As jobs unravel, it explores what comes next, from portfolio careers to deeper questions of identity, purpose, and life after jobs.
"Afterwork is a hidden gem. Iwana has the ability to break down complex ideas and offer practical solutions grounded in real-world experience."
"Iwana's newsletter is one of the few I read from start to finish. She explores the future of work and gives you practical guidance to design your own way of working in the age of AI."
With 6+ years in tech start-ups, I've built departments from scratch, led teams, and developed expertise in strategy, customer success, project management, and marketing. Now, I've built a portfolio career operating at the intersection of the future of work, tech and navigating change — combining systems thinking with writing, mentoring, and fractional or project work.
I support people in transitioning from jobs into portfolio careers. Using my own framework and lived experience, I help navigate the practical and psychological shift.
Learn more →Afterwork helps you navigate the biggest shift of our time as AI disrupts work as we know it. As jobs unravel, it explores what comes next: from portfolio careers to deeper questions of identity, purpose, and life after jobs.
Learn more →Depending on capacity, I offer fractional support to purpose-driven startups, combining strategic thinking with operational execution. I selectively take on aligned projects and consulting work.
Reach out →Working on anything in the future-of-work space, or have another idea for how we could collaborate? Let me know.
Reach out →I support people in transitioning from jobs into portfolio careers. Using my own framework and lived experience, I help navigate the practical and psychological shift to design an intentional way of working and living.
A portfolio career is an intentionally designed mix of work and income streams built around your passions and strengths that evolves with your life.
You might still be employed but curious, freshly quit, or somewhere in the early stages of building your portfolio career.
A multi-session 1:1 process to help you transition into a self-designed portfolio career. You'll get clarity, an action plan, and hands-on support.
"I think these kinds of transitions can be really tricky and having someone like you to support throughout is invaluable."
If you're curious, start with a few of the essays below to see what Afterwork is about and how I think.
I'm a curious, impact-driven generalist with almost a decade of living the future of work, tech and continuous reinvention. I left the start-up world after 6+ years to go solo and build a portfolio career: a mix of fractional roles, writing about the future of work, mentoring and creative projects.
I'm a big tech enthusiast and future-focused thinker who loves exploring AI, Web3, XR and the evolving world of work.
At the same time, I care deeply about sustainability and climate action, and I'm fascinated by how all of these forces can come together to shape a better future.
Originally from Germany, I've moved around a lot and am now based in Lisbon, Portugal, pretty good at making myself at home wherever I land.
Looking back on the past decade, my red thread is clear: I've always been circling the future of work and emerging tech.
I started in big tech at Microsoft and Autodesk, back when offices started to look like playgrounds. There were slides between floors, no fixed desks, a barista making coffee.
By 2017, I went fully remote working at a start-up. Back then, living and working abroad in Barcelona (pre-Covid) wasn't nearly as common as it is now. Remote work wasn't yet a lifestyle and the "best" jobs were still back home in Germany.
In 2019, I landed in what felt like science fiction to many: a virtual reality start-up building a VR office for remote teams. For four years, I was that odd girl at WeWork with giant VR glasses strapped to my face, looking like I was talking to myself while actually meeting clients in a virtual office. My team and I scribbled on VR whiteboards with BCG, ran agile sprints with German automakers, and jumped through cookie-shaped auditoriums with Mondelez. Totally normal workday.
By the time the Metaverse hype exploded in 2021, I was already in deep. Not just working daily in VR, but also building a Customer Success team and department fully remotely. And when AI arrived, we didn't just talk about it: it literally showed up as a co-worker inside our virtual office.
Fast forward to 2024, and I quit to build a portfolio career using AI as my team of one: a mix of fractional roles, writing about the future of work, mentoring and creative projects. On the side, I dove into Web3, fascinated by blockchain's potential to reshape how humans coordinate and earn. DAOs, decentralised ownership, new work models, another puzzle piece added.
So yes, there's a red thread when I look back. Future of work, emerging tech, reinvention. It's the story I've been living, and the one I'm here to tell, to help you shape your own.
Read what I write on Substack, follow along on LinkedIn, or just send me an email if any of this resonates.
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As jobs unravel, it explores what comes next: from portfolio careers to deeper questions of identity, purpose, and life after jobs.
"Afterwork is a hidden gem. Iwana has the ability to break down complex ideas and offer practical solutions grounded in real-world experience."
"Iwana's newsletter is one of the few I read from start to finish. She explores the future of work and gives you practical guidance to design your own way of working in the age of AI."
Visionary thinking on the future of work and life.
We're living through one of humanity's biggest shifts in how we work and live. As AI disrupts jobs, we need to explore the deeper questions about what we define as work, as well as about identity, purpose and how societies fund life after jobs (post-labour economics).
Diving deeper into what's currently changing.
What comes next when full-time jobs are no longer the default? Explorations of portfolio careers, fractional work, and new models of organisation and leadership.
Helping you navigate the shift.
Frameworks, prompts, mental models, and small experiments to help you design your own way of working in uncertain times, grounded in honest reflections and personal stories from my own reinvention journey.
We don't need more doom and collapse-thinking right now. We need a positive vision, big ideas, fresh perspectives, and practical tools that build the confidence to navigate this shift.
If you're curious, start with a few of the articles below to see what Afterwork is about and how I think.
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.
I support people in transitioning from jobs into portfolio careers. Based on my Five Pillars of Work framework and lived experience, I've designed the Portfolio Career Transition Package. It's a way to better understand where you are in your transition, which scripts you're still running, what areas you're already strong in, so we can see the gaps and build a plan together.
