Part Three: How to Go Fractional
This is the final post of my three-part series, Unattached: The Next Era of Knowledge Workers. I recommend first reading part one (Making the Case for Fractional Work) and part two (Fractional Work in a Post-Pandemic Era). In this post, I’ll talk about the personal benefits of going fractional at work, and a few tips on getting started.
One year after having my first child, I caught myself falling into my usual pattern of full-time job claustrofobia. Despite a steady job at an early-stage startup, I was spending my evenings voluntarily advising a nascent web3 builder community. On the weekends, I started hiring babysitters just to steal away for a few hours at a time to design a curriculum to get students excited about jobs in tech. Neither project paid me. On the contrary, I was literally paying someone else just for the privilege to spend time on them. That’s when I knew something had to give.
For the first time, rather than shy away from this discordant behavior, I leaned into it and finally asked, “Well…could I get paid for my side interests?” Much to my surprise, the answer in both cases was yes.
One month later, at 8 weeks pregnant with my second baby, I transformed one full-time job into three fractional ones. And I’m so glad I did.
Our societal scripts around work changed drastically during the peak of the pandemic. Job-seekers today have more power than ever to design their work around the kind of lives they want to lead. There’s no better time than right now to rethink your relationship with work. (And the past three years have already primed us to begin fractionalizing our lives.) Let’s talk about how to get started.
Shifting from Work-First to Lifestyle-First
I’m 35 years old but people still occasionally ask me, “What’s your dream job?”
The last time this happened, it caught me off-guard, and I didn’t quite know how to respond. Not because I hadn’t considered it (on the contrary, I obsess over it), but because my mental model around work is no longer constrained to the notion of just one job. I’ve retired the idea of a single, dream job, and moved on instead to a state of work that includes a collection of the things most important to me. That’s the power of independence.
As I shared earlier, the rise in independent, fractional work has grown exponentially since 2020. But while today’s technology makes fractional work possible, it doesn’t explain why it’s stuck so hard, so fast. After all, it’s hard work to juggle many things, simultaneously, for a long time. There’s something else at play to explain the mass exodus from full-time work in tech. I believe it’s due to the shifting role of employers (particularly, tech employers) in our lives.
Let’s circle back to 2009 — when I got my first job in tech right out of college. I’ll never forget the surprise on my mom’s face when I described my benefits package. Not only was I earning more than she’d expected, but the extra “perks” racked up far more quickly than she was accustomed to. Brand new computer, near-free healthcare, in-office lunches every day. My first day on the job was at an amusement park for a company-wide offsite. (Seriously.) When the co-founder noticed my penchant for getting deep work done in the lounge area of the office, he bought me my own cozy chair to store next to my desk. Ah, yes. Life was good.
Over the next decade, I witnessed first-hand how the tech industry responded to the “war on talent.” First, it was just free lunch. Then came ping pong. Then unlimited vacation days. Matching 401ks. Company-wide offsites in exotic locations. Free puppies for referring engineering hires. The list went on and on. By 2019, “working in tech” was no longer just a job — it was a lifestyle. Employees looked to their employers for everything — compensation, benefits, retirement savings, free meals, office space, unique experiences, gym memberships, bike shares, a community outside of work. Some CEOs asked, “Are we too paternalistic to our employees?” Others retorted, “Absolutely not!”
Then the pandemic hit. Overnight, we didn’t just lose access to a place to get our work done — we also lost our built-in social networks, our free meals, our travel itineraries. But here’s the thing: The reason working in tech got so sticky was because they really knew how to hit on the psychology of what humans need. And whether or not a company provided us with those things, we still needed them. At least, most of them.
We still needed a place to get work done. So we found corners in the tiniest crawl spaces in our 500 square foot apartments and made it happen. We still needed to eat. So we learned how to cook. From sourdough bread to cook-it-yourself pizzas, we did it ourselves. We idolized celebrities who tried it on their own in their kitchens.
We even lost our built-in work communities, and to be honest, this made a lot of us feel really lonely for a really long time. But then we went hyper-local. We made friends with our neighbors, we started dinner clubs and garden parties, we reconnected with old friends and family. Maybe, after a year or so, we even started to feel a little bit better about ourselves along the way. (After all, it’s nice to be in charge of your own destiny.)
And that brings us all the way back to the power of fractional work. Companies, actually, shouldn’t be our whole lives. Life should be our whole life. Fractional work keeps that in check, by keeping companies contained to just a fraction of our whole.
