When the rules of the game keep shifting, what does bold leadership look like? In this episode, Ben Schafer (Rev Op Leader and husband) joins Monique (Product Leader and Advisor) to explore a listener’s questions: do we make bold moves in uncertain times? And how do you, as a leader, show up with all this uncertainty? Together, Monique and Ben explore the nuances of courage, risk, why inaction is often the riskiest of all, and how to make decisions when the future refuses to give you clarity. This is a conversation that moves beyond easy answers and into the deeper work of leadership, navigating complexity, staying grounded in first principles, and helping others metabolize change.  Through both personal and professional stories, from parenting during the pandemic to the disruption of AI, Monique and Ben reveal what it takes to lead with intentionality when uncertainty is the only constant. You’ll walk away with clarity on why boldness doesn’t mean recklessness, how to navigate the risks of the status quo, and what it looks like to lead others through change without losing sight of your values or purpose. In this episode: (01:47) - The HBR headline that sparked this conversation (05:44) - What “being bold” really means (and doesn’t mean) (10:49) - Why even small bold moves carry hidden risks (13:20) - When not making a decision is a decision, and often the riskiest one (18:28) - Unpacking uncertainty at both personal and business levels (19:31) - Parenting during the pandemic: making bold moves when the stakes are high (23:38) - AI disruption and the temptation of reactive boldness (31:11) - Experiment over analysis over paralysis (35:47) - Time horizons and pacing bold decisions (39:51) - The boldness of speaking truth into leadership (47:24) - Playing your own game without losing your core strengths (50:37) - Lessons from hard choices: one-way vs two-way doors (55:44) - Final reflections: brave, intentional, uncomfortable action in uncertain times Links and Resources: • Harvard Business Review (September/October 2025) | https://store.hbr.org/product/harvard-business-review-september-october-2025/BR2505 Connect with Monique: • Website | https://www.thegreatlifeexperimentpodcast.com/  • Instagram - thegreatlifeexperiment_podcast | https://www.instagram.com/thegreatlifeexperiment_podcast • Instagram - @itsmoniqueschafer | https://www.instagram.com/itsmoniqueschafer  • YouTube | https://www.youtube.com/@GreatLifeExperiment  Ask Monique Got a question that’s keeping you up at night? Need a new way to look at a problem?  ’Ask Monique’ is your chance to get personalized insights. Submit your questions about business, professional life, or personal development, and let’s dive into the messy, beautiful, and ever-changing world together.  https://forms.gle/iGZv2bVnhBSXbnbc8