After countless conversations about portfolio careers over the past year, I recently realised something: I’ve been all-in on building one, writing about it, and mentoring others through it — but I’ve never actually written the post that steps back and explains what a portfolio career is, why I care about it so much, and why it matters right now.
Since so many new people have joined me here recently, this feels like the perfect moment to do that. So here it is.
(You can also listen to me talk more about my thinking with Jill Reilly)
What is a portfolio career?
A portfolio career is about combining different types of work and income streams into your own version of a working life, built around your strengths, passions, constraints and the life you actually want. Instead of one full-time job that defines everything, it can blend part-time roles, fractional work, consulting, creative projects, digital products, services, or volunteering into a deliberately designed mix. It is basically up to you to design the portfolio career that suits you.
The key word is designed. You’re not just juggling three jobs or hustling across gig platforms. It is about intentionally building multi-dimensional income, identity, and impact across different projects at the same time.
In my own case, I split my time between fractional or project work, which cover the basics, writing on the future of work on Substack, portfolio career mentoring and building additional offerings. Alongside this, I deliberately set time aside for continuous learning, investing, and contributing to the local climate community. None of these alone would be “the job.” Together, they are my work.
Others assemble different components into their very own portfolio career. Kacie Brennell splits her time between fractional operations leadership at a start-up for what she calls ‘financial income’, and teaching yoga and working at a clothing store for ‘energy income’. Linda Perry left a career as a federal criminal defense attorney and now intentionally mixes leadership coaching, strategic advisory, writing, and speaking. Ella Writer organises her portfolio in seasons rather than days: intensive consulting blocks in winter when demand and rates peak, one-on-one coaching and programmes through the summer months, and deliberate stretches carved out entirely for sports and cooking.
Why I'm excited about it.
For a long time, I kept looking for the perfect job. The one that would pay well, have impact, let me be creative, give me variety, let me work remotely. Over the years, I added fifteen more criteria to that list. Eventually, I realised that job didn’t exist — at least not in one single role. If I wanted work that truly fit me, I’d have to design it myself by building a portfolio career, intentionally and strategically.
Freedom to design your life how it best fits you: A portfolio career has allowed me to combine different interests, energy levels, and rhythms into a way of working that actually fits me. Work has become something I actively shape rather than something I squeeze myself into. I design my work on my own terms, around my values, and with people I truly want to work with. Of course there are constraints, but broadly I can decide what time I start, which days I work, what I work on, when I have calls, and who I work with.
One full-time job rarely fulfils all the reasons we work. A single job is expected to deliver income, meaning, growth, creativity, impact, and more. That’s an enormous ask, and it almost never delivers. In my portfolio career, each piece does its part — a fractional role for stability and stable income, writing for creative expression, local community engagement for impact, investing for long-term thinking. I don’t need a single job to do everything. I need each component to do its job.
They reflect the reality that humans are multidimensional: Industrial-era work pushed people into narrow specialisation. But I have strategic sides and creative sides, relational instincts and intellectual curiosities, things I want to build and things I want to explore. A portfolio career makes room for all of it instead of compressing everything into a single job description.
They evolve with you over time: Because it’s mine, it evolves with me. Components can be added, paused, expanded, or dropped as my energy, interests, and life circumstances change. Two years from now, my portfolio will probably look different from today’s. Realising that my career can be fluid, that it doesn’t have to be perfect or permanent, was one of the most freeing shifts I’ve experienced. I don’t need to worry about whether this will be fun for the rest of my life. I just need to follow what’s working now and adjust as I go.
A pragmatic response to a changing labor market.
The reasons above might simply be personal preferences. But portfolio careers also make structural sense right now when the world of work is shifting fast, and I think that is what makes them more than a lifestyle choice.
The structure of work is changing. The dominance of the single full-time job is fading. Fractional roles, project work, and independent collaboration are becoming more common. AI and automation are breaking traditional roles into smaller components. AI agents are quickly taking on lower-level tasks. As Rishad Tobaccowala puts it, we may have already reached peak full-time employment in 2025, and the workforce is now made up of full-time employees, contractors, freelancers, fractional professionals, and increasingly, AI agents.
