Meet Shinah Chang

Alright – so today we’ve got the honor of introducing you to Shinah Chang. We think you’ll enjoy our conversation, we’ve shared it below.

Shinah, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?

When I left my prestigious law career to start a creative business, I wasn’t exactly full of confidence. In fact, I felt like I was starting from zero – no fancy title, no clear path, just this knowing that I HAD to do something braver with my life. And the doubts were loud. Who was I to call myself an artist or start a business? What if I failed? What if all my old law colleagues found out I was trying to sell calligraphy for a living?

It took a lot of internal wrestling (and weekly meetings with a life coach) to understand why my self-worth was so tied to external achievements and other people’s approval. What finally helped me develop real confidence was realizing that the bravest, most admirable thing you can do is live for yourself instead of others.

My whole life, I had done everything I was “supposed” to do to be successful: got into Harvard, became a corporate attorney, and worked my butt off to please others. But even with those achievements, I felt disconnected from my life…like, this is it? I trudge through each day just waiting desperately for weekends and vacations?

I built my confidence by embracing the thing that makes my calligraphy — and my story — unique: imperfection. The usual pretty, polished aesthetic felt boring. That’s why I named my business Crooked Calligraphy because swear words and mistakes felt way more fun. People connected with me because I was sharing not just my art but my messy, honest journey. The more I tapped into my authentic voice, the quieter that inner critic became.

Confidence doesn’t come from overthinking — it comes from imperfect action. Don’t wait for confidence; build up your COURAGE instead. Every time I took action despite my doubts, my self-esteem grew a little stronger. I realized people weren’t looking for perfection; they were looking for something real. Now, I teach others not just how to write beautiful letters but how to find confidence in their real, flawed, creative selves.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?

I started Crooked Calligraphy in 2016 and have taught over 5,000 students how to write beautiful letters and make money from their art. Our signature offer is the “Pro Calligrapher Bundle”: a comprehensive trio of online courses that teaches students how to do pointed-pen calligraphy, develop a sellable calligraphy style, and launch their own profitable calligraphy side business.

I’ve watched so many of my students do things they NEVER thought they could do: create stunning art, put their creativity out into the world, even turn their passion into a profitable business. And that’s why Crooked Calligraphy has resonated so deeply – because it’s about so much more than perfect lettering. It’s about offering a space where people can take risks, make mistakes, and learn that their worth isn’t tied to perfection. It’s about rediscovering the joy of creating, building self-worth, and realizing that you don’t have to have it all figured out to start.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

My calligraphy education business has brought me more financial success and personal freedom than I ever could have imagined. But, I wouldn’t have been able to grow my business without three things: the willingness to 1) learn, 2) be uncomfortable, and 3) be vulnerable.

The Willingness to Learn: Building a business, building a life of your own, that requires constant growth and learning. It’s impossible to know all the steps in advance, so you just have to be willing to figure things out… even when it’s hard. My advice? Start before you’re ready. Take one small step toward that thing that excites you (and terrifies you) and trust that the next step will become clear.

The Willingness to be Uncomfortable. Phew, this is a huge one. Most people HATE the feeling of uncertainty, so we stay in corporate jobs that give us the illusion of safety. But you have to embrace risk when you’re making a living out of your own cleverness and creativity. And it doesn’t stop once you’ve gotten through the first few years; the more successful you become, the more criticism, misunderstanding and plain ol’ projection you’ll face. My advice? Tell yourself it’s normal to feel uncomfortable when you’re growing. Each new level takes you out of your comfort zone and that can be terrifying, but it sure makes life more fun.

The Willingness to be Vulnerable. Authenticity has been the heart of my business and my success. The more I showed up as my real, imperfect self — sharing not just my wins but my fears and missteps — the more people connected with my work. My advice? Don’t hide your weird. Attracting the right people to your business means repelling the wrong people. Especially in this age of A.I., people are desperate for real humanity. The more you embrace your true voice, the more you’ll attract the right opportunities and community.

If you’re early in your journey, know this: going after a truer life isn’t easy. The more you can embrace the full spectrum of human emotions and experiences, the stronger you’ll be. You don’t have to have it all figured out to start. You just have to trust that you CAN keep learning and stretching through discomfort and getting closer and closer to your real self.

How can folks who want to work with you connect?

I’ve been having a lot of fun lately teaching more advanced business strategies and messaging. I’ve built a million-dollar education business over the past 10 years, and I’m itching to share my wisdom and experience with others! If you’re a creative business owner, or have an audience of aspiring creative business owners, and you want an expert to come teach on:

– Profitable creation, marketing, and selling of creative online courses

– Messaging, copywriting and content that helps your business cut through the noise and become irresistible to your ideal customer

– Neuroscience-backed ways to move through fear, work past limiting beliefs, and reframe self-doubt so you can finally take action

… feel free to email me at [email protected] =)

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