How to Become a Freelance Writer, Part One: Why and When Experience Matters

How to Become a Freelance Writer Part 1Lately, this is the most common question I get from readers of my blog: How do I become a freelance writer? For those of you I never responded to, I apologize. I’ve been planning on addressing it on my actual blog, so, here is your answer. In a three-part mini series I’m going to, as best I can with the experience I have, address the big question of becoming a freelance writer.

For me, it all started with a coffee meeting.

A little over five years ago, I asked a friend to coffee who was a seasoned freelancer in the Nashville area. I set up the meeting because I wanted to know how to do what he did, and I had no idea how to get started. Maybe you don’t either. I’m glad you’re here. What occurred before, during and after that coffee meeting will be the framework for this mini series. I hope you find it helpful and feel free to ask questions in the comments section. I love that.

Let’s begin…

Before Coffee

What if I told you my first writing job was writing obituaries?

It’s true. My senior year of college I was a proofreader for our alumni magazine. One of my responsibilities was managing the “obits” sections. It was as glamorous and uplifting as you’d imagine. But it was also something invaluable. It was experience with the craft.

Before anyone becomes a freelance writer full time, they write. They write a lot and a lot of different things. Before that coffee meeting five years ago, I had logged hours in writing obits, I had spent a few semesters as a staff writer for my college paper, I had received a degree in English (read: I knew how to do research aside from Wikipedia), and I had been blogging for two years.

Why am I giving you my credentials? To explain that rarely does anyone simply jump into freelance writing. They’ve logged hours already. Maybe not in magazines and major websites, but in school. On their blogs. Writing a research paper. Writing a few obituaries.

The world of freelance opens up after the building up of experience here and there until you have a few things you can show a writer friend or a few links you can send to an editor. Freelance often happens after you’ve done quite a bit of work already.

For some of you, this is encouraging. You have years of writing experience and the tangible evidence to show for it. You’re ready to jump in.

For some of you, maybe this sounds discouraging. You are just starting. You have barely written a thing. To you I say, take heart. If writing is an interest but not something you’ve really done yet, start small. Start in a journal, a letter to a friend, an email. Start playing with words in the little ways and read my next post (about finding your writing niche) to see if this is something you want to pursue further. It might remain a personal interest. It might explode into a career. You’ll never know unless you start putting words down somewhere, anywhere, as often as possible.

For those of you with the experience but without the pay, think about all of the writing you’ve ever done. From research papers to a blog you’ve been piddling with to a press release you wrote for your company recently to a presentation you had to give or a pitch letter you had to write.

If you were going to have coffee with a local writer in your city, what could you send them before your meeting? What’s there? What is your base? Look at it. All of it.

To start, you have to know what you’re starting with.

My bet is, if the freelance writing bug won’t leave you alone, you probably have more experience than you realize. You’ve probably logged some hours that you’ve forgotten about. You’ve probably written more than you think. It might be time to start looking at it, and it might be time to start showing it to others.

I got a coffee meeting because my writer friend knew I blogged, and I knew I had samples I could send him later. You better believe I was blowing the dust off those college articles. When it comes to writing—you’ve heard this before—none of it is wasted. It could get you a meeting, and that meeting could get you an assignment, and that assignment could lead to a new career.

Take inventory. See what’s in your vault. Ask yourself if it’s time to jump in.

Part two of this three-part series will address what actually happened in the conversation over coffee: discussing the importance of having a writing niche. It was a game-changer for me, and I hope it will help you as you set out on this path.

A Few Thoughts on Quitting Your Job and Going Freelance

here A Few ThoughtsA little over a year ago I quit my job at a publishing house and went freelance full time. Freelance writing, that is. Which has also meant some freelance PR and some speaking and some other ways that I found out I can be “freelance.”

My overall thought on being a freelance writer is that 1. I really love it and 2. it’s really hard.

It’s not for everybody, I don’t think, and there were many times this year that I thought it wasn’t for me. Like the time in January when I had been working from a desk in my living room for four months, and I thought I was going insane, and then it turned out I just wasn’t around people enough. So in March I found an office listed on Craigslist in a building with other actual people, and I decided that my sanity was worth the extra cost per month to rent it. That turned out to be a really good decision.

There was also the time that I took on too much work. In the spring I said yes to four things, and then in the fall when all four things were under contract and happening, I thought I was going to die. It was great to have the money, but it was not great to be working at night and on weekends. I am not really one of those work-all-the-time kind of people, so I have learned to think about my calendar in advance and only say yes if I know it won’t make me crazy or want to die.

So there have been times that I didn’t feel cut out for this, and I haven’t even mentioned all of the times I’ve been in Excel, and looking at my taxes, and trying to do math and attempting all the business-y things that I am not naturally good at. I especially doubt my freelance abilities on my “get your finances in order” days.

But there have been some really good days too. Like when my sole task for an entire morning or afternoon or both is writing, just writing. I don’t have to be on email constantly or go to a meeting or feel pulled here and there because this is my job now, and my boss isn’t really a person anymore so much as it is a deadline, and deadlines? Well, I like them, and I can meet them, so they are just fine for me as a boss. That’s when I feel cut out for the freelance life.

There have been other times too when an opportunity came out of nowhere that let me work with former colleagues of mine but in a totally different capacity, and I think, “I never could have done this or had the time do this if I wasn’t a freelancer.”

And, there are perks. I can adjust my working hours so that I can grocery shop at 11am when Kroger isn’t a madhouse. I can wear whatever I want, though I do try and wear real clothes most days instead of yoga pants every day. But I have had weeks… And I have my office, but I can work at a coffee shop or on my couch or on a plane or just about anywhere else if I want to or need to.

The biggest thing for me though, the thing that makes me feel deep down that I am on the right track, has been how I feel at the end of the day. When the work is done, and I close my computer, I’m not zapped. I feel energized. I feel like I can go to the gym and to dinner with a friend instead of picking just one. I feel at peace in a way that work never made me feel before. I guess this it what it feels like to do what you’re supposed to do.

I didn’t know what that felt like before or that it was possible. I grew accustomed to the frenzy and the stress and the dread. I thought that was what work was supposed to be. But now, I don’t think that anymore.

One of my biggest emotions this year has been gratitude. If that’s an emotion. I am so grateful to get to do what I do. I think gratitude and peace are probably pretty good indicators that you’ve chosen a good career for yourself. You won’t feel grateful and peaceful all the time of course, that’s just ridiculous, but underneath the less desirable feelings you have on any given day, you will be saying thank you under your breath, instead of saying obscenities, and you will feel a rest in your soul that’s assuring.

I am thankful. So thankful for this past year, even the insane lonely months in my living room, and the headache I had from January to April doing taxes. I am even grateful for the stacks of un-filed, important documents lying around my office. They are a sign that I’m getting to do what I love, and that is a rare, rare opportunity for most.

I don’t think everyone should be a freelancer, or a writer. I certainly don’t. But I do think and hope that what you do brings you some gratitude and some peace, and if it doesn’t, I hope you challenge yourself to find something that will.


Psst! After writing this, I decided I might turn some of these paragraphs into longer articles, like “should you be a freelancer?” “what is it really like to be a ‘writer’” “how to know when it’s time to quit your job” “how to never miss a deadline again!” (haha) etc etc. I have thoughts on these things. Lots of thoughts. So be on the lookout for some more focused pieces on freelancing, writing and quitting your job. And shoot me a note to let me know some questions you have on these topics. There might be a Q&A session in our future.