All Episodes

In this episode of The Monday Break(Through), I dive into a truth that keeps surfacing in almost every conversation I’ve had with my podcast guests - and in my own life: no one really has it all figured out. Not the viral creatives, not the award-winning designers, not even the people we admire most. Behind every beautiful portfolio and curated Instagram feed are moments of doubt, unfinished work, and quiet confusion. From Ian Barnard to Carly Salzman to Adam Bosley and Will Paterson, every guest has shared some version of this same experience: they’re still figuring it out, just like the rest of us.This episode is a reminder that your path isn’t broken just because it’s messy. In fact, that mess might be where your best ideas come from. I talk about letting go of the myth of “one day,” the dangers of comparison, and why embracing uncertainty can actually set you free. If you’ve ever felt like you should be further along or like everyone else has it together - this one’s for you.

What do you do when your wife is watching Downton Abbey, your newborn needs feeding, and your creative spark is burning out?If you’re Ian Barnard—you pick up a “Calligraphy for Dummies” book and unknowingly set yourself on a path that leads to Creative Market bestsellers, fonts spotted in Starbucks, and a global community of lettering lovers.In this episode, Ian shares how his journey from a local graphic designer to an international lettering artist wasn’t driven by trends or flashy success—but by daily practice, small bets, and staying curious.We talk about: • The early days of learning calligraphy with zero experience • Building a thriving digital product business without losing the love for the craft • Making fonts that people actually use—and one that accidentally went viral • Teaching vs. creating vs. resting (and why Ian needs all three) • Parenting, faith, and finding balance as a one-man creative studioThis is one of those conversations that reminds you why you started—and why it’s worth continuing, even when no one’s watching.🎧 Listen now on Apple Podcasts, Spotify, YouTube, and everywhere you get your podcasts.👉 Check out Ian’s work on Instagram: @ianbarnard🌐 Explore his products, courses, and fonts at: www.ianbarnard.net

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.comhttps://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.—👀 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.designLet 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!

In this episode of Monday Break(Through), I reflect on a simple but crucial question: Are you truly in control of your time, or is it slipping away unnoticed? A recent conversation with Martina Flor left me thinking—time is the only resource we all have in equal measure, yet how we spend it defines everything.I dive into the quiet moments when I catch myself asking, ‘Is this really the best use of my time?’—not in a productivity-obsessed way, but in a deeper, more intentional sense. Are we investing our time in what matters, or just moving on autopilot? If time is the one thing we can never get back, maybe it’s time to start spending it differently. Tune in for this quick shift in perspective to start your week with clarity and purpose.

In this episode of The Type Convo, I’m joined by the incredible Martina Flor—lettering artist, author, mentor, and someone who’s built a life and career through bold moves and quiet dedication. We talk about her journey from Buenos Aires to Berlin, how she found her voice in lettering, and what success really means after 15 years in the industry.Martina opens up about the power of side projects, the beauty of sharing your work (before it’s perfect), and why asking for help might be the smartest thing you do for your business. We also dive into her two must-read books:✨ The Golden Secrets of Lettering – your go-to guide for mastering letterforms.✨ Make it! The Workbook – for turning your creative skills into a thriving business.If you’re dreaming of doing what you love—and making it last—this one’s for you.🎙 Listen now, and check out more of Martina’s work and projects at martinaflor.com.

After I shared why I stopped setting New Year’s resolutions in this episode, so many of you reached out asking “Okay, but how do you actually plan your weeks?”So here it is—a full breakdown of how I structure my time running a digital product business. I’m talking about my recurring weekly tasks, how I manage releasing new typefaces, balancing content, podcasts, client work, emails… and how I stay focused on one big goal every 12 weeks without getting totally overwhelmed.If you’re running a creative business (or want to), this is the exact system that helps me keep things clear, productive, and sustainable. Feel free to steal it, tweak it, and make it work for you.And if you do, let me know how it goes!

