How to transition from a job to a portfolio career.
Using my own framework and lived experience, I support people through both the practical and psychological shift, to design an intentional way of working and living.
You might still be employed but curious, freshly quit, or in the early stages of building your portfolio career. Chances are you're multi-passionate, drawn to variety, and already had a side project in your job. You sense that work is changing and you want to consciously change with it.
You're still in full-time employment, but you can feel the shifts happening in the world of work. You may not want to quit. Instead, you want to be strategic and explore what else is possible without destabilising your life. You'd like to build optionality, develop new skills, and test ideas on the side. You want clarity before making big decisions and a structured way to design your next steps.
You have already quit, were laid off, or are currently on a sabbatical. Now you're facing a blank calendar and a lot of open space. A portfolio career sounds interesting, but you're not sure where to start or how to make it sustainable. You don't want to drift or recreate your old job in a different format. You'd like structure, direction, and a clear plan to move forward with confidence.
You're already in the early stages of building a portfolio career, but it feels messy. Maybe you've taken on too much work, or you're unclear about your positioning and long-term direction. You sense that you might be repeating old patterns: overworking, saying yes too quickly, or chasing income without a clear strategy. You want to simplify, refine, and design your portfolio more deliberately so it supports the life you actually want to live.
Every job is built on five pillars: vision, structure, identity, money, community. They collapse one by one when you walk away and need to be consciously rebuilt in a portfolio career. The mentoring works through them in turn.
The goal of the programme is to help you successfully build a portfolio career. We go deep to understand what you want to build, why, and how to get there. The first two sessions focus on mapping your situation, goals, strengths, and challenges in depth. The remaining three sessions are dedicated to workshopping the areas with the biggest impact for you.
If you're curious whether this could support your own transition, let's have a short call to get to know each other and clarify your questions.
I left the start-up world after 6+ years to build my own portfolio career - a mix of fractional roles, writing about the future of work, mentoring, and creative projects. I've lived the pillars, made the mistakes, and built the systems I now share.
I write the Afterwork newsletter on Substack, where I explore how AI is reshaping work, careers, and identity. I mentor people through this transition because I wish someone had done it for me.
Real people I've supported through the transition.
"I learned about portfolio careers through Iwana, and she supported me throughout 2026 to make the leap towards one. I managed to land a fractional role instead of a full-time job and test my first offerings for my female finance community. What stood out was how she addressed not just strategy, but also the underlying fears and scripts shaping my decisions, so I felt confident building a career on my own terms."
Miriam went from a full-time job at a climate tech company to a portfolio career. She landed a fractional role in Customer Success, while building a female finance community and also offers nutrition coaching to her clients.
"I felt stuck between wanting more flexibility but not knowing how to move beyond my full-time role. Iwana helped me build a plan and the confidence to step into a portfolio career. Her ability to connect how the world of work is evolving with practical guidance on how to adapt is both unusual and invaluable. It's also pretty cool how she combines traditional mentoring with AI to deepen the process."
Fiona went from a full-time job to a portfolio career. She now does strategic ops and AI for purpose-led female founders while teaching yoga and building online products and services around her work on overcoming insomnia among high achievers.
"I've always been multi-passionate and doing many things has felt natural to me. But I've lost count of how often I was told to 'just pick one thing' and focus. Through working with Iwana, I realised that nothing was wrong with me. She introduced me to the concept of a portfolio career and helped me see that I could intentionally build a work life around multiple interests, strategically and sustainably."
After leaving her full-time role as a Marketing Lead, Carmen built a portfolio career combining freelance work in marketing with teaching pilates, organising retreats, and hosting a podcast, all while being a mum of two.
Read the articles below to learn what portfolio careers are and why they're gaining momentum.
The best way to reach me is over email, LinkedIn or Substack.
Email iwana@afterwork.one LinkedIn /in/iwanajohannsen Substack iwanajohannsen.substack.comPrefer to write freely? You can always email me via iwana@afterwork.one or find me on Substack / LinkedIn.
I'll get back to you as soon as possible.
