Freelancer Success Stories: Jenn Greenleaf

Name: Jenn Greenleaf

Location: Boothbay, ME


Bio: Jenn Greenleaf is a freelance writer hailing from the great state of Maine. She specializes in SEO, content marketing, and ghostwriting.

How long have you been doing freelance work?

More than 5 years.

Tell us about your freelance business, in 100 words or less.

I’ve been in the freelance writing and publishing industry since 1999 with ghostwriting and by-lined pieces as part of my background. I’ve covered a wide variety of topics including art, construction, education, finance, human resources, legal, lifestyle, marketing, medical, real estate, and software. My background also includes experience with article writing, blogging, content writing, ebook writing, SEO, web copy, and white papers.

What do you consider to be your specialty. How does it help you in your business?

I prefer not to be a “specialist” because I love writing about a variety of topics. While many writers like narrowing their writing down to a particular vertical or niche, I like covering topics that cater to a broader audience.

What made you become a freelancer?

I’ve been writing for as long as I can remember. So, becoming a freelance writer felt like a natural career move. Previously, I was working in retail management for music stores, a home decorating store, and a bookstore. Each of those opportunities allowed me to incorporate writing to a small degree, but it wasn’t fulfilling.

What do you love most about freelance work, and why?

I mentioned that I’ve been writing for as long as I can remember–the same has been my reality regarding reading and learning. I used to spend hours in libraries during summer break, as well as surrounding myself with books as often as I could. The reading and learning process carries onward into my career today. I love that part. Researching is a lot of fun for me.

What do you hate about it?

Search engine optimization . . . I can do it and I do it well. However, when a client asks me to use long-tail keywords a dozen times (give or take) and they aren’t grammatically correct in a 500 word blog post, that becomes a challenge.

Tell us about your first paid job. How did you land your first client?

Yes, it was for writing about Graphic Artists. My first piece was about M.C. Escher and it paid $25 for 500 words. They hired me to write a column after that, and then they hired me to continue writing how to complete mixed media art projects. I landed that first assignment by searching google for freelance writing jobs and applying.

Do you think aspiring freelancers should take unpaid work to gain experience? Why or why not?

You’ll find that this is a topic debated throughout the writing industry. I wrote about it here – What Does it Mean When People Say Freelancers Will Write for Free? – because I felt like the topic needed addressing.

Do you feel you’re charging what you’re worth?

For a long time, I wasn’t charging enough. It wasn’t until I started talking to other freelance writers in Facebook and LinkedIn groups that I got a feel for how to adjust rates. I wrote about it in an article titled The Great Rate Debate, because I’d received this question so often.

Describe your process for finding new clients? Where do you look?

I look in MANY places for freelance work and I do it for about one hour at the conclusion of each workday. If I have a stable of consistent work, then I won’t work through this process. But when the workload lightens, here’s what I do:

  1. Check out Twitter hashtags: #writingjobs, #freelancewritingjobs, #freelancewritingopportunities
  2. Search LinkedIn jobs: I use the search function to find remote freelance writing jobs, as well as those in my area.
  3. I belong to several Facebook and LinkedIn groups that post job leads daily.
  4. I look on websites including,, MediaBistro,, and
  5. I search google for leads, jobs, and calls for pitches that may not be showing up in social media or on the sites I’m checking.

Have you ever had to ‘fire’ a client? If so, why and how did you do it?

I haven’t had to deal with this situation.

Name 3 tools (apps, equipment) that you can’t live without. What makes them so great?

Grammarly, OneDrive, Buffer

What is your #1 productivity hack?

I start the day early (a lot of people think I’m crazy, but it works for me) with a to-do list, and map my day out in a paper daily planner, as well as a large desk calendar I keep hanging on the wall behind my monitor.

Do you outsource tasks? Why or why not? If so, which ones?

No, I secure enough work to keep myself busy and nothing more.

In your opinion, what is the most important skill required for freelance work, and why?

I think they need more than one. Freelance writers need good communication, time management, and grammar skills.

Do you consider yourself a strong time manager? How do you stay organized?

Yes, time management is critical for running a small business. I stay organized by writing my deadlines into my daily planner early as a “soft” deadline. Then, the actual date they’re due is the “hard” deadline.

Do you also work a 9-5? If so, how do you balance it with your freelance business?

No, I’m a full-time freelance writer.

Where do you do most of your work?

I have a small 12×12 out-building in my backyard.

Do you use a co-working space?


Name an entrepreneur/freelancer/influencer who inspires you. What is it about their story/message that resonates?

I have a couple – Yuwanda Black from Inkwell Editorial, and Carol Tice from Make a Living Writing.

Name 1 thing you would do differently, if you were starting over today?

I would have placed more value on my skills and abilities.

What is your #1 tip for aspiring freelancers?

Don’t doubt yourself!

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