Effort doesn’t have a price tag, but it changes everything. In this episode of Monday Break(Through), I dive into a powerful mantra from my recent chat with James Martin: the idea that effort is completely free—but also the most valuable thing you can invest. No excuses, no waiting for the perfect moment. Just showing up and putting in the work. If you’ve been overthinking, hesitating, or waiting for the right conditions, this one’s for you.

In this episode of The Type Convo, I sit down with one of the most influential voices in branding and logo design—James Martin, better known as Made by James. We dive into his incredible journey from struggling with self-doubt to becoming a creative powerhouse behind some of the most recognizable logos in the industry.James opens up about:• The truth behind his 20+ years in the design world• Navigating impostor syndrome and finding his voice• Why he left Adobe for Affinity and joined the Designer Advisory Board at Canva• The power of conversations and how one can change your life• His mission for free design education and the vision behind #Mission10Milli• His philosophy of “Effort is Free” and how it drives his successThis is not just another design podcast—it’s a raw, honest look into the mindset and experiences that shaped James into the creative force he is today. Whether you’re a designer, creative entrepreneur, or just looking for some real talk on navigating life and career, this episode is for you.Connect with James Martin:🔗 Instagram: @made.by.james🔗 Website: themadebyjames.com🎧 Tune in now and get inspired!

In this episode of Monday Break(Through), I reflect on a simple yet powerful question that hit me out of nowhere during lunch the other day: Am I in this for love, or am I in it for money? As creatives, we all navigate that balance between passion and practicality, but what happens when one takes over completely? Can creativity survive if it’s only about the paycheck? And if it’s fueled purely by love, will the money eventually come?I dive into this cliché—but undeniable truth—that loving what you do is what makes the work meaningful. And when that love is real, when you wake up excited to create, the money will follow. But if it’s all about the money, with no heart, no obsession, no soul—then maybe it’s time to rethink the path. Tune in for this quick hit of creative clarity to start your week with purpose.

Burnout is something every creative faces at some point, and yet, we rarely talk about how to handle it. It’s not just about working too much—it’s the mental exhaustion of constantly creating, staying relevant, and chasing perfection.In this episode, I share what’s helped me avoid burnout over the years, from stepping back without guilt to finding the right creative pace. Plus, I break down my own routine for staying creatively energized, including how I structure my work weeks and why taking real breaks is essential.If you’ve ever felt creatively drained, this one’s for you. Tune in, recharge, and remember—your creativity thrives when you take care of it. 🎧

In this episode of The Type Convo, I sit down with Jack Chitty, the designer and creative force behind ChittCo (www.chitt.co). Jack’s journey into design is far from conventional—he started in linguistics and advertising before making the leap into branding and graphic design.We dive into:✅ How he transitioned into design with no formal education✅ The impact of personal challenges on his creative career✅ How he built ChittCo and gained recognition through social media✅ His approach to branding, pricing strategies, and working with clientsJack’s story is one of resilience, self-learning, and building a creative business from the ground up. Whether you’re a designer, freelancer, or just love a good creative journey, this episode is packed with valuable insights.🎧 Listen now and connect with Jack:🔗 Instagram: @chittco🔗 Website: www.chitt.coWatch the full episode on Instagram or listen here on The Type Convo podcast! 🚀

In this Monday Break(Through), I’m diving into a feeling we’ve all faced at some point—imposter syndrome. But what if I told you it’s not a sign of failure, but actually proof that you’re growing? I’ll share my own experiences with self-doubt, from launching new fonts to starting ‘The Type Convo,’ and how those moments of uncertainty weren’t roadblocks—they were indicators that I was stepping into new territory. We’ll talk about why feeling like an imposter means you’re aware of your potential, how to reframe that discomfort as creative fuel, and why it’s a green light, not a red flag. If you’ve ever questioned your place in the room, this episode is for you.

