EPISODE 187 - My 3 Best and 3 Worst Moments in Business (10 Year Lookback)

Shinah Chang ·

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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 CALLIGRAPHY CHALLENGE STARTS SEPTEMBER 14, 2026!

FREE WORKSHOP:

ABOUT CROOKED CALLIGRAPHY

Hey - I'm Shinah! A former miserable corporate lawyer turned sassy calligrapher and teacher. Ten years ago, I was WISHING I could create beautiful calligraphy but feeling really un-creative and LOST about how to achieve that... and now I truly believe that ANYONE can learn this beautiful craft - because I've already taught it to THOUSANDS of people, from all different backgrounds.

Calligraphy has given me a gorgeous life. It's helped my students find PASSION, PURPOSE, and a reason to JUMP OUT OF BED each morning. What could it do for you? =)