Creative Business Real Talk

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 imperfec...

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 su...

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 fro...

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 s...

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...

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 actuall...

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 thi...

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 ma...

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...

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...

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 episode What...

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...

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...

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 c...

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 way...

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 ho...

Advanced Calligraphy Skills Studio - 50% off sale ends May 5, 2025! -- Struggling to find enough clients for your calligraphy business?   What if you didn’t need more clients—just better ways to serve the ones you already have? In this episode, we explore how to increase your revenue without constantly hunting for new leads. Learn to think of each customer as a journey, not just a transaction, and...

One of the biggest and scariest questions I get from those around me is, “ How did you know when it was time to leave? How did you choose the unknown over security?” Ooof, that’s a tough one.  If you aren’t familiar with my story, about 10 years ago I was an unhappy, overtired, pent up corporate lawyer who had reached the end of my rope and decided I needed to make a change. I quit my 6-figure sal...

One of the most common headaches for new business owners is figuring out where to find clients. I promise you, there is no “secret club” filled to the brim with potential clients just waiting for you to find it. The real truth? You don’t find clients, you grow them - through consistent, intentional outreach.  In this episode of The Shinah Show, I’m sharing how to reframe your mindset and take prac...

“The point of this isn’t actually to bring in a lot of money… the point is to get your name out there!” - Shinah We're back with an oldie but goodie - with even MORE advice packed into this episode! We’re entering into the Spring and Summer, and you know what that means! It’s time for craft fairs and outdoor markets! For creative entrepreneurs, this can be a very lucrative period of the year,...

It’s OK to Stop Growing Once in Awhile This is a short, light-hearted episode about a new podcast that's delighting me and a new creative endeavor (completely unrelated to calligraphy) that's really fueling me right now.  💁🏻‍♀️Listen in to hear: How I'm thinking about "self-improvement" now that I'm in my mid-40s What the wealthiest, oldest people are still worried...

LaTache began her calligraphy journey just a few short months ago – after dusting off a 4 – year old gifted calligraphy kit that had been sitting in the back of her closet. Now, she’s almost made her full course investment back off of one referral from a friend, that  just happened to be for a high end brand needing place cards for a Michelin Star dinner. Crazy, right?! Not as much as you think! ...

It’s been 10 years since I started Crooked Calligraphy – and I’m finally where my 2015 self always dreamed I’d be. I have a steady $200K a year business, 3-day workweek, and I’m more at peace than I ever have been. But the truth is, that peace has come from a lot of resilience, faith in myself, and ability to ride the waves (and it’s been *quite* a ride). And there are still times I have doubts an...

What if you wanted to start a calligraphy business… but you lived in the “wrong” place? Like a country where nobody speaks English (the one and only language you speak)?? That’s exactly what happened to Lisa MacIntyre, who has lived in a small town in Korea for the past 20 years. She found our MC201 course and, despite not being able to find ANY supplies, pursued her dream of learning calligraphy...

When a single corporate client paid me over $10K for one project — and $6K of that was digital calligraphy — I knew I had to pull back the curtain on this game-changing skill! While I would describe myself as a pen-and-paper calligrapher, digitized calligraphy has become a necessary add-on to most of my commissions. Of course, most of my clients initially contact me seeking handmade original piece...