If you prefer to start with fewer sessions, I also offer the Mini Portfolio Career Transformation Sprint, which consists of 2 × 60 min 1:1 sessions with me and the Portfolio Career Report (basically steps 1 to 3). 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 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 works fractionally in customer success 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.
"I don't necessarily want to quit my job, but I want to build optionality. Iwana helped explore what that can look like without unnecessary risk. We clarified my vision and defined first steps. What stood out was how she addressed not just strategy, but the underlying fears and scripts shaping my decisions. I left clearer and more confident that I can design work on my own terms."
Miriam is still in her full-time role at a climate tech company, while she is actively exploring and building projects on the side. She founded a female finance community and also offers nutrition coaching to her clients.
Read the articles below to learn what portfolio careers are and why they're gaining momentum.
"I wouldn't know what else to do" is the main reason people stay in jobs that don't fit. When you do leave, your sense of direction tends to go with it — and rebuilding it is the foundational work of any portfolio career. This 18-page PDF + Notion template walks you through that work at your own pace, with four exercises drawn from how I work with mentees on the Vision pillar and a worked example to follow.
This workbook is written for people in three different moments on their way into a portfolio career. Different on the surface, identical at the centre: a need for direction, a working set of principles, and a way to test both in real life.
You're still in full-time employment, but you can feel the shifts in the world of work. You want to be strategic and explore what else is possible without destabilising your life.
A working vision you can hold while still in your job, and a set of small, low-stakes exploration experiments you can run on the side. You won't have to quit anything to use it.
You've already quit, were laid off, or are on a sabbatical. A portfolio career sounds interesting, but you're not sure where to start, and the open space is starting to feel like pressure.
A rough first vision, principles to decide against, and a first round of experiments that point you somewhere new without forcing a five-year plan you can't yet write.
You're already in the early stages of a portfolio career, but it feels messy. You sense old patterns repeating: overworking, saying yes too quickly, chasing income without a clear strategy.
A chance to stop and update the vision against what you've actually lived. Sharper principles to use as filters for what to say no to, so the next round of work has a shape, not just a velocity.
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. This workbook helps you to rebuild the vision pillar.
A few sample pages so you know what you're getting. Click through the chapters on the right.
The portfolio career guiding principles describe how you want to build your portfolio career and what you think is non-negotiable along the way.
Clear statements of what you believe and how you want to operate, make decisions, find direction, and sustain progress.
Your principles are built directly from the self-discovery work you just did. Each category below draws from the answers in the table on the previous page. They're convictions you check in on at the end of a week to notice what's actually true.
Turn your "what does success mean to me now?" notes into a few clear statements about what a good work-life looks like to you. E.g. "I wake up excited about the day ahead."
Turn each success statement into something you can answer at the end of a week. Plain language, observable, week-bounded. E.g. "Most mornings this week, I woke up looking forward to the day."
Write down the core values you've defined for yourself, such as autonomy, contribution, or well-being.
Notice the patterns under your "what do I research for fun?" and "what makes me lose track of time?" answers. These are what fuel you regardless of pay. E.g. "Solving problems I find genuinely interesting."
Take your "what do I not want again?" list and translate it into specific limits. E.g. "No more than 25 paid hours per week."
These go on the calendar before anything else, the things you defend even when the week gets full. E.g. "Evenings are for family."
Build two parallel lists from your "what energises me, what drains me?" answers. E.g. yes to "generalist breadth", no to "always-on availability."
Take your "what does an aligned project or role look like now?" answer and turn it into a checklist. Use it to evaluate every yes. E.g. "Respect for async work and my hours."
Pick at least one stability experiment that uses your existing skills and helps cover your baseline. Pick at least one exploration experiment that follows your curiosity. The third can lean either way.
Keep them small enough to actually run in one quarter. After each experiment, use the reflection prompts below. Your answers feed back into your vision and guiding principles, sharpening both with each round.
| # | Experiment | What I want to test | How I'll test it | Timeline |
|---|---|---|---|---|
| 1 | Name or theme… | My hypothesis… | Concrete action… | e.g. Jan/Feb |
| 2 | Name or theme… | My hypothesis… | Concrete action… | e.g. Jan/Feb |
| 3 | Name or theme… | My hypothesis… | Concrete action… | e.g. Jan/Feb |
Concrete things on paper, written in your own words. Not motivation. Output.
From work, from life, from the next chapter — distilled into your own answers, not borrowed from others.
A working set of principles you can use to filter opportunities, say no faster, and choose what fits.
A directional sketch of the work-life you're moving toward — grounded enough to act on, flexible enough to revise.
Small, low-stakes, doable. Not a five-year plan. A way to test your direction with real life feedback.
The PDF stays yours. Run another round in three months and watch your answers evolve.
The single biggest unlock. The clarity you're waiting for arrives by doing the work — not before.
From button click to first exercise in roughly two minutes.
One click, secure checkout via Lemon Squeezy. €17, instant delivery.
Two minutes later, the workbook lands in your inbox. PDF link plus Notion template duplicate link.
Open the PDF. Read it through once. The exercises start making sense as you go.
Duplicate the Notion template. Work through it slowly. Come back as your thinking shifts.
€17. PDF and a duplicatable Notion template by email immediately after purchase. Lifetime access — yours to return to as your thinking evolves.
Sold by Lemon Squeezy as merchant of record. Receipt arrives separately from your workbook download email. VAT included where applicable. As a digital product, the workbook is non-refundable once delivered.
The best way to reach me is over email, LinkedIn or Substack.
Email iwana.johannsen@gmail.com LinkedIn /in/iwanajohannsen Substack iwanajohannsen.substack.com
