An Afterwork Update
Recap on what I've been building and what's next.
Building in public.
The last months I’ve been deep in laying the foundations of my work - and I’ve been doing it in public. I’ve been thinking out loud about my own career transition while connecting it to the bigger shifts reshaping how we live and work. With many new people having joined along the way, this feels like a good moment to recap.
I’ve poured an immense amount of time into writing out my five pillars of work framework to support people moving from a full-time job into a portfolio career. For most of us, the word ‘career pivot’ is much of an understatement for this transition. I’ve given up my five pillars of work (vision, structure, identity, money and community) with a bang, picking up the pieces slowly over the time to build my own portfolio career. I’ve gone (and am still going) through the identity unravelling, my own vision creation process, the money fears, re-structuring my day, building my portfolio components and my community outside of work. It often meant dismantling old scripts and limiting beliefs that unconsciously push us to recreate our jobs in self-employment form if we’re not careful. And with every article, it became clearer to me that this change is deeply psychological and, above all, an identity transition.
I’ve been revisiting my own journey, noticing what helped in each pillar and translating those lessons into repeatable frameworks others can use. My hope is that this framework offers a clearer view of what actually ‘breaks’ when you leave a job, and how to rebuild it into a self-authored portfolio career (or any form of self-employment).
If you’re new here, or haven’t had the chance yet, I’d love for you to dive in.
📚 The Five Pillars of Work:
The Five Pillars of Work: How To Transition From A Job To A Portfolio Career. An introduction to the five pillars and the transition struggles I’ve experienced myself and observed in countless conversations with others navigating career change.
Vision Pillar: Rebuilding Vision from the Inside Out
“I wouldn’t know what else to do” is one of the main reasons people stay in their current job. Most have simply never taken the time to find out. We often think we need a fully formed master plan before we can begin. Spoiler: you don’t. What you need is a rough, self-authored vision with your own success metrics, values, and boundaries and then slowly experiment your way towards it - while respecting your current constraints.
Structure Pillar: How To Structure Your Days When No One Tells You How
How do you structure your week if you’re sitting in front of a blank calendar and suddenly you’re the only one deciding everything? Structure translates your vision into day-to-day reality through rhythms, workflows, and decision-making habits that make your days sustainable. And one thing is certain: your definition of success will determine what your work life actually looks like.
Identity Pillar: The Hidden Identity Crisis of Portfolio Careers
Identity is our internal set of rules - our relationship to work, worth, and safety. It shapes what we believe matters, what’s enough, and how we respond to uncertainty. Over time, we absorb powerful scripts about who we are and what makes us worthwhile. If we don’t work with them on our journey, we don’t truly transition but we replicate. We rebuild our old jobs in self-employment, carrying the same fears and limiting beliefs, just without a boss. Identity work is the core work of any meaningful career shift.
Money Pillar: How To Feel Safe Without A Job
One of our most deeply ingrained beliefs is that security comes from employment. Leaving that security behind activates the core scripts we’ve been trained in for years. In a portfolio career, we need to update our mental models of security and learn to build internal safety - through diversified income streams, trust in our skills, adaptability, relationships, and our ability to respond to uncertainty.
Community Pillar: The Power of Intentional Community Building
In your transition, you may miss the sense of belonging that comes from working in a team. You may feel judged for exploring paths that don’t fit the traditional script. In a portfolio career, you consciously weave together micro-communities to create your own circles of belonging. It’s no longer a single office or city, but an ecosystem of people, places, and spaces that make you feel seen, safe, and inspired.
Why does this matter?
The more I worked on this framework, the more I realised this is not just about personal reinvention but also about the larger shift reshaping work itself.
I recently wrote my first guest post for Rick Foerster as part of his Alter Egos series (honest accounts from real people who are trying to push work past its limits). It captures some of my core thinking about portfolio careers but also how work could evolve over time.
In it, I explore whether portfolio careers might be a transitional model between the collapsing world of jobs and a post-labour society.
I do believe jobs are unravelling, but I also think ‘the end of work’ could look very different from how it’s often portrayed. Right now, our definition of work is simply incredibly narrow and mostly reduced to paid employment. That lens ignores much of what actually keeps our lives and society functioning: care work, relationships, learning, tending to our health, and contributing to our communities. All of these require real effort, time, and energy, yet rarely count as ‘real work’.
So I ask: could the disruption of jobs finally push us toward a broader definition of work - one that recognises the invisible and unpaid labour that has always been there?
Maybe portfolio careers are not just alternative career paths but rehearsal spaces for a different way of organising work altogether.
So what’s next?
Building this in public has shaped it into something real for me. Over the past months, I’ve spoken to many of you who reached out after reading my articles. You’ve helped me test and refine my mentoring offering. Through those conversations, both my thinking and my direction have sharpened.
And with that, I’ve just launched my website 👏:
In March, I’ll be opening three spots for my portfolio career mentoring. So if you’re curious, or you know someone that this could help, let me know. Just message me here on Substack or send an email and we can jump on a call to get to know each other.
And in the meanwhile, you’ll continue to receive my thinking here. I’ll be combining both - further reflections on portfolio careers and how to successfully transition - but also visionary thinking on how I see the world of work evolving.
Thank you for being here! 🫶🏻
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.
I love the steady effort you’ve put into this over the last year and the love evident in your work. Well done!
Excellent and timely!