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What You Need to Consider Before You Go Freelance: A Checklist

It seems like there's 1,000 blog posts every month about the joys of freelance. Real life, on the other hand, is a bit more complicated.

Chucking the corporate life for the freedom of working independently is the fantasy of many a cubicle monkey. But before you make the jump, ask yourself some hard questions to make sure that you can operate from a position of strength while on your own.

Before I joined 99U last fall, I freelanced full-time for five years in New York City, writing for places like ESPN The Magazine, Fast Company, and New York. While I was ultimately able to thrive on my own, the first year was rough. My life was a constant cycle of eeking out enough money to pay my monthly bills, relishing that accomplishment for about as long as it took me to sip a celebratory glass of whiskey and then realizing: This month nearly killed me. How in the world am I going to make it next month?

If I were to go back and do it all over again, I’d make one major change to vet the decision to freelance from the perspective of an entrepreneur, and not solely weigh it against my creative ambitions. While it feels clinical to think of your art as a “product”and asking yourself questions about money makes you feel vulnerable, this approach can help you make a decision informed by both creative desires and shrewd business sense. This combiniation pushes you to pinpoint why you really want to work independently, highlight your shortcomings and hopefully allows you to firm up any weaknesses so you make the move when you’re truly ready.  

Vet the decision to freelance from the perspective of an entrepreneur.

However, it’s hard to know what best prepares one for first year of freelancing without the benefit of hindsight. That’s why, whenever anyone asks me whether they should make the leap, I send them some version of these questions. Follow below and be honest with yourself to assure you’re in a position of strength to make a seamless transition to an independent career.

1. Why exactly do I want to strike out on my own?

If you are considering working independently, have a good reason for doing so. Hating your current role, loathing your boss or feeling exhausted from the long hours all are poor reasons to jet your current job. (You will still experience each of these as a freelancer under more trying and less stable circumstances.) Instead, determine what you can do as a freelancer that you can’t do in your current capacity. Vet the decision to freelance from the perspective of an entrepreneur, and not solely weigh it against my creative ambitions. 

Determine what you can do freelancing that you can’t do at your current job

Earning more money is one response that makes sense. Doing something that you love is another, though it’s more romantic than pragmatic. If it is the latter, first see if there is the chance to make your situation at work, well, work. Can you take on new tasks that better fit wth your interests? Can you more thoroughly apply your strengths to the business’s goals? Can you move to a different team that does what you’d like to do more of? The cottage industry of blog posts and books urging us to go freelance can make us think that the solution to everything is quitting our jobs. But that’s not always the best, or even a good, idea.

Try and solve the root of what’s chewing at you you while are you are protected by a steady salary and benefits. (Because jumping into freelance and trying to figure out something on the fly is an income-draining approach.) If you can’t and you believe the only way to accelerate your career is to be your own boss, then…

2. What makes you think you can do better than the people already on a company’s payroll?

When you become a freelancer, you’re now fighting for work from companies that already have in-house staffs and a roster of creatives on contract. So now you have to beat out people who are already tops in their fields and are getting paid by these businesses to drum up concepts. That is no easy feat.

Before you compete against that stacked lineup, evaluate the contributions you’re making to your current company. Are you an All-Star who consistently produces the best projects? Are you the person every client wants to work with? Are you responsible for driving a large chunk of your team’s revenue? If not, then you might hold off until you reach that point. Why? Because, if you’re not already generating the ideas that clients are spending heavily on when you’re surrounded by a team, then what makes you think you can be this person when you’re doing it all by yourself?  

3. What do you have to sell, and to whom?

I wish I would have asked myself these questions. I loved writing satirical stories about quirky characters, but the problem I learned after the fact is that there is no market for them. In hindsight, I should have identified my market niche and buyers before I went out and offered up my writing for sale.

Be realistic and specific in calculating your market. If you’re a photographer, don’t just say that there are tons of brands and magazines that need photos and that someone will want yours. Casting a wide net probably won’t work—it’s too general. One obvious place to piggyback off of is your current speciality. Did I try that? Of course not. I wasn’t interested in starting small and focused. Why do that, I figured, when I could lob pitches to the literary big dogs in hopes that one would see my genius and I’d be on my way, all of 26 years old and already a contributor to the New Yorker!

Identify your market niche and buyers before you offer your work for sale.

My strategy proved good at failing. Only after a few slow months did I realize that my best chance of getting work published was via what I knew well—the world of running. I had been a collegiate runner, befriended Olympic runners, and understood what running magazine readers were looking for in stories. Plus, running publications typically rely heavily on freelancers, because they have very few staff writers. By combining my insider knowledge and credible resume with a true market need for my ideas, I was eventually able to break into Runner’s World and Running Times.   

4. How do you really know if you can cut it?  

Prove to yourself that you’ve got what it takes to work independently, well before you do it full-time and even when you don’t feel like working.

This sounds dumb because everyone thinks that if they can just leave their current job, then it will be easier to create art. While it’s true that you will have more time for your craft, work is still work. There is a huge difference between enjoying these activies as a weekend hobby and depending on them to put bread on the table, all while a boss is hounding you for changes.  

I started writing my first book at age 22, a full four years before I left my corporate job. During that span, I wrote in the mornings before work and again at night—two hours every workday. On Saturdays, I put in a six-hour writing session. I never shrugged off these practices because I was too tired, needed a break, or whatever excuse works here. The commitment reinforced that I was willing to write even when the conditions weren’t perfect, like at 7 p.m. when I was hangry and beat from working since 7 a.m.

Prove to yourself that you can work independently before you do it full-time.

By taking this storytelling test drive, I discovered that I wasn’t just going to talk about “writing my novel one day when I have more time.” I would find time to make it happen. That discipline carried over to freelancing when I didn’t have any assignments, but desperately needed to come up with something—anything!—to sell to an editor. I kept chipping away into the night until I had something worthwhile to pitch.

Freelancing requires a boatload of initiative, so see where you fall on the self-motivation spectrum and use that to determine if branching out is really the best move for you.

5. How will you get off the ground?

So you’ve got it all covered: great ideas, a strong product, a bright passion and a killer work ethic. Before you take off, though, make sure that you’ve cleared the runway for yourself. Do this by establishing your key business contacts long before you go freelance.

Some people might suggest tapping your current company as your first client. It’s a smart idea in theory, but doing so often depends on the culture of your company. Are your bosses and co-workers genuinely happy for their colleagues when they move on to other pursuits? Or, do they feel betrayed? If it’s the latter, then you could be doing yourself more harm then good. In that case, start asking your connections for help: Who have you worked with that might be a potential customer, or know a potential customer?

Establish your key business contacts prior to starting freelancing.

Here is where you need that one-two punch of self-belief and no shame: My first big break into a national publication came when I asked a friend of a girl who I met at a party to introduce me to her editor at ESPN The Magazine, whom she barely knew at the time. An awkward networking tree? You bet. But I got a lunch with the ESPN The Magazine editor and ultimately made 40 percent of my income from ESPN in the ensuing years.

And start freelancing for a few new clients while you’re at your current job, so that you already have work (read: income!) on day one on your own. This will ensure that you’re taking a strong first step into this new chapter in your career.  

Matt McCue

Matt McCue is the Editor-in-Chief of 99U. He lives in New York City, but he is willing to travel long distances for a good meal. Find him @mattmccuewriter or email him at 

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