One of the most memorable pick-up lines directed my way was, “So, you’re a writer, huh?” The mystique of writing intoxicates; with the written word alone, a skilled craftsman can transport others to different places and times, elevate public discourse, share knowledge or provoke a hearty laugh or bitter tear. For the artistically inclined, writing reflects beauty. For others, writing is a form of denial — a psychological defense mechanism to salve the battered ego, insulating non-published, non-practicing aspirants from the existential shame of flipping burgers on the third shift to pay the rent while trying to figure out what to do with that English degree. From high art to punch line, few avocations inspire such disagreement about its nature and practitioners as does writing.
A dear friend of mine, a novelist with two published (and several unpublished) manuscripts under his belt, once told me that a writer is someone who can get someone else to pay for his work product. By that light, I’m a fairly successful writer; in the last two years, on a very part-time basis, I’ve broken into five figures of writing income. Another friend, a former newspaper editor, insists that writing is a craft and anyone who practices it is, ipso facto, a writer, even if the only place his writing appears is within the pages of his own private diary.
This diversity of opinion leads to the obvious first point: Finding success as a freelance writer requires the scribe to define success largely in self-referential terms. Each person’s needs, ambitions and skills will settle out at different levels. Some may wish to seek fame as a public intellectual, others as a pulp novelist. Some may content themselves with humor blogs or screenplays. Others still may write for income, or solely for the love of the craft. No matter the goal, the first task of any aspiring writer is to arrive at a clear personal teleology of writing, with a swift and confident answer to the question, “Why do you write?” Define a long-term goal commensurate with your purpose and keep it front-and-center. Let it be your Polaris to guide you through the darkness of rejection and writers’ block.
For it’s only after the “why” is answered that the “how” becomes relevant.
Part I. Formation.
The best writers are the most voracious readers. Reading exposes you to different voices, different words, different turns of phrase. Devour Vergil and Aquinas and Shakespeare and Milton. Survey the great histories and dusty tomes. Sample Stephen King and Milan Kundera and Anne Frank and J.R.R. Tolkien. Subscribe to magazines like First Things and Harpers and National Geographic. Scan USA Today or the Washington Post or The Wall Street Journal. Peruse blogs – dozens of them. Just read.
Part of your reading should focus on the craft of writing. Grab three or four books on the subject. Decent texts on my shelf that emphasize mechanics include Writing Tools by Roy Peter Clark, Woe is I by Patricia O’Conner, Usage and Abusage by Eric Partridge and Lapsing into a Comma by Bill Walsh. Good, general works about the business of writing include On Writing by Stephen King and The First Five Pages by Noah Lukeman. Kitty Burns Florey’s Sister Bernadette’s Barking Dog has its charms.
Digest a stylebook. Most writers benefit from an intimate relationship with The Associated Press Stylebook and Briefing on Media Law – and bonus points if you subscribe to the stylebook online. Read it cover-to-cover; you cannot know when to consult the style manual unless you have some appreciation for what’s in it. But don’t rest with AP alone. Select an auxiliary manual like The Chicago Manual of Style or The New York Times Manual of Style and Usage. Learn what’s in them. In a more general sense, become familiar with the major authorities on English syntax. Fowler’s A Dictionary of Modern English Usage is just old enough to satisfy traditionalists, while Garner’s Modern American Usage offers an in-depth overview of current trends in the language without being too permissive of the lit-crit zeitgeist.
Likewise, grab a dictionary. A real, paper-and-ink dictionary, not an online one. The AP’s official dictionary is Webster’s New World College Dictionary, 4th ed. Not all dictionaries are alike; different publishers have different standards for hyphenation, neologisms and non-standard usage. Use one dictionary, and use it consistently. One of my most prized possessions is an authentic, unabridged, single (massive) volume of Webster’s New International Dictionary, 2nd ed. – one of the finest one-volume dictionaries ever published in the English language. With the dictionary should come a robust thesaurus and supplementary vocabulary texts like William F. Buckley’s The Lexicon or Bill Bryson’s Bryson’s Dictionary of Troublesome Words.
