#006: How I Took My Writing Biz to the Six-Figure Level (Pt. 1 of 2)

Today, I’m taking a departure from the types of shows I’ve been doing since I launched this podcast. Instead of doing an interview, I’m going to share my story with you.

The story of how I stumbled into freelance writing and how I’ve turned it into a six-figure business.

I’ve shared parts of my journey in articles and video trainings. But I’ve never shared the whole thing in one place.

I’m going to do this over two episodes. I’ll share both the successes AND the struggles. I’ll show you why I truly believe that any writer with solid skills can do this. And I hope to satisfy much of the curiosity out there about what I do day to day, how I spend my time and where my income comes from.

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes or on Stitcher to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Born Out of Necessity

The decision to go out on my own came in January of 2003. My initial thought was to either start or buy a business sometime in the next five years.

We had just had first child, and I felt out of control of my own career and future. I wanted to take charge, make my own decisions. I didn’t know what exactly I would do, but I KNEW I’d find the answer.

Out of nowhere, I received “can you write a letter like this?” promo from American Writers and Artists, Inc. (AWAI), and I fell in love with this idea of writing for a living. Probably because I was already “selling on paper” to feed my family!

At the time, I was selling software for a small company with a very limited marketing budget. I had to find my own sales leads, which was nothing new. I faced the same challenge with my last two employers.

In an effort to find solutions to this challenge, I had learned how to write effective lead-generating letters. I read books on the subject by Dan Kennedy. I also studied and practiced the techniques in books such as Selling to VITO and The Power to Get In.

I used all this information to write and mail lead-generating letters and fax broadcasting campaigns (back when it was legal to do so). This stuff worked! It generated appointments that eventually turned into sales.

Accidental Salesperson

I was doing well in my sales career. But this was NOT a path I had planned. I never wanted to end up in sales. I was a finance major in college and wanted to work in that field.

Unfortunately, when I graduated from college the U.S. was still trying to come out of the recession of the early 1990s. All I could find were sales jobs. And I ended up selling for a company that distributed underground pipe, valves, fittings and fire hydrants.

As a junior salesperson, I was given very challenging virgin territories. These situations forced me to innovate because I HAD to meet sales targets … or I would be out of a job. In the process of finding, implementing and experimenting with different solutions, I became better at my craft.

Key lesson: every difficult situation has the seed of something great in it!

So when the idea of launching a freelance writing business presented itself, it seemed perfect. It had best of both worlds:

  • My own business
  • No employees
  • No inventory or suppliers
  • Little overhead

It also offered something that was very important to me: the ability to avoid weekly travel. Constant travel was an inevitable part of success as a sales professional in my industry.

Yes, I’m Going to Do This!

I spent most of 2003 studying the AWAI Accelerated Program for Six-Figure Copywriting. The program taught direct-response fundamentals for consumer products and services. So even though I ended up focusing on business writing and B2B copywriting, learning the fundamentals of persuasive writing was extremely helpful.

Oct/Nov 2003: I started prospecting for copywriting clients using sales letters. This generated one client that awarded me about $800 in project work over the next few months. I also wrote copy on spec for Nightingale Conant, which went nowhere.

Key lesson: Knowing how to write great copy is not enough; you HAVE to become very good at self-promotion! I was great at selling my product (at work), but not at selling myself and my copywriting services.

So I hired a coach: Chris Marlow. Worked with Chris for 3+ months. This was just what I needed. Chris helped me position my writing business and to leverage my strengths and talents.

Key lesson: Just because you have a solo business and the cost of entry is low doesn’t mean you should not invest in yourself and your business! That’s a mistake too many new freelancer make. Writing skills alone aren’t going to guarantee success. You need to learn and master the “business side” of launching, running and growing a writing business.

Once I got serious and regained my focus, it took me about six months to land my first real client. Once the first client came, the others came back to back. It seems like getting the first client is often the hardest milestone to achieve. Once you can get through that, it’s easier to gain momentum.

Key lesson: The emotions, beliefs, energy and confidence you bring into your prospecting efforts WILL determine how quickly you start landing clients. I would have probably landed my first client sooner, but I was starting to doubt whether there were actually freelance writing clients out there! It just didn’t seem real to me. So, guess what? That’s what I attracted—no clients!

So … go for quick wins! You need quick wins to feed your confidence and help you see that this is real. These wins don’t have to be monumental; they just have to be good enough to show you that you can do this. Even the smallest win can give you the self-confidence and motivation you need to push further.

Transitioning from Day Job to Freelancer

By late 2004 my plan was to work my freelance business part time, on the side, until I was ready to make the leap.

What did “ready” mean to me?

