Be a Freelancer, or be a "Freelancer", but be a Freelancer

This November marks the 5th anniversary of working for myself. I have mixed feelings about it. On the one hand, I feel as if I've blinked and built a business. On the other, I feel as though I've aged 20 years, through every challenge and triumph. But alas, I'm here, and 5 years feels significant enough to make full commitment to it: I'm a freelancer.

Despite how much I actually despise that word—more on that some other time—we'll go with it. According to Wikipedia (only the most trusted online source) freelancer is "a term commonly used for a person who is self-employed and is not necessarily committed to a particular employer long-term." And it seems, these days, everyone wants to be one. 

Who wouldn't? Freelancers look like they have it all: time, control, choice, autonomy, authority, no nagging bosses. Freedom!  That's the Instagram version. We have overhead, accountants, accountant fees, lawyers, lawyer fees, invoice collection, self-employment taxes, instability, fear, self-doubt, self-doubt. Did I say self-doubt?

For me, it works. I'm your classic "Jane of All Trades, Master of None," which makes me effectively good at the diverse range of tasks running your own business requires. I'm also self-disciplined, self-motivated, and good at managing my time, necessities for acquiring clients and delivering work as promised. But for a lot of people, it doesn't work. Cool.

Entrepreneurship is over-glorified and over-hyped, the details of which I'll leave to the subject matter experts in your Google search. And yet, I do believe there is value for everyone, in all work environments, in some of the practices of a freelancer. If I could turn back time to my days as a 9-7er, I'd stash a few insights in the time machine with me.

Here's my If You Aren't Going to be a Freelancer, be a "Freelancer" List

1. Network for a network, not for a job. You've probably heard the advice to 'always be networking' before: take a lunch, go to events, entertain prospects. I agree. It's smart to keep the doors open, and beneficial to meet people in your industry. It's also important to be connected to people outside your industry, which limiting yourself to networking for the purpose of a future position likely won't allow you to do. In my work, I need an army of people to help me get a job done: photographers, designers, publicists, models, interview subjects, web developers, etc. But a contact list of diverse professions won't only come in handy if you do decide to go out on your own someday. It'll be there if you decide to pivot paths, too. And, through conversation with people from different lines of work, you'll gain fresh perspective that can be contributive to your current role.

2. Broaden your skillset. Doing something on the side—whether it's creating a personal website or building and managing an Instagram account or developing a hobby like painting—will teach you stuff. Useful stuff that could allow you be seen for a more senior position or a department change. Take, for example, building a website. If you know intimately what it requires—the time, the content, the backend management—you're going to be better able to assess agency costs in a proposal you receive at work. Or, you'll be reminded to consider dimensions when you're out on your next photoshoot. 

3. Be smart about your taxes. Freelancers have a lot of responsibility when it comes to taxes: we have to calculate and pay quarterly estimated payments, account for all expenses, collect and distribute filing forms, and a whole bunch of other stuff. To be successful in business by yourself is to be smart about them. But just because the weight isn't so heavy on those with employers, doesn't mean they should be any less knowledgable of deductions and exemptions. I'm no expert here, as I'm still learning myself, but if you like money, pay attention.

4. Say no more than you say yes. I could write a book on this one. Or, I could just direct you to Oprah's. Anyway, this topic is rich, but it's particularly applicable to freelancers and 'freelancers.' When you're on your own, it's difficult to say no to any project that comes your way, for fear of it being the last, or over the excitement of the money you'll make. But this is an amateur move. Energy is a limited resource and putting it toward projects that don't excite or further your goals will only leave limited for those that do. In traditional work environments, this could mean saying no to favors from colleagues, or no to a meeting where you're not needed, or no to staying late. Someone once told me "a lack of boundaries welcomes a lack of respect." Just say no.

5. Structure your work if it isn't structured for you. My work with startups is manageable now, but it wasn't always. When I was on the inside, the environment was chaotic; objectives, priorities, and timing were unclear. But I would never allow these three critical pieces to be unclear today, or I'd be out of business. If they don't exist, create them. You wouldn't travel the highway without guardrails or a destination, would you?

Emily SchildtComment