In this episode of Monday Break(Through), I share the results of a simple challenge I gave myself last week: break the phone habit. After limiting Instagram to just 30 minutes a day, I quickly realized how much time I was wasting on mindless scrolling - and how little it actually impacted my business or engagement.

But the experiment didn’t stop there. It led me to uncover another sneaky time-waster: constantly checking emails out of habit, not necessity. So I’m taking action - and maybe this episode will inspire you to do the same.

If you’ve been feeling scattered, stressed, or stretched too thin, this one’s for you. Let’s talk about time, focus, boundaries, and the power of being intentional.

Plus, I share a quick announcement about this week’s live conversation with illustrator Ian Barnard on The Type Convo Instagram page - don’t miss it.

In this Monday Break(Through), I’m reflecting on a surprising insight I had after reviewing my digital wellbeing stats—I’ve been spending nearly 14 hours a week on my phone, with most of that time lost to mindless scrolling on Instagram. This episode isn’t about blaming tech or going off-grid. It’s about awareness. I talk about what sparked this realization (a powerful interview with Harbor), how small habits add up, and why our attention is our most valuable resource as creatives and entrepreneurs.

If you’ve ever caught yourself in a scroll spiral, felt guilty about your screen time, or wondered how much of your energy is going to things that don’t actually move you forward—this one’s for you. Tune in for a raw breakdown of my week, a simple action I’m taking to regain control, and an open invitation for you to do the same.

Let’s take back our time, one conscious choice at a time.

In this deeply honest conversation, Harbor Bickmore — the creative force behind That That Type — joins The Type Convo to share his incredible journey from small-town beginnings to building a bold and distinctive design career.

We dive into his early days of skating and graphic design, his decision to live without a smartphone, starting That That Type, preparing to launch Vanilla Type, and his bold philosophy about life, creativity, and self-worth.

Harbor talks candidly about why he left a ‘dream job’ at a top design studio, how he created his own definition of success, and why knowing yourself is the ultimate creative superpower.

A must-listen for anyone who dreams of doing things differently. 🎙️✨

https://www.thebestgraphicdesignerintheworld.com
https://www.thatthattype.com

In this episode of Monday Break(Through), I take you behind the scenes of a major milestone — the launch of my new Type Foundry website. But this isn’t just about celebrating a website going live; it’s about a deeper lesson I’ve learned over years of building creative projects: launch before you feel ready.

I share why I decided to publish the site even though it wasn’t finished — with missing product uploads, unfinished mobile layouts, and without a polished freebie section or newsletter signup in place. I explain why choosing progress over perfection has made all the difference not just in this launch, but across my entire creative career.

Through stories about my unexpected journey building both a design agency and a successful type foundry — neither of which were part of my original “plans” — I reveal how simply putting work into the world, even when it feels messy and incomplete, leads to real opportunities, growth, and surprising success.

You’ll hear practical insights on why endless tweaking behind closed doors doesn’t serve you, how feedback (not fear) drives real improvement, and why being visible — even imperfectly — matters far more than being flawless in hiding.

Whether you’re working on a portfolio, launching a side project, starting a freelance career, or simply battling perfectionism, this episode is a reminder that the bravest (and smartest) thing you can do is to show up — as you are, where you are.

If you’ve been waiting for the “perfect” moment to hit publish, this episode might just be the push you need.

Stay creative. Stay curious. Keep going.

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.

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👀 Takeaway: The ratio doesn’t matter as much as the rhythm.
💡 Quote to keep: “Create. Swing. Share. Repeat.”

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.

—

👀 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/