  • A year’s worth of living expenses socked away (not necessary for everyone, but I was my family’s sole breadwinner and was very conservative)
  • Steady client work
  • Ability to secure affordable health insurance for me and my family

How did I land work? It was a combination of several strategies:

  • Direct mail campaigns. I reworked my direct mail strategy and finally started seeing results. For a more detailed explanation of my direct mail effort, see pages 83 – 91 in my book, The Wealthy Freelancer .
  • Warm email prospecting: a very strategic and effective way to contact prospects with short, relevant and personalized email messages.
  • Networking at local, prospect-rich events and organizations
  • Tapping my network (one of my best and longest-running clients came from a friend of a friend. Lesson: take your friends out to lunch/coffee and explain what you’re doing. They might be able to refer to you potential prospects.
  • Online networking (very targeted forums such as SoftwareCEO.com)
  • SEO: after about a year, I stared getting ~ 1 inquiry a month from prospects who were searching for a copywriters via Google searches.

How Did I Juggle Both?

Juggling a very demanding sales job AND a writing business was not easy. My day job was performance-based. If I didn’t make my ever-rising sales numbers, I would be out of a job.

To make it worse, I had to be careful with the types of prospects I reached out to. I couldn’t use a big part of my professional network because I didn’t want to risk my employer finding out about my side gig.

I decided to focus on doing an amazing job at work; my income was variable, so the better I did, the more I’d earn, which meant that I would reach my savings goal faster.

I’d handle inquiries if/when they came in, but I tried automating as much of it as possible (standard response templates I could copy/paste).

How did I find the time? I worked my biz nights (8pm – 10pm+, some all-nighters) + weekends (Sat mornings from 6am – 12pm or 1pm). Tried to keep Sundays free.

This was NOT easy! But once I started earning $1k, $2k+ per month, I could see the light at the end of the tunnel.

Key lesson: Focus on baby steps. You can always take that next step, then the next one after that. Focus on today only. What can you do today? Don’t worry about tomorrow or next week or next month. Don’t worry so much about your target date for quitting your day job. It’s OK to set it as a goal, but stay focused on the next baby step.

Your First Set of Clients Won’t Be Dream Clients

At first, not every client was great, not every project was amazing. I wrote package copy for a potato chip company — a job that paid very little. I also remember writing dozens of bios for territory managers in a large telecom services company. They were very demanding and difficult to work with. And here again, the pay was not great.

My first few tech industry clients were WAY too technical for me. I had to do a ton of research just so I could understand what they did.

Key lesson: Balance meeting your savings and experience goals with trying to go after ideal clients only. Instead of telling yourself that this project or client is a waste of time or not worth doing because of the low pay, look at each opportunity as a stepping stone. Use each of to take you to the next step (e.g., each project is a new sample, a new opportunity to learn something, learn how to deal with a special situation, learn how to tackle a specific aspect of running or managing or producing something).

Momentum … Finally!

By the fall of 2005, I was consistently earning $2k – $3k a month part time. I was sending all after-tax dollars to savings.

I was extremely busy, working at least 4 nights/week + all Saturdays.

By early 2006, things were now out of control. I often worked 7 days a week and pulled an all-nighter every 2 or 3 weeks in order to meet client deadlines. Fortunately, I was getting close to my savings goal.

Then, something wonderful happened: my employer got acquired by a larger company. They offered me to stay in my current position, which I accepted … but only because I wanted to wait to cash in my stock options.

I began the health insurance application and underwriting process (there was no point in starting earlier). All went through OK, which was a great relief, because securing affordable health insurance was my last hurdle. I had the savings. I had the steady stream of clients and projects, I was making enough on a part-time basis that I knew that if I could just take my business full time, I would be fine.

But the weekend before I was going to turn in my notice … I got cold feet! I asked my wife if she thought I was making the right decision. She urged me to revisit my reasons for going solo. And that gave me the clarity I needed to move forward.

Key lesson: When in doubt, always go back to your core reasons for going out on your own. What’s your Big Why? Always have a solid “Why” that’s not just about the money. Because when you do, you’ll push through the tough times, and you’ll have a real, fundamental reason to get up every day.

So Long, Corporate America!

Mid-may of that year, I gave my 2 weeks’ notice. And on June 1st, I was fully self-employed!

Ironically, I was slammed! So even though I took a few minutes to savor the victory, I found that the real joy came earlier.

Key lesson: The real reason for setting a goal and going after something big is NOT the actual goal. It’s NOT the “thing.” The real value of going after something big is the person you become in pursuit of that goal!

This process had changed me. It had made me a better, more resilient person. I had grown personally and professionally in ways I wouldn’t have grown had I not pursued this big, hairy audacious goal.

That’s a priceless benefit!

I’ll continue this story next week. I’ll tell you about the year when I lost focus and my business nearly went under — and the unexpected victory that saved me.

So stay tuned for that.

Let’s Get This Message Out There

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Thanks again for your support!

Till next time,