Over the past week, I’ve been working in person with Hayden Miyamoto to fine-tune the curriculum for Second Brain Enterprise.

This week, we’re running the first practice sessions with our internal team and a few close partners—a kind of mini alpha cohort—to stress-test the content and make sure everything’s dialed in.

We kick off the live cohort on June 2nd, and applications will close in just under two weeks.

This program is built for entrepreneurs, executives, and team leaders who want to streamline how their business runs—across operations, hiring, marketing, and more—using practical, structured systems that leverage AI.

You’ll walk away with an operating system tailored to your business and the confidence to lead its implementation.

I Tried ONLY Working in Notion for a DAY - Here’s What Happened

So many productivity apps promise to be the all-in-one solution.

In this new video, I’ve challenged myself to test the one that might actually pull it off: Notion!

Using only our Second Brain Notion Template, Notion Calendar, and the brand-new Notion Mail, I attempted to spend my entire workday inside a single tool.

Do you think that’s possible? Let’s find out.

You can now connect your Gmail to Notion Mail for free! Give it a try.​

Thanks to Notion for sponsoring this video.

Reconnecting with Dormant Knowledge in Your Second Brain

Worried your best ideas might be gathering dust in your Second Brain, especially in that overflowing Resources folder? It’s a valid concern I’ve heard from many.

But the good news is that those insights are still there, waiting for the right moment to be useful again.

Here are three ways to reconnect with your dormant knowledge:

1. Do a mini “knowledge review.” During your Weekly Review, pick one folder or tag and give it a quick skim. It’s just a light pass to resurface forgotten ideas and reawaken connections.
2. Search with intent. Whenever you’re starting a new project, search your Second Brain for related keywords first. You’ll often find useful information—notes, quotes, or insights you forgot you captured.
3. Create a “Highlights” section. Tag your most impactful ideas with something like [Favorite], [To Use], or [Timeless]. This gives you a shortlist of high-value ideas to return to when you need a creative spark.

The goal isn’t to perfectly catalog everything. It’s to stay in conversation with your past self. And to make sure your best thinking doesn’t go to waste.

Infinite Loops Podcast: Unlocking the Power of the Annual Review

I had such a fun conversation with Jim O'Shaughnessy on the Infinite Loops podcast about a wide range of topics…

From digitizing 50,000+ words of personal data to build an AI-powered life coach, to the emotional intelligence hiding inside envy, to the surprising lessons I learned walking through a tiny historical museum in Coconut Grove.

We also dug into the messy magic of identity shifts and why letting go of productivity-as-performance might be the most productive thing you can do.

Plus: the power of NotebookLM, building AI-native systems of self-awareness, and why the future will belong to those who embrace the one-way door.

Start Learning AI in 2025 Everyone talks about AI, but no one has the time to learn it. So, we found the simplest way to learn AI in as little time as possible: The Rundown AI. It's a free AI newsletter that keeps you up-to-date on the latest AI news, and teaches you how to apply it in just 5 minutes a day. Plus, complete the quiz after signing up and they’ll recommend the best AI tools, guides, and courses – tailored to your needs. Sign up to start learning Thanks to The Rundown AI for sponsoring this newsletter.

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