Photo: rachfog

It’s raining.  Again.

It’s July 19, and so far this summer, Portland has had 12 days of sunshine. I’ve been keeping track. The City of Roses doesn’t get a lot of sunny days in June, so no one’s disappointed when they don’t materialize. But when July rolls around, the sun comes out and stays out well into October.

Only this year, the record rains we had during spring have hung on a little longer. No, a lot longer.

Right now, sitting in my office, mid-afternoon is as dark and gloomy as December.

This is not how it was supposed to be.

My writing business isn’t going according to plan either.

A client decided not to renew their contract for the remainder of the year. It wasn’t anything I did. They opted to stop buying what I’m selling while they retool their website and promotional efforts. Goodbye editing work. Goodbye steady monthly income. Goodbye writers, photo editor and proofreader I’d worked with on the project for so long.

And yet, I expect to wake up tomorrow or the day after that or the day after that to clear skies and dry pavement.

And I expect that sometime soon the clouds obscuring the horizon of my freelance business will clear away too, revealing a sunny future.

Until then, what else can I do but enjoy the rain.

Others take self employment one step further and turn a solo enterprise into an honest-to-goodness company.

At a time when fewer publications are making assignments based on unsolicited queries and aggregators like Demand Studios, Associated Content and Helium are encouraging more amateurs to try their hand at creating web content, running your own show sounds pretty darn good.

Taking your freelance game to the next level doesn’t have to take a huge cash investment, though getting some ventures up and running definitely costs more than others.

Here are 10 writing-related businesses an enterprising freelancer could start today. Each includes examples of at least one writer who’s done it. I purposely included not-so famous writers – no Tina Brown or Arianna Huffington on this list – to make the point that you don’t have to start out rich and famous to make a go of it as a journalist entrepreneur.

Here’s the list:

1. Hyperlocal news – The equivalent of yesterday’s neighborhood newspapers, hyperlocal news sites cover what’s happening by the block, voting precinct, parish or or school district. These sites have become so popular you can do the work yourself or use hyperlocal news templates and advertising networks from companies such as Outside.in and GrowthSpur. That’s the good news. The bad news is major digital media companies like AOL and Yahoo have figured out there’s money to be made in hyperlocal and are working on their own initiatives, though how successful they’ll be remains to be seen. Examples of hyperlocal news sites started by a single writer or small group include:

• OpenFile – Read a Q&A I ran last week with co-founder and Regret the Error blogger Craig Silverman for more details about this Toronto start up.
• Portland’s Neighborhood Notes
• Tasha Does Tulsa

2. Training – Amy Webb spent 15 years covering emerging technology, media and cultural trends for Newsweek (Tokyo) and the Wall Street Journal (Hong Kong) before starting Knowledgewebb.net, a training company that teaches journalists the tools they need to succeed in the age of digital media. Today, Webb heads a team of trainers who hold webinars and travel the country teaching at conferences and providing in-person, one-on-one training. But you don’t have a staff to train other writers on WordPress, Twitter, or other technology. If you know enough about tech tools for writers to teach someone else how to use them, you could offer your services as a consultant, write e-books on the subject, or do like Boston-based The Urban Muse blogger Susan Johnston and teach blogging classes at a local community college.

3. City magazine – Books aren’t the only things the DIY publishing revolution has made it easier to bring to market. Online-based publishing tools have also made it easier for writers become print magazine publishers, as Portland freelance journalist Michael Robinson is discovering. Robinson just launched Portland A Foot, a small format magazine for the famously bike-friendly city’s “low-car” culture.

4. Customized wire service – Nozzl Media is to raw facts what AP is to news. Steve Woodward, a long-time reporter and editor at the (Portland) Oregonian took a company buy out and collaborated with two other ex-Oregonian reporters to create Nozzl Media. A cross between a wire service and a software app, Nozzl provides news websites with a constant stream of public records, social web conversations and other data they can customize to fit their particular location or niche. Since the service launched early this year, Nozzl has signed up The (Vancouver, Wash.) Columbian, The LundReport and ParkroseGateway.com. Nozzl isn’t the only company providing constant news streams. EveryBlock helped pioneer the concept and was subsequently acquired by MSNBC.com.

