You discover something fascinating—maybe it’s vibe coding, sustainable investing, or sourdough baking. Your excitement builds as you imagine mastering this new skill. But then reality hits: Where do you even start?

The internet offers endless tutorials, courses, and “ultimate guides.” Your bookmarks folder grows heavy with resources you’ll “definitely check out later.” Weeks pass, and you’re still stuck in planning mode, no closer to actually learning anything.

Someone asked me recently in our monthly Q&A session for the Second Brain Membership: “When you learn a new tool or skill, do you have a strategy to do it? Like different stages of exploring and repeating?”

After thinking through it for a moment, I realized I actually do have a systematic approach to learning new skills—I’d just never formally documented it. 

It’s worked for me for years across everything from productivity systems to personal development. And in this blog post, I will share it with you.

Here’s the key: The goal isn’t to become an expert at everything you try. It’s to efficiently identify what’s worth pursuing and what’s not.

Stage 1: Immersion – Get Maximum Exposure

The first stage is about orienting yourself in the new field. Think of your content consumption time as a portfolio that you’re actively allocating.

When ChatGPT first came out, I immediately dedicated 20% of my content consumption time to AI. Instead of watching random YouTube videos during breaks, I’d pick something AI-related. During walks, I’d listen to AI podcasts instead of my usual rotation.

What this looks like practically:

• Subscribe to 3-5 newsletters or Substacks on the topic
• Follow key YouTubers and podcasters in the space
• Reallocate existing content consumption time (don’t add more, just redirect what you’re already consuming)
• Focus on getting a general sense of the landscape rather than deep expertise

The key insight: You automatically start learning through mere exposure. Your brain begins building mental models and recognizing patterns without conscious effort.

How to Find Quality Sources in a Noisy World

One challenge you’ll face in this stage is finding the signal among the noise. Here are my strategies:

Ask for recommendations: Post on social media asking for sources, or ask around your friend group. Personal recommendations are strong signals, especially if you hear the same name mentioned multiple times.

Ignore popularity metrics: Subscriber count, view count, and virality usually lead to mediocre quality. The best content is often shared person-to-person, not algorithmically promoted.

Seek out obscure sources: Some of the best content exists as “janky PDFs” passed between practitioners. I started a subreddit called “obscure PDFs” specifically for this kind of hidden knowledge.

Match your consumption preferences: I prefer text over video and audio because I don’t have a commute. Work with your natural preferences and lifestyle constraints rather than forcing yourself into formats that don’t fit.

Stage 2: Building – Make Something Real

Here’s where most people get stuck in tutorial hell. Instead of consuming more content, you need to try making something as quickly as possible.

There’s a completely different set of lessons that only come from building. You can watch hundreds of hours of coding tutorials, but you won’t understand programming until you try to build an actual project.

When I wanted to learn vibe coding, I gave myself one Saturday to create something. I built a “death clock” calculator that predicts your exact day of death. In this blog post, I share what I learned from this real project with real constraints.

What this looks like practically:

• Set a short deadline (one day to one week maximum)
• Choose a simple, concrete project
• Accept that it will be messy and imperfect
• Focus on completing something, not making it perfect

The key insight: Building reveals the gap between theoretical knowledge and practical application. This gap is where real learning happens.

Stage 3: Structured Learning – Find Your Mentors

After you’ve gotten exposure and tried building, you’ll have a much better sense of who actually knows what they’re talking about.

Now it’s time for more structured learning—but with a crucial twist. Instead of trying to learn from everyone, pick just 1-3 people max to treat as your mentors.

For example, in the realm of self-development, I’ve gone deep with the teachings of Joe Hudson and the Art of Accomplishment. In marketing, I’ve learned from and worked closely with Billy Broas. In writing, I modeled my work closely after Venkatesh Rao. In tech news and analysis, I’ve read everything Ben Thompson of Stratechery has written in the last decade. Currently, I’m studying YouTube scriptwriting intently under George Blackman (though he doesn’t know it). I’ve learned a ton about embodied self-awareness and biomimicry from adrienne maree brown. 

