#103: How Freelance Writer Jennifer Gregory Took Her Income to $100,000 in 6 Simple Steps 

North Carolina–based freelance writer Jennifer Gregory has had quite a ride over the past 18 months.

She took her business to the six-figure level in 2015. But then shortly after, she lost some of her anchor clients. And things started to fall apart.

Jennifer didn’t sit around for very long. She quickly went back to the drawing board, drafted a turnaround plan and took massive action.

Within weeks she was booked solid. And 2016 is shaping up to be a banner year for her.

In this interview, Jennifer details her wild journey to the $100,000 income level. She reveals the 6 things she did that enabled her to get there. And she walks us through the plan she executed to replace her lost anchor clients.

Regardless of where you are in your freelance business, I think you’ll find some great ideas and inspiration in Jennifer’s story.

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 to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Tell us about yourself 

Jennifer Gregory lives in Raleigh, North Carolina. She got her start in technical writing. About eight years ago, she started a freelance writing business when her kids entered school.

Today, she specializes in content marketing writing. Her clients have included some big names, such as IBM, Adobe, MS, Samsung, State Farm and All State.

In 2015, your income surpassed six-figures. How did you do it? 

1. She took on fewer clients

Jennifer’s income went down in 2014, partly because she had a lot of small and medium size clients. She realized these clients took up a disproportionate amount of her time because she had to get up to speed with each of them.

With bigger, longer-term clients, she could spend less time marketing, getting up to speed and waiting for new projects to come in.

In 2015, she started having 30-minute phone calls with every potential client before agreeing to work with them. It helps her make sure clients are a good fit, so they’re more likely to stay clients long term.

2. She narrowed her niche

Previously, Jennifer had identified her niche as personal finance and technology. But in 2015, she went further and targeted data analytics.

Data analytics is a hot topic with few qualified writers, so she could command a higher fee.

3. She learned how to negotiate better

Jennifer says she’s a terrible negotiator—especially on the phone. In 2015, she shifted negotiations from phone to email.

Negotiating by email gives her time to consider her responses and makes her bolder.

4. She started treating her business as a business

When people asked her what she does for a living, she used to say, “I’m a writer.”

Now, she says, “I own my own freelance writing business.”

This mindset shift from writer to business owner gave her the determination to invest in her business. As a result, she revamped her website, attended Content Marketing World and started outsourcing more work.

5. She decided to work only with nice people

Working with jerks is stressful. And when we’re stressed, we don’t do our best work.

Jennifer started turning down clients she didn’t really like. As a result, she spends less time procrastinating. She enjoys her work more and her productivity is up.

6. She made time for “fulfilling” writing 

While Jennifer likes writing about data analytics, it’s not always fulfilling. Most of us got into writing because it’s part of who we are. When it’s also your job, it’s easy to forget to feed the writer within.

In 2015, Jennifer took the time to write some essays for a parenting magazine. It didn’t pay much, but it was a lot of fun. She also enjoys writing for her blog.

clicktotweet When we feel good, we’re more productive. So make time for writing that makes you feel good.

In early 2016, you had some big setbacks. Can you tell us about that? 

Jennifer ended 2015 with three big anchor clients in the bag. But when she returned to work in January, she discovered the projects had been delayed or substantially reduced.

So she made a list of marketing activities and challenged herself to implement them.

After 45 days of marketing, she ended up with about $64,000 in contracts for the year as well as a number of warm prospects.

Some of the marketing activities she undertook:

  • Sent out 53 letters of introduction to content marketing agencies
  • Sent out five letters of introduction to trade publications
  • Followed up on 15 letters of introduction from 2015
  • Created an active Twitter presence
  • Targeted agencies and content marketing managers on Twitter
  • Replied to 15 online job ads
  • Updated her LinkedIn profile with new niches
  • Updated her website with new clips
  • Sent an email to three writers in her niche to see if they had any leads
  • Attended a local marketing conference
  • Checked in with five previous clients
  • Checked in with a new client whose project was delayed.

Which activities were most successful?

Most of her success came from checking in with previous clients. She ended up getting $36,000 in business from one of them.

When following up with past clients, point out new skills or experience that could benefit them.

What did you learn from this experience?

There’s plenty of work out there. If you’re not finding it, you need to reassess what you’re doing.

This is a great time to be a writer. With the growth of content marketing, every business is a potential client.

Where can listeners learn more about you?

Jennifer’s website: The Content Marketing Writer

Jennifer’s blog: The Content Marketing Writer Blog




  • Lori

    Jennifer is *great* — the real deal–a gifted writer *and* an all-around lovely individual. So delighted for her success!

    • edgandia

      I know, right? Love what she’s done and love her enthusiasm. 🙂

    • You made my day! I really appreciate all of your tweeting.

  • Great interview! I appreciated that Jennifer said she only worked with “nice” people because I can relate to this. Life is too short to be surrounded by people who drain your energy. If you deplete yourself not only will your writing suffer, but so will your life.

