Walking away from a secure city government job to eventually run one of the world's most recognizable handbag brands sounds like fiction. For Lew Frankfort, it became his career story, and the path between those two points is exactly what makes this conversation so valuable. Lew joins Joe Saul-Sehy and OG in the basement to break down how a combination of discipline, curiosity, and what he calls "magic and logic" shaped his journey from city hall to the corner office at Coach. This isn't just inspiration for aspiring executives. Lew's insights about making better decisions, taking calculated risks, and building a meaningful life apply whether you're 25 or 55, whether you're climbing the ladder or considering jumping to a different one entirely. Lew shares how preparation became his secret advantage, why curiosity beats confidence during major transitions, and what he learned about leadership while helping transform Coach into a global powerhouse. His framework for balancing intuition with analysis gives the Confident Explorer a practical lens for evaluating their own big moves, career pivots, or midlife reinventions. Then Joe and OG shift gears to tackle a different kind of transition. The first year of retirement. When excitement runs high and "go-go" energy meets newfound freedom, spending can spiral in ways that derail decades of careful planning. They break down the crucial financial decisions retirees face right out of the gate, why that first year can be surprisingly dangerous, and how to set yourself up for long-term stability without killing the joy of finally having time to live. Plus, Doug delivers trivia involving time travel and underwear, because even episodes about CEO wisdom and retirement planning need a reality check from the basement. What You'll Walk Away With: • How Lew Frankfort pivoted from city government work to leading Coach and what that path teaches about career reinvention • The "magic and logic" framework anyone can apply to big decisions and career moves • Why curiosity and thorough preparation matter more than confidence when making your next leap • Leadership lessons from someone who helped build a global brand from the inside • What retirees absolutely must understand about spending during that crucial first year • Why the "go-go years" of early retirement can wreck your finances if you're not careful • Strategies for aligning your early retirement excitement with long-term financial stability • Permission to reinvent yourself at any age, armed with both inspiration and practical wisdom This Episode Is For You If: • You're considering a career change but worried you're too far along to pivot • You want to understand how successful people actually made their big moves • You're approaching retirement and want to avoid the spending traps that catch most people • You're curious how to balance intuition with analysis when making major life decisions • You believe it's never too late to build something meaningful or try something new Before You Hit Play, Think About This: What's one career move or life transition you've been thinking about but haven't pulled the trigger on yet? What's actually holding you back? Drop your answer in the comments because Lew's story might be exactly the perspective shift you need to take that next step. FULL SHOW NOTES: https://www.stackingbenjamins.com/https-stackingbenjamins-com-lou-frankfort-bagman-1772/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 (https://www.stackingbenjamins.com/201) Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices