.

  1. Read for arguments. I read through my writing and try to spot any janky transitions and vague language. I do this on Ulysses because this pass creates the most changes in the document. After this pass, I export my Markdown to HTML and paste it into ConvertKit’s HTML editor.
  2. Read it through, out loud. Pasting clean HTML means I don’t have to worry about formatting the email in ConvertKit. I can focus on editing my work in a fresh environment, increasing the chance I’ll spot typos. And yes, I silently mouth each word when I do this edit — this really tests for rhythm and flow, regardless of grammatical correctness.
  3. Just read. I send myself a test email on desktop, mobile, or tablet and I read to experience my work the way my reader would. If I spot any mistakes, I make a note and change after I finish reading.

Even with my 500 - 1,000 word emails, this editing process takes 10 - 30 minutes and catches 99% of mistakes.

Part 3: How to deal with recurring projects in Building a Second Brain and P.A.R.A.

TL;DW I have an Area for each specific recurring project. I create a new project each occurrence of that recurring project.This was probably the biggest undocumented BASB/PARA problem that I’m proud to solve.

I don’t run through a comprehensive project completion checklist yet. I’m working on it. For now, the only thing I do after a project is start the next project as soon as I finish a one to maintain momentum (a.k.a. daisy-chaining or chainsmoking. H/T Austin Kleon).

Finally, I want to emphasize that the Evernote project for each newsletter only gets created after the Things 3 project is created. This rule respects my Things dashboard as my master projects list where all the other software’s project lists are synced to.

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How to Use Readwise to Get Notes and Highlights into Evernote

For an updated version of this article, check out this post: “How to Use Readwise to Get Notes and Highlights into Evernote”.

My main capture workflow is Hypothes.is/Instapaper/Twitter -> Readwise -> Evernote.

Thanks to Readwise after I highlight something or add a note, they automatically go into my Evernote’s “Readwise” notebook. From there I can move notes into other notebooks and they would still sync with any future updates and highlights.

Note that you’ll need a Readwise Full membership ($8/month) to unlock Evernote sync and tags/notes.

I outline my capture workflow in this video:

This post is a companion to that video. I’ll also talk about other methods I didn’t cover in the video like:

  • Mobile uploads/scans for physical books with Readwise app (beta)
  • When I use Hypothes.is vs Instapaper.
  • My read-it-later workflow for PDFs

Physical books and notes

For physical books, I’ve tried CSV bulk imports and the Readwise app’s scanning feature. As of this writing, I prefer CSV imports for physical books.Typing into a CSV is faster (for now).

Method 1: CSV Import

You can import a CSV of your notes through Readwise’s bulk import method.

Here’s the CSV I used for my Great by Choice notes.

The highlights field is the only requirement, but I’d recommend adding a Title and the URL for articles.

You can have multiple books and articles in each CSV. You don’t have to do a new import for each article or book.

The bulk import also works for podcast notes, video notes, etc. Basically any text notes that you can type in a CSV spreadsheet. (Personally, I don’t bother. I type in-the-moment thoughts and notes on Drafts then export them to Evernote.)

Method 2: The Mobile App

I didn’t cover this in the video.

With the Readwise app (still in beta), you can take a photo of the page or book. The optical character recognition within Readwise lets you highlight the passage you want to save.

I haven’t used this feature as much as I’d like to. I tend to highlight multiple passages in a page and as of this writing, I would need to take for each highlight I have on that page.

Online Articles & PDFs

Instapaper is for articles that I want to read later - mostly, non-work related articles - while Hypothes.is is for articles and PDFs that I read as I find them.

Method 1: Hypothes.is

Hypothes.is great for articles and PDFs. I don't use Hypothesi.is to collaborate with others.

I've tried LINER and Highly (RIP). Hypothes.is is better because it lets you annotate each highlight and it lets you annotate PDFs. This lets you use Readwise’s tagging syntax to identify headings (.h1, .h2, and .h3) and concatenate highlights (.c1, .c2, .c3 …).

You can’t do PDFs or annotations with any other highlighting tool (that I know of).

The only thing with Hypothes.is right now is that it’s pretty clunky. You need to log in for every new page you want to highlight. When you delete a comment, Hypothes.is also automatically scrolls the entire page up. But if you’re talking about the fundamentals - getting highlights and notes into Readwise - it’s perfect.

Method 2: Instapaper/Pocket

For articles I want to read in bulk or offline, I use Instapaper. Like all the other apps, any highlights and notes go into Readwise then Evernote. And like Hypothes.is, Readwise’s tagging syntax works, too!

Note that you’ll need Instapaper Premium ($3/month) to make more than 3 highlights per article. Pocket, I think, has unlimited highlights free (and integrates with Readwise, too). I’ve used both but I just like Instapaper better.

What about PDFs for later?

For PDFs that I want to read later, I AirDrop them to my iPad, read + annotate them on Good Notes 5 (I have an Apple Pen), then get the notes into Readwise following the physical books method.


If you bought the book from Amazon, highlights from Kindle eReaders sync automatically to Readwise. If it’s a personal document (PDF, mobi, etc) , you’ll have to manually connect your Kindle to your computer, search for the file that called “MyClippings.txt”, and manually upload it.

For ePubs (not compatible with Kindle), I’d use iBooks, although I haven’t explored this integration yet. The Readwise guys also have a Kobo integration in the works.

What about the Kindle app for mobile?

As far as I know, the Kindle mobile app for Android, iOS, and macOS only syncs Amazon-bought books. Not personal documents.

I haven’t found a way to get PDF highlights from my iPad Kindle app to Readwise. I’m hoping that converting those PDFs to ePub and reading with Apple’s iBooks will automatically get my highlights into Readwise.

