A Diversified Portfolio of Work
What do you do when jobs stop doing their job?
Let’s say you’re tired of the same-old at work, but not so naive to think you should just quit-and-follow-your-dreams (terrible advice unless you’re the one person it works out for).
Rather than believing a new, shiny job will fix your problems, or that you’ll need to wait until retirement to finally do what you want, it might be worth considering a new item on the menu: the portfolio career.
Iwana Johannsen is one of those people who’s experimenting at work’s edges. She’s been deconstructing “the jobs of a job” and rebuilding those pieces again through a new way of working, not only for herself, but advising others looking to make the same type of change.
Her way is one that doesn’t discount the value of an income (kinda useful), but creates the flexibility, accountability and experimentation that so many successful people want in a next step.
I invited Iwana here to talk about why work is evolving toward portfolio careers, and why you might want one.
Iwana is the first entrant to my new series, Alter Egos; honest accounts from real people who are trying to push work past its limits.
- Cheers, Rick
👉 P.S. If you’re interested in this topic, I urge you check out her writing at After Work. She’s one of the few people I recommend following.
From Jobs to Portfolio Careers to Portfolio Lives
The full-time job has long been the center of work and life. It shapes how we spend our time, how we earn money, and how we make sense of ourselves. None of us knows exactly how work will evolve in the coming years but we can all feel that something is changing. That our narrow definition of work may no longer fit the world we’re moving into.
Is it the end of work? Probably not yet, but it may be the beginning of the end of the full-time job as the dominant container through which work is organized.
A hint of what’s coming is already in the air: a world where ‘fractional’ might become the default, not the exception. Where people mix multiple roles, projects and income streams into portfolio careers.
Could the path ahead not be from job to job, or even from job to freedom, but from full-time jobs, to portfolio careers, and eventually to portfolio lives?
That thought has been circling my mind for a while and it’s the one I want to explore more deeply here.
Our Definition of Work
For a long time, I didn’t really question what we mean by work. Like most of us, I treated it as shorthand for paid employment: the job, the role, the title on a LinkedIn profile. For decades, the full-time job became the primary container for our time, energy, and attention. It absorbs most of our waking hours. Life is structured around the job, and everything else has to squeeze in around it.
But that narrow definition excludes much of what actually keeps our lives, and society, functioning. Care work, relationships, learning, tending to our health, contributing to society. All of this requires real effort, time, and energy, yet rarely counts as ‘real work’. We’ve learned to treat these activities as secondary, something to fit in around the edges of what’s considered productive. This is exhausting and it undervalues everything we do that keeps society alive, connected, and compassionate.
We’ve internalized the idea that value only shows up on a payslip. We’ve built a society that runs on invisible labor and then organized identity and security around the one form of work that pays.
So isn’t what we define as ‘work’ overdue for a massive reframe, for one that makes room for the full human experience?
The Job is Losing its Monopoly
What I’ve been describing is not necessarily new. The flaws of the system have been visible for a long time. What is changing now is the speed and the convergence of forces hitting the full-time job at once. AI, automation, and robotics are driving the cost of knowledge and labor toward zero. Tasks that once required whole teams are now being absorbed by technology, breaking traditional jobs into smaller components. As work becomes more modular, companies are increasingly hiring for projects, part-time, or fractional roles rather than permanent positions. A shift accelerated by digital platforms, the need for specialized skills on demand, and the desire to remain flexible in volatile markets.
Apart from that, the full-time job was never able to meet all our needs in the first place. We are multi-dimensional humans, yet industrialisation pushed us into ever narrower forms of specialization. Instead of chasing a perfect job that delivers income, meaning, security, creativity, and impact all at once, people break this bundle apart and reassemble it on their own terms.
And as work becomes more fragmented, modular, and unstable, people have started reorganizing themselves with a new model.
Portfolio Careers as a Transitional Model
Portfolio careers are a pragmatic response to these shifts. Rather than relying on a single full-time role, it combines different forms of work and income streams into a deliberately designed mix. That might include part-time or fractional roles, consulting, creative projects, digital products, services, or volunteering. Some parts generate income. Others provide meaning, learning, or connection. Together, they form one coherent working life.
There’s also the practical dimension. By diversifying work across multiple sources, people become less dependent on a single employer, more resilient to change and better able to adapt as industries shift. Instead of putting all your eggs in one basket, you spread your bets.
In practice, portfolio careers can take many forms. Most combine stable income streams with more exploratory work.
In my own case, I currently split my week between a fractional marketing role for two days, which covers the basics, one day writing on the future of work, and two days focused on portfolio career mentoring and further developing my offerings. Alongside this, I deliberately set time aside for investing, continuous learning, and contributing to the local climate community. Others assemble different components around the same logic.
