
The Stone in My Shoe
She Left the Job But Kept Grading Her Own Worth | Connie Kwan on Self-Worth & Identity Change
Why does your sense of self-worth disappear the moment there's nothing left to point to? Have you ever finished a day with nothing "produced" and felt strangely uneasy about it, like the day didn't quite count? In this episode of The Stone in My Shoe, Debbie Thompson sits down with Connie Kwan, a former Silicon Valley product executive who spent over twenty years in leadership roles at companies including Microsoft and Atlassian, to talk about the belief she's carried since childhood: that her worth comes from what she does. Connie traces this belief back to growing up in Hong Kong, where achievement was simply the language everyone around her spoke, through immigrating to Canada and needing something legible to be recognised by, and into two decades of a career that rewarded exactly this pattern with promotions, paycheques and praise. Seven years after stepping away from traditional corporate life to build something of her own, she's honest about what hasn't disappeared: the quiet audit she still runs on herself, and the moment she realised the real work wasn't a new career — it was identity change at the root. This is a thoughtful conversation about self-worth, achievement and what it actually takes to stop needing proof that you were enough today. What you'll hear: Why growing up between Hong Kong and Canada shaped Connie's relationship with achievement The contradiction of being entrepreneurial while calling yourself "a very low-risk person" What it looks like to still audit your own worth, seven years after leaving the system that used to do it for you Why she believes real purpose has no guarantee attached to it What she means by "getting rid of my stone" Sometimes the hardest part isn't leaving the job that measured you. It's learning to stop measuring yourself. Connect with Connie Kwan Website: https://conniekwan.com/ Newsletter (STORYHabits): https://conniekwan.substack.com LinkedIn: linkedin.com/in/conniekwan ✖️ X: x.com/ConnieKwan_ Product Maestro: productmaestro.com Connect with Debbie Thompson Facebook: facebook.com/thestoneinmyshoe Instagram: instagram.com/thestoneinmyshoe ▶️ YouTube: youtube.com/@stoneinmyshoepodcast Website: debbiethompson.lovable.app If this conversation resonated with you, please follow the podcast, leave a review and share it with someone who may need to hear it. Every conversation helps another person recognise the stone that's been quietly shaping their own journey.






