The Five Pillars of Work: Rebuilding Vision from the Inside Out
How to establish your own guiding principles for a portfolio career.
Returning to My Own Compass
The last two weeks I’ve been on a much-needed vacation and it reminded me why having your own guiding principles matters so much in a portfolio career. When you’re building something on your own, it’s dangerously easy to slip back into old patterns. We cut breaks, scrutinise every euro, and promise ourselves we’ll rest ‘once things are more stable’, but that moment rarely arrives on its own.
Building something from scratch demands real energy and creativity, and you simply can’t pour from an empty cup. Time off is not a distraction from the work; it is what keeps the spark, courage, and originality alive.
I almost skipped my trip to Rio de Janeiro for all the ‘responsible’ reasons. My Substack is gaining momentum, my five pillars of work framework has resonated strongly, and I’ve just run my first mentoring sessions and refined my offering. Staying home to ‘ride the wave’ seemed like the logical choice, but going turned out to be wiser and far more aligned. This trip gave me exactly what momentum alone couldn’t: fresh energy, new ideas, and a powerful reminder to take my own portfolio career guiding principles seriously.
This is the work of vision: learning to steer your life by your own principles, even when momentum tempts you away from them.
Back with a clearer head and a fuller tank, I’m excited to go deeper into the five pillars of work framework for transitioning from a traditional job to a portfolio career. As the year comes to an end and people start thinking about 2026, this might actually be a good moment to dive into vision.
Dismantling the Vision Pillar
In a traditional job, your vision comes pre-assembled. The company hands you a direction, a ladder, and a definition of success and your role is to fit yourself inside it. You get your next task from your manager, you grow by moving upward, you develop according to annual reviews, and you borrow meaning from the mission on the website. Even if you don’t fully resonate with it, it tells you where you’re going and why. You learned to align your ambitions with the organization’s direction rather than your own.
Leaving a job means stepping out of an architecture that once told you who to be and how to advance. Without a predefined path, the horizon suddenly stretches wide open. At first, that feels exciting and you might feel relief. And then it becomes paralyzing, because no one is there to tell you what comes next. There is no ladder, no manager, no ready-made roadmap; growth stops being a sequence of promotions and becomes something you have to design and defend for yourself. With endless possibilities in front of you, the fear of choosing ‘wrong’ creeps in, and the freedom that looked expansive from afar can feel terrifying up close.
At the same time, your inner compass is out of practice. Years of shaping your ambitions around external expectations make it hard to recognise your own curiosities and desires. You start confusing external success with internal success because that’s the only metric you’ve ever known. You may find yourself overthinking instead of experimenting, frozen by the pressure to figure out your ultimate purpose before taking a single step. And of course, your circle loves to ambush you with the one question guaranteed to trigger an existential crisis at every gathering:
“So, what’s your plan?”
Questions you never had to sit with before start to weigh heavily: What do I actually want now? What does success look like if I define it myself? You may realize there are skills, knowledge, or experiences you never needed in a traditional role, and now you face a new challenge: learning how to learn, choose, and navigate independently. That can feel disorienting, not because you are doing something wrong, but because you are switching from sitting in a train to steering your own sail boat.
Already feel your head spinning when reading this? Completely normal. The chaos is actually not a problem to solve, but a completely natural phase of rebuilding. And the willingness to exist in that undefined space is itself the work.
Vision is rarely available at the beginning
I quit my job without a plan because I couldn’t keep building a life around things that I didn’t want. I just didn’t know where to go next.
There’s endless talk about big visions and five-year plans. But knowing what you want is the prerequisite for that and I didn’t. Most people in transition don’t. Vision is rarely available at the beginning. In fact, trying to force clarity too early can strangle the very curiosity that is trying to lead you. Most of the time, you begin in the middle, build what you can see right now, and trust that the dots will connect later.
So let’s take the pressure off by reframing the void:
Vision emerges from trying, not thinking.
Curiosity is the new compass.
You don’t need clarity to begin but beginning creates clarity.
Your vision evolves as your portfolio career evolves.
‘Defining success internally’ becomes the new muscle.
One’s vision in a portfolio career is curiosity-led, emerging over time, iterative, and built through experiments.
Vision in Motion
Of course we want a plan. We want to feel like we’re at least moving in the right direction. And while I wouldn’t recommend mapping the next ten years, you can absolutely define the next steps.
Since we’re talking about portfolio careers, let’s assume the idea already resonates. You might still be employed but curious, freshly quit, or somewhere in the early stages of building your own path. Chances are you’re multi-passionate, drawn to variety, and maybe already had a side project in your job.
So what can be the first steps that you can take towards building a vision for your portfolio career?
Self-discovery – ask the questions that rebuild your inner clarity.
Define a rough emerging vision – keep the stakes low, remembering that vision is dynamic.
Choose first experiments – treat everything as a test and follow your curiosity.
Build your own portfolio career guiding principles – turn your insights into a practical system that guides your decisions.
