In this conversation, I sit down with Dave Kang, entrepreneur and brand strategist, to explore his bold experiment in building an “octopus-style” portfolio career. Dave shares how his journey began with a corporate layoff and a transformative sabbatical, leading him to embrace generalism and launch multiple ”tentacles” of work—from brand strategy consulting to e-commerce and even ambient music production. We dive into the philosophy behind his unique approach, including the importance of integrating work and life, the challenges of balancing multiple revenue streams, and the criteria he uses to decide which projects to pursue. Dave also discusses his vision for a future where generalists are valued, sharing his goal to create a community of portfolio careerists and, ultimately, innovation teams built entirely from generalists. From redefining work-life integration to challenging the specialist-driven job market, we cover why portfolio careers offer a compelling alternative for those seeking fulfillment, variety, and purpose in a fast-evolving world of work. P.S. - Check out Dave’s Life-at-a-Glance motivational calendar