AI is what makes the team of one realistic. Portfolio careerists operate across multiple domains, and AI agents can increasingly handle the work that used to require a whole team. This lowers the barrier significantly. What once demanded either deep pockets or constant context-switching can now be distributed to AI, allowing one person to sustain a genuinely multi-dimensional career.
Portfolio careers restructure risk and security for today's reality. We have been taught that a job equals safety. But when a single employer can restructure you out overnight, that sense of security was always more fragile than it appeared. A portfolio career does not eliminate risk, but it distributes it. Multiple income streams mean less dependence on one employer, more resilience to change, and a stronger ability to adapt as industries shift.
Diversification as security. Instead of putting all your eggs in one basket, you build multiple income streams. Less dependent on one employer, more resilient to change. If one stream slows down, others sustain you.
Adaptability as a core skill. Because you are constantly working across different contexts, you build broader skills, stronger networks, and the ability to pivot as opportunities evolve. Your identity shifts from "I am my job title" to "I am a portfolio of skills and I can adapt and reconfigure." Over time, this builds a different kind of confidence: the kind that comes from knowing you can adapt, not just from knowing you are employed.
Moving from external security to internal safety. In a job, security is outsourced to the company. In a portfolio career, you start building something different: the feeling that whatever happens, you can handle it. It lives in your skills, your adaptability, your relationships, your sense of agency, and your ability to respond to uncertainty. That kind of security does not disappear when a contract end. I unpacked this fully in my article on how to feel safe without a job.
So after all, portfolio careers might be a pragmatic response to a changing labor market shaped by volatility, automation, and institutional fragility.
How do you get started?
A portfolio career does not ask you to quit tomorrow and figure it out. You can actually build optionality without being reckless through combining stable income streams with more exploratory work.
Many people transition by starting a small side project alongside the job, testing it, learning from it, and slowly shifting the balance over time. Can you negotiate a four-day week? Can you carve out a few hours in your current job to learn something new? Start writing on Substack about a topic you care about?
Others take a sharper turn: quit, take a sabbatical, start from scratch. That path comes with more uncertainty but also more space to explore. Most people I see land a fractional role for part of the week using previous skills and expertise to cover the financial floor. And dedicate the rest of their time to experimentation, creative work, skill development, and working toward longer-term goals.
Either way, the real work is not just logistical but especially psychological. Leaving the structure of a job means rebuilding your sense of direction, your relationship with money, your identity, your daily rhythms, and your community from scratch. That is why I developed the five pillars of work framework to help people navigate the transition more consciously. If you are considering this path, that is probably the best next read.
Where I think this is going.
Portfolio careers are still early. The infrastructure, the language and the cultural acceptance — all of it is catching up. But they’re clearly part of a broader shift. People are learning to unbundle the job and design work that fits their lives, instead of the other way around.
I don’t see portfolio careers as the destination, though. They’re a bridge toward a portfolio life. Right now, many of us are learning to unbundle work splitting a single job into multiple streams of income, meaning, and impact. But the same logic applies to life more broadly. Care work, relationships, learning, health, contribution, play or resting — these are not extras to squeeze in the margins around work. They are the activities that make life meaningful. Instead of organising life around a job, you organise life around a portfolio of everything that matters to you.
That's the conversation I'm most interested in. And if you're reading this for the first time, welcome to Afterwork!
About Afterwork.
I’m building Afterwork to help people navigate the biggest shift of our time as AI disrupts work as we know it. I write about what comes next - from portfolio careers to deeper questions of identity, purpose, and life beyond employment.
Through my mentoring, I work 1:1 with professionals transitioning from jobs into portfolio careers. My Vision Workbook is a way for you to work through this self-paced.
This is the post I’ve been looking for. Thank you for writing it! Mid-January my job was eliminated and seeing my job prospects at this point in my life is making me think that a portfolio career is a much better option. One question: I keep reading about fractional work but what does that mean?
Thanks for breaking this down so clearly. Have recently started writing in Substack about some my pov on some of these topics after having quit the traditional 9-5 and building my fractional ops biz. You have been one of the greatest inspirations to start doing so! Love the idea of the "portfolio life". Things are changing, but how cool we get to build new ones.