In this unscripted Monday Break(Through), I finally take a leap I’ve avoided since the start of this podcast—recording solo without a script. It’s raw, imperfect, and real.

I talk about pushing through fear, showing up even when you’re unsure, and the underestimated power of side projects. From recording in a noisy apartment to learning new skills outside of font design, this episode is a love letter to doing the thing—even when it’s scary.

Plus, I share a major lesson from Elliot Jay Stocks about why side projects matter more than we think, and how they can actually help us avoid burnout, spark new ideas, and reignite passion for our main work.

If you’ve been waiting for a sign to start something on the side—this is it. Let’s talk fear, creativity, and why the messy beginning is often the most powerful part.

We live in a world obsessed with the highlight reel — the bestselling book, the viral moment, the overnight success. But what if the real magic is in the volume of work no one ever sees?

In this Monday Break(Through), I reflect on a single post by @mattgottesman that hit me hard — and how it led me to discover a feed full of wisdom, perspective, and quiet truth. From Frank Sinatra’s 1,300 songs to Picasso’s 150,000 artworks, this episode is about the unseen effort behind every masterpiece… and what that means for the rest of us who are still creating in the quiet.

🎙️ Plus — a little behind-the-scenes: Matt Gottesman will be joining me for an Instagram Live this Friday on The Type Convo. Don’t miss it.

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👀 Takeaway: The ratio doesn’t matter as much as the rhythm.

💡 Quote to keep: “Create. Swing. Share. Repeat.”

In this episode, I’m talking about the one thing that keeps coming up in almost every Type Convo I’ve done so far—the so-called cliché of “loving what you do” and “having fun with it.” It might sound overused, but there’s a reason it keeps showing up. In just a few minutes, I explore why joy, curiosity, and play are often the real secret to creative longevity. A soft reminder to bring the fun back into your work—especially when things start to feel heavy.