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S1E6. Failing (up) at work

Reinvented | Season 1 | Jenny Wu | Failing (up) at work


Jenny Wu has accomplished more in the first 15 years of her career than most of us will in a lifetime.

The key to her success? Finding a way to “fail her way up.”

Jenny and I relive some of her biggest career setbacks, talk about what she learned, and explore how each of us can make better career choices.


1:20 – The most millennial resume in the world

2:30 – If you’re not failing 90% of the time, you’re not trying hard enough

4:45 – The immigrant struggle + a rebellious personality

7:30 – Theoretical career choices vs. real-world data

12:15 – Being scared to make the wrong decision + not quitting soon enough

13:00 – Cultural norms around resumes, quitting, and failure

15:00 – Economic rationale for millennial behavior

16:30 – Reliving her favorite failures

19:00 – How you react in the moment vs. with the benefit of time

20:45 – Landmark = turning point in reframing failures

21:30 – Needing to prove yourself vs. finding unconditional love

24:30 – Reframing your failures and forcing yourself to tell a new story

30:00 – The rationale for moving into the social sector

32:15 – Features vs. flaws and finding the right fit when you’re an “acquired taste”

40:00 – The role of mentorship in career development

42:30 – The impact of privilege

46:00 – Finding what works for you

49:00 – Does failure teach you more than success?

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Thanks so much for listening!