I strongly believe that this focused approach enabled me to make leaps in growth that wouldn’t have been possible if I had just dabbled in a lot of different approaches.

What this looks like practically:

• Choose teachers based on results, not popularity
• Follow specific instructions rather than cherry-picking from multiple sources
• Use them as a filter for all incoming information
• Invest in their courses, programs, or coaching if available

The key insight: One focused teacher is worth more than twenty scattered resources. Use your mentors as filters to cut through information overload.

Stage 4: Connection – Build Real Relationships

The final stage is about tapping into our innate drive to share information and ideas with others. 

Some of the most transformative learning happens when you join a community of practitioners and even step into a leadership role. You might organize meetups, start a discussion group, or even host your own events around shared interests.

Every year, I host a mastermind-style retreat largely for this purpose—to turn online relationships into real friendships and collaborations. There’s nothing quite like that personal connection for accelerating learning.

What this looks like practically:

• Reach out to people you’ve learned from
• Attend conferences, workshops, or retreats in the field
• Create collaborations or projects together
• Host or join communities around the topic
• Take on leadership roles in existing communities
• Organize your own gatherings or events to bring people together

The key insight: Learning becomes exponentially more powerful when you’re part of a community of practitioners. And when you become a leader who brings others together, you accelerate not just your own learning but everyone else’s, too.

The Secret Ingredient: Cultivating Play in Learning

There’s one element that can transform every stage of this framework: playfulness.

As one community member beautifully put it during our discussion, “Anything that I can turn into a sort of boyish feeling of play speeds my learning and takes me more to the heart of whatever I’m feeling drawn to.” This wisdom about play isn’t just personal preference—it’s backed by compelling research.

In his book Free to Learn, developmental psychologist Peter Gray demonstrates that curiosity, playfulness, and sociability are the three natural drives that are inherently educational. These aren’t just nice-to-haves—they’re the fundamental biological mechanisms through which humans learn most effectively.

Gray’s research shows that play is nature’s way of ensuring children acquire the skills necessary for survival. When we approach learning with a playful mindset, we activate the same biological drives that make children such incredible learning machines before they ever set foot in a classroom.

How to cultivate playfulness in your learning:

• Approach new subjects like a curious child – What would happen if you just started experimenting without reading all the manuals first?
• Give yourself permission to “waste time” exploring – Follow interesting tangents even if they seem unproductive
• Turn challenges into games – Can you learn 10 new concepts in a week? Can you build something silly with your new skill?
• Embrace the “beginner’s mind” – Let go of the need to look competent or professional while learning

The beautiful paradox is that when we stop taking learning so seriously, we often learn more effectively. As Gray notes, the shift from exploration to play is one from a focused, serious facial expression to a more relaxed, smiling one—and it’s in this relaxed state that deeper learning often occurs.

This sense of play doesn’t diminish with age—it just gets “beaten out of us” by formal educational systems. But we can reclaim it. The next time you’re learning something new, ask yourself: How can I make this feel more like play and less like work?

The Hidden Truth About Learning

Here’s what might surprise you: Most of your learning attempts should fizzle out. And that’s not just okay—it’s optimal.

You have limited time and energy. Most interests are meant to be explored for a season, not turned into lifelong pursuits. The idea that you should finish every book you start or master every skill you try is a maximalist trap that actually prevents deep learning.

The real test of any skill isn’t how you feel about it—it’s whether you can produce externally verifiable results in the real world. Can you make a sale? Can someone exchange their hard-earned money or time for what you’ve created? That’s an exceedingly high standard, which is exactly why it’s meaningful.

Most importantly, give yourself permission to stop at any stage. If something doesn’t spark continued interest after Stage 1 or 2, let it go without shame. That’s not failure—that’s efficient filtering.

The skills worth pursuing to mastery will reveal themselves through this process. When something passes through all four stages and you’re still energized by it, you’ve found something worth serious investment.

I used AI to help draft this post based on my spoken insights, then edited it to ensure it captures my authentic voice and experience.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.