My Path to Freelance Success (And So Can You)

January 10, 2011 by Dean Rieck
Filed under: Freelancing 

freelance successOkay, I stole that headline idea from comedian Stephen Colbert. But it kinda makes sense if you read this whole post.

You see, I get a lot of emails from aspiring copywriters who want to know how to break into freelancing and find success.

And I have to admit, that’s a difficult question to answer. There is no one right path.

I’m not aware of any college curriculum that teaches freelance business practices. And I wouldn’t trust a professor to provide good advice on a topic like freelancing anyway.

Every freelancer I know has a different story to tell. Each has different advice.

I might suggest that you seek a job in marketing or advertising, get a few years of experience, freelance on the side for a while, then launch your own business. That’s because most successful freelance copywriters have some area of expertise that makes them more valuable than an ordinary writer.

But instead of pontificating about what I think you should do, why don’t I just tell you about how I actually came to freelancing? I had nothing like a plan, yet in a strange way, it was the perfect path for me to get to where I am today.

I graduated with a double degree in English and Science. My intention was to teach in a public school. However, I discovered that I had more interest in the subject matter than in teaching.

So I applied for a number of jobs, finally landing a gig as a salesman at a top-40 radio station in Wheeling, WV, my hometown. I hated the selling part, but loved creating the radio commercials for my clients. This led to a 5-year stint at a TV station where I wrote and produced commercials and news promos.

I had a knack for advertising, but the pay at the station sucked. I never made more than around $5 an hour, barely above minimum wage at the time. Eventually, I wised up and decided to move on.

My college degree had gathered some dust, but my teaching certificate was still valid, so I made the fateful decision to give teaching a go. I moved to Las Vegas, taught 7th grade English for 3 weeks and 3 days, then quit. Why I quit is a long story, but let’s just say that I had a “life is too short” moment and walked out. I knew there must be something better.

I had been thinking about getting into advertising, but my experience consisted of small-market TV and radio spots, which didn’t impress big-city ad executives. So after many depressing interviews over the course of 3 months, I loaded my car and drove cross country back to my apartment in WV, where my wife had become highly displeased with the (lack of) direction of my career.

This was a difficult time. We were poor. My wife had packed everything to move to Las Vegas. And now here I was calling it off and jobless.

The day I arrived home, I picked up the phone and called a client from the TV station. He ran a small ad agency and printing firm. I asked if I could do any work for him. He said no.

The next day, he called me back. “Well, maybe I could use your help with a few things.” I met with him and negotiated some freelance work for a whopping $10 an hour. I thought I was in heaven.

This arrangement lasted for nearly a year and I made more money than ever before in my life. I fell in love with the idea of freelancing and being my own boss. However, this was in the early 90s, before the World Wide Web, email, and all the other wonders we enjoy today. So I had to move to a larger city to find additional opportunities.

I applied for some full-time freelance work in Columbus, OH, as a writer for a “book packager,” a firm that develops published products for major textbook companies.

In a span of less than two years, I variously researched, wrote, and edited 22 science and social studies textbooks. It paid $13.74 per hour, but I found the work hellish. I would often work 48 hours without sleep to meet deadlines.

In my spare time, I started to take on freelance work as a direct response specialist. I had no qualifications, just an interest in direct mail and related marketing tactics. I learned to “fake it to make it.”

Most of the work I got was pretty small stuff, such as writing sales letters, newspaper ads, and newsletters.  But just as I reached the point of burnout with writing books, I had a meeting with a big local ad agency which had just started doing direct marketing and needed a copywriter.

While summoning the courage to ask for the astonishing sum of $3,000 to write two direct mail packages, an agency executive took me aside and apologetically ask if I could do the job for a measly $9,000.

Time stood still.

Giving an Oscar-winning performance, I nodded slowly and in a firm voice managed to say, “Well, if you think that’s what the job is worth, I’ll trust your judgment. Somehow, I’ll make it work.”

On the inside, I was squealing, “Yippee! Who hoo! I’ve hit the jackpot!”

That project gave me the financial and emotional boost I needed to turn things around. After all, $9,000 was about as much as I made in a full year at my former TV job.

From that point forward, I freelanced full time. I learned how to land clients, manage my time, and become an expert in several disciplines, including direct mail, lead generation, and business-to-business. Soon I was making six-figures a year with my income growing year after year.

Today, I find myself with more business than I can handle, well-known in my field, making hundreds of thousands a year, and doing work I can be proud of.

So that’s my story. I made lots of mistakes. I had the wrong education and no career path. But it all worked out. All my twists and turns have given me a unique set of skills and experiences that no step-by-step plan could possibly duplicate.

What’s your story? How did you get into freelance copywriting?

Related posts:

  1. $#!* Happens! A dirty story about freelancing success

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Smart Comments

8 Comments on My Path to Freelance Success (And So Can You)

  1. Pervara Kapadia on Jan 10th, 2011 2:34 pm
  2. Good all the best Dean

  3. Joseph on Jan 10th, 2011 3:44 pm
  4. Dean, this is awesome. Thanks for the story.

  5. Andrew B. on Jan 10th, 2011 4:15 pm
  6. Hi Dean,

    Great story! I knew a little bit of your background (I’ve been reading your stuff since the mid 90s!) but not the whole picture.

    Here’s a question about freelancing: Do you think it’s better to start with small no-name jobs that hopefully get progressively bigger and better? Or is getting a big household name (from the beginning) worth the considerable investment of time? That is, am I more likely to find more work by showcasing dozens of local mom-and-pop projects or one big Microsoft or Pfizer?

  7. Dean Rieck on Jan 10th, 2011 4:47 pm
  8. Andrew,
    First, thanks for making me feel old. Sigh. Second, great question. I think you should get the best jobs you can get. Generally, you have to take what you can get anyway when you’re starting out. If it comes to showing samples, you’ll want to show samples that most closely match the business you’re trying to land, though as a rule, the more impressive the business, the more impressive the sample. “Name Brand” business samples are worth a thousand times their weight in gold.

    What people will want to know is … do you understand my business and have you done this kind of work before (direct mail, online, radio, etc.)?

  9. Debra Torres on Jan 11th, 2011 2:15 pm
  10. Great to hear your story. I’m at a crossroads in my freelance career I think. I’ve done the mom and pop stuff and now I’m seeking higher paying clients. I’ve just finished my website and this week I’m updating my business card. My site is ranking well for my state (PA). Just waiting for the next step, I guess. Any words of wisdom or better yet, leads for an affordable freelance copywriter (specializing in web writing and SEO)?

  11. Anita Cooper on Jan 12th, 2011 8:47 am
  12. Loved the story, Dean. Thanks for sharing with us!

  13. Chrystal Johnson on Jan 12th, 2011 5:59 pm
  14. Thanks for sharing your story! I came into freelancing in a roundabout way. I worked in corporate marketing communications for about a decade when my oldest daughter was born. Coincidentally, I got laid off from my job at a Fortune 20 healthcare corporation right around that same time–along with several hundred other people. It was kind of my push to do it on my own. And I had lots of contacts who needed my services at that point. They were actually beating on my door before I decided to go it alone. So, I have never really had to market myself. I’ve worked purely off of referrals (mostly in the healthcare technology realm, but in other areas as well). I mostly do freelance writing, but also a little marketing consulting here and there. I’ve recently been thinking about marketing myself more in case my “big” clients fall off at some point… Anyhow, it’s very true that we all come into it from different angles and there isn’t one clear path on how to do it right.

  15. Dean Rieck on Jan 12th, 2011 6:58 pm
  16. Debra,
    Think about some additional specialties. Everyone now says they specialize in web and SEO.