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A weekly kick-in-the-pants to go after your creative dreams. From a former Harvard corporate lawyer who built a million-dollar calligraphy education business… and then scaled it down intentionally to create a life full of creativity and freedom. Every week, I share a tactical business lesson + powerful brain reframe that will help you get unstuck. The perfect mix of strategy and warmth that never shies away from the truth. Welcome to Creative Business Real Talk - Shinah, Founder of Crooked Calligraphy
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Lots of my students have become successful Pro Calligraphers, but WILL IT REALLY WORK FOR YOU? I got some very good questions recently from a busy mom who wanted a reality check and asked me: What’s a realistic first-year income for a 5-10hr/week side hustle?Can a busy working mom really make this work?How can new calligraphers stand out and get clients?Should a new business start with local services or online?My informal answers in this episode and a surprising result? My answer to qu...
What if your breakthrough was just two simple steps away? This week on Creative Business Real Talk, you’ll meet Sophilia - a student who proves that you’re closer than you think. She enrolled in our Modern Calligraphy 101 Program in January 2025. By October 2025, her calligraphy was pro-level. But she still felt stuck, unsure, and desperate for direction. So I gave her two clear action steps… and what happened next will blow your mind!! In just 60 days, Sophilia booked her first calligr...
There’s nothing “wrong” with you if you haven’t found your “creative passion” yet! In fact, let’s stop thinking about creative passion in a romantic fantasy, fairytale prince kinda way and let’s actually make it HAPPEN for ourselves (‘cause women in our middle years know how to get shit done, right?) In this episode of Creative Business Real Talk, I’m busting three myths that keep us from sticking to a creative hobby: Myth #1: The LOVE of the craft itself should be enoughMyth #2: You should...
Who makes more $$$? An accountant or a calligrapher? In this inspiring episode of Creative Business Real Talk, I sit down with Laura Hess of Getrie’s Calligraphy - a former accountant who took our calligraphy courses in 2020 thinking, “I’m not even artistic.” Fast forward to today: she quit her 20-year corporate job, runs a thriving calligraphy business, and now earns way more PER HOUR for her calligraphy than for her accounting services!! Here’s what you’ll learn from Laura’s journey: ...
FREE Calligraphy Classes start 1/19/2026 --> crookedcalligraphy.com/challenge -- Still waiting for your craft to be “perfect” before launching your biz? Big mistake. I’m busting the myth that you need flawless technique to start making money as a creative. When I launched Crooked Calligraphy, I’d only been practicing for three months. THREE. But I didn’t wait to be perfect. I shared my imperfect, beginner calligraphy and built a real, thriving business by learning in real life. Here’s wha...
Failure isn't the end! It’s a -requirement- for success. But no one taught us that in school, right? Most people don’t quit because they fail once… They quit because they decide that failure means something is wrong with them. In this episode, I’m breaking down why failure is essential to building a thriving creative business, and how learning to fail correctly is what separates people who succeed from people who stay stuck. You’ll hear: (1:30) The fear one of my students had before joini...
Have you ever been too afraid to put yourself out there for fear of what people might say? Yeah…me too. Especially when I searched my own business on Reddit and found a thread calling me a snake (Word of advice - DON’T do what I did, unless you have thick skin).... In this episode of Creative Business Real Talk, I’m getting honest about the fear of criticism, how it’s shown up in my journey from lawyer to calligrapher, and the three powerful mindset shifts that changed everything....
Think building a calligraphy business means you need a full-blown plan, a perfect brand portfolio, and a social media master? Think again. In this video, I share two real stories—of students who started scared, took action, and booked their first gigs within weeks. I’ll tell you exactly what to focus on in order to get your business going with your very first paying clients. In this episode, I’m sharing: (0:57) “I need all of the things!!” - Why this myth holds people back SO often(2:08) The ...
Is AI about to put calligraphers out of business? I put it to the test…and what I found might surprise you. In this episode of Creative Business Real Talk, I share my honest reaction after testing a “calligraphy generator” inside ChatGPT, and why it shook me… initially. I have a lot of students who send me questions about AI replacing calligraphy jobs,, and the question I hear constantly is, “Is it even worth starting a calligraphy business now?”. Join me as I discuss the future o...
If calling yourself an "artist" makes you cringe... I get you, and it doesn't always have to feel that way. In this warm n’ fuzzy episode, I’m taking you back to the exact moment one tiny click on Instagram changed the entire trajectory of my life. If you’ve ever wondered whether you’re “creative enough,” “artistic enough,” or whether calligraphy is something you could ever actually do… this one’s for you. (0:50) Part 1: The One Instagram Click That Changed My Life I share the true sto...
