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.

What Creatives Can Learn from Harper Lee

to kill a mockingbird

You’ve probably seen the news about the upcoming release of the sequel to To Kill a Mockingbird by Harper Lee. Lee’s much anticipated follow-up, Go Set a Watchman, will come out this July, 55 years after the release of To Kill a Mockingbird.

I’ve read a lot about the excitement over the discovery of the manuscript, and a lot about the skepticism over it. Could the reclusive author who claimed again and again to not want to release another book really be deciding now, in her weak state of mind and body at the age of 88, to release a sequel that was “recently discovered”? It is certainly suspicious, but regardless of Lee’s involvement and willingness, this news can serve as a lesson, and maybe a warning, to those who create art, in whatever form.

A little over a year ago, I attended Donald Miller’s Storyline conference, a conference where attendees are encouraged to determine their dreams and passions and then create a plan to begin achieving those dreams. At one point in the conference we broke up into small groups and were asked to go around the circle answering this question: What will the world miss out on if you don’t tell your story?

The way this question was formed has been helpful to me in my creative pursuits because it takes the focus off of the creator and puts the focus on the potential recipients of the creator’s work. The pressure’s off. Now, you can view yourself as a servant of art, rather than an artist of art. Your job is to help people with what you do, and if you don’t do it, people will miss out.

It’s easy, and natural, for creative people to get bogged down in the perfection of their craft. I think—and she has been known to say this in not so many words—Harper Lee was afraid of failure, and this prevented her from releasing a second novel. It also prevented criticism from coming her way. It prevented comparison to her first work that has been hailed a masterpiece, and truly is. It kept her safe from these things, but look at her readers. It’s been 55 years, and the announcement of a follow-up novel has us cheering and clapping and standing in our seats. And we would have done this 50 years ago, had Lee decided to release another novel at that time.

I wonder if the encouragement would have encouraged her to keep going. I wonder if she would have kept writing, expanding into other genres, written children’s books, or lectured in universities. I wonder what the world has missed out on from this great novelist because, in her words, “When you’re at the top, there’s only one way to go.”

Lee has said the story in To Kill a Mockingbird was the only story she had to share. Something in me says that is not true. Something in me says that a person who can write a novel like that has much, much more to say about society, family, race, and culture. So while I’m thrilled about Go Set a Watchman and will be pre-ordering a copy soon, I’m sad that we, the world, have had to miss out on so much Harper Lee could have said to us and taught us over the last 55 years.

May we vow to be giving of our art; it’s a gift we’ve been given to share.

Are You Overthinking It? The Dangers of Introspection

no text bike image

I’ve written about this tendency of mine before—to daydream, to overthink, to create scenarios in my head and then have a difficult time returning to reality. I’m one of those people who’s been journaling since age eight and will disappear from time to time to sit on a beach, climb a tree or ride a bike simply to get away and think.

I am of the overanalyzing persuasion. It’s something I’ve grown to accept about myself, but it’s also something I’m learning to watch about myself. I think it’s important for we over-analyticals to be aware of when it’s time to JUST STOP THINKING ABOUT IT.

Now that I’m a writer by trade and work from home, my job is to think. This is great, and this is dangerous. Since I no longer work in the 8-to-5, fast-paced corporate environment, I have time and space to really flesh out my thoughts. Any problem, obstacle or doubt that’s arisen in the last few months has received extra attention. I’ve thought about it, run through various scenarios a million times. I’ve journaled and talked to myself about it. And now look, here I am analyzing my over-analyzing.

Through all of this, I’ve realized something. My tendency to overthink is really an attempt to control things in my life I can’t control. Think about it. How often to do you overthink circumstances that are beyond your control? For me, it’s the past and the future that I obsess over–as if thinking about them enough will change my past and make certain events occur in my future. It’s ridiculous. It’s a joke. But it’s what I do.

Being introspective is a good gift, but when your thoughts become a desire or attempt to control the person, place or thing you’re thinking about, it’s gone too far. That’s when we are not just thinking, but overthinking.

