Why Listen: Grabbing a hold of your own career narrative.
David Kang, a Brand Strategist, shares his journey from a specialist to a generalist, using the metaphor of an octopus to illustrate the benefits of having diverse interests and skills. He discusses his new venture, the criteria for his “tentacles,” and the importance of balancing work with personal passions. David also explores the potential advantages of generalists in an AI-driven world and offers practical advice for those looking to embrace a more holistic and fulfilling career path.
Conversation Highlights
- David’s New Venture: David explained how his sabbatical led him to embrace his generalist side and develop the octopus metaphor for his career. He started writing about this on Substack and received positive responses, which encouraged him to fully embrace this approach in his career.
- Portfolio Career Concept: David described his approach to a portfolio career, which involves having multiple income streams from different areas of expertise. He emphasized the importance of not relying on a single source of income and the value of having diverse interests and skills.
- Criteria for Tentacles: David outlined the criteria for his tentacles, including the need for multiple income sources and at least one non-income-earning activity. He stressed the importance of enjoying work and having a well-rounded existence.
- Inspiration for Tentacles: David and Julie discussed how to find inspiration for tentacles, including reflecting on childhood interests and identifying latent passions. They emphasized the importance of staying curious and exploring new areas.
- Balancing Work and Interests: David and Julie talked about the challenges of balancing a full-time job with personal interests. They suggested starting small by dedicating a few hours a week to explore one tentacle and gradually expanding from there.
- Advantages of the Octopus Life: David highlighted the benefits of embracing the octopus life, such as expressing more of oneself, enjoying work, and having a more holistic approach to life. He encouraged people to find ways to integrate their diverse interests into their daily lives.
- Experimentation and Boundaries: Julie shared her experience of experimenting with new interests and setting boundaries to make time for personal growth. They discussed the importance of giving oneself permission to explore and try new things.
- Generalists and AI: David and Julie explored the potential advantages of generalists in an AI-driven world. They discussed how generalists’ natural curiosity and ability to learn quickly could help them adapt to new technologies and find innovative ways to use AI.
- Advice for Aspiring Octopuses: David advised those interested in the octopus life to stay curious, explore their interests, and learn from the capabilities of octopuses. He also mentioned his Substack and upcoming book as resources for further exploration.

Dave Kang is a solopreneur attempting to make a living doing up to 8 different “jobs” in an Octopus style portfolio career. A brand strategist and marketer for over 20 years, Dave has worked at Silicon Valley startups and Fortune 100 corporations, but following a year long sabbatical decided to leave corporate life and pursue a creative career that utilizes his multiple interests. He writes about the octopus as a metaphor for a generalist who enjoys doing multiple things at once.
LinkedIn: Dave Kang
https://davekang.substack.com/
https://www.neworbitlab.com
https://www.neworbitmarketing.com