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How To Fail At Freelancing

For 10 years, I’d been working as a freelance writer and editor, making money but not a living. It was a good arrangement family-wise, allowing me to stay home with our daughter, but not so great financially or, sometimes, ego-wise. — Will Allison
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I’ll be turning 31-years old in January, which will mark six years of living in Los Angeles and six years since I started freelancing. Within my first month of arriving, I booked a screenwriting gig for $10,000 off the strength of a spec script I had written the prior summer. The job was to write a draft based off a concept by the producer who hired me and do basic revisions. I got half up front to expedite the process. I really want you to focus on the writing, the producer said. I was promised the remaining $5,000 upon completion of the work. Once I got the upfront fee, I hammered out a first draft and turned it in. He came back with revisions which I promptly did and turned in the updated draft. And then, I never heard from him again.

I had mixed feelings about the experience. On one hand, I told myself, well, that’s kinda how Hollywood works right? At least I got that first five-thousand. But I was also bothered that I did the full amount of work and didn’t get the full amount of pay. It also didn’t matter that we had contracts; a legal pursuit would cost too much both in money and time. Also, I was semi-homeless going on to full-homeless. I had bigger things to sweat about.

My biggest mistake from that whole experience was that I was naive enough to believe another gig will come. Give me a month and I’ll be collecting another $5,000 fee to work on another screenplay, and that’ll be the routine. But of course, that didn’t happen. It took maybe another year before I booked my next gig. And not a screenwriting gig but rather a gig where I got paid breadcrumbs to write reviews for self-published e-books, usually following some type of script prepared by the client.

Fast-forward to (almost) six-years later and I’m still learning the ins and outs of the freelance world. It’s still a constant hop from lily pad to lily pad while the bass lurk underneath waiting for the opportunity to devour you. A bit melodramatic but sometimes it feels like that.

Milling over the years spent freelancing, if I have anything to offer aspiring creatives is not so much secrets to success but rather things to avoid as you pursue your freelance career. Basically, do these things if you want to fuck things up for yourself.


1. Doing Free Work For The Wrong Reasons

Doing free work isn’t bad but it should be avoided as often as possible. Yet, sometimes doing a gig pro-bono can warrant some great results for you creatively and personally and you may decide to commit to one. What ultimately makes the difference is why you choose to do something for free.

The big hook a lot of non-paying gigs use is that their project will provide you with “ future opportunities at paid gigs” or that it will “open the door” for you in some shape or form. Most often this will not be the case, so doing a gig based on the hope it will elevate you to the success fantasy you have in your head is a recipe for disappointment.

Even if a client has legitimate connections that could provide a step-up in your career, at the end of the day your client isn’t obligated to put you in a position to have access to that connection. I’ve been in those situations — so-and-so’s friend is an agent here or an associate producer at x-studio and you get strung along for months chasing that dangling carrot.

It took me a bit of time but eventually I came up with a very strict set of standards that need to be met in order for me to even consider committing to a free gig. The reasons are a balance of both creative and personal needs and I made a promise to myself to never budge, never compromise on these rules of engagement.

Figure out what those are for yourself and stick to them with a vengeance.

2. Not Talking Money Up Front

Yes I know. It’s not always comfortable to talk money up front with a potential client. Often, it can shoot you right in the foot because it can give the impression that your only motivation is the money. After all, client’s want you to be authentically passionate about their project too.

Regardless of that notion, it’s not about the money, it’s about survival. You have bills to pay, a mouth to feed, and time to set aside to actually work on your client’s project. How can any client expect you to clock in 20, 30, 40-hours a week and be able to meet your basic living needs?

I screwed myself over many times by not talking about money up front. I let things drag on until I was uncomfortably obligated to ask how much does this pay and was met with a “ums” and “well my budget is really low” responses. All it does is collapse any bit of enthusiasm and hope from right underneath you.

Address money up front and get that out of the way early. On top of that, it’s a great way to gauge how transparent your potential client will be with you from the get go. The more they dance around the subject the more likely they’re wasting your time.

3. Letting Money Be The Sole Reason You Take A Gig

There’s been a few times where I would have multiple gigs on the table and I would always pick the highest paying one. Makes sense right? If you got a gig that pays $1,000 versus one that pays $250, it should be a no-brainer.

Except it’s not. The thing is sometimes that better paying gig can turn into a nightmare to the point where the money isn’t even worth it. Inclusively, the bigger the paycheck the more married you are to that project. The more it has to take priority over smaller jobs and your own personal projects.

The other harsh reality is you’re more likely to get ripped off from the higher paying jobs. Maybe I’m unlucky, but it wasn’t uncommon for me to have to chase down clients of these types of gigs to collect my last payment.

With a low-pay gig, most of the time they are quick and painless. Plus, if you’re savvy enough it’s not out of the realm of possibility to lock down multiple ones and make more money collectively than that single high-paying gig.

4. Not Having A Financial Safety Net

At some point or another you’re going to be in famine mode. There’s no special blueprint for this because it’s pretty straight forward. Either have money saved to keep you afloat when the well dries or have a job to do the same, even if it’s part-time. You will always need funds to save you in a time a crisis.

I know it’s an ego boost to tell people you freelance full-time and don’t need to work at the pizza shop on the weekends but your landlord won’t accept your ego to cover rent. And if you’re in a city with a high cost of living, it will only amplify the stress that comes with slow-to-no income.

There’s no shame in having a common man’s job but there is shame in thinking you’re better than it.

5. Expecting Your Client To Do More

This essentially hearkens back to the discussion about free work and those clients often promising “new opportunities”. Likewise, your client is not expected to give you anything beyond what’s agreed upon in the contract. They don’t owe you another gig, they don’t owe you a line to any of their contacts, they don’t owe you shit except what’s on that paper you signed.

In the past, when I would finish a gig with flying colors I’d anticipate a follow-up email or phone call from the client enthusiastically asking me to work for them again. Or them referring to me to friend or colleague who just couldn’t wait to hire me. But nine times out of ten I would end up frantically scouring freelance sites for job postings and submitting my application to countless employers.

Just because you do a good job doesn’t mean you’ll keep getting jobs. You have to remember, everyone has a lot of things going on in the creative world and they can be on a completely different wavelength the following week. Hell sometimes they may have just found someone better than you.

It’s vital to see each gig as a standalone. I’m not saying don’t get your hopes up, just be realistic as to what’s legitimately on the table and what isn’t.

6. Putting Yourself In A (Creative) Box

A big thing that stalled my ability to progress in my freelancing was stubbornness. Not just any kind of stubbornness but the creative kind. I would only pursue jobs in the screenwriting realm and nothing else. Sure, I would book a job here and there and some paid well while others didn’t but the amount of time I put into searching for gigs was exhausting.

Eventually, I had to swallow my pride and pursue writing opportunities in editing, coverage writing, web content et cetera. A lot of the jobs I got were unsatisfying and low-pay but I was working almost full time. At one point I had lined up close to 15 gigs that covered two weeks. The lowest paying one was $50 and the highest was $300. When it was all said and done, I had worked roughly 50-hours total over those two weeks and made close to $2,000.

These small jobs, as uninspiring as they tended to be, turned out to be great stepping stones that would eventually lead to better gigs.


Even after six-years I’m still constantly learning and adapting to the freelance world. I can say with confidence that this list of fuck-ups are constant go-to’s for me when I’m pursuing a gig and have made the process less stressful and more efficient.

I have not failed. I’ve just found 10,000 ways that won’t work. — Thomas A. Edison

That is all.

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