My career as a freelance writer began quite serendipitously. And throughout my career I have been able to take advantage of opportunities.

I had been working for several years as a director of student financial aid (which I also entered serendipitously, but that’s a whole other story). A good part of that job involves writing: brochures, consumer information, memos, even research papers, and I always enjoyed that part most.

When I lost my job I used my contacts to get hired to help write materials for a federal training contract. When that project ended, I spoke with another of my contacts in financial aid – at the Law School Admission Council – who needed to revise his brochures and create better consumer information.

After we got started it became clear that instead of just revising the materials he had, we needed to create a whole book about financing a law school education. After that book, I approached the Graduate Management Admission Council and convinced them that they, too, needed a similar book. This led to several other books on similar topics.

At the same time I started my own newsletter on college planning. Because I had worked in the field for so long, I was able to recruit professionals to write many of the articles. While the newsletter wasn’t very successful, it opened some doors. One of the people I met at one of the newsletter publishers association meetings – it’s important to get involved with these types of organizations – had taken a job with a publisher and asked me if I wanted to help out there.

For a few years I worked part time as an editor and subject matter expert at Peterson’s, which published books on higher education. One of the editors left there and took a job at Macmillan publishing. And when together we came up with an idea for a series of books on admission and financial aid, I was hired as series editor and co-author.

Once you are a published author, the public, including those hiring people, considers you an expert. It then becomes easier to convince them to hire you. And that, of course, builds on itself. But there are always those times when things aren’t quite so rosy. Those are the tough times and you need to do whatever you need to do.

One time, for example, because I had no work I took a job as a driver. For a few months on an on-call basis, I drove corporate executives to and from the airport. During one of those drives, the executive and I talked. And when he realized that I could write, I applied for and got hired in the company advertising department as a copy writer. He and I had already established a relationship. The only thing needed was for me to prove I could write. I worked there for a year while continuing to freelance.

The road continues to be bumpy, despite the fact that I have written 12 books. I am continually marketing myself to just about everyone I know professionally. Even to those I know from other, non-professional areas. You just never know where your next opportunity will come from.

At my college reunion, for example, I reconnected with a friend who has since hired me several times to work on his company’s materials. At a social gathering, a friend from financial aid days asked me if I could write documentation for new software in financial aid. “Of course,” I responded. And this project led to almost five years of ongoing work within the same organization. And just the other day I talked with someone at my gym about what I do and about her work. You just never know.

Last fall I wrote to my publisher, who had moved up in the company, and asked if she had or knew of any projects on which I could work. Soon after I was contacted by one of the editors and, as a result, got a contract to write another book.

The point of all this is that you must always be looking for opportunities. At the same time, you don’t want to “market” everyone you meet. That’s a balance you have to find for yourself.

Here’s how I view it:
1.       You let people know what you do (i.e. freelance writer)
2.       You let people know that you’re available for work
3.       If they indicate an interest, you let them know that a good writer can write on any topic
4.       You continue to work on your craft

The key is, I believe, you have to be willing to say yes to opportunities, even if you’re unsure of your ability to carry it off successfully. You have to check craigslist.org, monster.com, your local newspapers, and, of course, inkwelleditorial.com. And you have to let your circle of colleagues know you’re looking and available for work.

Most freelancers have difficulty responding to the question of what they charge. I really like my answer. I say, “it depends.” That sounds like a cop-out, but I don’t leave it there. I say, “It depends on whether it’s a long-term or short-term project.” I explain that for short-term or one-time projects I have to charge more, and that usually goes over well.

The other thing about fees is that most people have in mind what they want to spend. So I ask them and make it clear that a ballpark figure is fine. They usually respond and if I feel that’s reasonable, I either accept or ask if they might consider going up a little (you’d be surprised how many times the figure is higher than what you would have asked for).

If it’s too low, I will say so – nicely, of course – and say that while I’d like to do the project, I need a bit more. If they ask how much, then I know it’s now not a question of whether they’re interested but one of coming up with the right amount. Since they’ve already given you a starting point, you can use your best judgment to figure out how much higher they’ll go. And whether you want to risk losing the job for just a few more dollars. Sometimes it’s worth it, sometimes it’s not.

To me, lifestyle is more important than money. Of course, that’s easy for me to say because my wife has a good job and we’re not hurting for money. Nevertheless, I could get a good job (I’ve actually had some along the way). But now I enjoy being able to go on trips with my wife who travels frequently. And I enjoy staying at home, not having to commute. It’s a tradeoff, of course. You have to like being by yourself. And you have to enjoy spending half or more of your time marketing yourself – unless you’re extraordinarily lucky.

Freelancing is not for the faint of heart. And I have been successfully working as a writer only because I didn’t have the total responsibility for bringing home the bacon.