Should we all have portfolio careers?
Former Google Europe COO and Portfolio Collective co-founder Ben Legg joins us to unpack why more people than ever are choosing to earn in multiple ways. With AI, remote work and economic uncertainty reshaping the landscape, workers are diversifying their income not as a nice-to-have, but as a form of risk management. Ben calls it the shift from “wage slave” to “company of one”.
What a portfolio career actually is
Forget the old ladder. A portfolio career simply means you’re not dependent on a single employer — you earn through a mix of consulting, fractional roles, side hustles, creative projects or products. Ben breaks it down into four types: the Side-Hustler, the Freelancer, the Focused Expert and the Multi-Hyphenate. The common thread? You design the mix that works for your life.
The mindset shift: life design, not career design
Ben argues that careers will increasingly move in stages: learning in your 20s, earning in your 30s, chaos in your 40s, and reinvention or mentoring later on. Traditional retirement becomes less relevant; instead, we evolve toward work that flexes with our energy, finances and values over decades.
Organisations aren’t ready, but they need to be
We explore why today’s hiring and org-design models can’t keep up with the speed of change. If half of all work becomes fractional, companies will need to master rapid onboarding, flexible project teams, and new ways of maintaining culture with people who may only be around for weeks or months at a time.
The real challenges of going solo
Portfolio careers aren’t all freedom and fulfilment. Ben calls out the tough bits: the complexity of running a one-person business, the loneliness of not having built-in colleagues, and the income volatility that comes with project-based work. Discipline, community and a strong pipeline become essential.
AI as accelerator, not threat
AI isn’t replacing portfolio work — it’s expanding what’s possible. Ben suggests using AI to speed up the middle of tasks, freeing humans to focus on defining the real problem and shaping the story. Learning AI becomes one of the most important skills for future-proofing your portfolio.
Preparing the next generation
We talk about how children may need to start building skills for portfolio work long before adulthood. Ben advocates for project-based learning, entrepreneurship and experimentation — because education systems are still preparing young people for jobs that may not exist.
Inside The Portfolio Collective
Ben shares how The Portfolio Collective has grown into a global community of 15,000+ people navigating portfolio careers together. It’s designed to solve the two biggest blockers he sees: complexity and loneliness. Members learn from each other, collaborate, and often hire one another too.
Learn more about the Portfolio Collective here.