Are you trying to turn your love for calligraphy into real income - but feel stuck, overwhelmed, or like you need to go viral to make it work? Good news: You don’t. In this video, I’m sharing two proven calligraphy business pathways that can help you start earning - no huge audience required - and breaking them down step-by-step so it actually feels DOABLE! ✨ Inside this video: (00:52) The 3 things to focus on to grow your creative business - what to focus on & what to ignore (05:38) Ac...
What’s the secret to building a million-dollar creative business? It’s not hustle…it’s focus. In this episode of Creative Business Real Talk, I break down the real numbers behind my million-dollar course sales - and the sneaky way I kept sabotaging my own success. If you’ve ever felt pulled in a million directions, this is your permission to simplify, focus, and finally scale so you can start making profits! Here’s what you’ll learn: (1:07) The math behind the $1 million - how many did I...
In this episode, I share how I was able to scale my small calligraphy business... because I had a mentor who believed I could do it. You’ll hear: (1:30) The three things that allowed me to scale my business successfully (5:30) The pandemic - being prepared at the right time for your moment of opportunity (6:50) Why believing it’s possible is a MANDATORY step in going after your passion (8:40) How much money I'm making now in my business Stop looking at the reasons why you CAN’T. Start l...
From Corporate to Creative: a 10-Year Journey What if the career you worked so hard to build… turned out to be a giant soul-suck? In this episode, I share my real journey from miserable Ivy League lawyer to building a wildly successful $900K/year calligraphy business to scaling down to a leaner "enough" business. I’m breaking down my revenue, year by year, from 2016 to 2025! Inside you’ll hear: (1:00) Personal updates from the last 5 months(7:54) The unexpected moment that ...
Direct links to the most popular, valuable and impactful episodes of the show right here: crookedcalligraphy.com/bestof -- Why I'm taking a little break from the weekly podcast and how it might be changing next season! Including: A quick business lesson on lead, nurture & sales content (and which one Podcasts are best for)Why I started this podcast and kept it going for 145 episodeWhat I'm thinking of changing for the next seasonFREE WORKSHOP: “How to Become a Calligraphy Pro” Educationa...
This inspiring interview with student Lisa Doty will fire you up! Lisa didn’t learn calligraphy from me (she studied under a traditional master calligrapher) but she still found herself stuck and scared to start her business. Then she joined our Calligraphy Biz Starter Course, and in under a year, everything shifted. She went from hiding her calligraphy in her room to confidently demoing in front of crowds and landing big gigs, like a department store grand opening. Lisa shares what hel...
Rome wasn’t built in a day – and neither was any (decent) business. It was built over thousands of tiny micro-decisions, leading to compounding effects that eventually became BIG. Gorgeous buildings, architecture that has inspired masses, and historical significance spanning centuries. Likewise, when you’re establishing a business, you can’t just completely quit your job and start turning a profit if you haven’t already laid the groundwork. You have to consciously choose to show up every day ...
Looking for a confidence boost or wondering how creative hobbies like calligraphy can change your life? Elisha took one of my very first in-person workshops back in 2016… and walked away with her entire life turned upside down. She joined that workshop in her early 20s, feeling like there was something wrong with her. But now, 8 years later, pursuing a calligraphy business has turned her into a completely different, more confident person. 🎧 In this episode, you’ll hear: The one comment ...
You finally hit the goal. You should feel proud, satisfied, even a little celebratory. But instead? Your brain whispers, “Okay, cool… what’s next?” In this episode, I unpack the arrival fallacy and why it keeps creative business owners stuck in a cycle of never-enough, even when we’re living the life we once dreamed of: What “arrival fallacy” is and how it steals your joy in a really sneaky wayConcrete steps to free yourself from the cycle so you can finally enjoy exactly where you are ...
Think a brand partnership is just a one-time gig? Think again! When you find the right brand partnership, it can be a win-win(win) for everyone involved! Early in my career, Apolis, a national retail brand, brought me in to customize their jute tote bags. When I started working with them, never could I have known the multi-beneficial aspects of our relationship. In this episode, I’m diving into how long-term collaborations fueled my creative business in the beginning and how you, too, can tur...
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I first learned about Shinah when I took one of her calligraghy workshops and she has a way of teaching you that makes a light bulb go off. I'm so happy to get more of her in podcast form. She's insightful and inspiring.
you're an inspiration! I started teaching myself calligraphy about 3 years ago and after discovering you I'm waiting for your course to open again. Shinah has a nice voice and navigates through the creative journey in a real and exciting way that speaks to me.