Making (and Securing) Your Second Brain

This presentation explores why having a “Second Brain” matters, how Tiago Forte’s PARA and CODE frameworks help you organize information, and why Obsidian is an excellent tool to implement these ideas. It highlights Obsidian’s local-first design, powerful linking features, and customizability—and then dives into how to keep your vault secure, from full-disk encryption and cloud-sync strategies to Apple’s new Advanced Data Protection (ADP) for end-to-end encrypted iCloud storage. By the end, you’ll see how to build a future-proof digital system for capturing, organizing, and safeguarding everything you learn.

This is for the January 2025 Austin Cryptoparty for OWASP Austin

Transcript

1. MAKING (& SECURING) YOUR SECOND BRAIN ! /in/wickett || @wickett james@dryrun.security
2. ! Hi, I'm James Wickett, founder of DryRun Security. We're solving incredibly hard AppSec problems, like IDOR, using Contextual Security Analysis. It's really amazing, especially if you're tired of the pain of SAST. Because I've seen the power of context, I'm currently on a journey of building a second brain for my whole life.
3. ! SLEEP ON THIS, IF
4. ! SLEEP ON THIS, IF • You think that AI knows all, so why try
5. ! SLEEP ON THIS, IF • You think that AI knows all, so why try • You don't like learning
6. ! SLEEP ON THIS, IF • You think that AI knows all, so why try • You don't like learning • You trust companies to steward your data
7. THE BENEFITS
8. THE BENEFITS • Reduced Mental Overload
9. THE BENEFITS • Reduced Mental Overload • Enhanced Creativity
10. THE BENEFITS • Reduced Mental Overload • Enhanced Creativity • Increased Efficiency
11. THE BENEFITS • Reduced Mental Overload • Enhanced Creativity • Increased Efficiency • Future Ready for your personal AI
13. THE PARA FRAMEWORK
14. THE PARA FRAMEWORK • Projects: Short-term efforts with a clear goal and a deadline.
15. THE PARA FRAMEWORK • Projects: Short-term efforts with a clear goal and a deadline. • Areas: Ongoing responsibilities that need maintenance (e.g., health, finances, relationships).
16. THE PARA FRAMEWORK • Projects: Short-term efforts with a clear goal and a deadline. • Areas: Ongoing responsibilities that need maintenance (e.g., health, finances, relationships). • Resources: Topics or interests that don’t have a specific deadline but hold value
17. THE PARA FRAMEWORK • Projects: Short-term efforts with a clear goal and a deadline. • Areas: Ongoing responsibilities that need maintenance (e.g., health, finances, relationships). • Resources: Topics or interests that don’t have a specific deadline but hold value • Archives: Inactive or completed items you want to keep for reference but don’t need in your main workspace anymore.
18. THE CODE PROCESS
19. THE CODE PROCESS • Capture: Gather articles, books, conversations, emails...
20. THE CODE PROCESS • Capture: Gather articles, books, conversations, emails... • Organize: Sort and label captured items into your PARA categories.
21. THE CODE PROCESS • Capture: Gather articles, books, conversations, emails... • Organize: Sort and label captured items into your PARA categories. • Distill: Review and condense notes to their most essential parts.
22. THE CODE PROCESS • Capture: Gather articles, books, conversations, emails... • Organize: Sort and label captured items into your PARA categories. • Distill: Review and condense notes to their most essential parts. • Express: Write an article, creating a presentation, or planning a project.
23. WHY OBSIDIAN IS A GOOD SECOND BRAIN CANDIDATE?
24. MARKDOWN & LOCAL Obsidian stores your notes as plain text Markdown files on your local machine, giving you true ownership over your data. There’s no proprietary lock-in, and Markdown is text, and text is forever (except YAML ).
25. POWERFUL LINKING Bi-directional links let you easily connect concepts, and the built-in graph view visualizes your notes as an interconnected web. This networked approach fosters insights you might miss in a strictly linear setup. !
26. HIGHLY CUSTOMIZABLE From third-party plugins (task management, spaced repetition) to custom themes and CSS tweaks, Obsidian offers a vast ecosystem for tailoring your workspace. Including slides! !
27. OFFLINE & PRIVATE By default, Obsidian works entirely offline. Combine that with tools like full-disk encryption so you get total control over how (and where) your notes are stored. !
28. BYOC BRING YOUR OWN CLOUD Use Obsidian's Sync service or use your own, like Apple iCloud. ☁
29. SPEED Obsidian is designed for lightning-fast note creation and navigation. You can quickly add links, tags, or nested folders on the fly, while the advanced search keeps your growing vault responsive and easy to explore. !
30. ADAPTABLE Whether you follow PARA, GTD, or your own system, Obsidian’s flexible structure and linking capabilities let you evolve your knowledge base over time—without ever losing track of your ideas. !
31. Securing Your Second Brain Securing Obsidian Securing a bunch of markdown files !
32. FULL-DISK ENCRYPTION FIRST !
33. FULL-DISK ENCRYPTION FIRST • macOS: Use FileVault to encrypt your entire drive. !
34. FULL-DISK ENCRYPTION FIRST • macOS: Use FileVault to encrypt your entire drive. • Every OS has easy-to-setup full disk encryption !
35. FULL-DISK ENCRYPTION FIRST • macOS: Use FileVault to encrypt your entire drive. • Every OS has easy-to-setup full disk encryption • Protects against: physical access lost laptop/SSD, ... !
36. But, You Have Multiple Devices Because It's not the 90s !
37. OBSIDIAN VAULT IN ICLOUD By default, iCloud encrypts data in transit (between your device and Apple’s servers) and at rest (on Apple’s servers). However, in most cases, Apple also holds the decryption keys. !
38. ADVANCED DATA PROTECTION (ADP)
39. ADVANCED DATA PROTECTION (ADP) • You control the encryption keys on your devices, not Apple.
40. ADVANCED DATA PROTECTION (ADP) • You control the encryption keys on your devices, not Apple. • Apple no longer has the technical ability to decrypt those services’ data—even under subpoena or other legal demands.
42. A Secure, Fully-Synced, Second Brain * Obsidian * iCloud * Advanced Data Protection (ADP) !"
43. NEXT STEPS !
44. NEXT STEPS 1. Set up your first vault: Start small—create a new Obsidian vault and organize it with PARA. !
45. NEXT STEPS 1. Set up your first vault: Start small—create a new Obsidian vault and organize it with PARA. 2. Enable security: Turn on full-disk encryption and ADP for iCloud to lock down your notes. !
46. NEXT STEPS 1. Set up your first vault: Start small—create a new Obsidian vault and organize it with PARA. 2. Enable security: Turn on full-disk encryption and ADP for iCloud to lock down your notes. 3. Tweak and grow: Add plugins or adapt workflows over time. !
47. QUESTIONS OR IDEAS? Let's chat: - james@dryrun.security - X: @wickett - LinkedIn: /in/wickett !