For years, I’ve collected questions and prompts that reveal hidden truths about our lives.

As the end of 2025 approaches, here are 3 of my favorites that never fail to give me insight:

1. When did you feel most alive? What was happening around you to fuel that aliveness?

This helps you identify the conditions that make you feel alive, so you can recreate them in the future.

2. What hardships are you carrying with you into this time of year?

This surfaces the disappointments, heartbreaks, and pain you’ve been avoiding, so you can process and heal them.

3. In which areas of life are you still holding back until you feel like you know what you’re doing?

This reveals where fear or perfectionism keeps you from bringing your full self forward.

Can you feel the power of these questions? Your subconscious already has the beginnings of an answer—it just takes time and honesty to surface them.

That’s exactly what an annual review does: it gives you the time and space to have an honest conversation with yourself about what’s going on right now, what matters and is being neglected, and ultimately what you want.

Join The Annual Review 2026 and I’ll show you a series of surprisingly powerful tools for asking and answering these kinds of soul-searching questions.

Enrollment starts next Monday, Nov. 24!

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I Need a Pause (Here’s Why)

After years of teaching annual reviews, I’m finally taking my own advice.

With my book manuscript due in two months, programs launching, and life throwing curveballs, I realized I need to retreat instead of pushing through.

​My book is about creating space for annual renewal, and I can’t authentically write it while doing the opposite.

So in this video, I share an update on what’s changing over the next month.

Watch on YouTube

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Eliminating Friction: A Small Change Can Make a Big Impact

This month in the Second Brain Membership, we’re focusing on optimizing our toolset and removing friction from our workflows.

Often, it’s not necessary to overhaul your entire system. You can refine what’s already there.

Here’s a simple two-part exercise to try:

1. Reflect: Think of moments in the past week when a tool slowed you down or made your work harder. (Example: Maybe you spent too much time deciding where to save your notes.)
2. Adjust: Identify one small change that could reduce that friction. (Example: Instead of deciding each time where to save, create a single inbox and sort your notes weekly.)

Progress comes from small experiments that add up over time.

Now, I’d love to hear from you! What’s one small change you’ll make to improve your workflow? Reply and let me know.

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Book Recommendation: Big Trust by Shadé Zahrai

In Big Trust, Shadé Zahrai offers the perfect inner complement to Building a Second Brain.

My work helps people organize what they know; hers helps them believe in what they know.

Zahrai shows that productivity without self-trust leads only to burnout and doubt—that knowledge alone isn’t enough without the confidence to act on it.

Her framework of Acceptance, Agency, Autonomy, and Adaptability gives readers the missing operating system for their inner world: a way to move through self-doubt with clarity, courage, and composure.

This book is essential reading for anyone who’s built external systems of knowledge and is now ready to cultivate the internal trust to use them fully.

Pre-order your copy

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Take Your Focus Seriously With Bento

I’ve been watching my friend Francesco D’Alessio (who many of you know from the Tool Finder YouTube channel) work on something that cuts through the productivity noise: Bento Focus.

What makes it different: you pick just three tasks each day. That’s it. No endless lists, no guilt about what you didn’t do.

The app uses calm, animated focus scenes inspired by Japanese simplicity to help you work through those three priorities. It’s built around the idea that doing what matters beats doing everything.

If you’re drowning in task managers that make you feel worse instead of better, this is worth trying.

Try Bento