Creative Business Real Talk

Hosted by Shinah Chang

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188

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Aug 2026

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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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August 26, 2026Episode 18728 min

187: Turning 45. 3 Best and 3 Worst Business Moments EVER

Free Calligraphy Challenge : crookedcalligraphy.com/challenge I turn 45 today, so I'm looking back at the moments that shaped this decade of entrepreneurship: the highs that taught me the joys of business, and the lows that taught me even more. 3 FAVORITE MOMENTS Buzzfeed Listicle Feature! Just 8 months into my biz, I got featured in list of Sweary Stationery… but I learned the hard way that exposure and real business growth are not the same thing Glenomorangie Live Calligraphy . A year later, I got flown up to San Francisco to do live calligraphy on whisky bottles and I got the job by sending on “thank you” card to the right person Summit Success. Ten years in, I watched my first Summit come together and realized the power of being a connector, not just a lone wolf 3 HARDEST MOMENTS: Cheated by a Trusted Client. 80 massive signs, an impossible deadline, months of being strung along, and a client who ultimately didn't pay me and said my work wasn't good enough Losing 4 Employees . After massive growth, I made the hard decision to scale way down and go on an indefinite sabbatical. Turns out, bigger is not always better. My Abysmal Launch Failure. I wanted to sell 30 spots. I sold 2. What I learned from analyzing exactly why it happened. The through-line in all of it: failure doesn't mean you are a failure. Rejection doesn't mean something is wrong with you. And the life you didn't plan for might be the one that makes you the most free, most resilient version of yourself. FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

August 19, 2026Episode 18631 min

186: The Calligraphy Elitism Debate (let's say the quiet part out loud)

There’s been a dark divide whispered in the calligraphy community for years. This summer, a single Instagram post brought it into the light. And I have thoughts. The post argued that calligraphy is "suffering" - that the rapid popularization of calligraphy has led to aesthetics over discipline, too much commercialization, and a dilution of standards. It got 400+ comments, divided the community, and made a lot of beginners feel like they'd never be good enough. I posted a response Reel, but now I'm doing a deeper analysis. In this episode: (0:52) Summary of the original post - what it actually said, why it resonated with some calligraphers, and why it landed so badly for so many others (7:51) Is Calligraphy really suffering? - It’s more popular than ever. But is there too much of the "wrong kind"? (10:51) The Legitimate Concerns - about people mis-representing their skills during the hiring process and what we calligraphers can do about that. (16:56) The Human Fear and Selfishness Underneath - the quiet part that everyone’s afraid to say out loud, but that would lead to a more honest conversation and actual solutions And finally, why it’s so important to me that calligraphy can be fun AND serious, welcoming AND disciplined, easily accessible and deep, all at the same time This is one of the most nuanced, invigorating debates I've had in this space and I’m so thankful we get to have it in this wonderful, respectful community, with brave people starting the conversation. THE ORIGINAL POST : https://www.instagram.com/p/DY7GWSlDFAM/?img_index=2 MY RESPONSE REEL: https://www.instagram.com/reel/DZGB9GVvnzT/ FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

August 12, 2026Episode 18521 min

185: Launching a Biz without feeling like a FRAUD (Callifest excerpt)

I asked over 5,000 calligraphers: “What's ONE QUESTION you would ask your favorite calligraphy business owner?” The result surprised me because one theme kept coming up again and again. And it wasn’t permits or portfolios or pricing or websites… The question that kept getting asked is: “When did you know you were READY to go from hobby to business?” “What was the a-ha moment when you realized your passion could become a business?” “When did you feel confident enough to actually go for it?” Most aspiring business owners aren’t worried about the nitty-gritty. What’s stopping them is PERMISSION. So if you’re waiting for a light-bulb, burning-bush moment where you suddenly realize you’re worthy enough… you’re gonna wait forever. In today’s episode, I’m bringing you an excerpt from an hour-long, brand-new training I’m teaching called “Launching a Calligraphy Business without Feeling like a Fraud” I created it for The Manuscript Pen Company’s Callifest 2026. It’s 3 days of juicy workshops from beloved calligraphy instructors… completely for free. You don’t even need to enter your email address to sign up! All you have to do is join this Facebook Group: https://www.facebook.com/groups/themanuscriptpenclub My workshop will be airing on Friday, August 14… so if you like this excerpt, make sure to sign up to join the full 3 Days of Callifest! But mostly, I hope you walk away from this episode believing that there is room for you in the calligraphy industry. There’s always a demand for newer, up-and-coming artists, You don’t need to be perfect before you start putting yourself out there, and You can create a calligraphy business that suits your personality and desires… it doesn’t have to look like anyone else’s! FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

