Careers don’t come in one size
Field notes from a year of career reinvention.
It’s almost September, which means we’re three-quarters through the year. It’s been a year that has been pretty transformative for me. But here’s the funny thing: it’s easy to forget transformation when you’re living it. What felt mind-blowingly new six months ago now feels obvious, like everyone’s already talking about it. That’s the thing about learning - once it clicks, it just becomes your new normal.
A few weeks ago, I had a three-hour conversation with a friend who’s in the middle of starting over. It was like talking to an earlier version of myself: the same doubts, the same fears, the same ‘but how does this actually work?’ questions. And while I was giving him ideas and reassurance, I had this moment of realization: wow, I’ve actually learned a lot this year.
The truth is, at the start of 2025, I didn’t even know any of the terms I’m about to share with you. Now they’re part of my everyday vocabulary. They’ve turned what once felt like an experiment into something with shape and direction.
So here it is: the three biggest realizations I had this year that changed how I think about my career.
Generalist
It all started with a single word: Generalist. I stumbled across it earlier this year and instantly thought ‘Oh. That’s me.’ Multi-passionate, multi-skilled, adaptable, the type who can jump into a dozen roles and somehow make them all work.
Suddenly, my whole career path made more sense. Of course I’d thrived in early-stage startups. They needed people to wear every hat, connect the dots, and figure things out on the fly. That’s my natural habitat.
It also explained why LinkedIn has always felt like a dead end. Most roles feel too narrow. The world still tends to reward specialists. My very first role at a big American software company was proof as every morning I walked into the office already knowing exactly what I’d do all day - the same thing as yesterday. For me, that was suffocating.
My biggest realizations:
What once felt like a weakness is actually my strength. I’m a generalist and being broad, multi-skilled and adaptable is exactly what makes me valuable.
Generalists thrive in uncertainty. In today’s world that changes by the minute, we can pivot fast, juggle different things at once and learn new skills on the fly. It’s basically a hedge against obsolescence in the age of AI.
Context is everything. Not every environment values generalists (yet). In the wrong place, we’re overlooked but in the right places we become indispensable.
Looking back, I basically reframed my identity as a generalist, connected it to the needs of today’s fast-changing world and figured out where I can best put it to work.
(Side thought: I do question if the whole ‘generalist vs. specialist’ divide is even real. To some extent, we’re all multi-passionate and multi-skilled, it’s just that the industrial age trained us to pick a lane and stick to it.)
Portfolio Career
Once I understood myself as a generalist, the next question was what do I actually do with that on the job front?
For most of my career, I thought there were only two real options on the table: get a full-time job or start my own company. Then, through Substack, I came across the term Portfolio Career and suddenly a whole new universe of possibilities opened up how I can design my professional life.
A portfolio career is defined as having several part-time jobs or multiple income streams rather than one full-time gig. It involves pursuing multiple passions, interests and types of work. In other words: a generalist’s dream.
My biggest realizations:
There are more than two paths. Work isn’t limited to employment or starting a company. A portfolio career opens up the whole space in between and puts you in charge of designing your own mix.
A portfolio career is the generalist’s world. Freelancing is the specialist’s term, selling the same set of skills to multiple clients, usually tied to billable hours. The portfolio career is the generalist’s world, combining different types of work and income streams, built around a unique mix of passions and strengths. It’s a narrative that ties them all together, for yourself but also to present to the outside.
Diversification is the new security. Contrary to mainstream belief, it’s way safer to diversify your income streams than to rely on one employer. A portfolio career makes you less dependent, more resilient to shocks, and better able to adapt as industries shift. Instead of putting all your eggs in one basket, you spread your bets.
Starting to build my portfolio career, I’ve created work on my own terms, around my values, choosing who I work with and what I work on. If you’re interested, you can read more about my portfolio career journey here.
Fractional Work
If a portfolio career gave me the framework, then fractional work was a great way to get it started.
Fractional work means taking on a part-time role - usually one to three days a week - where you contribute your expertise without being tied to a full-time contract. You’re paid on a monthly retainer for a set commitment of hours, becoming an embedded part of the team. It’s not a one-off project with a fixed cost, but typically a medium-to long-term relationship.
The question I get most often is: ‘But why would anyone hire you fractionally?’ It seems counterintuitive at first - wouldn’t companies want someone full-time? The truth is many, especially startups, don’t need (or can’t afford) a senior role at 100%. What they do need is someone who can step in a few days a week, bring expertise, build systems and move things forward without overcommitting headcount. Fractional work lets both sides test a work relationship, access senior talent and stay agile as priorities shift.
For me, it’s been the sweet spot: combining the steadiness of ongoing work with the flexibility of a portfolio career. I get to contribute where my skills matter most, while keeping space for writing, creative projects, and other ventures. The future of work isn’t rigid or one-size-fits-all but it’s agile, smart, and flexible for both professionals and businesses.
My biggest realizations:
Fractional roles solve a real need. Especially startups and founders often need experience and momentum without the cost, risk, or commitment of a full-time hire. Fractional work lets them plug in senior talent quickly, get results, and scale support up or down as needed.
It’s a win-win. Companies get senior skills without the cost of a full-time role, while I gain flexibility, variety, and the freedom not to be tied to one employer.
Both worlds in one. In a portfolio career, fractional work provides stability - a consistent retainer and a team to work with - while still leaving plenty of time each week to explore passions and build other income streams.
This is why, in my opinion, fractional work is a great start for anyone considering a career shift. It can even start with re-negotiating your current role to stay on fractionally while freeing up time to experiment on the side.
The bigger shift
Looking back on that long conversation with my friend, I realized that so much of what felt confusing and messy a year ago now has language and shape. At the start of this year, I didn’t even know these terms existed and now they’re part of my everyday.
And who knows - what still feels like ‘figuring it out on my own’ might actually be part of a much bigger shift in how we work. The old model of one job, one employer, one title is cracking. Technology is moving faster than organizations can keep up with. AI is automating tasks, entire industries are reinventing themselves and the world we’re operating in is far less stable than the one careers were designed for in the industrial age.
In that context, portfolio careers and fractional work could be smart adaptations. They’re how we diversify our bets, stay resilient and design lives that actually fit who we are. The future of work won’t be built on narrow paths, but on people mixing skills, passions, and income streams into something that evolves with them.
Maybe the biggest gift of sharing my journey was realizing this: I’m not just building a career for myself but hopefully I’m also building a story that might help someone else find their own way.
If any of this resonates with you, if you’re on a similar journey or just discovering these terms for the first time - I’d love to hear from you.
Where you can learn more.
Generalists. Check out Generalist World. You’ll find articles, podcasts, videos, a job board and a community of generalists.
Portfolio careers. Subscribe to Anna Mackenzie’s newsletter and check out her offerings. Also Portfolio Career Lab and The Portfolio Career-ist speak a lot about it. There is also a community called The Portfolio Collective.
Fractional work. There is more specialised job boards such as Go Fractional or Fractional Jobs, platforms such as Braintrust, initiatives for parents like the Five Hour Club or I find it simply in communities that are more in my interest field such as climate change e.g Work on Climate, or freelancing for good.
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.
Great notes. The generalist role is one that I predict will explode in the next few years. Especially generalists with some experience and powered by AI.
Thanks for sharing this Iwana. Your field notes become someone else's permission slip.