Leading Up: The Work Shift "I Don't Know" Is Actually Knowing: Top Leaders on Career Uncertainty
Feb 17, 2026
Anna Kriacic, Oliver Wyman leader who champions serendipity and nonlinear career moves. Ray Wong, tech analyst and founder who was pushed to ask “what are you worth?” before launching his company. Dr. Becky Kennedy, clinical psychologist who turned therapy into parenting guidance by embracing “I don’t know.” They discuss career pivots, reframing uncertainty as insight, and practical ways to navigate work shifts.
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Father's Question Triggered Entrepreneurship
- Ray Wong's father asked him, "How much do you make? What are you worth?" which pushed Ray to realize salary and personal worth differ.
- That distinction led him to start his own company to build a culture rewarding risk and ownership.
I Don't Know Sparked a New Approach
- Becky Kennedy realized parenting advice using punishments conflicted with her therapeutic approach to adults.
- Saying "I don't know" in a session pushed her to write new ideas that became Good Inside.
Use I Don't Know To Journal And Act
- Becky Kennedy advises using "I don't know" as data: journal what you do know and spend minutes building an "I know" circuit.
- Take small actions; behavior change precedes identity change and builds confidence by surviving missteps.