This episode explores how life-altering moments can fundamentally reshape our definition of success, work, and legacy. After losing his mother, globally recognized people leader Alex Seiler confronted the illusion of unlimited time and re-evaluated goals that no longer fit who he had become. Grief became a clarifying force, prompting deeper questions about identity, purpose, and what it truly means to live, and be known for, a meaningful life, rather than chasing success for an outdated version of oneself.

From that clarity emerged a reimagined approach to career and leadership. Alex shares why he stepped away from traditional career ladders to design a portfolio career blending executive leadership, advising, writing, speaking, and partnerships, each chosen for income, impact, learning, or legacy. The conversation challenges narrow definitions of loyalty, titles, and progression, arguing instead for values alignment, optionality, and being “brilliant at the basics.” Practical insights span early-career guidance (building transferable skills, saving for choice, finding community beyond one employer) to senior leadership lessons on pacing change, meeting organizations where they are, and leading without judgment.

At its core, the episode is about relationships, reflection, and intentional change. Alex discusses building a personal board of advisors, creating trust through accountability, and making reflection a daily practice rather than a crisis response. The conversation ultimately returns to legacy: not “Have I been successful?” but “What do I want to be known for next?” For anyone questioning whether their career still fits the life they want, this episode offers a thoughtful, humane blueprint for choosing work that evolves with who you are becoming.