6 questions to ask yourself before making the switch to an independent career

Since I adopted a fully fractional way of work a few months ago, I've been getting a lot more inbound from friends, colleagues, and interested peers all wondering the same thing: "Should I go fractional, too?"

Given the relatively new nature and nuance of the role (not to mention the term "fractional" itself), I wanted to share more about what "fractional" means to me, my own decision-making process, and offer a few questions you might consider before taking the plunge in your own career.

Let's start by getting three things straight.

1. Fractional work doesn't mean less work. Today, as a fractional worker, I split my time between three places: At Bolster, where I continue to work alongside our GTM teams, at Zeitgeist, a web3 builder community where I conduct research into decentralized communities, and at Tech:NYC, a non-profit where I oversee the launch for an educational initiative for city youth. When you add it all together, I'm working a lot more than I would in a single full-time job. There's always a project that needs my attention, and I'm also always keeping an eye on 3 and 6 months down the road: What do I want my next projects to be? Yes, fractional work may mean more flexibility and autonomy, but it also means a lot more hustle.

2. Fractional work is not consulting. As Bolster, we tend to think about fractional work as ongoing, part-time work. This can either be a persistent gap that you're filling over some period of time. Or it might be a fixed scope, project-based assignment. Like full-time employees, fractional workers tend to be responsible both for the design and the execution of their project. But unlike regular hires, the range of your work scope is much tighter. While the project may change over time, it's important to be clear about what the job is (and what it isn't).

3. Fractional work relationships are more like colleagues than clients. I tend to think of the people I work with not as clients but as colleagues. We are on the same team, I'm just less involved in some of the bigger picture planning pieces. (And by the way, it's important to be okay with that.) While this might feel like a subtle distinction, an important key to effective fractional work is a shared sense of ownership. This builds trust, accountability, and ultimately, better outcomes. I know my personal performance is best when I'm bought in, not just when I'm earning a paycheck, so I'm picky about the type of work I take on. Now that we've framed fractional work a bit more, let's look into how to determine whether it's right for you.

Reality check: Is fractional work right for you?

I'm not going to lie: Fractional work can be a lot to manage. Some weeks are tougher than others, and the balance never quite feels 100% spot on. But for me, the payoff - of maintaining an expansive network, of having my feet in many different types of work, and of managing my own time - make it worth it. In 2022, I wanted to put myself in a position where I could jump into new projects quickly, to say yes to things, and to tinker. And that's exactly where I am today. If you're thinking about taking the plunge to a more independent, fractional career, here are some important questions to consider.

1. What's your risk tolerance?

   As a fractional worker, it's important to think outside the box, basically all of the time. If you get anxious about not knowing what your work projects may look like six months from now, you'll be a ball of nerves working fractionally. I've gotten a lot of exposure to gig economy work through my husband's career in theatre - and I've seen a lot of people ultimately decide that the inherent "job to job" nature of the entertainment industry doesn't fit their own lifestyle. But trust me on this: It's a process, and hard work pays off. The further established you get in your career, the further in advance you'll be able to see in your future (though likely still not more than 9–12 months out).

As an added challenge, in fractional work, you can no longer rely upon the "package deal" of a 9–5 job with built-in accountability structures, consistent work, retirement plans, and healthcare coverage. Of course, all of these things are possible to find on your own - companies like Stride Health (one of our partners at Bolster) can provide access to pooled health insurance. You can design your own retirement savings plan through IRAs or through investing in a financial advisor. It just takes a few extra brain cycles - and creativity.

1. Will your network support you? Have you validated your own MVP or brand? Before I decided to go fully fractional, I spent several months testing the waters by discussing my potential new work mode with dozens of professional connections. I heard a lot of validating responses: "Oh! That makes so much sense for you. Let me know when you make the switch, I may have some projects for you." Much to my surprise, this decision was met with equal enthusiasm across many disparate parts of my network: VCs, startup founders, crypto builders, non-profit educators, and other fellow fractional professionals.