Something I know to be true but often disregard is that I rarely find peace in trying to control my life through my imagination. In fact, the opposite happens. When I get lost too deep in thought, I come out of it more anxious and confused than I was before I entered it. So nowadays, when my thinking becomes overthinking, I try to focus on what is true. Because that’s what the Bible says to do: “Whatever things are true, whatever things are noble…whatever things are pure, whatever things are lovely…meditate on these things” (Phil. 4:8).

Whatever things are true.

The true things for me right now are simple and basic: God is good. God is faithful. God is sovereign.

Even though I wish I could, I’ve learned I cannot think my life into being better or different than it is, and I cannot think my problems into being fixed. I can, however, force (and it does take an act of force) myself to meditate on what is true. Eventually the truth that God is good overcomes whatever lie or uncertainty had been occupying my brain, and very slowly but very surely, I am more at peace. The fog caused by the anxiety clears, and a path toward hope becomes visible.

Kicking Your Critics Out of the Arena

Kicking the Critics Out of Your Arena

Brene Brown, much like Taylor Swift, really speaks to my soul. I talk about her here a lot, and a friend recently introduced me to a fabulous talk Brown gave at a conference for creatives. You can watch it here.

In it, she uses the metaphor of a coliseum-type arena as the place where we display our work, art, ourselves. The place where we must be vulnerable and put it out there. Whatever “it” happens to be. In the audience of the arena are many people, including the critics. Brene says that there are always four internal critics present in our arena:

  1. Scarcity – which asks, “What am I doing that’s original?”
  2. Shame – which says, “You’re not enough. Who do you think are trying to act like you belong here?”
  3. Comparison – Does this one even need an explanation?
  4. Fill in the blank

Only you know who occupies seat number four, and I think the critic in this seat rotates depending on what you’re up to in the arena. I imagined one particular person in my fourth seat that I had almost completely forgotten about. My 12th grade math teacher.

I went to a small Episcopalian high school and one of its (many) traditions was The Senior Chapel Talk. The entire school attended chapel every day at 10 a.m., and at some point during the year instead of our chaplain speaking, a senior would get up and give a 15-minute speech. I was very nervous about my chapel talk. I liked theater and choir and performing, but when it came to being on stage and acting like myself, I was terrified and had little to no experience.

I remember my dad sat down with me at our kitchen table and helped me write my Senior Chapel Talk. Then I practiced saying it aloud in front my mirror about 17 times. When the day came to give my talk, my mouth was dry and my hands were shaking, but I got through it and was so relieved when it was over. After chapel I had math class, and the first thing my teacher said when she saw me was, “Wow, I’ve never heard anyone give a speech so fast!” I was mortified. I was so nervous I didn’t even know I had talked fast and flown through my speech. Her comment echoed in my head for a long time, and since that day, I’ve always told people I that hate public speaking and I’m terrible at it.

We have so many voices like this don’t we? Maybe we have some we’re not even aware of that are taunting us from the nosebleed section, and we’re listening to them even though they’re mean. In her talk, Brown suggests replacing these voices with kind, trusted ones. With the people who love us and cheer for us no matter what and with a picture of the strong person we know deep down we’re capable of being.

One way of conquering my math teacher’s voice was volunteering to do chapel for the company I used to work for. I had 15 minutes (again) and the crowd would be 20-30 people. It sounds small but it was a really big deal for me. And you know what? I was ok. I received kind feedback and I even enjoyed the experience.

Sometimes you have to do the thing that one person told you weren’t good at in order to kick them out of your arena. They don’t belong there. Don’t let them have a seat.

The Parts of Us That We’ve Forgotten

The Parts of Us We've Forgotteb

I continue my time of rest from a place my family has returned to almost every summer since I was 15 years old. This place, oh this place.

I got to thinking as I was walking on the familiar beach path a few days ago that I’ve walked that path as many different girls: a teenage girl, a college girl, a girl in love, a heartbroken girl, a confused, sad, joyful and excited girl. A girl arm and arm with her mom, her dad, her best friends and her sisters. No matter who happened to show up as me that summer, I consistently walked or ran that path by the water and the lava rocks and the giant sea turtles as many times as possible before the sad departure day arrived.