Tired of setting New Year’s resolutions that fall apart by February? In this episode, I dive into the game-changing concept of The 12 Week Year by Brian P. Moran and Michael Lennington. I’ll share how adopting this system helped me go from releasing 20 fonts in 2023 to 41 fonts and updates in 2024—all without working more hours. Learn how to break free from the traditional yearly goal-setting trap, create urgency, and achieve more in less time.Check out the book here!

In this episode of The Type Convo, I’m joined by two incredible creatives who’ve inspired me for years: Adam Vicarel, the mastermind behind Vicarel Studios, and Carly Salzman, an incredibly talented type designer. This was such a special conversation as we dove deep into their journeys, challenges, and creative philosophies.Adam shares his story of discovering hand-lettering while backpacking in Southeast Asia and how it led him to start a studio that blends art, design, and massive murals. Carly talks about her unexpected path to type design and how a serendipitous misunderstanding brought her and Adam together at Vicarel Studios.We discuss the process behind some of their standout projects—like designing a building-sized mural and creating the heartfelt “Grandma’s Recipe” font—and explore the importance of embracing imperfection, staying inspired, and finding joy in the creative process. Adam also opens up about starting a coffee company that gives back to the Cleveland community and why chasing curiosity is at the heart of everything he does.This episode is packed with insights, laughs, and plenty of inspiration for anyone passionate about design, creativity, or simply following their own path. I can’t wait for you to hear this one!🎨 Check out Adam’s work at Vicarel Studios and follow him on Instagram at @adamvicarel.✏️ Explore Carly’s type design journey and follow her on Instagram at @carlyincursive.

In this episode of Monday Break(Through), I talk about the challenges of dealing with change and how embracing it can lead to creativity and growth. Using Instagram’s recent profile design update as an example, I share my thoughts on why stepping out of the familiar and leaning into discomfort can open up new possibilities, whether in design, work, or life. Change might be uncomfortable, but it’s where the best breakthroughs happen.

In this episode of The Type Convo, I reflect on my decision to step away from designing hand-drawn fonts and what led me to rediscover my passion for them. I share insights from past struggles, lessons learned from my podcast guests, and the exciting announcement of a brand-new hand-drawn font that’s on its way. Join me as I explore what it means to give up—and why it’s sometimes just a step in the creative process.

In this episode of The Type Convo, I chat with Adam Bosley, better known as Adam the Illustrator. Adam shares his journey from a track scholarship student to becoming a sought-after illustrator and designer who has worked with global brands like Adobe, Nike, and Reebok.We explore his transition into graphic design, how he found his unique style, and how uplifting messages and community projects like “Nothing But Net” have become hallmarks of his work. Adam offers insights on navigating creative burnout, the impact of the pandemic on his career, and his aspirations to bring his designs into the physical world with projects like plush toys, vinyl figures, and art shows.🎥 Watch the full conversation here: Live Reel📲 Follow Adam on Instagram: @adamtheillustrator🌐 Explore his work: adamtheillustrator.comWhether you’re a designer, illustrator, or creative dreamer, Adam’s story is packed with inspiration, practical advice, and encouragement to keep chasing your dreams. Don’t miss it! 🎨✨

In this unplugged episode of Monday Break(Through), I share my personal approach to staying on track when life doesn’t go as planned. From why I’ve ditched New Year’s resolutions to how I embrace the mantra of “do better every day,” this episode dives into the realities of goal-setting, setbacks, and finding growth in small, consistent improvements. If you’ve ever struggled to keep your resolutions or wondered how to move forward when things fall apart, this one’s for you. Tune in for a dose of real talk and practical tips for making progress—no matter what life throws your way.

I recently realized how easy it is to get swept up in the whirlwind of the design world, always striving for the next project, the next deadline. But I've learned that true creativity requires moments of pause, moments of disconnection. In this week's Monday Break(Through), I share my own journey toward prioritizing rest and offer insights I've gathered along the way.Tune in to discover practical strategies for making breaks a regular part of your routine, from scheduling downtime to changing your environment. Let's explore how to recharge our creative batteries and find more balance in our lives.