My friend Fiona works fractionally in customer success at a tech start-up while teaching yoga and building products and services around her work on overcoming insomnia among high achievers. Her current split is roughly 30% fractional work, 20% yoga, and 50% focused on insomnia-related content creation, coaching, and digital products.
Many actually transition from a job to a portfolio career by developing a side project alongside a job and then gradually shifting the balance over time. It’s a way to experiment without jumping off a cliff building skills, confidence, and optionality as you go. Importantly, portfolio careers are not static. They evolve with life stages, interests, and responsibilities. Workloads scale up and down. Components are added, paused, or dropped. That flexibility is precisely the point.
Lately, I’ve been thinking that portfolio careers may not be the end of the story, but a transitional model. A practical way of navigating the gap between the collapsing world of jobs and a more self-authored way of working and living.
Portfolio Lives: Beyond the Job as the Centre of Life
For decades, the job has shaped how we allocate our time, define success, and decide what counts as valuable. As that structure weakens, something important becomes visible again: much of what keeps life and society functioning was never absent but it was clearly pushed to the margins.
Seen in this light, the shift toward portfolio careers is not just a labor market adjustment. It is a first step toward recalibrating what we value. A move away from treating paid employment as the sole legitimate form of work, and toward recognising the full range of activities that sustain a meaningful and resilient life. A larger shift from organizing life around a job to organizing life around a portfolio: of work, care, relationships, health, learning, contribution.
It’s understandably hard to imagine life without jobs at the center. For most of us, work has been synonymous with survival, structure, and legitimacy. But once AI and automation performs most labor better, faster, cheaper, and safer, we may be forced to confront a new reality. One where questions of identity, contribution, and meaning can no longer be outsourced to employment alone.1
As Rick Foerster points out in this article, this is not about abandoning ambition or productivity. It’s about taking a more deliberate, multi-dimensional approach to life that doesn’t collapse identity into a single role, but allows different sources of motivation and meaning to coexist and evolve over time.
The example Rick shares of how his own portfolio has shifted across life stages makes this tangible. It’s not a rigid framework or a calculated formula, but a living composition shaped by circumstances, priorities, and personal values. Just like a portfolio career, a portfolio of life is never finished. It adapts as we do.
The transition from full-time jobs, to portfolio careers, and eventually to portfolio lives won’t be easy. But rather than being abruptly pushed into a post-labor future, it could offer a gradual way out of job-centered living.
That pace matters. Not just economically, but especially psychologically, because the hardest part will be letting go of identities, routines, and measures of worth shaped by decades of job-centered living.2
Navigating it will require new forms of guidance - culturally, politically, and personally. But if we get it right, it may also be our best chance to build a society that values what actually makes life work.
Postscript from Rick: Iwana is the first entrant to my new series, Alter Egos; honest accounts from real people who are trying to push work past its limits. Stay tuned for more guest posts and interviews
I’m sure, you’re now thinking about how we replace household income as jobs collapse, so I recommend to read this article and explore David Shapiro’s work on post-labor economics.
 | A guest post by
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I looove this. I couldn't agreemore: a portfolio career isn’t the destination, it’s a bridge. The deeper longing isn’t for multiple income streams. It’s for agency, self-determination, and alignment between how we live and who we are. We’ve built a dependency on an economic structure that extracts more than it nourishes. We optimized for productivity. But a life is more than sustaining yourself while paying the price of existing. And the solution is fundamentally different from simply redesigning employment (or curating a more diversified work portfolio).
Many argue that for someone struggling to cover rent, “self-actualization” is a luxury. Stability comes first. Survival comes first. Yet even those who “just need any job” are already experiencing the cost of the system: burnout, precarity, anxiety, loss of meaning.
That longing for life isn’t exclusive. It lives in all of us. The desire for dignity, agency, and alignment isn’t a luxury need, it’s human. And what differs is not the depth of that need, but the degree of freedom we have to respond to it.
Those with more privilege often have more room to experiment, to redesign, to say no, to take risks. And still, many don’t. Not because the desire isn’t there, but because the inner shift can feel even riskier than the external one. It requires questioning inherited definitions of success, productivity, and worth. Yet, many are trapped and don't dare to make this transition. That’s why inner transformation matters so much. When those with the capacity to choose begin choosing differently, they expand what becomes imaginable, and eventually possible, for all of us.
This makes total sense. I have also realised (thanks to my 6-7 months of sabbatical) the importance of balancing other aspects of life and not to detach your identity from "career" or the job role you're in!