Around The Ladder: The Growing Disconnect Between People and Their Jobs With Alex McCann

What happens when your career looks good on paper, but still feels off? In this episode of Around the Ladder, Erika Steinberg talks with Alex McCann about career pivots, the pressure to “have it figured out,” and why so many people are questioning the old rules of work. Alex shares the through line behind his own shifts from engineering to music to marketing and now to founding Rumbo: curiosity, experimentation, and a willingness to test assumptions about himself. He and Erika also dig into his viral essay, The Death of the Corporate Job, and why it resonated with so many people who feel disconnected from the jobs they’re supposed to value. The conversation explores the gap between how work looks and how it actually feels, the role of social media and comparison culture, and why “imposter syndrome” may not always be the right language for what people are experiencing. They also discuss AI, automation, and what happens when white-collar work becomes increasingly easy to simulate or obscure. Later in the episode, Alex explains how his experience with a career coach inspired Rumbo, a platform designed to help people move beyond tactical job-search advice and get clearer on strategy, direction, and what they actually want from work. The episode closes with a thoughtful reminder: if something feels wrong in your career, it may be worth stepping back and connecting your work to a problem you genuinely care about solving. Connect With Alex Substack: Still Wandering Company: Rumbo LinkedIn: Alex McCann