Calligraphy Biz Corner

Has setting up your customer relationship management (CRM) system been on your “someday” list? Dubsado specialist and client experience strategist Kelly McCracken joins me to make systems feel approachable even if you don't consider yourself tech savvy, and shares how implementing just the basic features of Dubsado can help you book more clients from day one. 

We talk about: 

• The first thing to do for a successful set up (before even logging into the system!)
• Kelly’s top 3 Dubsado features to help calligraphers save time and get paid
• How much aesthetics matter in the booking process 
• New features in Dubsado 3.0 that will make customizations even easier
• Kelly’s advice for balancing business while raising kids

About our Guest:

Kelly McCracken is a client experience strategist and Certified Dubsado Specialist who helps service providers create thoughtful client experiences and simplify the work behind the scenes. A former teacher and mom, Kelly believes business growth should leave room for the life you want to live. Through strategic systems and automation, she helps entrepreneurs spend less time managing their businesses and more time doing what they love. She also leads the Boston chapter of Made for Mothers, bringing local moms in business together for connection and community, and is the host of The Kitchen Island HQ podcast.

Links Mentioned in this Episode: 

• Freebie: Create your Dubsado Inquiry Workflow
• Freebie: Dubsado 3.0 Scavenger Hunt
• Free Dubsado Trial + 20% Off
• Connect with Kelly on Instagram: @kellymccracken.co
• Work with Kelly: kellymccracken.co

 The Dubsado link above is an affiliate link, which means we may earn a small commission if you sign up, at no extra cost to you.

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

In this episode, I'm bringing you a short but important conversation pulled from inside my Ascent coaching community. Feeling behind is a sentiment I hear often - and one I also experience myself. I share some ways to flip the script to help you feel more supported as you navigate different seasons in your business, including ones where your business may not be getting as much attention as you'd like.  

Want to hear more insider coaching conversations? Message @calligraphybizcorner and let me know! 

 🔗 Links mentioned in this episode:

• Ascent Coaching Mastermind for Calligraphers - Only 2 spots left! 
• Your CEO Partner 1:1 Coaching Program
• Message Shaochen @monstera.gold to learn about how coaching can help your business 

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

Only a fraction of small businesses make it past the five-year mark, so I wanted to break down some strategies and mindsets that have helped me stay resilient through the highs and lows of business ownership as I look forward to year 8. This episode is shared from the private podcast inside my Ascent coaching program. 

Inside we talk about: 

• Making decisions like your future self
• How happiness isn't a constant - and why that can be a good thing
• Removing the shoulds from your business 
• How rest is not a luxury, but required 

1. Journal Prompts: 
   1. What are some actions and decisions the future version of you running your ideal business would make, that you could apply to your business today? 
   2. What “shoulds” are weighing on you? What can you do instead to achieve a similar outcome, in a way that feels more fun? 
   3. What does “fully booked” mean to you? How does this translate to revenue and/or client goals? 
   4. What are some boundaries you can put around your business to ensure that you have time for rest?

🔗 Links mentioned in this episode:

• Ascent Coaching Mastermind for Calligraphers
• Your CEO Partner 1:1 Coaching Program
• Coaching Interest Form

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

I'm so excited to have Kristine of Kristine P. Calligraphy on as our first guest interview in a year! Kristine's story is a perfect example of how a business can transform based on your interests, your physical wellbeing, and what season of life you're in. From chalkboard signs to digital templates to now running a full-service, large-scale wedding signage business, Kristine walks us through every pivot — including the moment in 2025 when she was ready to give up entirely, and how joining my CEO Partner 1:1 coaching program helped her completely reposition her business, leading to a booked-out 2026.

In this episode, we cover:

• How Kristine's business evolved from a 2017 hobby into full-service wedding signage today
• Why hand pain and burnout led her to pivot into a passive digital template shop — and why that pivot didn't stick
• The moment she realized large-scale signage installs were her true passion (and the family connection behind it)
• What we worked on inside the CEO Partner coaching program to rebuild her positioning, pricing, and clientele in just 12 weeks
• Kristine's advice on whether a coaching program is worth it 

🔗 Links mentioned in this episode:

• Connect with Kristine on Instagram @KristinePCalligraphy
• Getting married in Northern California in 2027? Kristine's books are open, inquire at kristinepcalligraphy.com
• Apply for Business Coaching
• Learn about Your CEO Partner 1:1 Coaching (Kristine's Program) 
• Learn about Ascent Coaching Program
• Learn about the Pro Wedding Calligrapher course that started Kristine's business

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

Clients and brands are seeking out live event artists like never before, creating a booming new revenue opportunity for calligraphers, engravers, and other creative entrepreneurs. If you're looking to add an income stream that can bring several thousands of dollars per month, this is it.

In this training, you'll learn how to add take your calligraphy, engraving, bottle painting, watercolor portraits, or other art form from your studio, to performing in front of guests. 

We'll cover:

• How to find and reach your ideal live event clients (including corporate clients, brand activations, and weddings)
• The best pricing strategy for live events, which increased my rates by 30% without losing bookings
• The steps to making your first live event a success

Whether you're a calligrapher looking to diversify, an engraver wanting to break into events, or a creative entrepreneur exploring live art as a business, this episode will show you how to turn your artistic skill into a scalable, sustainable income stream.

Download the Freebie: Live Events Supplies Guide

Get the best deal when the Live Events Course launches: Join the Waitlist

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

Introducing a new look for Calligraphy Biz Corner! I hope the art reflects how I want this show to make business feel for you - easier and lighter, with more room to play and experiment. And you're not building this thing alone, because when you're tuning in, you've got a whole community of calligraphers and creatives learning right alongside you. My mission on the show and as a business coach is to empower you to not only thrive as an artist, but be confident as an entrepreneur.