August 5, 2026Episode 18422 min

184: Summer Confessional - The "slump" no one talks about

I took 2 allergy pills, passed out for most of the day... and it was still good for my business. This episode is my honest, unfiltered check-in on where I'm at after a hectic year and a wildly successful Summit - and why I'm choosing rest over hustle right now, even with a Challenge coming up in September. In this episode: The unglamorous truth about my "day off" - mosquito bites, allergy pills, and a nap that turned into an entire day My "Permission Slip" philosophy - motivation goes up and down, business goes up and down, and none of it means something's broken "Regenerative Business" - why fallow seasons are doing just as much work as busy ones Does turning calligraphy into a business change your relationship with it? My real answer If you're in your own summer slump (or regenerative season) right now, this one's for you. -- FRIDAY PRACTICE PROMPTS: https://www.instagram.com/crookedcalligraphy FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

July 29, 2026Episode 18331 min

183: Lawyer, Burnout, Calligraphy, and the Business Jackpot - My Story in One Episode

I've never told my whole story in one episode. Until now. This is the one where I go all the way back - the Korean American kid who peed her seat in third grade rather than raise her hand, the Harvard grad who didn't know what to do once she got there, the corporate lawyer who hit a health scare at 31 and finally started asking the question she'd been avoiding for years. And then: calligraphy. And what happened after that. The four eras: 3:10 - The "Should" Years (ages 5–30) — straight A's, classical piano, Harvard, NYU Law, corporate law in New York. Doing everything right. Feeling nothing. 12:54 - The Questioning (30–34) — a health scare that changed everything, a leave of absence, two years of trying blogging, knitting, cooking, and creative classes before finally finding calligraphy 18:30 - The Business Jackpot (35–40) — starting Crooked Calligraphy with $0 profit in year one, hitting six figures by year three, landing Dom Perignon and Apolis, going viral on Instagram, and building a course business during the pandemic 23:05 - The Second Questioning (41–now) — burnout, stepping away, coming back, and figuring out what a leaner, more creative, more life-serving business actually looks like at 42 Plus - 20:00 the year-by-year revenue breakdown from 2016–2022. Because I believe in showing the actual numbers. My mission has always been to give people a sense of what's possible — that a more creative, unconventional life is real and reachable. It's hard and risky and requires confronting every uncomfortable thing about yourself. But it's worth it. This episode is proof. FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

July 22, 2026Episode 18220 min

182: Mid-Year Recap - Rock Bottom to Summit High and Grateful for it all

How I went from WORST YEAR EVER…. to a bulging business bank account. It’s time for our 2026 Mid-Year Recap: an honest behind-the-scenes of a true rollercoaster of a year. And I'm doing after getting back from vacation literally last night. I’m jet-lagged, I’m teaching a live training tonight — and honestly? Not mad about any of it. Because I chose it. And that feels like the whole point of this episode. What we get into: (1:40) The 6-Month Recap — feeling like I finally had it figured out, then watching February completely unravel that story and my brain deciding everything was permanently broken (7:27) The thing about "arriving" — after 10+ years, what I actually know now about business ownership, hedonic adaptation, and why you never really figure it out for good (10:50) The Summit’s Unexpected Gift — watching other people get excited about building a calligraphy business brought me all the way back to why I started mine (13:30) The lawyer dread vs. the jetlagged calligrapher — the comparison that still gets me every time The takeaway isn't that it gets easier. It's that when it's yours, hard feels different. (P.S. Free live training tonight 7/21 and tomorrow 7/22 — crookedcalligraphy.com/training. Doors open to the Pro Calligrapher Bundle through Tuesday 7/28.) FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

July 15, 2026Episode 18129 min

181: Burned-Out Nurse to Full-Time Calligrapher

Belle thought in 2019 she had her dream job as a nurse helping take care of terminally ill patients on a daily basis… until the real burnout hit her. Between COVID taking over in her job, and needing a creative outlet, Belle started dreaming about calligraphy as a source of relaxation at a time when she needed an escape the most. Join me as I chat with Belle about how she went from an overworked nurse, to borrowing money from her mom to invest in her calligraphy education, to transitioning to calligrapher as her full time job (only 8 months ago!). We’re sharing… (2:50) How Belle went from a burnt out training nurse to finding joy in calligraphy when she needed it most (6:20) How calligraphy went from the backburner to her main career (and how the Pro Calligrapher Bundle pushed her into starting her creative business) (13:20) How Belle took the leap to full time calligrapher 8 months ago (17:35) The best part of becoming a full time calligrapher & the most challenging part (and the advice Belle would give to those aspiring creative business owners) (24:30) My takeaways from our interview - the financial analysis, the “deathbed regret” feeling, and how DOING IT SCARED is still doing it (27:50) How the Pro Calligrapher Bundle can help you, like it did Belle, move toward your goals Remember - ready is not a feeling, it's a decision. You might never feel like it's truly the right time, but you don’t want to find yourself on your deathbed saying, “I wish I would have done that.” Because at the end of the day, time is fleeting. If you’re ready to start moving closer to your creative goals, our Pro Calligrapher Bundle enrollment opens Jul 21, 2026 and I’m celebrating with 2 FREE hour-long strategic workshops to help you see the path forward. Visit https://learn.crookedcalligraphy.com/webinar/ to sign up for one of 2 LIVE Webinars happening July 21st, 2026 & July 22, 2026! Find Belle Here: IG: @handwrittenbybelle https://handwrittenbybelle.com/ FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