    • edgandia

      Amen to that!

    • You are totally right – it’s not just your writing that suffers, but everything. I’m glad you can relate. I was nervous about stating this as one of my strategies and it’s nice to see others can related!

  • Dave

    I’m happy for Jennifer’s success. Her experience in losing a few big clients, or in having her clients delay projects, is similar to my own. I foolishly let one client become so important that their retainer accounted for more than 80% of my available time.

    It was a great ride for two years. But it was a very hard landing when it ended. You might say it was like an addiction to crack. It took my attention away from the marketing activities I should have been doing all along.

    Now I’m working to establish a rule that comes from David Ogilvy, the famous ad man: Never let any one client account for more than about 12% of your billings.

    • edgandia

      “Like an addiction to crack!” — love that because it’s so true! Never heard anyone put it that way before. Lol!

    • Thank you for the kind words! Yeah, someone told me recently that you can expect all projects to end. I try to keep about no more 20 percent for one client because that feels right to me and going down to 80 percent of my income isn’t a huge lose. I do better with a few anchor clients so that’s why I like 20 percent as my max.

  • Raj Chander

    Congratulations to Jennifer on her success, and I’m grateful she could share her story. 100% agree with everything here, but especially the “nice people” thing.

    I think it’s one of the less obvious benefits of the work we do, yet it’s so important. How many times have you heard a friend or relative complain about that annoying coworker in the office? When you’re self-employed, you choose who you work with. If someone’s personality doesn’t agree with yours, you aren’t obligated to interact with them like you would be at a day job. And as Ed points out, if you’re feeling like you must take on any work no matter who it’s from, you’re not doing enough marketing/prospecting for new and better clients. I deal with this struggle almost every day!

    @Dave – thanks for sharing the Ogilvy rule, and I can totally relate. He’s always a great source for inspiration and direction!

    • edgandia

      Thanks for checking it out and for your comments, Raj!

    • Thank you for the congratulations! I totally agree with you about being able to choose who you work with as one of the biggest advantages of freelancing. I realized that last year and that’s why I instituted the nice people rule.

  • Lisa Stockwell

    Great to hear a fellow writer is enjoying success! I need to listen to the entire interview (versus reading the highlights), but I’m curious to know whether the content marketing agencies are worth pitching. (Did anything come of the 53 letters?) I haven’t contacted any in a few years because initially I had no success and now I imagine they pay lower fees and don’t want to work through a middle person. Also, did she send paper letters or emails? I do think that keeping in touch with old clients is a must, but I’ve had good success with my warm emailing and plan to keep that as a top strategy.

    • Thank you for the kind words! Yes, I find content agencies to worth pitching. Most of my clients are actually agencies and I prefer agencies over direct businesses. I actually find that I can often make more with agencies and that I can get a lot more volume of work because an agency has multiple clients. Here is a post that I wrote on this topic. http://www.jennifergregorywriter.com/2016/01/14/do-you-make-more-money-working-for-direct-clients-or-content-marketing-agencies/

      I got one gig from those 53, but I typically get the gigs with agencies from following up and I haven’t followed up with these. It can take a while to get a gig with an agency and usually takes regular follow up. I have gotten gigs two years later. An agency must have a project that meets you expertise so if they don’t hire you then it doesn’t mean that they don’t like you just that they don’t have a specific project that is perfect. I really find that the trick is the follow up.

      Definitely emails. I’ve never sent paper letters.

  • Dave Vigna

    Congratulations on your success Jennifer and thank you and Ed for sharing your story with us. Very helpful and encouraging!!!

  • markarmstrong

    Especially liked Jennifer’s targeting potential clients via Twitter and negotiating by email to give her time to think and consider. Best of all: her example; namely, demonstrating the supreme importance of being a very proactive self-marketer. Great post, thanks for sharing.

    • I’m so glad that you liked the podcast. I continued to do the email negotiation throughout 2016 to great success. The two times I did phone negotiation were utter disasters – one I told the client that I wanted to the job so bad that I would take whatever they paid and the other I ended up arguing with the client for a lower rate. Seriously. That’s how bad I am at negotiating. Interestingly enough, both times the client gave me a much higher rate than I expected because they said I must really want the job. But I wouldn’t recommend this technique.

      And yes, you have to be a very proactive marketer to be successful. It has to be consistent and targeted throughout the year, no matter how busy or not busy you are.

      After I did this podcast, my year took another crazy turn. I had a serious health issue and ended up taking about 3 months pretty much totally off work and 2 other months only working part-time. But was able to ramp my business back up a second time on September when I went back to work, again relying mainly on former clients. And I ended the year with four consecutive $10K months. So while I only earned $70K in 2016, I consider that to be as Ed says the part-time equivalent of 6 figures based on how much I worked. And in many ways, even after 9 years of freelancing, I learned the most this year about freelancing, than any year previously.