A Letter to Friends Looking to Break into a Part-Time Writing Career

Dear friend who wrote to ask me for writing career advice:

Thanks for writing. It’s always good to hear from you, and I am both humbled and honored that you would seek me out for advice. I want to take the time to give you a thorough response, and I also want to be perfectly frank with you about what challenges lie ahead.

Writing has never been my “full-time” pursuit; even now, making my living as a freelancer, writing only accounts for about 25% of my total income. I get the sense from the other writers I know that the number of them that make their entire living as a writer is very small indeed; thus, I am pleased to have as much opportunity to publish as I do.

My Path So Far

Maybe it will help to remind you of how I got started writing. I started writing seriously (meaning, with the intention of pursuing publication) in 1998, and my first piece was published in the following year. Okay, it was just a 200-word sidebar for an article that someone else wrote, but it was my writing, in print, and I was paid for it. That made me a published writer in my book!

Over the next few years, I continued in my writing pursuits, despite finishing my college degree, working for a couple of years in a full-time job, and beginning a graduate degree while teaching full-time at a small private school. Needless to say, I had less time than before—but I was also compelled that writing was an important part of who I was; it was part of my calling, if you will. So I found the time for it.

Over the years I have worked up from scrounging for a legit full article publication to having regular columns at online “webzines” to becoming a regular contributor to a print magazine to… now, where I get regular assignments from one magazine, have several others that will eagerly consider my queries, and have a book publisher interested in a new project from me. At this point, I could write and publish more than I actually do, mostly because my other freelancing tasks take so much time.

So you see, maybe the first thing to realize is that, if you want something kind of like what I have, then it takes a while. I’ve been at this for almost two decades, and working regularly at it all that time.

Learning to Write Takes Time

Now, this is where the rubber really hits the road for you. Nobody is born a good writer. Some people have a natural gift for taking the accumulated knowledge and experience they have gathered and using that to express themselves well on paper. Others don’t have any such innate ability but have learned how to work hard at writing well. But it doesn’t just happen.

It also probably won’t happen just because you’ve gone to school and/or done a lot of academic work. Remember that year in college when I wrote more than 60 papers for assignments? Looking back, only a little of what I wrote then was useful toward my writing career, in terms of learning to express ideas in a creative and engaging way. (I like to think I had improved on this a bit by graduate school, and those papers were more like writing exercises.) Most of my writing education and training didn’t come in formal school but from actually writing.

I figured out early on that I needed to improve my writing; while this didn’t keep me from making a pitch here and there, or from keeping my ear to the ground for new opportunities, it prevented me from taking myself too seriously or from being overconfident about what I offered as a writer (or, really, an aspiring one). It wasn’t until I began to get trustworthy feedback from writers who I took seriously about the quality of my writing (mostly from a blog I wrote for a long time) that I began to really dig in. That was in 2004. From there, I relied heavily on the additional voices of the editors I worked with.

In fact, I think this is probably the biggest obstacle between you and a regular writing thing. Is your writing really ready for publication? Don’t just ask yourself; ask others. Be ready for criticism, feedback of all sorts, and outright rejection. (More on these in a little bit.) Until you’ve gotten feedback like I did—substantive, meaningful words from writers whom you respect and appreciate, and from editors you submit to—then you may do well to second-guess yourself.

Gathering the Knowledge

Writing is one thing; many people write for years with no aspiration (or at least, little or no success) toward publication. Becoming a paid, published writer is another thing altogether.

There is a growing wealth of information about the “work” of writing—meaning, the practices and business of becoming a working writer. Many a book has been penned on the subject by accomplished writers and writing instructors; Anne Lamotte’s Bird By Bird, Stephen King’s On Writing, and William Zinsser’s On Writing Well are some of my favorites, but there are plenty of others (Brenda Ueland’s If You Want To Write is often listed among the most favorite/popular ones, though it has never really resonated with me). These days there are also countless blogs, including a handful from literary agents (which may be more or less interesting to those who don’t yet aspire to publishing books), that offer great insight. And podcasts now, as well, are an easy way to gain a lot of wisdom about the profession; the Longform Podcast is one of my favorite ways to pass the time in the car.

