Advice from the trenches.

Nineteen years ago, I left my full-time job as a Senior Financial Analyst for a Fortune 100 corporation to begin a career as a freelance writer.

Some Ancient History

The job I left was a good job. I was in my late 20s, bringing in more than $45K a year. In 1990, that was a pretty good salary. I’d been with the company for two and a half years after five years with the New York City Comptroller’s Office and was on the fast track for upper financial management. If I’d stuck around, I probably would have doubled my salary in two to three years.

But although I was good at what I did and I didn’t mind the work, it wasn’t what I wanted to do with my life. I didn’t want to be just another corporate grunt, working 40 to 60 hours a week in an office park 30 miles from home, living for weekends and vacation time. I was tired of wearing suits and heels and pretending that the work I did was important or even meaningful. I was a number cruncher, drawing the conclusions my bosses wanted from numbers we couldn’t change. It was bullshit.

I’d gotten to where I was by going to college — I was the first one in my family to do so — and getting a BBA in accounting. I liked working with numbers and I was good at it. When you’re starting college at 17, what do you know about life or careers? I came from a lower middle class family and all I knew is that I didn’t want to be poor. Accountants made a lot of money, I liked working with numbers. It seemed like the right answer.

Until I got into my junior year at college. That’s when I started to realize that what I did in college would determine what I did for a living when I finished. And I didn’t want to be an accountant. I wanted to be a writer.

I remember calling up my mother and telling her that I wanted to change my major to journalism. I remember her freaking out, telling me I’d never make a living as a writer, that I’d starve. She wanted me to become a CPA. She, like so many mothers out there, wanted her children to succeed in careers she could brag about. “My daughter is a CPA” sounds a lot better than “My daughter is a reporter for Newsday.” (Newsday was the daily newspaper out on Long Island in New York, where we lived at the time.) That’s not to say I planned to write for Newsday, but it was probably what she was thinking.

So I backed down and stuck with accounting. It was a decision I’ve regretted for nearly 30 years.

It was also the last time I listened to my mother.

As you might imagine, in May of 1990, when I called my mother to tell her I was leaving my secure, high-paying job to become a freelance writer, she freaked out. But there really wasn’t anything she could say to stop me.

Don’t Leap before You Look

Now those of you who are reading this might think I was very brave to take this rash step. But it wasn’t rash. It was well thought out and executed.

You see, I didn’t just throw away a career and start scrambling for work. I already had a project lined up. A company I’d done some part-time training for wanted a five day computer course about using computers for auditing. Computers were relatively new at the time and laptops were cutting edge technology. Some of the better funded corporate internal auditing departments — including the one I’d spent two years in — were buying laptops for their staff. The training organization saw a market for a course written by a computer “expert” with a background in auditing. Someone with writing skills. Me.

The course paid $10,000. It wasn’t something I could work on while continuing my full-time job — it was just too intense. My boss wouldn’t give me a leave of absence, so I quit. Simple as that.

But $10,000 certainly wasn’t enough to live on, so I needed to line up other work. I got a job as a per diem instructor for a computer training organization. They called me in when they needed me and paid me by the day. Some weeks I’d get just one day of work. Other weeks I’d get four days. They tried to hire me as a full-timer, but I wanted no part of that.

As I worked on the auditing with computers course and did some per-diem training, I started networking. I got other, better paying contract computer work. I sent out queries and book proposals. I got an assignment as a ghost writer for four chapters of a computer book. I built a relationship with one of the co-authors of that book. Together, we sold another book to another publisher. I sent out other proposals on my own. I got my first solo book contract. I got assignments from computer magazines. I got my own column in one.

All this happened over a period of three years. By then, I was securely entrenched in my new career as a computer how-to writer and trainer. Within two more years of hard work, publishers were coming to me, offering me books.

The point is, I didn’t jump ship without a solid plan that would keep me earning money while I could build my writing career.

I think I was smart. And I think some other people are dumb.