Finally, pick up a grammar primer. I’m fond of George Curme’s English Grammar, although the text is a bit old. Hint: Before you buy a grammar, check its entry about masculine pronouns. If the advice is to use “they” with singular antecedents or to deploy “inclusive language,” put it down and pick up something different. Err on the side of being too conservative; you will get much less grief from curmudgeonly copy editors later in your career. No matter your politics, being transgressive works better in performance art than in the performance of the craft of writing.
English isn’t as black-and-white as some may wish. Writers who receive conflicting advice from editors sometimes fail to grasp that writing is more of an art than a science. For that matter, some editors also fail to attend to that point. Take the time to arm yourself with the tools and counsels of the trade. Writing, like playing the piano, requires much practice and study before you achieve true mastery of the discipline.
Part II. Development.
Let us assume, for the rest of this essay, that you’ve decided that writing for publication – and therefore compensation – tops your bucket list. Armed with the skills you’ve learned from extensive reading and writing, the next step on your journey sets the foundation for a solid career.
Begin by assembling a portfolio. A portfolio is the one absolute necessity for writers of all stripes and experience levels. At first, it might include meager content. Your chief objective is to beef this up. Portfolios are fundamentally paper documents, so developing a PDF is helpful. Keep a dozen or so of your best works handy, and highlight your diversity by including a variety of formats and publications. You may wish to share several public portfolios depending on the nature of your work: If you mostly write for newspapers, then keep a current newspaper clips packet but also maintain a more general file of clips for other opportunities.
Tips: Always keep a master file of everything you write and if possible include full tear sheets from a print publication. Each item in the portfolio should include the publication venue (including URL as necessary), publication date, publisher and relative location (e.g., page A5). It’s better to scan images of your work into a PDF than to send the same content as a plain-text Word file.
The best portfolios emphasize your range of talent and depth of expertise. Accordingly, new writers should aim for diversity of content and format. Many local mid- and small-market newspapers will accept string reporters and photographers for little or no compensation; your reward is the clip. Trade industry newsletters often seek freelancers, as do some blogs. Avoid the trap of writing solely for the Web. If your portfolio consists mostly of articles posted to revenue-share content-mill sites, diversify. Quickly! Include grad-school papers, grant applications, technical papers, substantial blog posts, whatever – just don’t rely on your online articles alone.
Concurrently, cultivate a niche. Find something that makes you unique and valuable to potential clients. Do you raise pet snakes? Have a degree in medieval studies? Experience as a technical scuba diver? The various skills and experiences you’ve accumulated in life can help shape a niche. Make yourself known for being an expert (or at least highly skilled or connected) in some subject, then use this subject as a marketing lever with clients.
Find a mentor, a peer writer or an editor who will look at your body of work and give you frank advice on what you do well and what needs work. Writers are notoriously prickly about their competence; every writer thinks his own skill is above reproach and any suggestion that his work has some material deficiency sometimes leads to fist fights or online feuds or blacklisting. Have the grace to receive the counsel of others and be open about improvement opportunities. Any writer who refuses to grow is an embarrassment to the profession.
Finally – start a business. Some hobbyist writers with minimal income can get by on their own Social Security Number. Freelancers with more substantial income or who sign contracts that could entail liability should protect themselves with some sort of company structure. Indeed, some clients will only work on a business-to-business level. Limited liability companies are good choices, but consult with a certified public accountant or business lawyer about what option is best for you.
Irrespective of your business structure, after you’ve built the foundation your next step is to solicit clients. Follow two parallel paths.
