Dear WordCount:

I have been praised for my writing ever since I was a kid. I’ve always been told I should become a writer. Years ago, I moved to the West Coast before I finished college because I was dying to escape to the big city. I needed to pay the bills, and I fell into word processing because it turned out I can type like the wind. As a result, for my entire work life, I have functioned as a de facto editor, writer, proofreader, and fact checker, but with nothing to show for it. I am always prettying up someone else’s work, or flat out rewriting it for them. “Uncredited ghostwriter” is my middle name. These days, technology and off-shoring have defoliated the job market of word processing work, permanently. It did not satisfy me anyway. I am trying to transition into freelance writing, but I do not have the writing samples to prove that I can do it. If you have any suggestions I would be very grateful. No one will help me and I am just about at the end of my rope.

Yours, Jane S.

Dear Jane:

There’s no easy way to do what you want to do, but it’s not impossible.

You don’t really say what type of writing you want to do. I’ll assume it’s journalism because that’s what I know best.

If you’re interested in working as a freelance journalist, you need training and practice.

For training, take classes through a local community college or university extension program. Not only will you learn basics like the inverted pyramid, nut graph, how to conduct an interview, etc., you’ll meet teachers who are likely to be in the business and who can give you good feedback and introduce you to publications that might need writers.

For writing practice, start a blog. Pick a topic and write about it – a lot. Since you don’t have other clips, blog posts can serve as clips.

Post your resume online. Put it on your blog, and emphasize your writing experience. Join LinkedIn and fill out a profile – that will help you show up in searches of people with your qualifications. Reach out to people you’ve worked for before and ask them to write LinkedIn recommendations for you, again emphasizing your writing and editing skills.

Join a local writers’ group, or start one; these days writers’ groups can be online too. Use the group to give you feedback on your work.

Collect ideas and craft them into queries that you pitch to the appropriate publications. If you’re nervous querying big publications start with little ones, but not so little that they don’t pay anything.

Treasure feedback you get from any editor who takes the time to explain why they didn’t accept your query. Use it to make the next one better.

When you get assignments, drink in everything the editor tells you to do – or not to do.

Meet your deadlines.

Send an idea for a second assignment when you turn in the first.

Rinse. Repeat.

How did you break into freelancing? Share your experience by leaving a comment.

Got a question for Dear WordCount? Email it to me at wordcountfreelance@gmail.com.

Last month I took my 18-year-old to a two-day freshman orientation at the university he’ll be attending in just a few weeks. While he registered for courses, met fellow classmates and checked out the residence halls, I sat through a series of presentations for parents on the realities of college life circa 2011.

Sometime during the second day it occurred to me that a lot had changed since we sent our oldest off to school four years ago. It also got me thinking  about the things parents sending a kid off to college for the first time should know but won’t get from a presentation or brochure, for example, that if your student gets sick, the campus health center won’t bill your insurance company.

The Anatomy of a Story Idea

Flash forward to the following week. I’m back in the office and getting ready to send ideas for blog posts to my editor at SecondAct, Entrepreneur Media’s website for people over 40. I considered including a pitch for a post about what parents need to know when sending a freshman off to college. But I’m not sure she’ll like it, so I don’t put it on the list. But at the last minute I tack it onto the end.

Turns out she loved the idea. I wrote this post within the week and it got good amount of tweets and comments.

Good Idea Goes Viral

That was in mid-August. A couple weeks later, I discovered that MSNBC.com, which is a SecondAct content partner, re-ran the post with a new headline and deck – you can read the updated version here. It racked up even more page views, comments, tweets and shares on other social networks.

The Washington Post‘s personal finance blogger, Michelle Singletary, spotted the post on MSNBC.com and used it as the basis for this Aug. 25 post; her post reiterates a lot of my original points, with some of her own comments.

Late last week, I found out the original post was the third highest trafficked story on SecondAct in August.

And to think, I almost didn’t pitch it.

All of this is a great example of why it pays to trust your gut. If you think you’ve got an idea that would make a great story you’re probably right. Granted, you have to know which story is right for which publication, and how to cast a story to fit a particular publication’s readership and mission. But if you write for the same publications on a regular basis, you’re probably good at that already. (That’s another reason why I’ve always advocated cultivating ongoing relationships with a handful of publications over writing for dozens).

That’s my story, but what about you: have you trusted your gut about a story and had things work out even better than expected? Share your experience by leaving a comment.

But when it comes to how you conduct your freelance business, you do have lots of choices. Well, OK, maybe not as many choices as you used to, given that newspaper and magazine freelance budgets have dried up quicker than a mud puddle in August.

But there are choices, in the genre you pursue, the subjects you specialize in, the clients you work with, even how you get your work done.

So how to get started? I’ve compiled the following list of Freelance 101 helpful hints gleaned from 18 months of posts on this blog and 12+ years of  freelancing I’ve done for international wire services,  daily newspapers, geeky tech magazines and Web-based publishers. You’ll find information on writing basics, finding story ideas, working with editors, blogging and other resources.

Writing Basics

• 10 great places writers can find story ideas – Tune in to your surroundings and story ideas are everywhere.
• Prepping for the big one – A dozen ways to ace a VIP interview.
• Keeping sources on the subject – Get in, get the quote, get out.
• A few words about writing short – 500 words is the new 1,000.
• How to write fast. – Setting the timer is just the start.
• Why good writing is all about context – Putting in the why.
• When the words won’t come – Dealing with writer’s block.
• 7 steps to cutting a story that’s too long – Why let someone else hack away when you can easily trim that extra graph or two yourself.

Plugging In

• A writer’s guide to getting the most out of Twitter – After avoiding it forever, I finally caved – and boy, what a difference.
• Delicious and Google News Alerts – Web-based research tools even non-techies can understand.
• Top 10 Web tools for freelancers – Firefox, WordPress and more.
• HARO rescues writers stuck for sources – Crowdsourcing meets journalism.
• How to be a blog star – Take a class or teach yourself.
• The secret to my LinkedIn success – Hint: it’s not the number of connections, but who you’re connecting with.

The Business of the Freelance Business

• How to write queries that sell – Know who you’re pitching to, and other helpful hints.
• Just say no to assignments that aren’t a good fit – If they make you miserable, even well-paid jobs aren’t worth the money.
• Why freelance queries get rejected – It happens, even to the best of us.
• 10 ways to promote your freelance writing business – Writing’s just the beginning, you have to sell yourself.
• You may be desperate for work, just don’t act like it – Editors smell fear.
• Writing for free is not a business model – Giving it away ain’t gonna get you anything but poor.
• 13 warning signs a magazine may be in trouble – Checks slowing to a trickle? Uh oh.

In Their Own Words

• How to build the freelance writing career that you want – Words of wisdom for newcomers from long-time freelancer Gwen Moran.
• Sometimes all it takes is saying ‘I can do that.’ – Being in the right place at the right time is just the start – to get the good jobs, you have to ask for them.
• Going freelance in a down economy – Bad times didn’t stop former copywriter Susan Johnston from pursuing her dream to freelance full-time.
• One writer’s journey from print to online – Reporter Michelle Nicolosi got the online news bug back in the 1990s. Today she’s executive director of the now online-only SeattlePI.com.