Me, Myself and AI: The Portfolio Career In An Agentic Economy
When AI stops being a tool and starts being a team member.
It’s Advancing Fast.
Six months ago I wrote a piece called Me, Myself and AI: How To Portfolio Career with a Team of One. I spoke about using AI as my ‘team of one’ in my portfolio career and described five roles it had started playing such as co-founder, ops manager, coach, creative partner, growth partner.
AI was already actively supporting me in my day-to-day back then. The vision of AI taking over things that an entire team does inside a company was clearly there. I suspected that with AI agents coming in, this would be taken to the next level. I knew the ground was already shifting when I wrote the article. What fascinates me is how fast the next layer arrived.
Over the past months, I've watched the agentic ecosystem develop and people starting to do genuinely wild things with it. I've been diving deep into setting up my own agentic workflows in Claude Cowork and using Claude Code to turn ideas into reality. I watched my husband build an entire business plan and working app - planned, coded, and deployed - in less than a week. I watched my friend in Lisbon build a full AI team of five agents with OpenClaw running 24/7 on his Mac Mini, all coordinating with each other through Discord while he sleeps. His chief of staff ‘Henry’ reporting on the happenings every morning. And these aren't niche people on the internet. This is my own circle, suddenly able to do real things. It all blew my mind once more.
The shift happening now is that AI is not just getting better at helping us but it’s starting to act. The agentic economy is here, even if still in its infancy.
The Agentic Economy: AI Agents Are Becoming Economic Actors.
The agentic economy begins when AI agents don’t just support economic activity but they start to behave like participants within it. What’s emerging is a new layer of agent-to-agent interaction inside the existing economy.
Agents acting on behalf of individuals interact with other agents on the seller, logistics, and payment side. Booking services. Paying for data. Negotiating rates. Running parts of businesses in the background, 24/7. Entire workflows that once required teams can increasingly run with minimal human involvement.
Large parts of the commercial supply chain could become agent-to-agent. And a growing share of purchasing decisions will be mediated by agents rather than made directly by humans. The agent sitting on your client’s device may increasingly become the first point of contact. Agents could pool micro-investments, fund a project in minutes, and dissolve the structure when it’s done.
It’s already happening at a small scale, and the protocols making it possible are being built in real time. But what does this mean for portfolio careers?
The Agentic Portfolio Career.
For companies, the agentic economy is a disruption story. Work is being decomposed into smaller units, with parts of roles increasingly handled by agents. The result is fewer full-time positions and more work that is fractional, modular, and project-based.
For portfolio careerists, it’s something else as independent work becomes more viable to run. Portfolio careers are already modular, already project-based, often already structured around outcomes rather than hours. Portfolio careerists are great at orchestrating tasks and projects. And now, instead of doing everything yourself, you can design systems, delegate to AI agents, and curate the output. Agents run in the background, manage workflows end-to-end, and collaborate with each other. You’re still the brain and the heart, but you’ve got a team that never sleeps and costs a fraction of a human assistant. You move from worker to orchestrator shaping the direction, setting parameters, and reviewing output. The agents run things between your decisions.
The portfolio career has always been a good idea with the wrong infrastructure. Traditional productivity systems were never designed for this kind of self-directed, fragmented, multi-identity work. Agents are the infrastructure it’s been waiting for.
The Stages Of The Agentic Portfolio Career.
None of this will arrive overnight. I could see the agentic portfolio career unfolding in three stages, with blurred lines between them. Most of us sit across two at once having one foot in how we work today, one foot in what's coming.
Stage 1: The Portfolio Career (No AI)
You do everything yourself. You coach, you write, you market, you invoice, you schedule, you admin. You’re the CEO, the intern, and the entire marketing department. Only a fraction of your time goes into the work you’re actually paid for or care about.
Stage 2: The AI-Assisted Portfolio Career (where most of us with AI are now)
AI enters the toolkit but stays in the seat of collaborator, not actor. You prompt, it drafts. You review, it iterates. You use it as a thinking partner, a first draft, an ops assistant. This is the world I described in part one of Me, Myself and AI.
Some of the work also starts to get automated through predefined workflows you kick off yourself. In my case, skills in Claude Cowork that log every call into my Notion network database, brief me for my day, prep me for my calls or build my IP into tools and apps (check it here). The human is still at the centre of every task but the execution gets lighter.
Stage 3: The Agentic Portfolio Career (where we’re heading)
AI stops being a tool you pick up and starts acting as team members working on your behalf. A chief of staff agent coordinates the whole setup of your portfolio career team and briefs you every morning. Department-head agents run their areas: your discovery agent identifies potential clients before they even know they need you; your negotiation agent handles rate discussions based on parameters you’ve set; your publishing agent packages and licenses your intellectual property to other agents.
Picture a portfolio careerist in Madrid serving clients in Seoul, São Paulo, and Stockholm because her agents handle discovery, intake, and follow-up overnight. She wakes up to a briefing: three inquiries pre-qualified while she slept, a licensing deal for her framework negotiated and signed, a collaboration with a researcher in Tokyo whose work complements hers.
Her role shifts toward what no agent can replicate: direction, judgment, taste and synthesis. Her original thinking. Creativity. The deep conversation she has with a client or collaborator. The human connection. The ability to define what matters, and what's worth working on.
Setting Yourself Up For The Agentic Portfolio Career.
The early version of Stage 3 is already here, and much of it is is doable in some form but still comes with the friction of being early. You have to invest time to learn it yourself. The infrastructure is still forming. New tools appear constantly. And parts of what makes Stage 3 really work won’t land properly until more of the economy catches up: agents transacting cleanly with other agents, mainstream services exposing agent-ready APIs, and payment rails designed for machine speed.
Late Stage 2 into early Stage 3 is the ambitious-but-rewarding sweet spot I’d recommend pursuing right now. It’s where the biggest practical unlock sits for a portfolio careerist, and being early here is going to matter once the rest of the economy becomes agentic.
The base for all of it is getting comfortable inside the Claude ecosystem: learning how to use it, automating your first workflows, setting up the skills and context files that let it support the way you actually work. Using Claude Code to build your first website, app, or internal tool. The value is seeing how fast the gap between idea and working thing is closing. Portfolio careerists who experiment now and get fluent with agents as collaborators before they become colleagues, will have a real head start once Stage 3 arrives in earnest.
I’d like to write a more in-depth piece on how I’m setting myself up for Stage 3: what workflows are already running, what I’m building, what’s still aspirational, what I’d do differently if I started over. If that’s something you’d want to read, let me know in the comments.
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 Vision Workbook is a way for you to work through this self-paced.
Amazing Iwana. I've read this twice now and I'm still trying to grasp the breadth of the impact! Thank you for expanding, no, blowing my mind!
I remember reading the original, and this is such an interesting follow up. For me the question is no longer how do I build out an idea, but which one deserves my attention and focus.