Creative Business Real Talk

Teaching, either in-person or online, can be an amazing way to connect with other creative souls, hone your craft, and have fun sharing your passion. 

So in this episode, I’m revisiting my 2024 interview with one of my former students, Melissa, and sharing with you how she went from making $140 with her calligraphy in 2024, to over $5200 in 2026 (all while keeping her day job managing thousands of people at a large corporation!! 

I’m also breaking down exactly how you can teach your first class, even if you’re still growing your skills.

The secret is to only teach what matters, and not try to teach EVERYTHING.

Inside this episode:

• (0:47) Why my in-person calligraphy classes generate wait lists
• (1:45) Roadmap to teaching calligraphy workshops - NOW - no matter your skill level
• (7:00) The easiest and *best* way to host your first workshop, without the stress
• (10:23) (Say it with me!) How to PITCH yourself & promote your workshops
• (13:15) How to fastrack teaching workshops
• (15:32) Choose your path to profiting! 

If you’ve been thinking about teaching calligraphy but don’t feel ”ready”, remember that sometimes more is less, and stepping out of your comfort zone can lead to SO many opportunities. 

Heads up!!! Our “How to Teach Profitable Calligraphy Workshops” training will be on 50% sale during our Five Days of Deals - happening at the end of November. Get on the waitlist at crookedcalligraphy.com/fivedays so you don’t miss it!

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!

Brands are booking their holiday activations right now. Envelopes need addressing. Shops are planning their December events. And if you’ve been waiting to feel “ready” - this is your window.

This is a short, tactical episode with three things you can actually do this week to land holiday calligraphy work. No fancy website required. No huge following. Just a skill that’s good enough and the willingness to put yourself out there.

What we cover:

• (1:20) Step 1: Get your portfolio to “good enough” - exactly what you need (hint: it’s less than you think) and how to practice specifically for the holiday jobs you want
• (3:33) Step 2: Reach out to your own network - Mian said “I’m a calligrapher” to a florist and ended up at Louis Vuitton. Melissa texted her network and booked nine jobs in her first year. You don’t need Instagram. You need three texts.
• (6:07) Step 3: Pitch local shops and boutiques NOW - the brands that hire calligraphers for holiday activations book 4-8 weeks out, which means this week is your window. What to say, who to contact, and why it’s not just luxury stores you should be targeting

Sophilia started with our calligraphy courses in August and made $1,500 by December. You’re closer than your brain is telling you.

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“How to Pitch Yourself” Episode 137: https://www.crookedcalligraphy.com/podcast/137

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!

How can my profits be booming in the worst year of my personal life like… ever? 

2026 has been a lot. Dad in the hospital. A family member in crisis. A dog with terminal cancer. A sinking patio, a leaking car, and just... the world.

And yet - my business is strong even though I’ve had very little creative energy to pour into it. I want to show you exactly why, based on the data.

What we get into:

• (2:48) What I created new vs. what I reused - and why people aren’t paying nearly as much attention as you think they are
• (6:03) The scary launch I never gave up on - 20 sales vs. 33 the same time last year, webinar attendance cut in half, a conversion rate that made me nervous
• (10:29) Core Business Drivers - I focused correctly on some of these… and totally ignored others
• (16:15) The actual lesson - why conversion rate matters more than total registrations, and how letting metrics drive decisions (instead of feelings) changed everything

The business stuff is working, even though life is a shitshow. And I’m feeling really friggin’ grateful for that right now. 

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50% off my “Style in 20-Minutes-a-Day” Practice Workbook https://crookedcalligraphy.lpages.co/quickie/#style

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!

A potential student asked me something recently that struck me DEEP:

"What if you've already chased so many dreams and they've all failed… a voice inside says don’t even try again, it won't work."

I’m so glad she asked because this is a feeling a lot of people are quietly carrying around. So I wanted to answer her out loud (and my response is a lot more nuanced than just “GO FOR IT!”)

Instead, I want you to ask yourself two questions: 

1. What does "failure" actually mean? I had two creative businesses that didn't work out, and what I got from them wasn't failure, it was the whole foundation of what I built next.

• What’s the alternative to trying? If it’s pause and learn and heal myself… wonderful! But if it’s “do nothing for fear of failing” … then we gotta re-examine that. 

Because "not trying" has a cost too. Staying in the dreaming phase can feel really pleasurable and comfortable. But actually going for it gets you so much more satisfaction, joy, growth, confidence, and self-discovery. That's what your fear is actually costing you

She joined. I can't wait to watch what happens next.

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!

This is a story about what's possible when you just don't give up - even when life gets in the way, even when progress is slow, even when you're still figuring it out. And finding a passion that funds the kind of lifestyle you want.

Jasmine learned calligraphy with us in 2020. She spent years dabbling - charging $50 for friend's weddings, putting her business on the back burner through grad school, her behavioral analyst career, and all the usual life stuff. Then she went all in on live events, invested in community and coaching, and built something that now genuinely changes the math of her life.

