Being a Freelancer in New York

Why You Should be a Freelancer

1. Gas is expensive; chances are you can do some of your work from home.
2. You set your own hours: are you a night owl? Work then and go to sleep at 3 a.m. Is there an afternoon book reading? Go to it! Make up for it later…
3. Have no one to complain about but yourself when all your friends are whining about their demanding bosses. You ARE your own boss. And NO office politics.
4. Work from wherever you want: if your freelancing gigs involve you and your laptop, then you can work wherever Wi-Fi exists. The downside to this is that, you can work wherever Wi-Fi exists. Catch my drift? That beach house? That mountain resort? Your parents’ basement? We’re all a little too connected…
5. It’s fun! Usually. Freelancing is still a lot of work, and takes a certain amount of discipline, but the work tends to be engaging and enjoyable. Like writing here on Guidespot!

Join the Freelancers Union

Before I go any further head over to the Freelancers Union and join already. It’s free! You can find all sorts of information about gigs, events, and discounts. Once you do that, peruse the Health Insurance options, which is what most people join for.

The Dreaded Health Insurance Issue

One of the biggest downsides to freelancing is that you are, more often than not, uninsured. You may be thinking, but I’m healthy! Well, be realistic: everyone gets sick at some point, you could fall down the subway steps and break your leg, you may need prescription drugs and they are mad expensive out-of-pocket.


If you are really unlucky, you could get struck down with a chronic illness totally insurance-less. Speaking from experience, this is NOT fun. So, shell out the money for
some decent health care so that you don’t have to worry about that innocuous vegetable-chopping gone wrong experience making you bankrupt.

The Freelancers Union plans in New York are some of the best in the country, so until the government figures out how to follow all other developed and developing nations, you’re stuck figuring it out yourself.

Look for Jobs

Job websites will vary depending on your freelancing field, but here a few general ones that offer a variety.

Tools of the Trade

Some, but not all, of us freelancers use laptops as our primary freelancing tool (well, first our brains, I guess). Whether you are a blogger, writer, journalist, graphic designer, web designer, developer, photographer, etc., you probably find yourself working from home sometimes and working elsewhere, at cafes, libraries, or anywhere with a decent internet connection.

Doing such sounds like a cake walk: you work at HOME?  You do work at your favorite COFFEE SHOP? But it’s no easy task to work in environments that are, well, normally fun places to BE, not WORK. Self-discipline is difficult and must be learned.

Working from Home

Make your space comfortable, but not too comfortable, i.e, buy some shite from Ikea. Take coffee breaks. Eat real lunches. Check out that thing called “outside” once in a while.

Working away from Home

Sometimes you just get sick of moving around the same 12 square feet of your apartment. Get ye to a coffee shop! Wi-Fi spots are sprouting up everywhere, but look for the ones that don’t cost more than your token latte. Or you’ll have to figure the extra internet costs into your hourly/project wage, and that’s no fun.