First, cultivate and publicize a brand. Build a Web presence. Blogs are ideal for writers and easy to maintain. Rent space from Site5 or BlueHost or the provider of your choice; commercial hosting space is inexpensive and owning your own domain name allows you to send emails from a professional address rather than that tired old Yahoo! account you’ve had since 1997. Build a site or hire Gillikin Consulting to develop a Web presence for you. Include a reasonable logo and tagline, but avoid being cutesy or using the Comic Sans font. Grow a social media presence using your Web site as a hub. Start a Twitter account; follow people who may be strategically significant for you and post frequently (perhaps two or three posts per day) but avoid being too self-promotional. Start a Facebook Fan page, if your target market resonates for it – for example, if you pursue commercial writing for companies in your community. Put together a detailed profile on LinkedIn and join local groups and networks for writers. Purchase high-quality business cards.
Second, cultivate relationships. Professionals transact business with people they know, like and trust. Join a local BNI chapter or the chamber of commerce. Use LinkedIn or MeetUp to attend networking events to meet people in person. Networking will be the most time-consuming part of being successful as a freelancer – don’t assume that you can just build a blog and people will come to you. You need to nurture relationships with others to earn their trust and their dollars. Look at networking as a strategic investment that may not pay off for years, instead of as a shakedown opportunity. Refer business to others to get business referred to you, and make sure your pricing strategy is competitive without disturbing the market or reducing your chances of landing an assignment. Build a rate card based on industry-standard data (e.g., from Writer’s Market or the Editorial Freelancer’s Association) augmented with your take on the local market.
In the online space, put your eggs in multiple baskets. If you focus on writing for the Web, pick three or four sites to write for. Follow online marketplaces like Elance or Guru or ODesk but stay away from the pennies-per-word stuff if possible. Low-pay online assignments are like a tar pit: Easy to fall into, hard to get out of. Some writers use pseudonyms but be aware that this practice may limit your exposure.
A word of caution, though. Some charlatans will try to persuade you that real online writing income flows from gaming SEO. They advocate creating what amounts to crap sites and then raking back AdSense dollars from unsuspecting Web surfers who land on a page in the site. Although with the right time and attention to detail, you can profit in the short term by doing this, the practice is disreputable and the entire house of cards could collapse with just one algorithm change to Google. Better to practice writing honorably and earn steady income over time.
For national media opportunities, grab a copy of Writer’s Market to guide your querying of various magazines and journals. Follow submission requirements precisely lest you risk silence or outright rejection. Use your niche to help guide you to the right publications. Read back issues of periodicals before sending a query letter to make sure you get the tone and general editorial direction of the magazine, and opt against sending marginal queries.
Oh, one more thing. Master the art of accepting rude rejections with serenity. It’s a skill you will have plenty of chances to hone.
Part IV. Refinement.
Sustain your momentum by joining professional organizations. Groups like the Society of Professional Journalists, the National Writer’s Union and the Editorial Freelancer’s Association offer various networking opportunities, job lists and sundry benefits that could be useful, and announcing your membership in these groups may be a sign of professionalism that helps close certain deals. Contribute to these groups and always be helpful and polite, as you never know when a peer may ask you to do some ghostwriting for hire in a pinch. One of the worst mistakes any writing professional can make is to act like a jackass in a public discussion forum or in someone’s blog comments.
Keep building your portfolio – tend to it as if it were a rose garden, and let the loveliest blooms grace your clips package.
Study your past works to gain a fresh perspective on your strengths and weaknesses as a writer. Look for any style tics in your writing (I noticed I tend to repeat the same word in consecutive clauses and use too many unnecessary commas and hyphens). Get a peer review from a trusted fellow writer or editor.
Take time for yourself. Don’t stop reading for pleasure. Shut off the computer and venture outdoors from time to time to reduce the risk of burnout.
Part V. Giving Back.
When you hit the point where you think, “I’m successful,” share your experiences with others. Be a mentor to new or struggling writers. You will find that teaching is the best way of learning, and coaching others helps to sharpen your own game. Whether you take new local writers under your wing or volunteer to critique writing samples for students or fellow writers, mentoring makes you challenge your assumptions about your own skills and habits and shows you just how little about writing is genuinely monochrome.
And don’t forget to grab a glass of Scotch and a premium cigar then sit back and congratulate yourself for being a writer. Go on, you’ve earned it.