In the meantime, I read and markup PDF in my iPad’s Good Notes 5 app. When I’m done, I follow the physical books method to get my highlights into Readwise/Evernote.


There’s 2 ways to save tweets to Readwise:

  1. Reply “@readwiseio save” to the tweet. Kinda like the Unroll app.
  2. DM the tweet to @readwise.io. (I prefer this latter method because it’s less intrusive.)

For threads or tweetstorms, I don’t think you can do the less-intrusive DM method. You’ll have to reply “@readwiseio save thread” to the last tweet in the thread.

More Info

If you want more details on how tagging works in Readwise (I use this a lot), check out these guides from Readwise:

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Why I’m Still Using Evernote

In the past few months I've gone through almost every note-taking app out there. I also wrote this article for College Info Geek a while back. But since then, my criteria for a note-taking app has changed.

It's not just about the writing experiece anymore. It's about personal knowledge management. In this post, I'll be using the 3-step personal knowledge management framework that Tiago Forte lays out in his Building a Second Brain course to outline how I use Evernote's features.

  1. Capture - how easy is it to get things into Evernote?
  2. Organize - how easy is it to make sense of the things I add to Evernote?
  3. Share - how easy is it to pull my knowledge together, remix them, and push them out to the world?

This post isn't meant to be a thorough review of all the possible Evernote alternatives out there. I just tested the apps that are supposed to give me features and functionality that Evernote doesn't:

  • Drafts
  • Roam Research
  • Bear
  • Notion
  • GoodNotes
  • Ulysses

Here's how I use Evernote.

Evernote for capture

My favourite Evernote feature is that I can get stuff into Evernote without ever opening it.

  • If I want to keep an email for reference, I can easily forward that to my Evernote email,
  • Any articles or eBooks I read and highlight appear in Evernote automatically thanks to Readwise (more on that later)
  • After reading and marking PDFs on my iPad's Good Notes app, I can export from my iPad straight to Evernote. All the text and my annotations within the PDF are searchable, too.

Ironically, the only thing Evernote doesn't capture well is text. Evernote's mobile app is cumbersome to open for on-the-go note-taking. And even then, its formatting -- bullets and shortcuts, in particular -- is closer to Microsoft Word than a modern note-taking app. Text capture should be table stakes for a note-taking app and I'm frustrated that Evernote does it so poorly. Because of that I use the Drafts app for quick text capture with Markdown support. I then use Drafts' built-in export features to process Markdown into rich text and upload my notes to Evernote.

Evernote for organization

Evernote's organization is simple, for better or for worse. Individual notes go into notebooks, and notebooks go into stacks. Frustratingly, you can't drag-and-drop notebooks into different stacks from Evernote's side panel.

For the most part, Evernote lets you access your notes fairly easily. With its search function, you can search for text within PDFs and images. It also has optical character recognition which makes handwriting searchable, too. This function only works 50% of the time, though - a poor showing, especially since I write in very legible block letters and not cursive (but better than nothing). You can also save searches in Evernote to create the equivalent of filters in apps liike Ulysses and nested tags in Bear.

On the flip side, Evernote doesn't have the in-line note linking/search that Roam and Bear have (on these apps, typing "[[" pulls up all the notes that you can link to). Nor does it the universal command function that Notion has (typing "\" pulls up every functional feature available, inluding note-linking).

Evernote for creating & sharing

Evernote's (in)ability to take the knowledge I've saved in it and share it with the world is the #1 reason I keep testing other apps.

For one, Evernote doesn't have Markdown support, which would solve both its text quick capture problem and exporting problem. Once a note is in Evernote, you can't export it as clean HTML (just tags, no spans). Even if you just want to copy what you wrote on Evernote to Microsoft Word or Google Docs, the text doesn't retain any links, headings, or formatting, aside from bold and italics.

In contrast, Ulysses is my go-to writing app because it has the most powerful export features. You can highlight an entire block of markdown in Ulysses and paste it as HTML, rich text, or plain text. It automatically converts markdown to HTML, upload images from your post to WordPress, and publish the post. You can also export your work as a Word document, rich text document, or a PDF, using CSS to style the documents and create templates.

Why I still use Evernote

Despite how much it fails me for content creation and sharing, I can't leave Evernote. Its universal capture capabilities are the biggest switching cost for me. Plus, it deals with images best among the note-taking apps I've tested. Of course, you can also embed images and maybe other file formats in apps like Standard Notes, Bear, and Ulysses. Other apps can barely do images and can't do other file formats (Roam, looking at you). While others just straight up do not deal with anything other than text (Drafts). Regardless of functionality, none of these apps come close to having Evernote's OCR and searchability.

The second biggest switching cost for me is Readwise's Evernote integration. Readwise talks to Kindle, Instapaper, and Hypothes.is, grabs my notes and highlights, then automatically exports them to an Evernote notebook called "Readwise". This saves me so much time and effort. I don't have to think about exporting my notes after I mark up a great article or finish a book. They're just there in Evernote whenever I need them.

Finally, unless other apps develop full offline functionality (cough Notion cough), I'll keep my notes in Evernote. Unlike Roam or Notion, Evernote Pro's full offline mode lets me have all my notes with me wherever I go. This means I can write on Ulysses, Standard Notes, or Google Docs whether or not the coffeeshop I'm at has wi-fi or not.

Evernote is great at getting everything in one place. But It sucks at getting things out of it. After months of testing, I find that the best workflow uses Evernote to capture other people's knowledge and then uses other, more specialized tools to make that knowledge my own.

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