Hard Lessons From the Early Days of Online Writing That Still Apply Today

Ten years ago, I was just another fresh-off-the-bus kid from the Midwest looking to make it big in New York publishing. Today, I’m still gainfully employed, I’ve transitioned from print media to online media and I’ve even managed to escape New York, which is as close to a success story as you’re going to find in this heartbreaker of an industry.

Looking back on my resume, it strikes me that every job I’ve held over the last decade has left me with an important lesson, most of which I learned the hard way. So, for the benefit of those who are starting out in their writing careers, I figured I’d share my accumulated wisdom and save you all some trouble. Let’s begin___

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1. Great Internet writing is both an art and a science.

Editorial Assistant, MaximNet (August 2002 ___ February 2004)

My first gig out of college primarily consisted of HTML coding, mixed with some low-impact entertainment writing. One day, I was assigned to interview System of a Down vocalist Serj Tankian, who let me fire questions at him for nearly an hour before his publicist threw in the towel. I spent the next two days transcribing our entire conversation, before submitting it as my article, virtually unchanged.

Shortly after I turned in the piece, my boss called me over and explained the principal irony of writing for websites: Although there’s a nearly infinite amount of space at your disposal, attention spans are lower online. Most Internet users will simply click a headline that grabs their eye, scan the first two paragraphs for the important points, and then click away to the next shiny object. And, according to Rob Weatherhead, head of digital operations of MediaCom, endless blocks of text are the biggest eBuzzkill of all.

“When a user lands on a page, you have three to five seconds to make your impression and convince them to stay,” Weatherhead explained. “So make your content easily viewable in length, and sign-post it with sub-headings and bullets, so that readers can understand the key points you are making. Long, wordy paragraphs and a lack of sections can turn people off. Readers need to pick out the key topics and be enticed to read more.”

In other words, your writing needs to be as concise online as it does when you’re dealing with physical limitations like magazine page-counts and newspaper column inches. In fact, it needs to be even sharper nowadays, since you’re competing with 140-character tweets and two-word memes. The Internet may allow writers unlimited freedom, but if you want to hold your audience’s attention, you__?ll have to earn it.

2. If you’re not fending off job offers, you’re doing something wrong.

Assistant Editor, Associate Editor, Giant (February 2004 ___ September 2006)

When I joined the launch staff of Giant, it was a witty and affectionate entertainment bimonthly aimed at young, culturally obsessed males (nerds, basically). Two years later, it was an “urban,” “aspirational,” “luxury” title run by entirely different management. One by one, my original crew successfully jumped ship until I was the last man standing, spending my days at a magazine that would otherwise never find its way into my bathroom. I had no exit strategy. I hadn’t bothered to network at media events, create a personal website to showcase my past work or reach out to other writers and editors who I admired to start a dialogue. I was stuck.

“The best way to not only advance in your career but also create new relationships is to pursue professional-development opportunities,” said Charles Purdy, senior editor of career site Monster. “Classes and workshops related to your profession are great places to meet people. The teachers are often experts who are still working in the field, and the other students and attendees will be professionals like you. And, of course, there’s the side benefit of learning something new.”

Even if you’re happy at your current position, building relationships outside of your bubble could lead to job offers that will give you leverage if you’re overdue for a raise. Just don’t be shady about it; publishing is a small world, after all.

“Always be positive and enthusiastic about your current employer,” Purdy recommended. “And talk to your boss about your networking activities: ‘I met so-and-so from Company XYZ, and we talked a bit about how our companies are similar. Here’s what I learned.'”

3. It could all go away tomorrow, so plan ahead.

Senior Associate Editor, Stuff (October 2006 ___ August 2007)

Just when I was beginning to despair, I was hired by a men’s magazine editor who I’d interned for in college. I came into the job with long-term plans for the kinds of features I’d be writing after I got my feet wet and of how I could steadily progress up the editorial ladder. Ten months later, I was laid off. It was business, not personal. But I wasn’t ready for it.

Luckily, I found my next job before my severance pay and unemployment benefits ran out, but it could have been a disaster — like, a moving-back-in-with-your-parents kind of disaster. The lesson I learned here was a practical one: Don’t live paycheck to paycheck. Unemployment can strike at any time, so if you don’t have enough cash in the bank to cover a few months’ worth of expenses, do whatever it takes to adjust your lifestyle so that you can create a financial cushion for yourself.

According to Claire David, manager of member services for Freelancers Union, you should also become very familiar with your employment agreement at the start of any new writing gig, so that there are no nasty surprises when the axe comes down.

“If you’re on a contract, it matters whether you’re being paid as an independent worker, or if you’re being paid on a W-2,” David said. “If you’re a W-2 employee, you likely qualify for unemployment. If you’re not, there really isn’t a safety net. And misclassification — being classified as an employee when you’re a freelancer, or vice versa — can impact everything from taxation, to access to company benefits, to specific employment protections, like the right to file a wage claim if you don’t get paid.”

4. Do more than just write and edit.

Managing Editor, CagePotato.com (October 2007 ___ present)

Starting a blog is easy, which is why so many people start blogs. But rising above the noise and finding an audience that shows up every day? Well, that’s a bit harder. When I was hired to launch a mixed martial arts news site in 2007, I quickly learned that creating great content is just one part of the equation. To make sure that your words aren’t swallowed up in the vast sea of the Internet, you also need to be a social media director, an SEO expert, a traffic analytics wonk and a marketing guru. (Coming up with million-dollar advertising and product ideas once in a while doesn’t hurt, either.)

Being multi-talented — and having a working understanding of all the factors that go into building a successful entertainment brand — means that there’s more than one reason for people to hire you. All other things being equal, the job will go to the person who brings the most to the table. But keep in mind that “skill sets” and “added value” are no substitute for actual writing ability.

“There will always be a demand for people who can think straight and then put those thoughts in writing in a way that makes sense,” said Mark Remy, editor-at-large for RunnersWorld.com. “Being SEO-savvy, or a social media expert — those are all good skills — but, if you can’t write or edit, I’m not going to hire you, period. Any time I see young people who actually can write and edit, I tell them not to worry. They have a future in publishing, whether it’s in print or digital or some technology not yet invented.”

Encouraging words — but just to be safe, you might as well learn Photoshop.

Ben Goldstein has written for the New York Post, Time Out New York, MensFitness.com, Maxim, Fight! Magazine, and BloodSweatandCheers.com. He can be reached at bjgoldst@gmail.com.