It’s strange how a place can remind you of who you once were and what you once were like. I’m laughing now at how timely it is for me to visit that path at this point in my own path when I’m starting a new career and hoping for the best and trying not to be terrified of the worst. This path has been good for me these past few days to remember why I’m doing this, to remember the parts of me that love and have always loved to write. The part of me that told people at age five that I was going to be an Author. The eight-year-old me that made up stories and read them aloud to my class. The college me that competed in a slam poetry contest (yes, yes I did that).

Those parts of us. Remember them? They’re still there, but sometimes we quiet them and hush them until we convince ourselves they’ve gone away. We do this because we are clinging to the reliable things like schedules, and financial goals and to-do lists and things that aren’t bad but when they are our rock, we feel no need for anything else—a hobby, a passion, a savior.

On my beach path, I’ve been assured the parts of me I’d forgotten have not actually gone away. Neither have yours. I’ve also been assured that we owe it to ourselves to be honest about who we are. To let what we’ve let die a little come back to life. This often means taking little steps like signing up to be in the chorus of a community theater production, taking a substitute teaching gig, knitting a scarf for a friend. Whatever it is that taps into that part of you you’ve been keeping under the surface, into that thing you once loved and were good at and others told you so.

Find the walking path, or the city, or the house or the park that will remind you of this. Go there, walk around and remember what it was. Remember who you were.

And He Will Make Your Paths Straight

And He Will Make Your Path Straight

My fourth summer in Nashville and I’m still not accustomed to it—the fast and furious rain storms that interrupt your day in the rudest way and leave you, just as suddenly as they came, walking along steamy pavement. This girl from the desert of south Texas is still surprised that rain in the summer even happens.

I watched a downpour like this the other day from the safety of my living room. People were on the street one minute and then nowhere to be seen the next. They had wisely run for cover. This particular rain was the vision-impairing kind that wouldn’t allow you to get anywhere fast anyways. A thick sheet of rain.

I haven’t made a major life change in almost five years. My last one was moving to Nashville, where I live now, to work at a book publishing house where I worked until this last Friday. This is the first Monday in 23 years that I have woken up neither an “employee” nor a “student.” It would be fair to say I am looking at a thick sheet of rain. I will probably be looking at it tomorrow too and many days thereafter. This is what it feels like to have an uncertain future. To leave a job you love and people you loved working with to do something you’ve known for a while now that you are supposed to do.

About a year ago after a succession of events I will write about in due time, I knew I was ready to start to pray about a job transition. And a few months ago I knew it was time to start to plan for said transition. And a few weeks ago, it was time to make it. I put in a five weeks notice, and here I sit on my stone on my uncertain path staring at the thick sheet of rain.

This is as descriptive as I can be about my next step at the moment: I’m going to be Doing My Writing Thing. At best, I’ve piddled in writing since I started a full-time job. I’ve freelanced here and there, been on and off this blog, taken a few weekends to work on longer creative pieces that are more fun than they are focused, and it’s time to get real about it.

I’ve never leapt like this before. My life to date has been about sensible choices. College, graduate school, career. I have felt safe in these decisions and yes they were challenging and scary when they started, but nothing has been quite so unclear as this next step. Never has my future looked so blurry. I can do nothing to get it into focus, squint as I may.

Sometimes several stones ahead of us on the path are illuminated. It’s so nice when that happens, isn’t it? When you kinda know what’s coming next, and the education and career track you are on are clear. Then there are those times when it seems only the stone you stand on and maybe one or two ahead of you are lit. Everything else? Dark.

We can’t know what’s next, and that’s difficult for we humans still not convinced of our mortality. But we can trust what’s next.

As I stand on my one illuminated stone, I don’t know what else to do except cling to this: “In all your ways acknowledge him, and he will make your paths straight” (Prov. 3:6). And he will make your paths straight. Not clear. Straight. We aren’t promised that we will know what’s next, we are promised something better: that what’s next will be in the right direction. It will be straight ahead because he will make it so.