Me, Myself and AI: How to Portfolio Career With a Team of One
The backstage crew that keeps me afloat.
Portfolio careers are on the rise
Traditional jobs are unbundling and the 9-to-5, single-employer model is cracking at the same time AI becomes widely accessible. The amount of power an individual has today is vastly more than any other moment in the past and that will only continue to increase. Together, these forces are accelerating the rise of portfolio careers.
A portfolio career means juggling multiple projects, clients, side hustles and creative outlets instead of having a traditional full-time job. Multiple deadlines, identities and ideas.
It’s exciting, but it can feel like spinning plates without a backstage crew to catch them when they wobble. Portfolio careers demand quick context-switching, constant output and relationships built on trust. All without the safety net of a team. And traditional productivity systems were never designed for this kind of self-directed, fragmented, multi-identity work either.
AI as your team of one
AI will disrupt traditional jobs, no question. But the same technology that threatens old structures also empowers individuals. With AI, one person can do what once took an entire team, creating new freedom to design work on their own terms.
AI acts like the missing backstage crew keeping the plates from crashing. It gives generalists in a portfolio career their edge by lending just enough specialist depth to thrive across different roles. And it smoothens the exhausting jumps between identities (strategist in one call, creator in the next) by summarizing, reframing and translating so context-switching doesn’t drain all your energy. Most importantly, it’s portable: a team that follows you wherever your career takes you.
Me, Myself and AI
Every portfolio career looks different. Each portfolio careerist has different needs and so each AI support team will look different too.
When I left full-time employment to build a portfolio career, I kept things simple. No overload of apps or endless tool-hopping. My foundation has been ChatGPT as a flexible generalist that I rely on for clear, everyday co-pilot workflows, complemented by a handful of other tools when needed.
Over time, my own AI team has taken shape: the Co-Founder, the Ops Manager, the Coach, the Creative Partner and the Growth Partner. The invisible ‘team of one’ that makes my portfolio career workable. It’s my expert team that answers my questions, it complements my strengths, covers my blind spots, helps me test ideas quickly and sometimes even lifts me up when I hit a wall.
1. The Co-Founder
Role: Acts as the sparring partner, you’d usually have in a co-founder
Support: Mapping out vision & strategy, challenging my thinking, brainstorming big ideas, stress-testing decisions, fills in gaps in my skills or perspectives
Example: Act as my co-founder. I’m choosing between another fractional role or investing in building out services/products around Substack. Compare both (short vs. long-term impact, stability vs. growth, vision fit), point out blind spots, challenge my assumptions, and suggest decision criteria.
2. The Ops Manager
Role: The Ops Manager supports me in the day-to-day of my portfolio career
Support: Research assistant, drafting and refining emails, meeting prep, turns call notes into action steps, drafts project timelines, admin tasks
Example: Here is my meeting transcript [paste]. Create a summary with 3 key decisions, 5 next actions and a short client update I can send.
3. The Coach
Role: The AI Coach lightens my mental load and supports my personal growth
Support: Reframes doubts or challenges, surfaces thinking patterns, helps increase confidence, builds weekly reflections, helps me with personal growth
Example: I’m second-guessing myself in my career reinvention. Act like a coach and reflect back my strengths and progress so far, based on what I’ve shared with you in past conversations. Remind me what I’ve already achieved and why I’m on the right path.
3. The Creative Partner
Role: The Creative Partner supports to make my creative vision real from branding and storytelling to illustrations and design.
Support: create my branding, craft story telling, editor for my Substack drafts, creating newsletter illustrations and design sketches, test creative concepts
Example: Create a minimalist fine-line illustration in black vector-style line art for this Substack newsletter. I sit cross-legged in the center, surrounded by my invisible AI team in a dotted circle with icons and labels. Clean lines, no shading, transparent background.
2. The Growth Partner
Role: The Growth Partner supports me in marketing and sales efforts
Support: Content planning & repurposing (Substack + LinkedIn), post refinement, analytics, research potential clients or partners, drafting outreach emails & proposals
Example: Act as my Growth Partner. Based on my recent Afterwork posts [paste topics or links], brainstorm 10 suitable content ideas I could write about next that build on these themes and resonate with portfolio career readers.
With AI agents this will be taken to the next level. Instead of just responding to prompts, agents will be able to run in the background, manage workflows end-to-end and even collaborate with each other. That means my team of one will increasingly anticipate needs, take initiative and execute on its own.
Knowing when not to use AI
The real art of working with AI is knowing when to leave it out and where to draw the line. It’s about finding your authentic balance, doubling down on uniquely human qualities and leaning on your own strengths. The power of AI is in handling the scaffolding but the heart of the work stays with me.
Don’t use it too early in the process. If I hand over the whole thinking process to AI, the result is flat. I have to begin with my own ideas and then let AI sharpen and challenge them.
Don’t outsource your strengths: I let AI complement my weaknesses and handle the mundane but keep the things I’m uniquely good at or love doing.
Don’t forget your voice. AI makes it easy to just produce more output. But quality, depth, taste, authenticity and creativity are the first to go. The final touch has to come from me so that my work keeps its unique edge.
Take care of your relationships. I could automate engaging with readers, clients and collaborators. But real relationships and authentic community building come from showing up myself. That’s the part I want to double down on, not hand off.
AI makes portfolio careers workable but it’s not meant to replace the essence of your work. The trick is letting it carry the load without stealing the soul.
Why it matters
Portfolio workers are already living a reality that may soon be the norm. They act less like employees with fixed jobs and more like conductors orchestrating tasks and projects. Instead of doing everything themselves, they design systems, delegate to AI agents and curate the output.
In a world that’s more uncertain, diversification, the ability to pivot fast, juggle roles, and learn on the fly might be key. AI doesn’t replace that, it amplifies it.
AI may democratize new work models and empower individuals to design work on their own terms. It may well accelerate the shift away from job-centric work toward more purpose-driven lives with more space for the things only we can do and those we care about.
That is a useful take! I feel like in many cases people believe Ai makes the more productive, but it doesn't, really. Yes, "they" produce more, but mostly pedalling a stationary bike that just adds overwhelm & to the paradox of choice pile.