When information is everywhere and costs nothing, what actually makes any of it worth having?
Nick Milo is the founder of the wildly popular program and YouTube channel Linking Your Thinking and a former student of mine who is now a leading voice in the world of personal knowledge management. In this conversation, Nick and I talk about why information on its own has never been less valuable, and why the real value comes from your ability to connect ideas and take action on them. We discuss where AI can reduce the bad friction in our lives, but also where handing over your thinking to the robots can lead to what Nick calls "cognitive surrender." You'll also get a first look (or listen) at the mind-bending Obsidian knowledge vault we built for The Connection Conference, so you can see what linked ideas actually look like in practice. And we may even talk you out of letting the robots clean your closet.
If you're buried in podcasts, articles, and AI summaries you never do anything with, or if you've started letting the chatbots do your thinking because it's just easier, this conversation will show you that the value of ideas is in the struggle to turn them into action.
Key Takeaways
Use linked notes to move from organization into ideation. Connecting ideas gives you a trail you can return to, helping you recall, re-internalize, and build on what matters.
Protect your cognition when using AI. AI can save time, but turning to it whenever you are tired can become “cognitive surrender” and sacrifice the ability to cultivate wisdom.
Make AI bring ideas to you, then engage with them in your own words. The goal is not to have AI create your thinking, but to use it as scaffolding that helps you interact with and internalize what matters.
Episode Highlights
Nick’s unexpected journey from engineering to becoming "Mr. Obsidian."
Where the real value lies in an abundance of information
The danger of “cognitive surrender” when we let AI do the thinking
What Obsidian actually is, and why "digital sovereignty" matters
The joy of typing a link and being serendipitously reminded of "cognitive affordances"
Embracing the mess: the architect and the gardener in all of us
A live tour of an early beta knowledge base of the Connection Conference
Why direct quotes from the source can beat AI interpretation
How to turning AI output into your own words
Finding the sweet spot between ready-made systems and the work that creates real learning
Nick Milo is the founder of Linking Your Thinking, the creator of the LYT framework, and a leading voice in personal knowledge management. A former civil engineer, he co-founded an international fitness boxing business, produced independent feature films, and worked as a film and TV editor. Today he guides people to link their thinking, generate value, and rediscover the joy of thinking itself. His upcoming book, Linking Your Thinking, will be published by Simon & Schuster in Spring 2027.
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