Tune in to learn more about your host, Shaochen (that's me!) and what's in store for Calligraphy Biz Corner! 

Starbucks gift card has been spent! Thanks for participating! 

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

Have you ever gotten an inquiry that you just knew you couldn't turn down, even though you'd never done that exact thing before? That's what happened when I booked my first live engraving event - without ever having touched an engraver. 

In this episode, I'm sharing the full story of how I said yes to an engraving live event, learned to engrave in one week, and pulled off a wildly successful event. I'm sharing what that experience and other similar experiences have taught me about putting an idea into action fast for your business. 

This isn't about winging it. It's about knowing when you have the skills to go for it, and deciding that you're ready.

In this episode we talk about:

• How to confidently take on something new, without taking on too much risk
• Why readiness is a decision, not a feeling
• The key to booking jobs you've never done before

🔗 Links to resources mentioned in this episode:

• Learn about Ascent 6 Month Coaching Program
• Learn about Your CEO Partner 1:1 Coaching Accelerator
• DM me to chat about your business
• All the engraving supplies I purchased
• FREEBIE: Live Event Supplies Guide (Including Engraving Supplies)

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

We’re back with a real, honest, and slightly emotional life + business update. This one’s going to feel a little different than our usual episodes, but these are the conversations that matter just as much as business strategy.

If you’re in a season where your calligraphy business or creative business feels a little… unclear, messy, or like you’re outgrowing things faster than you can keep up with, this episode is going to resonate.

We’re pulling back the curtain and sharing what’s actually been happening behind the scenes, why we took a break, and what this next chapter looks like for both of us. From big life changes to making those “I know this is right, but it still feels hard” decisions, this conversation is all about the real side of creative entrepreneurship—not just the highlight reel. 

We’re diving into what it really looks like to grow and evolve a creative business, including stepping into the “messy middle” where things feel unclear, uncomfortable, and uncertain—but also full of potential. The part no one really prepares you for. Tune in if you’ve ever questioned your direction, felt pulled between multiple paths, or wondered how to create a business that truly supports your life.

What we get into in this episode:

•  What calligraphy business growth actually looks like 
•  The “messy middle” of creative entrepreneurship and why it’s actually a good thing 
•  Making big CEO decisions in your creative business (even when you don’t feel ready) 
•  Letting go of things you love so you can grow 
•  Building a creative business that actually supports your life—not the other way around 
•  Why not having all the answers is… kind of the whole point 

This episode is a reminder that calligraphy business growth and creative entrepreneurship aren’t linear. Sometimes the most powerful growth happens in the quiet, uncertain moments where you’re redefining everything.

If you’ve been feeling like you’re in a season of transition in your creative business, you’re not alone - and this conversation might be exactly what you need to hear right now.

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

Have you been wanting to launch a new service for your calligraphy business, but aren't sure how to do so without getting overwhelmed or messing up what's already working? In this episode, I'm letting you be a fly on the wall for one of my introductory coaching calls with Laura of The Letter Grain where we talk about how to grow her business through new income streams. 

Laura is a calligrapher based in central Pennsylvania who has a steady window mural business, but found herself missing calligraphy and feeling stuck on how to bring it back. In just under 30 minutes, I take her from feeling unsure of where and how to proceed, to narrowing down one service to start with, and identifying some actionable next steps. 

In this episode we talk about: 

• The value of getting specific with your ideas and audience before growing
• How to focus your energy when you have multiple services and limited time
• Practical first steps for building out a new live calligraphy income stream

🔗 Links to resources mentioned in this episode:

• Apply for Your CEO Partner 1:1 Coaching Accelerator: https://www.calligraphyceo.com/ceo-partner
• DM me "Partner" to get recommendations for your business: https://www.instagram.com/monstera.gold
• Unsure whether coaching is right for you? Read this: https://www.calligraphyceo.com/tips/when-to-hire-a-calligraphy-business-coach
• Connect with Laura of TheLettergrain: https://www.instagram.com/thelettergrain/

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website

Taking leave as a business owner can feel overwhelming — whether you're planning for maternity leave, a medical procedure, a family commitment, or an extended vacation. In this episode of Calligraphy Biz Corner, Shaochen shares exactly how she navigated maternity leave twice as a creative business owner, and what she'd tell anyone who wants to step away from their business. If you've ever wondered whether your business will survive while you're away, this episode is for you!

We'll talk about: 

Financial Prep:

• Extending your cash runway 
• Boosting income before you go
• Getting assistance through leave programs 
• Cutting expenses before you leave  

Important Mindset Shifts: 

• How referring out inquiries can be good for business 
• Why you don't need to keep posting, emailing, or marketing
• How to handle the fear of missing a busy season
• What really happens to your business when you step away

If you've been putting off a break because you're not sure your business can handle it, this episode will help you see that not only is it possible, but an intentional break will help you come back even more motivated and poised for growth! 

🔗 Links to resources mentioned in this episode:

• Apply for CEO Partner 1:1 Coaching: https://www.calligraphyceo.com/ceo-partner
• DM Shaochen "PARTNER" and see if coaching is right for you: https://www.instagram.com/monstera.gold

Support the show

👩‍💻 Learn From Me: 

• Start Your Profitable Calligraphy Business: Join Shaochen's Free Masterclass
• Get Hands On Support from Shaochen: 
  • Ascent 6 Month Coaching Program
  • Your CEO Partner 1:1 Coaching Accelerator
  • Apply for Business Coaching
• Freebie! Download my free tech guide for the programs you need to run your business

👯‍♀️ Keep In Touch:

• Follow Calligraphy Biz Corner on Instagram
• Follow Shaochen on Instagram
• Visit the website