Ask a Freelancer

Ask a Freelancer: Will You Still Be Freelancing in 10 Years?

By Nicole Dieker November 18th, 2014

Do you think you’ll still be freelancing in 10 years? If so, how do you realistically see the next decade playing out for you professionally?

—Skipping Ahead to the End of the Book

I’d love to think that I’ll still be freelancing in 10 years. The trick will be to figure out how the freelance world is going to change in the next decade.

Ten years ago, for example, I might have thought about working towards a highly visible byline in a highly visible publication, the way Emily Nussbaum became the television critic for The New Yorker.

But, as Nussbaum told Rookie, those jobs are now few and far between: “I was super lucky—I aged in at a point where, when a really desirable job became available that I was actually suited for, I had enough experience to already have the clips in place. But how often does the television critic for The New Yorker step down?”

I would still love to write for The New Yorker or New York magazine’s Vulture or another premier publication someday, but I can’t play my career like that is going to be the endgame. Instead, I have to think about creating what Penelope Trunk calls a “braided career“—combining many different types of jobs and shifting focuses as the freelancing world changes.

Right now, for example, we are experiencing a renaissance of smart, funny specialty blogs and online publications. This is great for my skill set, and I am lucky to have a wealth of writing opportunities that line up with what I do well.

But I’m wise enough to know I can’t bank on this particular blogging career for the next decade. I was reminded of this last week when Say Media announced it was selling many of its online publications, including the popular XOJane. It’s a bit early to tell whether that means XOJane is going to launch a farewell issue, but it’s a good reminder that no publication lasts forever.

I can predict, however, that there will always be a market for good writing. Individual publications may change, and the method by which we access and read those publications might change, but the concept of collecting interesting stories under a single masthead isn’t going anywhere. Readers value specialty publications because they know they are going to get a specific, vetted perspective on events and issues important to them. I don’t think that model of sharing information will disappear.

Likewise, I don’t see copywriting going away any time soon. In fact, I suspect there might be more jobs for copywriters in the future. Companies need unique, original copy for websites, mobile sites, apps, social networks, and email campaigns. In the next decade, we will probably see companies optimizing copy for smartwatches, Google Glass, and whatever new technology becomes ubiquitous.

So I could absolutely see myself balancing copywriting, journalism, blogging, ghostwriting, and corporate writing for the next decade. To be successful, I will have to stay on top of technological trends—when someone says, “We need you to write a story for our Google Glass audience,” I can’t respond, “Well, I don’t know how Google Glass works.”

One of the reasons I think this plan might work is I am not emotionally tied to any particular type of writing. To persevere, freelancers have to be willing to ride the inevitable economic ups and downs. I love working as a blogger, for example, but I do not only identity as a blogger. There was a period of time in my freelance career when I earned more money writing website copy for companies, and if my career shifts back in that direction, I’m fine with it. Writing is writing, as far as I’m concerned.

This also means, over the next decade, I need to make sure I’m staying active in multiple lines of work. Last week, on my personal blog, I realized I hadn’t done a copywriting assignment since mid-October and was now making 100 percent of my income from blogging. Although that sounds like it could be a step forward in my career, I’m also aware it could just as easily be a career mistake to focus only on one field.

As a long-term career strategy, I need to start seeking out some new copywriting work. If you’re planning a braided career, you need to make sure you keep one finger on each strand. Otherwise, the whole braid falls apart.

Daniel Pink, in his book Free Agent Nation (one of the first books I read when I considered making the switch to freelancing), describes this type of flexibility as “My Size Fits Me,” vs. the “One Size Fits All” of traditional employment. You can, in theory, make a freelancing career fit a changing life—as long as you build a solid foundation of clients, clips, and reputation, and as long as you’re ready to evolve with your industry.

So where do I see myself in 10 years? Still freelancing, I hope, writing for people who value original content. I can’t see what’s on the monitor a decade from now, but I can see myself at the keyboard.

Nicole Dieker hopes her Ask a Freelancer column will still be running a decade from now and that you’ll read it on some kind of amazing technological device that will be invented in 2022. For now, please continue to send your Ask a Freelancer questions to

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