So let’s dive deeper!
1) Self-discovery
When endless paths are available and you can’t turn outward to your manager anymore for guidance, you’ll need to turn inward: knowing yourself becomes the anchor. During this phase of my journey, I did a lot of inner work to understand what energizes me, what I care about, what feels aligned with the life I want, and what I’m genuinely good at. This became the foundation for everything else and the launchpad for experiments to test whether I actually enjoy the things I thought I wanted. Below, I’ve collected self-discovery questions that I found useful and grouped them into categories.
Choose the ones that resonate and give yourself time to reflect, but resist the urge to overthink the process. It is completely normal not to have all the answers right away, so treat this as an iterative practice rather than a one-time exercise. Don’t think too much about how you can monetize things or what the market needs but for now explore what you want more of in your work and life, your values, energisers, boundaries, and what a fulfilling, sustainable workweek means to you.
Tip: Reflect on the question yourself first, and then feel free to ask ChatGPT to answer it about you. If you’ve been using it regularly, you’ll be surprised by what it notices that you might not see yourself.
2) Define a rough vision
Look at the raw material from Step 1, pull out the strongest themes and ask: if these connect, what kind of work-life direction begins to emerge?
Since we’re at the end of the year, it may help to write an imperfect sketch of what you’d like your work/life to look like in 2026. Keep your vision simple and directional: something grounded in what’s true now and flexible enough to change.
3) Choose first experiments
Once you have a rough direction, the goal is to test it, not fully commit to it yet. Experiments help you learn what actually works for you. Of course people’s realities differ: some need income quickly, some are still in full-time jobs with limited time, some have more freedom to explore. Your experiments should reflect your moment and constraints.
Pick 2–3 themes from your vision: What feels most exiting or most urgent to try?
At this point, it can be helpful to narrow your horizon. Instead of envisioning all of 2026, choose some experiments you’d like to try in Q1.
An experiment can take all forms or shapes:
Want to write? → publish one short post per week.
Need income soon? → take one mini freelance project to test fit or look into landing a fractional role.
Curious about mentoring? → offer 1–2 free sessions.
Still in a full-time job? → one 90-minute block per week for a micro-experiment.
Exploring a new field? → talk to three people working in it.
At the end, ask yourself: What did I learn? Did this energise me or drain me? Is there potential here? Do I want more of this in my portfolio?
4) Build your portfolio career guiding principles
After each experiment, fold your learnings back into what you’ve already defined. Perhaps your vision needs a small adjustment, a new success criteria emerges, or a component of your portfolio career becomes validated.
By now, you’ve gathered the raw ingredients of a self-authored vision: a clearer sense of who you are, a rough sketch of where you’d like to go, and a handful of early experiments to build on. Step by step, you’re shaping guiding principles that replace the structures of a traditional job: your personal compass for making decisions, finding direction, and sustaining progress.
An Ever-Evolving Portfolio Career
I’ll leave you with this for now in the true spirit of launching and iterating my five pillars (more to come on this in the ‘structure’ pillar). Since quitting my job, I’ve cycled through many versions of my own vision and portfolio career guiding principles. Each round of self-discovery, experiments, and reflection didn’t give me a final answer, but it did give me a better way to navigate.
At first, I only knew what I didn’t want anymore. I sketched my values, clarified my skills, and defined my boundaries. I imagined working in climate change and experimenting with alternative ways of working and financing life. But I’m glad I didn’t narrow my goal too early, like ‘get a full-time job in climate’. That would have limited the journey. I might never have discovered portfolio careers or started writing, which began as a spontaneous experiment and turned into something I enjoy. The same goes for shaping the branding and focus for this Substack or launching portfolio career mentoring. All results of small experiments.
So when you strip it down, a portfolio career doesn’t require a perfect vision at the start. It requires a few core anchors: a sense of what matters to you, a rough direction that feels “more you,” your own success criteria, and the courage to keep following your curiosities in small, low-stakes ways. The rest emerges over time.
You don’t have to get this right on the first try. Your vision is allowed to be fuzzy, your path non-linear, your experiments messy. What matters is that you’re no longer sitting in the train, waiting for someone else to announce the next stop. You’re learning to steer your own sailboat by adjusting the sails, reading the wind, and trusting that clarity grows with every mile you travel.
📚 Read the full Five Pillars of Work series:
The Five Pillars of Work: How To Transition From A Job To A Portfolio Career
The Five Pillars of Work: Rebuilding Vision from the Inside Out (this one!)
The Five Pillars of Work: How You Define Success Shapes How You Structure Your Work
The Five Pillars of Work: The Hidden Identity Crisis of Portfolio Careers
The Five Pillars of Work: The Power of Intentional Community Building
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 problem is, if one is exploring and trying, then how do we decide what is worth doing and what is distraction? And how much is too much? Especially as different eggs is different baskets means a lot a mental and skill energy going in different directions.
This is so helpful!! Thank you for laying it out so clearly. 🥲🥲🥲