Beating the Career Catch-22: How I Became a Web Copywriter

Chase Roberts posted this in
Inside Rocket Media
on November 18th, 2014

“To get a job, you need to have experience. To get experience, you need a job.”

For ages, this career catch-22 has left college students frustrated—almost to the point of despair.

But it’s not just college students either; it’s anyone who wants to get into a completely different field that requires X years of experience, and you have zero.

That’s the struggle I had.

I discovered I wanted to become a copywriter after 5 1/2 years of college (4 years for the communications degree and 1 1/2 years for the MBA).

While these degrees lended themselves to copywriting, I was still in a bad position: I was overeducated, inexperienced, and portfolio-less. In short—screwed.

So how did I finally become Rocket Media’s Web Copywriter?

Read on, dear digital traveler. I’ll show you the tools, resources and, most importantly, the mindset I used to get my job.

If you’re looking for a web writing job, every bit of this blog post will be useful to you.

If you’re just looking to start a new career in anything else, you’ll still find the lessons I learned useful. Especially this first one:

Asking the “correct questions”

So here’s what happened: When I graduated college in 2010, I was just a simple law firm courier with 0 copywriting experience.

As I continuously applied for copywriting jobs online, I kept asking myself these questions:

  • “Why do all companies ask for junior copywriters with 2+ years of experience? Do they not understand the meaning of ‘junior’?”
  • “When will I meet the connection I need to get my foot in the door?”
  • “Why won’t anyone give me a chance?”
  • “When will I get the money I need to get the proper education/certification I need to start in my field?”
  • “Why didn’t I figure out that I wanted to do this sooner?”

According to John G Miller’s book QBQ! The Question Behind the Question, these are called “incorrect questions.” They’re “incorrect” because they turn you into a powerless victim—one who’s not actually looking for a solution or personal accountability.

Now, I had not read QBQ at the time, but looking back I can see how I eventually applied

Miller’s advice: Only ask yourself “correct questions”:

  • What can I do now?
  • How can I do it?

Questions that start with “what” or “how” and have “I” in them force your brain to start looking for solutions instead of whining and waiting for a solution to magically appear.

Here are a few practical ways I applied correct questions:

  • “OK, I have zero copywriting experience. So what can I do now to get some? Where can I start?”
  • “It seems people who want web copywriters require that they have some SEO experience. How can I learn SEO and apply it to copywriting?”

These questions made me personally accountable and forced me to think of actionable steps (which I detail in the rest of this article).

Watch your mindset when trying to pry into a new field. If all you do is ask incorrect questions, you’ll whine yourself to inaction.

Start asking “what” and “how” and make yourself accountable. That’s your starting point.

Narrowing my focus and picking a specialty

Applying for jobs is almost a full-time job. (Have you seen how long online applications are? They’re like digital marathons. Anyway…) So I knew I needed to use my time wisely.

The best way to do that? Narrow my focus on what jobs I should apply for.

I discovered that companies are looking for different types of copywriters. Roughly, they fall into 2 broad categories:

  • Traditional (writing for TV, radio, print, etc.)
  • Digital/Web (writing general web page content, landing pages, PPC ads, banner ads, blog posts, ebooks, etc.)

Because there’s such a high demand for digital copy, that’s where I put my focus for learning and job hunting.

Hooray for time efficiency!

Working towards the skills to pays the bills

OK, so now I could focus on learning a specialty—web copywriting. Now what?

I started a LinkedIn profile and used the job search function to find the job titles that companies were using to describe my specialty.

Here’s a sample:

  • Digital copywriter
  • Web content writer
  • Web copywriter
  • Junior copywriter (could be traditional focused, but I searched for this anyway)
  • Web communications specialist (I just made this up, but it’s probably out there)
  • And the list goes on.

Then I looked at the “skills required” section for each position and made a mental list of the most frequently mentioned required skills.

Looking back now I know that companies, especially digital ones, are demanding that people have a T-shaped skill set, someone who:

  • Has deep knowledge and experience in one or two fields and
  • Has a general breadth of knowledge in related field

For example, the deep knowledge I needed was how to write compelling copy for every stage of the online marketing funnel. The general knowledge I needed in related fields was an intro knowledge of HTML and on-page SEO.

Now I had a specialty and a set of primary and secondary skills I needed to learn. So next I started…

Reading ALL the things!

Stephen King wrote in On Writing, “If you want to be a writer, you must do two things above all other: read a lot, and write a lot. There’s no way around these two things that I’m aware of, no shortcut.”

I don’t think it’s a coincidence that he lists reading first and writing second.

So what should you read to become a web writer? I would first read “how-to” material. Here’s a long list of what I had, and still do, read:

Free online resources:

Good books:

Once I understood the basics of web copywriting, I started reading web content mindfully, trying to notice web content I found persuasive and why.

Try this exercise:

  1. When you find persuasive web content (a headline, email subject line or sales page), copy it into a Word or Google Doc.
  2. Then, later, examine why you found it so persuasive. Make notes of the writing techniques they used. After learning the basics, this should be easy.

Your big takeaway: Learn the basics, then emulate someone’s style that you admire.

Getting my foot in the door by freelancing

Now that I had some copywriting knowledge in my head, I needed to apply it.

A web design friend of mine suggested I try out Odesk, a free freelancing website that:

  • Connects employers to freelancers
  • Handles the payment between the employer and freelancer
  • Gives you software for time tracking (if you bill hourly)
  • Allows you to post your work on your profile, giving you an online portfolio

But how could I get a job on Odesk if I didn’t have any copywriting experience? Well, Odesk is full of small, annoying jobs that digital marketers with full-time jobs would rather outsource.

For example, I started with one easy, low-paying job that was easy to get: Writing descriptive meta titles and meta descriptions, making sure to include keywords the client provided. That’s all.

That seems mundane (it was), but it got me experience and a 5-star rating—and that’s what was important.

As time went on, I slowly built up my T-shaped skill set doing a variety of jobs, including:

  • Compiling Google Analytics reports, which introduced me to interpreting web metrics in context
  • Doing keyword research and brainstorming content ideas from those keywords
  • Writing blog posts, press releases and landing pages

Besides building a portfolio, freelancing came with some hidden benefits. I learned how to:

  • Interact with clients and deal with their feedback
  • Juggle multiple projects
  • Sell myself
  • Manage my time to complete assignments on a deadline

Breaking into the field

Finally, after 10 months of job hunting and freelancing, Rocket Media’s HR Manager called. She liked that I freelanced because it showed that I had the motivation to be a self starter.

Friends, I cannot tell you the number of tears I cried after that phone call. About 3 writing tests and 5 interviews later, I finally became a web copywriter.

All that research, all that reading, all that freelancing—it paid off.

Last words of encouragement

Stop. Summary time:

  • Have the right mindset—Stop whining and start asking the right questions.
  • Do your research—Find a specialty, learn the skills you need—then learn them.
  • Practice—Find even the smallest way to get started. Then do it.

Finally—and most importantly—don’t give up. You might screw up along the way, and that’s OK. Growing pains are just that—painful.

Got questions, complaints, or concerns? Comment below. Or hit me up at or I love nerding out about this topic.

Chase Roberts

Web Copywriter

Yes, ladies, that southern drawl is authentic. Chase hails from a small town in Alabama. He loves sweet tea and all the bacon. But, in between consumption of these favorite treats, he plans and writes the copy for Rocket Media’s clients.