What I learned building a fractional executive career

As a graduate of Harvard Law School and Harvard Business School I believed full-time roles were the only way to succeed, until an unexpected Bollywood acting opportunity opened my eyes to freelance-forward careers. Since then, I have toggled between holding full-time executive roles and fractional ones. 

If you’re not familiar with the phrase, you can think of fractional work as the executive version of freelancing. Fractional leaders work in a C-suite or other senior role part-time, usually for multiple companies simultaneously.   

Landing a fractional role

I landed my first fractional General Counsel role when I attended an industry conference in the hopes of finding my next job. Instead, I met a startup founder who needed legal support but didn’t have enough work to justify hiring somebody full-time. A month later, I got my second fractional General Counsel role from a different founder in similar circumstances. 

Job postings for fractional work are fairly limited, owing to their custom nature and partial workload. Instead, this job type relies heavily on the “hidden job market”. To maximize your chances of getting a fractional role, seek out events that your future manager would attend. Fractional roles are often at startups and SMBs, so prioritize conferences attracting those companies’ founders, leadership, or investors. If you can’t meet your prospective clients organically, try to have a mutual friend introduce you, engage on social media, or send a thoughtful cold email directly. 

After securing your first fractional role, you can follow the same path to get your second, or ask your existing client for a referral. Building a book of business takes time. Depending on your circumstances, it might make sense to seek out other freelance or even full-time work while growing your fractional career. 

A day in the life

Here’s what my day usually looks like when I’m doing fractional work. I wake up by 7 am, do yoga, then scan messages to see if any fire drills came in overnight. If not, I’ll eat breakfast and get to my desk by 9 a.m. Then I log in to each of my company accounts.

Since I have a different calendar for each company, I confirm I don’t have any double-booked meetings or deadlines. I’ll then triage the requests that came in overnight, and make a master to-do list mapping out the day’s tasks for each client, as well as administrative tasks for running my own business. Inevitably, new work comes in during the day and I’ll triage that by urgency too.

Some days, I’ll spend the entire day in meetings and have to catch up on deliverables at night. Other days, I’ll be heads down on documents and have an open calendar. When client work is light, I focus on my own business admin or brand building. In the evening, I usually break for family dinner or a dance class. I’ll log back on afterward if needed to finish anything due by end of day and start making the next day’s to-do list.

The Biggest Upsides of Fractional Work

These are the biggest benefits of fractional careers that I didn’t know before I started:

1. Financial
As a fractional executive you often command a rate that is high for the number of hours worked (though often still cheaper for any company than hiring a full-time employee). As you continue to increase your rate and build a portfolio of clients, you may quickly out-earn your full-time salary while also working fewer hours.

2. Flexibility
Perhaps the biggest advantage of fractional work is its flexibility. Because you negotiate with each client individually, you choose when and how you work, in addition to the actual work itself. If you love being in an office, you can probably join your client in person. If you thrive remotely, that’s often available fractionally even if it wouldn’t be possible full-time. And when the workload expands, you decide whether the extra responsibility is within the scope of your part-time role.

3. Diversification

Working for multiple clients benefits your finances, skills, and brand. Financially, the loss of any one client is less catastrophic than a layoff. Educationally, diversification uplevels your skills. You can learn from each client’s business and see industry patterns from different angles. Lastly, diversification benefits your brand. With more than one client, you have multiple shots at earning a success story that can land you lucrative clients in the future. And if one company stumbles, you’re not gambling with your whole resume the way you would in a full-time job.

The Hidden Risks of Fractional Work

The benefits of fractional work come at a cost. Here are the biggest downsides I’ve seen: 

1. Financial
You have to keep selling, and income can vary substantially. There may be seasons where you don’t earn anything at all. You have to plan for your retirement and possibly set up a solo 401(k). And it’s not always possible to get equity at the companies where you work, which means you’d miss the financial upside of what you’re building. You might also miss upside if the role grows so much that the company needs someone full-time instead of fractional.

2. Health
Staying healthy as a fractional worker can be tricky. Health insurance when you’re self-employed is hard to get, expensive, and does not always cover what you need. Paid time off is not guaranteed if you get sick. Deadlines and work commitments also have a way of colliding such that your busy seasons take extra finesse to negotiate. You often can’t tell one client that another is keeping you busy, and there may be no team you can delegate tasks to.

3. Community
Fractional work can be lonely. The flip side of being sheltered from office politics is that you’re also insulated from team bonding. You’ll likely miss some company retreats, all-hands meetings, and parties. You might also lose the feeling of building something bigger than yourself, and the tidy sense of identity that comes with having a job title people at cocktail parties understand. 

How Do You Balance These Tradeoffs? 

Neither full-time nor fractional work alone is the promised land. Each working style brings its own set of opportunities and tradeoffs. But the thing that surprised me most was that fractional and full-time work feed off each other. As your title and responsibility in the full-time world grows, you can earn better titles and pay as a contractor. This progression helped me become a fractional executive instead of staying a project-based freelancer. The reverse was also true. More clients equals more experiences you can share in interviews to show future employers that you can solve their problems. 

Most of us are seeking money, enjoyable work and a sense of stability where our livelihood won’t be ripped out from under our feet. Both fractional and full-time work can accomplish these goals. But the most potent elixir to future-proof yourself? Creating a career that has both full-time and fractional elements. With this kind of dual-track career, wherever the market goes next, you can go with it.