5. E-newsletter – Speaking of TheLundReport, Diane Lund is a Portland health-care industry watchdog who for years published a well-regarded monthly print newsletter covering the industry in Oregon. After some time away, Lund re-launched her efforts, only this time as a weekly e-newsletter with a matching website. Lund is a strong believer in nonprofit journalism and has structured TheLundReport accordingly. According to her website, since launching last year, she’s collected contributions from 100 supporters – with donations capped at $1,000 per person. She makes it easy for readers to donate by prominently displaying a Support the Lund Report page on the website. Though Lund writes a lot of her own stories, she uses freelancers on a regular basis.

6. Blog network – There’s power in numbers. That’s the philosophy behind blog networks, groups of blogs linked by a common theme. By aggregating content and traffic numbers, blog networks can go after companies that might not have been interested in advertising on a single property. BlogHer, which now has about 2,500 women-run blogs in its network, was started five years ago by former journalist Lisa Stone and two other partners and today competes with some of the largest women’s magazine publishers for Fortune 500 advertising dollars (Disclaimer: I’m a member of the BlogHer network. Examples of other blog networks include:

• NewWest.net – A news and blog network covering the Rocky Mountain West
• Cities on the Cheap – A network of 60 independent blogs run by freelance writers offering “insider information on your city’s best deals.”

7. Turnkey editorial services – Why let Demand and Helium have all the fun when you, too, can become a content aggregator. I’m not joking. Magazines, news websites, custom publishers have a constant need for fresh information and many would rather work with one source that can provide them with a steady, dependable stream of high-quality breaking news, feature stories or SEO-enabled web copy than deal with individual contributors. Some enterprising freelancers have figured this out and created editorial services companies to fill this need. One of them is Gina LaGuardia, proprietress of Gina LaGuardia Editorial Services, who not so jokingly calls herself a content pimp. LaGuardia started her New York City metro area-based company after a dozen years as a magazine editor and editorial director, and since then has handled content syndication management for AOL.com, MSN Encarta, the Internet Broadcasting System (IBSYS), WorldNow, Salary.com, BellSouth, and more. LaGuardia uses freelancers – a lot of them. I counted 28 on the GLES contributors page. If you’re super organized, have editing experience, contacts in the publishing industry and know a lot of freelancers, this could be for you.

8. Pop up website – In October 2008, Conde Nast laid off most of the editors who’d been working on Portfolio.com, the website for its then new-ish and since shuttered business monthly. Two of those suddenly jobless editors were Laura Rich and Sara Clemence, who were experienced enough business journalists to know a trend when they saw one. Along with a partner, they quickly built a website to track the personal and cultural fall out of the bad economy and called it RecessionWire, with the tag line “The upside of the downturn.” The founders dubbed it a pop-up site, after those retail stories that show up just in time for Christmas crowds and close once the post-holiday bargains are gone. The thinking behind RecessionWire and other pop-up sites is that the founders will keep them alive as long as the trend they cover lasts. However, in a March 2010 interview with BusinessWeek, Clemence said she thinks the site will live on, though with less frequent updates.

9. Netcasts – Leo LaPorte has been around the tech industry since the early days of the personal computer. After pitching shows to radio, TV and publishing companies with varying degrees of success, LaPorte used the advent of relatively cheap podcasting technology to start an Internet-based netcast called Twit.tv, and it’s paid off in spades. Today, Twit.tv consists of 15 separate shows covering some aspect of technology available via live streaming video and downloadable audio and video. Talking at the 2009 Online News Association conference last fall, LaPorte said he’s making approximately $1.5 million in advertising a year for shows that cost about $350,00 a year to produce, which he does with a staff of seven.