It also means becoming proficient with the professional skills of writing. When you write for yourself, the way that you punctuate (or not) and the attention you give to matters of grammar and even spelling are of peripheral concern. Not so much, though, when you write for publication; you need to be familiar with, and committed to, the care and attention needed for these. Likewise, you need to break free from writing in a colloquial style, avoiding slang or jargon that may strike you as quaint (or more: one friend peppered an essay with what he said was “just how he talks” but which left me scratching my head frequently; I’m sure it would an editor, as well) but that don’t fit for the publication you write for. Which isn’t to say that you must cut out words/phrases that readers would uniformly know and understand! Learning this part can take time and patience, and maybe even study.

Be careful here, though: I’m sure many writers have found what I did, that it is easy to become so engrossed in reading about writing that it cuts deeply into time spent actually writing. You’re not a writer because you know about writing or talk about it, but because you actually write. I eventually stopped reading books on writing precisely because of this—and because eventually it seemed like the next book had so few new insights, compared to the half-dozen I had already read, that it was an effort of diminishing return.

Building a Network

Who do you know? Relationships are so crucial for almost everything we do, and although actually writing is typically a solitary activity, publishing is anything but! I wouldn’t have gotten anywhere if it weren’t for relationships.

That goes all the way back to that early feedback I mentioned. The way that I connected with those writers whose critique was so invaluable was because we read and commented on each other’s blogs (this was in the heyday of the early blog movement; today it might be following each other on Twitter or Medium, and next year it may be something else altogether). For a while I even pulled together some of these writers for a collaborative blog.

Along the way, most of the editors and others in publishing that I have worked with are people whom I connected with relationally, at least at some level, before sending them a pitch or query. Whether it was a LinkedIn or Facebook connection, someone I met face-to-face for a meal or a cup of coffee, or something in between, building these relationships has been vital to also building my writing career.

A great example of how this is a benefit to my writng is a friend of mine named Alissa, who I met because of that collaborative writers’ blog. From then until now, however, Alissa has busted her tail knocking down doors and advancing her own writing career, and is now an editor for a major publication. I sent her a pitch once that didn’t quite fit what she was looking for; had it been from someone she didn’t know at all, I’m sure it would have merited a quick and simple rejection. Because of our existing friendship, though, we bounced a few e-mails back and forth, clarifying both what my ideas were and what she was looking for, and the result was an article that appeared in a major magazine.

That’s just one example. But—and this is incredibly important—don’t do any of this just because it will increase the possibility of writing opportunities. The main reason why these relationships are fruitful now is because they have, from the start, been genuine. These are people that I like having in my life, who I enjoy getting to know. They are real friends, at some level, and not merely business contacts. Don’t even bother if all you’re doing it for is the toe in the door for a query.

Learning Your Markets

When I first got started, I had it in my head that I would take any assignment that I was offered. And, in fact, the first full-length article that I wrote was just such an assignment (from an editor I had met for breakfast a week earlier); fortunately, it was a profile of someone in a field I had some familiarity with.

What I didn’t realize then, but has become crystal clear to me since, is that there are topics that I simply shouldn’t write on, regardless of how great the opportunity may seem. Likewise, there are particular publications that, no matter how much I admire them and the quality of the writing and content they publish, I could never write for them—either because of a difference in style or because the subjects they cover simply aren’t my thing.

What will you write about? Consider that a single standard-length article (approximately 3000 words) may require 20–30, or even 50–60, hours of time in reading, research, writing, and re-writing on your part. If the subject is not one that is familiar to you, those hours could double or more; and if it’s a topic that isn’t interesting to you, every hour will feel like drudgery. Neither scenario is a productive or worthwhile use of your time.

You need to know your markets: what types of articles you will write (essay? personal reflection/opinion? profile? Exposé? Expository writing?), what topics and subjects you are both interested and qualified to write on, and which publications cover those topics. Until you have figured this out, you will waste a lot of time—your own, and the editors you contact.

One resource that is vital for at least the last part is called Writer’s Market (and, for Christian writers, there’s also The Christian Writer’s Market Guide, though many of the major publications are also covered in the standard Writer’s Market). This is an annually-released collection of information on magazines, book publishers, and other markets for salable writing. Of course, it’s almost immediately out of date upon publication, because many of the editors and other staff will have moved or been promoted, but it can be immensely helpful to get started finding which markets are viable for your topics and style of writing. (Then the trick is getting to know someone at that market.)