July 1, 2026Episode 18024 min

180: Choosing To Be A Premium Calligrapher

"How do people actually generate a living as a calligrapher? I thought it was all $3 place cards and making a few dollars for painstakingly writing envelopes...” If you've ever thought that, this episode is for you. In this episode, I’m sharing excerpts from 3 different speaker presentations from my “Art & Business of Modern Calligraphy Summit”: (2:38) Shaochen of Monstera Gold shares how to turn a $100 order into a $1000 order (product-based vs. service-based calligraphy) (8:27) Rosie of WanderCrafter shares how she changed her side hobby calligraphy business into a full-time income not through talent, but rather clarity, trust and visibility (14:13) Kristin of Kreative Blends shares how your calligraphy doesn’t make you a great calligrapher - it's your confidence and what kind of experience you’re delivering to the client (20:25) Sneak peeks of some of the other business presentation topics in the Summit (22:50) How to get INSTANT & LIFETIME ACCESS to over 20 presentations right now!! These are just excerpts of 3 presentations — and all of the presentations run 20-30 minutes (so there's a lot more where this came from)! SO MUCH is covered - legal, finances, stationery, how to teach workshops, and for beginners, exactly how to make your first $1,000 (with email templates included). Whether you are a seasoned calligrapher with years of experience, or have never held a calligraphy pen in your life, there is something for everyone in this Summit - and I can’t wait to share all these AMAZING teachers and presentations with you! Make sure to sign up HERE!! FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

June 24, 202618 min

179: Your 9-Question Calligraphy Business Plan

Forget the 40-page business plan. Here's what actually works when you're just starting out. In this episode, I'm walking you through my Calligraphy Starter Business Plan: 3 categories, 9 questions, and zero room for overthinking yourself into paralysis. 1. 🖊️Your Product/Service - What to offer first (choose one for now!) - What related upgrades you could add for the same clients - The focused practice so you can deliver it well 2. 👰Your Clients & Pricing - How to get clear on your dream client - How to build a portfolio that speaks directly to them - Where to focus to land your first 3 clients (hint: start closer than you think) - A simple pricing exercise that gets you past the fear 3. 💰Your Finances & Legal - The 3 financial steps to set up first - Sole prop, LLC, or S-corp — what decision you actually need to make right now Traditional business plans didn't work for me. This did. It's scrappy, focused, and designed to get you moving with intention — not spinning in place. --- 📝 Want this in a snazzy PDF you can fill out on your own? You can download the Summit Business Plan Builder when you sign up for my free Art and Business of Modern Calligraphy Online Summit (July 7–9) at crookedcalligraphy.com/summit FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!

June 17, 2026Episode 17817 min

178: The Summit I Was Too Scared To Build (Until Now)

What if I told you I sat on something for years that I REALLY wanted to do - but the fear overwhelmed me? Sounds QUITE the opposite of the, “go for it” and, “YOU can do it” mentality I put out to the world, right?? As comfortable as I look online with a camera in front of me, you should see me at a party… Stuck to my husband. Biding my time in a corner till we leave. Worried no one wants to be my friend or talk to me (total lone wolf mentality) Needing a FULL recharge after social interaction (if you’re an introvert, you know this all too well). After getting out of my own head and realizing I needed to take my own advice, I rolled the dice and started creating the very first Art & Business of Modern Calligraphy Online Summit - a passion project literally years in the making. And boy has it been a rollercoaster designing it (because perhaps it wasn’t the best timing - but that's life, right?) In this episode, I’m sharing: (0:37) The Art & Business of Modern Calligraphy Summit details! (1:55) Class & teacher previews (4:13) VIP All Access Pass (5:30) Why I was so scared to build this summit (10:15) The things that matter when building a summit (and what can take second priority) (13:40) Always remember what matters the most in the grand scheme of things Let this be a testament to the fact that the more you can try new things, and grow your personal toolkit, the better off you are (even if you’re doing things imperfectly). I hope you guys enjoy the summit and I am so excited to bring this to you! FREE WORKSHOP: “How to Become a Calligraphy Pro” Educational Workshop FOLLOW SHINAH : Join our community of creativity-seeking souls over on Instagram: @crookedcalligraphy SUBSCRIBE: Love podcasts? Listen to The Shinah Show wherever you get your podcasts, and leave us a review on Apple Podcasts!