“I decided to become a designer, but I had no design skills… So I taught myself—everyday I would do my day job in record time and rush home to learn design. Super talented people go to RISD for 4 years and learn design properly. I hacked together my piecemeal design education in 6 months—there was no way I was ready to become a designer. But I was so ready to leave Microsoft. So I started the job search and got rejected a few times. Then I got the job at Exec.”—
Cheng’s after-hours side hustle is evidence of one of the principles of building an antifragile career: When you have a secure but unsatisfying day job, you can take an unbridled bent to your next calling by night.