Transitioning to a portfolio career: The beginning
- Riccardo Decarolis
- Jan 2
- 3 min read

Over the past months, I’ve found myself increasingly asked the same question:
Why a portfolio career? And what does it really take to make the shift?
For me, this transition is not a finished story. It has just begun.
After multiple years in demanding roles across consulting, sustainability, and organizational transformation, I reached a point where a single, linear role no longer reflected how I want to work, learn, and contribute. Rather than choosing one next step, I decided to consciously explore a combination of roles and to see what emerges from that process.
Over recent months, this has taken shape in a few concrete ways: I’ve launched Tranclarity and am in the process of building it out; I’ve started a contract engagement in the public sector; and I’m actively exploring teaching and guest lecturing opportunities by reconnecting with people in my network. Together, these elements form the early edges of a portfolio. Not fully defined yet, but connected by a common thread.
Why a portfolio career feels right even at the start
Even at this early stage, some of the advantages of a portfolio approach are already becoming visible. Working across different contexts in the public sector, advisory work, and emerging academic engagement, creates contrast and sharpens thinking. Insights from one role immediately inform the others. Policy discussions influence advisory work, while reflecting on teaching material forces clarity of thought.
Equally important, this way of working aligns well with my personal motivation. I draw energy from change, from learning, and from engaging with people in different settings. A portfolio allows me to design work around that energy rather than compressing it into a single role. At the same time, it creates optionality. Not the comfort of knowing everything in advance, but the freedom to test, learn, and adjust as I go.
The challenges show up early
What also becomes clear very quickly is that a portfolio career is not automatically easier, especially at the beginning. Ambiguity is part of the deal. Roles are fluid, structures are evolving, and answering the question “what do you do?” becomes an ongoing exercise.
With several threads in play, focus and prioritization require active effort. There is no predefined rhythm or external structure to rely on. Momentum has to be built deliberately, and confidence often follows action rather than preceding it. This can feel uncomfortable at times, but it is also where learning happens fastest.
What I’m learning so far
Although the journey is still unfolding, a few early lessons already stand out. Waiting for full certainty would have delayed the transition for a long time. Starting before everything is clear turned out to be essential.
Anchoring the portfolio in a clear theme has helped create coherence. For me, that theme is transformation, of organizations, systems, and people. It provides a common lens across different activities and decisions. Equally, I’ve been reminded that relationships matter more than plans. Conversations open doors, challenge assumptions, and shape direction in ways no spreadsheet ever could.
Finally, reflection is not optional. Without regular reflection, a portfolio risks becoming reactive instead of intentional. Creating space to pause, reassess, and adjust is part of the work.
An ongoing experiment
I don’t see a portfolio career as a destination. I see it as an ongoing experiment. One that will evolve as opportunities, interests, and life circumstances change.
At this stage, my focus is not on building many things at once, but on building the right foundations. Clarity of intent, quality of relationships, and space to learn. For those considering a similar path, my current reflection is simple. A portfolio career doesn’t start with a perfect structure. It starts with curiosity, commitment, and the willingness to take responsibility for shaping one’s own direction.
I’m looking forward to seeing where this journey leads and to sharing further reflections along the way. If you’re currently reflecting on your own career direction, whether that means a portfolio approach or something else entirely, I’d be glad to exchange perspectives. Sometimes clarity emerges not from answers, but from thoughtful conversation.



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