Working: Freelance

I have worked as a freelance employee in a number of capacities: as a theater stage manager and producer, as intern, and as a project-based worker. My first “real” job after college was a freelance job, though I didn’t realize it until the next year at tax time that I had been working full-time on commission and the company had not paid any taxes on me (ah, youth!/well, they had bigger problems and went bankrupt that year).

Working as a freelancer can be really difficult, and there are a number of problems associated with contract work, including companies failing to pay workers in a timely fashion, the high tax burden, and lack of benefits. Earning all one’s money from freelance or contract work can be really hard to manage. Essentially, you are running a sole-proprietor business. For several years I worked with artists in a professional development context, virtually all of whom worked as freelancers in some capacity. It was always really interesting and intense to hear their stories: very low pay rates for activities like teaching, not getting paid at all by galleries and presenters, using freelance work to subsidize their artwork, navigating the tax system as an independent contractor, setting prices for their labor and products, and so on. These are extremely complicated issues, obviously. As a stage manager, I often was paid so little that my fee didn’t even cover the cost of traveling too and from rehearsals over the life of the show. That was a byproduct of the budget size of the theaters I worked with. I was okay with it, at the time, because I was networking professionally, and broke and young and dumb. It was fun. I was actually “lucky” to be getting paid at all (but that is another post!).

As an “office” worker, I have different issues around freelance work, they almost all have to do with two issues: time and expectations.

I think freelance projects can make an excellent use of time, both for the employee and the employer. I have worked with a number of consultants who had both time and expertise to bring to a specific, discrete project. They (almost) always did extraordinary work, especially research projects, that full-time staff would not have had the time to execute well. Because the organization is outsourcing some aspect of the work, it creates efficiency. The staff’s time is reserved for more important or essential functions, and the consultant’s time can be fully committed to the project at hand. The cost of the project would presumably be in time with the consultant’s fees, the scope fo the project, and the benefit of saving the staff’s time.

Time, for the consultant, can also be used to maximum efficiency. The work can often be accomplished outside of typical business hours, or very intensely over a few weeks, so that earning capacity can be maximized by efficiently organizing one’s time. When I took on a freelance project while I was also working full-time, I was able to increase my monthly income by 50% over the two months of the project, while working full-time, but making myself available at strategic times during the work day for calls. It was stressful, but it was definitely worth it. However, if travel or other extraneous activities are involved, the consultant’s time can be abused (for instance, traveling cross-country hours to teach a workshop could cause a teacher to lose an entire day of work to travel). Managing the consultant’s time to maximum efficiency is key to building a sustainable freelance career. But if it is done right, I think it can also allow the consultant to work extremely effectively, to manage a variety of projects simultaneously, and not to waste time .

Where freelance workers often run into issues with organizations is around the expectations around their work. If expectations are not clear, and especially if they are not clearly memorialized in the contract, it can be an arduous experience trying to negotiate after the fact. I know many consultants who are obsessive about breaking down their workflows and assigning each a time estimate, and who build in contingencies for overages. This kind of conscientious self-analysis is so important. I have also seen the opposite–usually it happens with consultants who haven’t thoroughly prepared, or a project that hasn’t been adequately spec-ed out. There are also sometimes unreasonable expectations on behalf of the organization, that go above and beyond the scope of the project. I would also say that the key to this issue is healthy communication.

There are other issues at play, of course. Like hourly workers, freelancers don’t get paid when they take time off, so it is important to build vacation and downtime into the fees that consultants charge. Freelance workers might also have difficulty organizing consistent work projects, and end up working intensely for a few weeks or months, and then not at all. This inconsistent earning can be very stressful.

But consultants can also specialize very highly, which might be enjoyable. Conversely, they can work on a variety of projects, and that variety is enjoyable. They are not tied to a desk, or to “face time” in an office, which might be really desirable (especially for parents who want the flexibility to stay home or pick up their kids from school, or just more independent personalities, like mine).

But then, the ultimate reward, being you own boss….almost.



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