Hwei-Yi Lee spent the first two thirds of her career making every move count on paper. She earned a prestigious MBA. She took a strategic step down in title. Then she (almost) perfectly timed her corporate exit. She optimized everything for how her resume would be perceived by her next employer. The strategy worked until the linear career path no longer made sense.
In this conversation, Hwei-Yi talks about the motivations and market forces shaping her “third arc,” why she’s learning software development at 48, and how she’s treating this next chapter as a living sandbox, with a clear sense of purpose and the rigor to figure it out along the way.
If you’ve ever made a career decision based on how it would look on paper instead of how it felt, this one’s for you.
Are you navigating your own crossroads? I’d love to have you on the show.