   Through this process, I established not only a first bench of projects ready to pay me, but I also heard what aspects of my professional toolkit were more sellable. Once a few of those conversations started to convert into discussions around paid work, I decided to make the switch. If you're just kicking off your own decision-making process, start by making a list of influential people in your network. Meet with many of them to validate the MVP version of you as a fractional worker.

2. Do you know your own value? You'd be surprised how many people - even super senior people - minimize their compensation expectations or get really uncomfortable talking about it. Trust me, I've been there. Even though I've worked in tech for over a decade, I have largely taken a backseat role in my own compensation decisions. Compensation was something that happened to me vs. something I controlled.

   While this is certainly problematic in full-time work, it's entirely untenable to operate this way as a fractional worker. When you work for yourself, you're in the driver's seat for all of your money discussions, all the time. It's essential to get comfortable quickly at setting competitive rates, advocating on your own behalf, and negotiating contracts. If you don't yet feel comfortable putting a price on your own value, you might consider doing some work there first before plunging into an independent career.

3. How good are you at self-management? Unlike a full-time job, where all of your work responsibilities fall within one organization, as a fractional worker, you'll be the only one with full visibility of everything that you need to get done. Essentially, you must operate as both the CEO and COO of your own work output. If you struggle with time management, motivation, or personal accountability, it'll be a lot harder to get yourself out of bed and into the grind, day in and day out.

   Another under-rated element of self-management is knowing your performance peaks so you can operationalize a schedule around how you get your own best work done. Due to the flexible nature of my role at Union Square Ventures for five years, I got very accustomed to designing a version of a daily schedule that worked best for me - deep work in the mornings, meetings in the afternoons. I'm thankful to have had that relatively independent opportunity to figure out my own work cadence, but it certainly takes some habit-building in order to get good at it, starting with calendar management and knowing your productivity peaks.

4. How good are you at context shifting? Context shifting is so important in fractional work that it's worth calling out as entirely separate from the self-management category. One of the most common questions that I get about working fractionally is, "How do you divide the hours or days you work at each place?" At least for me, in the work I'm doing, it's not that simple. Because every company exists without me, every job has meetings and emergencies and needs on a day-to-day basis. This means I may need to take a call about a decentralized crypto community gaming protocol back-to-back with a candidate interview for a junior marketing hire. (And yes, this actually happened this week.)

   When I first started at USV, context shifting was really hard for me. I realized I would harbor a lot of emotional load and "action items" at the end of every call, then get super stressed out when I didn't have time to close the book on one loop in my brain before kicking off another completely disparate thread. My therapist and I spoke a lot about how to manage this and worked through tactics that taught me how to work more efficiently, listen for the most important details, and move on swiftly. What I found was - I got so good at this skill (and the pattern matching that goes along with it) that I severely missed it when I no longer had a job that required such divergent changes from one hour to the next. For me, this is a feature (not a bug) of fractional work. But it takes a lot of time to get right.

5. Do you have adequate support structures in place for your own personal development? One of the best parts about working independently is that you have freedom, possibility, and endless opportunity. But one of the toughest parts can be that you might feel lonely, isolated, or without community. While I love nothing more than a dynamic whiteboard brainstorming collaboration with a group, I've consistently gravitated in my career to roles where I'm one of one, as opposed to one of many.

   Over many years, this pattern of independence led me to uncover peers, mentors, and advisors in non-traditional places. Today I feel lucky to have friends in many diverse places, whom I can call upon for different types of advice or guidance. I've also explored some of my own personal and professional tendencies through both therapy and executive coaching. For the most part, I have a good understanding how to get support, who to go to when I need it, and when to seek it out. Before jumping into fractional work, you might explore what structures currently exist in your own support system and whether you have what you need to succeed in your personal and professional development goals.

Needless to say, deciding to go fractional was not a decision that I took lightly - and nor should you! But I've been delighted to discover the grounded sense I feel of having a lot more autonomy and control over my own destiny. And I hope you do, too.