5 Lessons Learned from My Years as a Professional Freelancer

*Originally published on Copypress.com in October 2013, #ThrowbackThursday

On the surface, working for yourself as a professional freelancer seems like a pretty sweet gig. You don’t have to answer to a boss, and you have the ostensible advantage of determining your own destiny.

But all is not candy canes and lollipops in the land of freelancing, as you will shortly see. You’re essentially running your own business, and it takes a lot of effort and know-how to really succeed.

I learned this for myself, and I often did it the hard way. After working off and on in the freelance writing game for nearly a decade, here are a few of the more important lessons I’ve managed to learn.

Lesson 1: Understand the Freelancer-Client Relationship

On a few occasions, I’ve had conversations with other freelance writers where my jaw dropped. Some of them seemed to believe that these companies owed them benefits, while others talked of “customer service” from the editing staff as though they (the freelancer) were actually the client. In both cases, those individuals fundamentally misunderstood their relationship with the companies for which they were working.

This attitude undermines the the primary reasons for hiring freelancers in the first place. From your client’s perspective (and yes, they are your clients), the entire point of getting freelance help is that they aren’t hiring an employee, and that they’re getting someone to complete a project (presumably) for their client. As a freelancer, then, your attention should be focused on completing the work and maintaining the relationship with your client.

If you’re busy demanding benefits and expecting to be “serviced” by some customer representative, then you’re probably going to alienate a potential source of ongoing revenue. And, as even the novice businessperson knows, ongoing clients are worth their weight in gold. If you know how to recognize bad customers, it’s okay to cut some of the more problematic ones loose. Just don’t do it because you’re failing to comprehend how freelancing works.

Lesson 2: Always Get Your Assignments in Writing

A couple years ago, I got a frantic phone call from the managing editor for a Tampa Bay area magazine that I won’t name here. One of her writers had gone incommunicado, and she suddenly had two very large, feature-sized gaps in her editorial calendar. Since I’d recently pitched a couple feature ideas to her magazine, she was hoping that I’d agree to write the articles for her on a very tight deadline. Immediately following the phone call, I went about sourcing and writing the articles in question as quickly as I could.

In the meantime, the original writer re-emerged from the rock under which they’d disappeared and submitted the articles. Instead of refusing the late submissions, the decision apparently was made to publish the articles without notifying me. When I attempted to send the two articles a day later, I was told that the magazine had never actually commissioned the work from me. The editor insisted that she had just been “trying to see if she had options” — wholly ignoring the fact that she’d set a deadline, specified a pay rate, and told me explicitly that she needed the articles “right away.”

This, of course, meant that my articles wouldn’t get published, and that I was now holding the bag for roughly $500 worth of writing. Although I eventually managed to shop these pieces of content out to another publication (at a significantly lower per-word rate), I ended up writing the whole thing off as a learning experience. From that time forward, when a client approached me with a project, I would make sure to get the assignment in writing before doing any actual work on it.

For first-time clients, I now always make sure there’s a formal written agreement, even if I have to supply my own contract (making sure, of course, that the specified jurisdiction is in my own city unless the client demands otherwise).  With any subsequent assignments, I at least get them confirmed in an email before proceeding to write them. So far, I haven’t had any real issues, but if I do, I at least have a leg to stand on if I need to pursue legal remediation.

Lesson 3: Realize You Are Your Accounts Department

Prepare yourself to work with a company that will have a pay schedule that can delay payments. Most will take 30 to 60 days to cough up the cash, and this is usually done via a physical check sent through snail mail. Frankly, I can’t tell you how many times I was told, “the check is in the mail” when chasing down payments.

I even had a couple clients who’d only process invoices at the end of the month and it was only then that the 30 to 60 day wait would begin. If my deadline were at the beginning of the month, that would easily be a 60 to 90 day wait from my original submission. And these weren’t small businesses — this was common among some relatively large, fairly successful magazines.

One California start-up took nearly 6 months to pay me. I can’t say I was particularly happy about that.

Subsequently, I became very good at managing my money. The freelancing lifestyle can be one of feast or famine, so I always tried to keep a few pokers in the fire to mitigate this. Of the hundreds of articles and blog posts I’ve written, I’ve only had to make one entry on the wold’s longest invoice.

Most (legit) companies will pay up as agreed, even if some of them take their sweet time to do so.

Lesson 4: Learn to Pitch Stories to Your Advantage

Simply put, you’re going to have to learn how to pitch your writing to succeed as a freelance writer. It’s an endeavor that takes two parts confidence and one part humility — while it’s key to be convinced that your idea is interesting and compelling, you also have to be willing to change it  to meet your client’s needs.

Sometimes you’ll pitch them an idea, and they’ll come back at you with something that’s almost entirely different. This is actually a good thing, though, so don’t despair.

On the surface, this counter-pitch might seem like a rejection of your carefully crafted ideation, but it’s actually to your advantage. Not only have you succeeded in prompting the client to pitch an idea to you (instead of vice versa), but your original story concept is now completely free to be shopped elsewhere. This, of course, is a win-win situation for you, because you essentially get two assignments for the price of one idea.

Lesson 5: Market Yourself and Keep Your Skills Sharp

If you aren’t doing anything to market yourself as a freelancer, you’re just leaving money on the table and needlessly turning yourself into a starving artist in the process. You need to spend some time networking and building relationships, both online and offline. I found particular success on Twitter (I tend to tweet about things related to writing) and by interacting on various writing groups on LinkedIn.

And, you’ll want to write constantly — even when no one is paying you. It keeps your skills sharp and allows you to maintain good writing habits. Perhaps even more importantly, though,  this will help you in building a strong online portfolio, which you can then leverage as part of your marketing strategy to find paying clients.

So there you have it: Five fairly useful tips to kick off your freelance writing career. It’s not always an easy lifestyle, but it certainly can be really rewarding if you approach it in a conscientious fashion. What about you? Have you learned any other freelance writing lessons that you’d like to share?