What we get into:

• (3:34) The slow build - how she went from chalkboard creations and rewriting college notes to pointed pen calligraphy and a real business (in her downtime!)
• (6:25) How she got her first live event jobs - community, calligrapher connections, and how polynesian dancing parlayed into gaining clients - despite the imposter syndrome a new business brings
• (13:27) The Super Bowl story and why persistence pays off -  being rejected by the 49ers committee, but still ending up doing four events that weekend for the LA Rams
• (16:44) The numbers - $48K in revenue last year, and potentially doubling it this year? Why multiple streams of income is KEY
• (22:05) Her advice for anyone in the doubt spiral - you don't need it all figured out, and you don't have to do it alone
• (23:30) HOLY MOLY - The confidence build from learning a talent you KNOW is niche

You don’t have to have a perfect plan. You just need to KEEP GOING and not give up on yourself. 

Our Courses were Jasmine’s “first and best investment” in her calligraphy journey. Could they be yours, too? Doors close Sept 30, 2026. 

🔗 crookedcalligraphy.com/courses

Follow Jasmine’s Journey 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!

Pro Calligrapher Bundle open through Sept 30 → https://crookedcalligraphy.lpages.co/courses/
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In 2024, Melissa emailed me excited... she was two months into learning calligraphy from me and had just landed her first PAID JOB:  $140 for wedding envelopes.

She was loving calligraphy, but felt a little nervous about competing with other, more established calligraphers in South Florida.

Two years later... her calligraphy side business looks completely different.

She's made over $9000 (!!) from all sorts of clients, and somehow, she turned her biggest competition into her greatest business joy.

Join me as I share Melissa’s powerful update, how calligraphy has continued to shape her life a few years later, and what has driven her to build a successful business that she loves and continues to be proud of - all while STILL maintaining her full time job!

(2:00) Melissa’s intro and how she found herself drawn to calligraphy
(3:40) New calligraphers BIGGEST struggles & insecurities
(10:45) Where Melissa sees her business going in the future
(12:35) How Melissa has utilized her courses and how they have helped her
(16:00) Update on Melissa and her business in 2026 (spoiler alert! Her jobs this year have  totaled over $5k and included Montblanc, luxury boutiques, and Christmas event calligraphy booked!)
(17:30) Melissa’s update in her own words, and how coaching, staying the course, and networking have become invaluable to her

Melissa's best advice? “Stay the course, it's a slow start sometimes… Even in this tech heavy AI world, there is nothing more special than a human made item because people really appreciate the tender loving care that it took to personalize something special just for them.”

Even if calligraphy is just a side job for you, it can create multiple streams of income in your life. It can set you up to retire, stay home with your kids, or just have the time freedom you desire. Don’t underestimate your gusto and drive - it can TRULY change your life, imperfectly.

***Find Melissa At:
https://www.sunshinecalligraphy.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!

What if your breakthrough is just two simple steps away?

This week on the podcast, 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 calligraphy job, made $1,500, and even landed a better day job… all because she finally stopped overthinking and started showing up.

Inside this episode:

• (7:59) Sophilia's business journey (and if she even wanted to launch a business in the first place given her intimidation!)
• (11:50) How gaining strength from calligraphy spills over to other areas of your life
• (15:45) Recap of Sophilia's journey and how courses have changed her life
• (18:00) You don’t need to do as much as you think to gain clients (simple websites still gain traction!)
• (19:20) You’re never 100% ready - procrasti-learning is real!

I LOVE sharing this inspiring story of how focusing on the important things can TRULY start you on your creative business journey sooner than you think!

I hope this episode will inspire you to move now, with what you have (because you really have WAY more than you think at your disposal).

Find Sophilia here:

https://www.instagram.com/sophiliamarcellestudios/

https://www.sophiliamarcellestudios.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!

I’ve watched calligraphers go from $1 place cards to $10,000+ events, all in the past decade… and in this episode I break down exactly why.

This will help YOU better understand the psychology behind sophisticated, luxury pricing.

We cover 3 Pricing Mindsets I’ve seen since I started my business in 2016:

• Per-piece pricing: The “starving artist turned grateful business owner” mindset
• Hourly pricing: Starting to value our time with hourly rates, minimums, setup + rush fees
• Package pricing: Why clients are now paying five figures for event strategy + experience…not just lettering

I explain the psychology behind package pricing, why per-piece/per-hour can make you feel interchangeable, when hourly still makes sense, and the key shift that changes everything: pricing based on **value to the client**, not how long it takes.

00:56 Per Piece Pricing Era (2012–2016)
03:38 Hourly Pricing Era (2016–2019)
05:48 Package Pricing Era (Post-COVID)
15:22 The Key Mindset Shift

Listen now so you can take your creative business to the next level and generating profits NOW!

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!

LEARN CALLIGRAPHY FOR FREE: https://crookedcalligraphy.lpages.co/challenge/
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Live events are one of the most fun and lucrative things you can do as a calligrapher. 

In this tactical episode, I’ll tell you everything you need to know: who to pitch, what to charge, and how to show up so brands actually hire you again.

What I cover:

• (2:57) What live calligraphy looks like — engraving, bottle painting, hot foiling, paper calligraphy, at everything from luxury boutiques to pop-up markets
• (6:33) What you can charge — how I went from $75/hr at a small jewelry store to $150–$250/hr working directly with brands like Jo Malone, Anthropologie, and Mont Blanc
• (12:22) How to get the jobs — agencies, inbound SEO, and exactly how to pitch boutiques, flower shops, liquor stores, and wedding venues
• (19:37) How to be great at it — the skill level you need, what to wear, how to prep, and how to show up as an expert so you get hired again and again

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!

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!