Rather than, “What’s your dream job?” consider instead this contemporary reframe: “What’s your dream lifestyle?”
How to “Unattach” Yourself
Since I started writing about independent and fractional work, I’ve had a lot of people come out of the woodwork to ask how to get started. In addition to the question set I outlined in my earlier post, “Should You Go Fractional At Work?” there are a few guiding practices I’ve started recommending to anyone interested in “unattaching” themselves from the single-job mindset.
1. Decouple the jobs you’ve held from the skills you possess.
One of the biggest disservices to the standardization of job titles across industries is that it lets us take shortcuts in describing the actual work we do. “I work in marketing,” you might say. “I’m a VP of Operations.” While either of those facts may be true, it’ll be hard for you to find a broader array of project-based work if you fixate too much on the title of your current or past job.
Instead, take a look at all the jobs you’ve had and try to boil them down to the raw material skills. If you consider yourself a marketer, you might be good at telling stories, writing explanations of complex topics, and understanding user psychology and behaviors. But an entirely separate set of skills a marketer might have could include being able to get strangers excited about something, plan the best events, or convene the best-in-class people in a community. You need to know your strengths back and front — because those are the assets you’ll pitch to others when soliciting potential business.
2. Test the waters to find your person-market-fit.
A lot of people tell me that they wouldn’t have the stomach to work in a fully freelance or fractional capacity. This is perfectly understandable. I used to feel the same way when I observed my husband’s work as a permanent freelancer in the Broadway sound industry. “I could never work show to show, or deal with an inconsistent paycheck,” I’d tell him. But just like anything, the more you do it, the more consistent it feels — and the more patterns emerge. As my childhood flute teacher used to say, “practice makes permanent.” The more reps you get in, the more likely you’ll be to figure out how to make it work for you for the long term.
For most of us, fractional work isn’t a switch you simply turn on one day. It’s a gradual process of understanding how the job market around you might partake of your standout, superpower skills. The good news is, this is easy to test. Make a list of the 10 most important people to your professional network. Tell them you’re considering fractional or freelance work, and wait for their reaction. If other people can articulate your own unique value — or if they invite you to collaborate with them on a project — you’re one step closer to identifying your unique person-market-fit.
3. Start with a project. See how it feels.
The other great thing about fractional work is that you can start small. Don’t commit to a lifestyle, a career, or a direction. Take baby steps. Start by finding a project. Work on it for a while. See how it feels. Take note both of the process — how hard is it for you to find a project to work on? And also the outcome — how do you feel while splitting your brain into two different types of work?
It’d be great if you can land a paid project, but it doesn’t necessarily need to be paid, so long as you can squeeze in time to work on it (on nights and weekends, in all likelihood). For what it’s worth, in nearly every job switch I’ve had, I’ve done a little work for free before fully committing. Before I got hired at Union Square Ventures, I had already been volunteering my time to coordinate community sessions for people across USV portfolio companies. Last year, when I was interested in immersing myself more in web3 job opportunities, I rode shotgun alongside a nascent developer and builder community, Zeitgeist that continues to do great work today. I don’t consider this to be exploitive (and I don’t actively encourage companies to expect people to work for free). But I do think it’s important to note where you are innately driven toward “curiosity-driven learning.” After all, if you like something enough to tinker with it for fun, maybe you should convert it into something that pays.
A few weeks ago, I reconnected with my former executive coach for coffee. As soon as I sat down, she took one look at me, smiled and remarked: “Wow! You look…happy!”
After shaking off the insinuation that I clearly had not exuded happiness during our coaching sessions a few years earlier, I took her observation in stride.
“I am happy,” I acknowledged.
It feels good to do what you want. We’ve been primed to work one way — to pick one path and stick with it. But, as Paul Millerd writes in his book, The Pathless Path, it takes deliberate intention (and a lot of second-guessing) to untangle yourself from these prewritten expectations and social scripts.
Fractional employment is a surefire way to practice the art of expanding your range and building bridges, both of which very well may become the new essential skills of the modern workplace. I hope this post has shown that a different approach to work is not only intrinsically valuable, it’s also externally in-demand. That’s why the future of work is fractional — for me, and maybe for everyone.
(By the way — the more of us go fractional, the easier it is to find great teammates on short-term work. So if you’re looking for a collaborator on project-based work, you know where to find me.)