Like my old friend Mary (not her real name). I wrote about her once before in this blog. She always wanted to be a novelist and one day she decided her full-time job was holding her back from succeeding. She quit and spent her days in her apartment, supposedly writing. A year later, she was out of money and deep in debt with her family. Her novel wasn’t done, either. She was forced to go back to work. To my knowledge, she still hasn’t had a novel published.

That’s the dumb way of starting a career as a writer.

Take Things Seriously

I think Mary’s story is a good example of someone who simply isn’t taking a writing career seriously. Unless you’re independently wealthy or have the financial support of someone with a lot of patience, you can’t just throw away a real job to try your hand at writing.

And yes, I did just say “real job.” A real job is a job that pays you money. When I left my real job, I had two other real jobs lined up: the big writing project and the computer training work. Mary had nothing lined up. She just had a vague idea about writing a novel. She didn’t even have any ideas about who would publish it. And in case you don’t realize it, it’s tough to make s living as a novelist unless your work is published so people can buy it.

Of course, nowadays many people don’t have a choice about leaving a real job. Their employers or the economy itself might have made the choice for them. Layoffs and business closings currently have over 15 million Americans out of work. That’s as of now — who knows what the situation might be like in six months or a year? If you’ve always dreamed about starting that writing career and you suddenly find yourself out of a real job and with plenty of time on your hands, this might be the time to start work on that freelance career. In between job hunting exercises — and I certainly don’t suggest that you forget about getting a new real job — start writing.

No matter what your situation is, you need to take a career change seriously. Start by doing some soul searching. Answer the following questions as honestly as possible:

This is a real writer’s keyboard.
• Do you have the skills to be a writer? As professional journalist Dan Tynan recently wrote in his blog, “Just because you know how to operate a keyboard doesn’t make you a writer.” I couldn’t have said this any better. Too many typists out there think they’re writers. Get real. Look at your work objectively. Have other people read it — people who will give you objective feedback. If you’re not a writer, you’d better build some skills before you try to make it a career. Unless the topics you write about are in great demand, no editor is going to want to spend time repairing your prose prior to publication.
• Do you understand the importance of getting your work published? You can’t make money on what you write unless it’s published someplace for people to read. While print publishing appears to be in a slow spiral to death, that’s not your only publishing option. But you do need to find a way to publish that’ll earn you money. The way I see it, your options range from starting your own blog and hoping to get advertising revenues to support you (good luck, especially as online advertising declines) to building a relationship with a traditional print publisher who pays under formal contract by the word, assignment, or book.
• Do you have the business skills to connect with paying markets? That’s really what it’s all about. You can be the best writer in the world, but unless you can find a match for your work with a publisher willing to pay for it, you’re simply not going to succeed on your own. If you’re trying to write books, that’s when you might consider an agent — and kiss away 10% to 15% of your gross earnings.
• Do you have a plan for getting started as a writer? If you don’t, can you make one that’ll work? As detailed above, I had a plan. My friend, Mary, didn’t. The plan is one of the reasons I succeeded and she didn’t. (The other reasons may be in this bulleted list.) The plan was reasonable and it required a lot of hard work. I didn’t whine or complain when I got a rejection letter for a book idea. I just developed other ideas and kept trying to sell them. I also didn’t sponge off my future husband or family to get by during the lean times. I always had some kind of work, some kind of revenue source. It simply isn’t fair to your friends or family to build your writing career on their backs.

Right now, real journalism is in serious decline. Who knows what position I’d be in now, if I’d made that major switch in college? Would I have gone into pure journalism and be a victim of the cutbacks we’re seeing today? Or would I have used the writing skills and insights I’d gained during my college education to branch into some other kind of writing?

Perhaps the kind of writing I do now?

Who knows?

I like to think that there will always be a need for talented writers. I like to think that it’s still something that a person can make into a career.

But until you’re able to earn at least half of your income from writing, don’t quit your day job.