Mastering the Pitch

There are countless books and articles—including many good ones online—for learning this, so I won’t dwell on this for long. (I might mention that Writer’s Market actually also has a lot of valuable help with this.) But ignore this at your peril, as a would-be published writer.

Editors are terribly busy; they always have far more tasks and assignments than they can reasonably handle, and acquisition of new pieces for their publication is usually just one small part. Of course, it’s a vital part, but most don’t have the time to negotiate over numerous lengthy e-mails whether an idea might have the potential for their upcoming issue.

Therefore, they are dependent on writers helping them see that potential quickly and easily. This usually translates into something of a formula, which can feel like a stifling constraint; in actuality, it is a good exercise for writers who aspire to publishing great articles. Until you know your concept and subject matter well enough to pitch it effectively, you probably aren’t ready to take on an assignment in the first place.

One more comment on pitching: a lot of publications will help you out a lot with it, in one (or both) of two ways. Almost every magazine or website will have, somewhere, some guidelines for how to pitch them. Follow these to the letter, and you will be better for it. Also, many publications (or editors) will frequently ask for queries on a particular theme, concept, or subject that they are planning a future issue about. Once you find these, they can be a great source of inspiration, as well as a filter for saving you (and their acquisitions editor) time.

Growing Thick Skin

Friend, this isn’t the hardest part (I’ve already ascribed that superlative to the “learning to write” aspect) of your budding writing career, but it will be the part that, for most people anyway, is the most emotionally taxing.

The fact is, you will face rejection—a lot of it. It may come in a quick dismissal of an idea that you’ve already invested a good bit of time into considering and drafting a pitch for. It might be that your favorite idea of the past 12 months, which you sent to an editor you know at a publication that you are sure it is perfect for, never even gets a reply. Or it may even be that you do all of the work to write an article that interest was expressed about, only for it to get “killed” (what a horrible label) before publication.

Serious writers get more rejection than they do acceptance. It’s nothing personal, though it can feel awfully so—especially in the cumulative effect.

The same can be true of facing the editing process: are you prepared to see the words and phrases you so carefully crafted cut entirely for the sake of a word count? Are you willing to re-write entire sections of an article upon request? Will you feel defensive of your finished article to the point where you won’t accept the critique of the person who will authorize its publication (and the check to be written to you)? If not, then you won’t fare well in writing for publication.

There is a “give and take” in the editing process, and you can defend your word choices and other decisions as much as you wish. Too much, however, and editors will deem you difficult to work with (“his/her work is too ‘precious’”), and may not invite you to write for them again. Better to grow thicker skin and trust that the editors you work with are working with you on your writing, not out to destroy it.

Getting Your Hustle On

Finally, it takes commitment to a lot of hard work. That may already be clear from my comments above, but let me take it one step further.

What has made the difference for me through my years of writing has been a dogged endurance and dedication to keep at it, in spite of many temptations to give up, and to press on with the next idea or pitch. Not a week goes by, and hardly a day, when I don’t do something toward advancing my writing in some way, however small.

I’m always scanning for “calls for pitches” and other ways to find another opportunity to potentially write. I work hard to maintain my network of friends, especially attending to social media. I set goals for myself: one year, a goal was to get an article into at least two new publications; another year, one was to pitch at least twice a month.

And, keep writing! If you have an idea that deserves being put into words, write it. If you don’t find a publisher for it, then start a blog or create a Medium account and put it out there yourself. Some will flop, but others may be just what the world needs to read and could gain great traction. (My Medium stats range from one piece with just 4 clicks to another with 1.2K; I’m undaunted by the former, and humbled by the latter.) The practice of writing—and putting it out for public consumption—will be good for you.

Some writers find that joining a writing community (either locally or online) can help them through all of this: accountability for their goals, encouragement to keep moving forward, constructive feedback about the pieces they write. You might look into this as well.

Wrapping Up

Surely, some of what I’ve written above is redundant to what you have read or heard elsewhere; perhaps the repetition only serves to underscore the importance of it. At any rate, I hope that some of my thoughts above will encourage you. The fact that you cared enough to write to me and ask for yourself means that you are serious, on some level, about writing for publication—and as much as I want you to have a realistic understanding of what is ahead of you in that endeavor, I also want to to be an encouragement to you.

Go forth and write! And may your success and readership far exceed mine.

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