10. Creative services – To market themselves effectively in the age of digital media, writers need a website, blog, letterhead, business cards, Twitter background page, e-book design and so on. To make the best impression, all those marketing pieces should sport a common, professional caliber graphic design. Writers who are comfortable with HTML code or have a flair for design can do this work themselves. But many aren’t or would rather pay someone to do the work for them so they can focus on other things, like clients. That’s opened up an opportunity for freelancers with a degree of technical skill and design sensibility to provide creative services for other writers. Denver freelancer Ron S. Doyle started designing blogs and websites for other writers a year ago (Disclaimer: I’m a client). By the end of 2009, such work accounted for 40 percent of his income. So far this year, it’s up to 75 percent. Writers make up 80 percent of his business, but that number’s shrinking as he picks up work from other types of businesses. Doyle’s using web design as a base to branch into offering print and online marketing materials, online publicity campaigns, copywriting and video editing.Things are going so well he expects to add a business partner by March 2011, possibly sooner.

Are you a freelance writer who’s started a small business? If so, I’d love to hear from you.

I’m talking about flat in the sense that with so many newspaper and magazine staff jobs going by the wayside, publications don’t have as many middle managers or mid-level editors as there used to be. As a result, many publications are farming work out to independent contractors, editors and writers.

With so much in flux, at any given time the hierarchy of who’s working for whom could change, and the editor you wrote for yesterday maybe the writer you edit tomorrow.

It’s happened to me in the past couple months, as I’ve taken on a new editing project. I’ve found myself assigning stories to not one, not two but three freelance writer/editors who at one time or another I’ve written for while they were either staff or freelance editors. Another writer I’m working with is also a freelance editor who may eventually throw some assignments my way.

If it’s happening to me, it’s got to be happening to other writers too.

So how do you act when your boss today may be the person reporting to you tomorrow?

1. Quit thinking of writer-editor relationships as ‘us v. them.’ Constantly pitting yourself against editors because of perceived bad treatment – lousy contract language, unreasonable deadlines, crummy editing or late payments -  makes you a victim. If you’re not happy about aspects of a writing opportunity you have the power to make a choice: negotiate new terms, walk away, or accept the fact that the terms are lousy but you’re taking the assignment anyway. Yes, sometimes the editor you’re dealing with is disorganized, mean or incompetent. But in many situations, problems you encounter may be beyond their control. If you run into trouble the best thing to do is talk, via email or better yet, by phone.

2. Approach the editor-writer relationship as one of equals. One’s not better than the other, just responsible for different things. Editors translate ideas into stories suitable for their audience, sit through a lot of meetings, buffer writers from demands – reasonable or otherwise – of editors and other publication staff higher up the food chain and prep articles for prime time. Writers are editors’ eyes and ears on the front lines, keeping tabs on what’s happening out in the world to come up with interesting, relevant stories. If you think of what editors and writers do as being different parts of the same enterprise, you’ll have more appreciation for what the other does, and it’ll show in your working relationships.

3. If you’re a writer, think like an editor. Editors keep track of multiple details for multiple projects for multiple issues simultaneously. Some go so far as to use Excel spreadsheets or project management apps to keep things straight. If you’re a writer, you can help them and yourself by thinking like an editor. Don’t turn in stories until you’ve gone over them with the eyes of a copyeditor. If you’re responsible for turning in elements that run with the story such as headlines, decks, inks, file art, sidebars, subheads, etc., send everything with your original draft – along with your invoice – instead of waiting for an editor to remind you. If you have aspirations to work as an editor, being organized about those types of details is good practice, gets you noticed, and it could pay off if you ever want to ask for a recommendation.

4. If you’re an editor, think like a writer. As an editor, if you say yes to a query, talk through what your expectations are of the writer and for the story at the very beginning so everyone’s expectations are the same. Because of their status, editors often have access to people and information writers might not. Sharing that information with a writer could help them with a story they’re working on, which helps you in the long run.

5. Be considerate in all your business relationships. I write a lot about workplace issues and in the last couple months have done a few pieces of employee rewards and recognition programs. My take away – you don’t have to give people money or stuff to make them feel good about doing their job, or about working with you. A small amount of courtesy goes a long way – an email to say thanks for an assignment, or a Twitter status update on how awesome someone is to work with. When the holidays roll around, you don’t necessarily need to send gifts to editors you work for – though last Christmas I did send something small to editors I’d worked with over the year.

Do you work as an editor and writer? What advice do you have for getting along in a flatter media world?