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.

In this inspiring and laid-back conversation, I sit down with Tom Cunningham, the founder of Tropical Type, to talk about his seven-year journey from surf-loving freelancer to building one of the most recognizable font foundries on the internet. We explore how Tom’s “fast font” philosophy democratized high-impact typography for everyday designers, why he ditched clients for creative freedom, and how he stays grounded in a rapidly evolving design world.

Tom shares personal stories about launching his business with zero formal training, watching his fonts end up in Billie Eilish & Ed Sheeran videos, designing a typeface with his 5-year-old son, and how he’s navigating the rise of AI. If you’re a creative tired of design elitism or just someone trying to balance creativity with life, this one’s for you.

Find more about Tom and Tropical Type:
Intagram: https://www.instagram.com/tropical_type/
Website: https://tropicaltype.com/

In this episode, I talk about something we don’t address enough: creative copying. After Jen Wagner shared a recent example of font theft, I reflected on my own experiences with people releasing work that feels too close to mine—and others, like Sam Parrett or Tropical Type.

Copying might feel like a shortcut, but it leads nowhere meaningful. It’s not just unfair to the original creator—it’s empty. True success comes from putting in the work, finding your voice, and staying honest with your process.

Whether you’ve ever been copied—or felt tempted to copy—this episode is a reminder of where the real creative power lives.

In today’s Monday Break(Through), I’m sharing a simple principle that has shaped my entire creative journey: Build first, perfect later. Whether you’re designing fonts, launching a product, building a website, or creating anything from scratch—waiting for perfection will only slow you down. I’m sharing personal stories from my own path as a type designer, lessons from guests on The Type Convo, and a gentle push to get your work out there, even if it’s not “ready.”

If you’ve been stuck in planning mode, this episode is your sign to start messy, learn fast, and refine as you go. Because momentum beats perfection every time.

In this episode of The Type Convo, I had the pleasure of chatting with Will Paterson—a logo & brand designer, lettering artist, and YouTube educator with nearly a million followers. 🎙️

We dived deep into:

🔥 The power of backengineering in design – how Will deconstructed work to teach himself design from scratch.

🎨 Why failing more makes you a better designer – embracing mistakes as part of the process.

💡 The art of branding & typography – why Will creates fonts for clients and how it transforms brand identity.

📣 Communication & creativity – the secret skill that separates good designers from great ones.

👥 Working with his wife in design – the real challenges & benefits of building a business together.

😈 Imposter syndrome & self-doubt – why it never fully goes away and how to use it as a superpower.

Will’s journey from struggling in school to running his own agency and building a massive online presence is packed with insights for any designer, creative, or entrepreneur.

📺 Watch Will on YouTube: https://www.youtube.com/@WillPatersonDesign

📸 Follow him on Instagram: https://www.instagram.com/willpat/

🌐 Check out his work & agency: https://www.willpaterson.design

Let me know your biggest takeaway from this conversation! 💬🔥 #TheTypeConvo #Branding #Typography #SelfTaughtDesigner #CreativeProcess

In this episode of Monday Breakthrough, I’m talking about the power of conversations—how they shape careers, relationships, and unexpected opportunities. Inspired by my chat with James Martin on The Type Convo, this is a reminder that every big moment starts with a simple conversation.

So, what’s stopping you from starting the convo that could change everything? This week, I challenge you to reach out, speak up, and open doors—because the best things in life don’t happen in silence.

🎙️ Listen now and take that first step!