Are You a Writer, Freelancer, or Entrepreneur?

One of the most challenging things about being a freelance writer is that there isn’t really a well-defined career path laid out for you.

In a regular career, there are specific rungs on your ladder that are pretty well identified. For example, when I worked in IT, I started out answering phones for a help desk. After a few months and after earning some certifications, I moved up to desktop support. From there, it was a step up to being a systems administrator. I ended my career as a network engineer, just a stone’s throw away from going into IT management.

As a freelancer, though, my career has been more of a zig-zag pattern. I started out doing web content articles, which I still do today. Along the way, I’ve added certain types of skills and tasks, such as copywriting, website content, ebooks, sales letters, and even the occasional print article. In many ways, I’m still doing the same things today that I was when I started out.

Still, if I look across the entire path of my writing career, I can see specific points where it was time to make a decision about how that career would go. You might recognize some of these points from your own career.

The Web Writer

Like many folks, I started out writing articles. When I first began, I was working, primarily, for a single client. That client had plenty of work to keep me busy, as I was still working on my master’s degree at the time. I was happy as a writer, doing one type of content and working for one client. There came a time, though, when I needed more. I finished my degree, and working for a single client wasn’t good enough. So, I had to take a step up on the career ladder.

The Freelancer

I realized, before too long, that there was plenty of demand for what I was doing. I started to throw out feelers here and there. I began bidding on work at freelance websites. I piddled around in some writer forums, and eventually found myself with a small but steady list of clients. “This is it. This is what a writing career is all about,” I thought to myself. Now, I take pride in the work that I do. I’m a good writer. I’m not the best out there, but I have a decent grasp of the rules of the language and I have a good ear for what clients like. I’ve worked hard to hone certain skills that clients want out of their writers. Believe it or not, doing a good job eventually became a problem. I found that there was not only plenty of work for me to do, but there was actually more work to do that what I could finish on my own. I found myself, yet again, making changes.

The Entrepreneur

I can’t say exactly when it happened. Maybe it was when I first outsourced some of my work. Maybe it was when I hired an administrative assistant. Heck, maybe it was when I started my blog. But at some point, I found that I wasn’t just writing for money anymore. I wasn’t just freelancing; I was running a business. Now, I don’t know if entrepreneur is the last stage of this career path. I suppose there are, if I think about it, some other peaks I can hit. Editor, publisher, maybe even web writing mogul. But entrepreneur is where I’m at right now, and it’s where I’m most comfortable. So, what about you? Where is your writing career taking you?


Photo by Paul Worthington


  1. says

    I can definitely say I am all three. I have overused the word “freelance” in the past and now use business owner and writer much more often. However, with your definitions I am a freelancer more than the others.

  2. says

    I never was a single client gal. So I would place myself in the freelancer and entrepreneur categories. And more and more leaning to the entrepreneurial side…as I am doing more of my writing for myself…with ebooks, blogs, etc.

  3. says

    @ Nicole – To be sure, there’s some overlap between the categories. I still write, of course; I don’t work for a single client, so I’m definitely a freelancer; but overall, my path has taken me into the entrepreneur realm, where I’m trying to look much more at the big picture.

    @ Tina – I think that’s a big part of being an entrepreneur – taking your own ideas, or your own writing, and running with it. Good stuff!

  4. says

    One of the things I love best about freelancing is the ability to zig-zag. After spending most of my life slowly climbing academic rungs, then going into a career in tech support (big mistake – really not “me”), I’m loving the freedom.

    Like you, Bob, I started off with web writing (first for one blog, then a couple, then a couple more), and initially focused on web content. I’ve branched out into magazine pieces, ebook editing and writing, proofreading and what you might call “entrepreneurial” projects if you were feeling kind: basically a couple of blogs!

    Like Tina, I want to do more writing for myself rather than just for clients, and I’m trying to schedule time for that — it’s sometimes tricky to give it the same priority as paid work, though.

  5. says

    I know what you mean. I have to schedule time for my own websites, books and columns. I make sure I spend some time every day on my own work. Otherwise, I would end up completing work for my clients all the time and not getting any of my own work done. There needs to be some balance there, and that takes self-discipline.

  6. says

    Ok, Let’s start again….

    1st I’m a freelancer then i turn up as a successful entrepreneur and then finally a dumb writer (I’m like a Alice in wonderland in that specific field).

    Now I’m improving my writing stage. usually trying to visit some selective blogs for good tips.

  7. says

    Oh dear. Is it okay to be all of the above? I often refer to myself as a “Freelance Writer and Entrepreneur”. I try to spend only half my time freelancing for clients, and the other half pursuing my own business efforts. But I try to always make time for the business… I don’t want to work for clients forever. =)

  8. says

    Hey Bob, interesting topic! I’ve been a freelance writer for about 15 months…and I’m finally entering the “entrepreneur” role – as I finally realized that I have too much work on my plate that I need to outsource about half of it to others so I can specialize in the projects I enjoy the most while still ensuring my clients continue to get the quality of work they deserve.

    So my question…what are the next few levels?

  9. says

    @ Ali – I’ve often said that freelance writing is the perfect career for someone with ADHD – the zig-zagging comes with the territory.

    @ Nicole – It is a balancing act, for sure. My blog has led to some of my biggest clients in recent days, and more than a few business opportunities. But If I hadn’t spent the time to start it up and to post, I’d have missed out.

    @ Infected – Good luck as you continue on your journey.

    @ Dkumar – Heh. Well, that’s one way to do it. Here’s to hoping you turn it around!

    @ Monica – Absolutely. I still write, I still have client work, and I’m building a business that’s ever-expanding. But for me, entrepreneur is where my vision is centered.

    @ Chad – I’m not sure what’s next. Perhaps millionaire beach bum, ala Tim Ferris?

    @ Dainis – Glad you enjoyed it.

  10. serj says

    when you do jobs for big clients, I think that writing gives you some edge, because the “sapiens” in the industry or not are looking for people that know what to do, know how to implement a personality to a site, brand it, not copy paste some design and “voila, I AM A WEB DESIGNER” . I think the moust of you got hired by clients that saw your work or just loved a article, I know I did:D.As for the entrepeneur and freelancer part it depends on your goals.

    My advice is … BRAND YOURSELF, you dont have to wear nike or adidas, think difrent and you’ll be a brand. This is a advice for everydoby, it doesnt matter how many years you have under the “belt” .

  11. says

    In my opinion you CAN be all three. If you want to be an entrepreneur it’s very beneficial to be a good writer. If you want to effectively promote your businesses it’ll get too expensive if you have to pay someone to do all your writing.

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