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As a freelancer, I think you need to ask yourself, “Where do I want to be in 25 years?"

Since 3rd grade, New York native Lee Matthew Goldberg knew, that he wanted to write. Having published his first two novels, with the latest being The Mentor, he tells us about the long way to the top, his master plan, and how rejection makes him a better freelance writer.

LEE MATTHEW GOLDBERG – Freelance Writer & Author – New York

What is your background in a nutshell?

I have an undergraduate degree from Connecticut College and an MFA from the New School. I’ve been writing since I was a little kid, so I’ve always known what I wanted to do. It’s a really strange field to get into, the path is not that easy.

How would you describe your occupation?

I’m a writer and a professor. I’ve been a professor for about 7 years. I used to teach at LaGuardia in Queens and I’ve been at the college in New Rochelle for the last 2 years. I teach mostly literature writing. My main career, or main job, is as a writer. I have about a dozen stories that I’ve published in magazines, and last year my debut novel came out with an independent press. This year, my novel The Mentor just came out with Thomas Dunne Books/St. Martin’s Press.
I usually work on a bunch of different projects at once, be it novels or a TV show that I’m writing. I kind of try to plan my week that way. Teaching is definitely my secondary occupation. I’m one hundred percent a writer first. I teach once a week because I enjoy it, and I think I will always keep that. But I would never teach full time.

“I’m a better boss to myself than any other bosses that I ever had in all honesty.”

Would you call yourself a freelancer?

I am somewhat of a freelancer. Now that I am selling things, working under contract for a certain publisher. But that’s kind of new for me. (Before that) I would pick up freelance stuff here and there. Most of it was unpaid, and was just building up my writing résumé.

What do you like about that lifestyle?

I would get very claustrophobic at a deskjob. Any job I had like that, after six months I’d get really bored, plus I didn’t like working for somebody else. I like working for me. I’m my own boss, and I’m very diligent, I get shit done. I’m a better boss to myself than any other bosses that I ever had in all honesty.

What does a busy day look like for you?

I have the same schedule Tuesdays through Fridays. I usually wake up somewhere in the 8’s. I eat breakfast, work out, do some editing, eat lunch, and then I really start writing around 1 o’clock. I write for about 4 hours straight and then that’s it. There was a writer that said, that you’re only good for about four hours. That’s your best. I could work on stuff at night, but I’m happy when I get about 5 pages a day done when I’m really working on something.

What do you look for in a client or project partner?

I just recently started co-writing on a few projects in screenwriting and TV pilots. All my co-writers have been great so far. So, for any project I would take on in the future, I would look for a good fit, and if I would enjoy working on the project itself. If I can tell that I would not enjoy (working on it), I would not do it.

So would your partner have to have certain character traits that you would be looking for?

Not really. I pretty much get along with anybody. More a good fit on a business level. That’s enough. There has to be some trust. My ideas have to be heard, and I’m also listening to your ideas. I want to work with somebody who inspires me, as much as I inspire them.

“The challenge is to motivate yourself, when there is not an actual dollar sign behind it, yet.”

What are the most difficult challenges about freelancing?

All my books I’ve written on spec, that means I have to do all the work up front, which sometimes takes years without seeing a dime for it. So the challenge is to motivate yourself, when there is not an actual dollar sign behind it, yet. With my latest work I got 50% paid up front, which I never had before, which made me perform better because I had such an incentive every day. Also, the writing comes easy to me but the business end is very difficult and complicated.

You do need people, like an agent, taking care of stuff and looking out for you. But at the same time, you also need to make sure, to steer things in the direction you want them to go. Like, what do I want my next book to be? Which is the smartest one, saleswise? Do I want to sell something very similar to the previous one, or do I want to try to sell the book that I love so much? Those are things that I’m wrestling with on a daily basis. I’ve been very premeditative in terms of how I’m planning my career, and slowly inching up. It’s been taking me a long time. It certainly hasn’t been just handed to me.

Do you have any tips on how to manage your project partner?

Listen to each other. When you disagree, you have to make sure to work through that disagreement. You kind of have to ask, what’s worth it. If it’s something like a sentence that somebody loves, and you’re fighting over that, when it comes to that level, lose the sentence.

Have you hired a freelancer before?

Yes. I’ve hired somebody to do my website. He listened exactly to what I wanted, and at the same time steered me…

“I feel much more in control if I am the one who is hiring.”

What is the difference for you, being on the freelancer side versus hiring someone?

There is definitely less pressure, I think, when you hire somebody. When you are getting hired, you obviously want to do the best job you can, and there is the pressure to make sure that (the project) goes well. When you are hiring somebody, you want THEM to do a good job.

Do you manage your client differently than you would manage a freelancer?

When I am hiring somebody, I know what I want, so it’s very stable. When I am being hired, I initially don’t know exactly what my client wants, what they are looking for. Or if (the client) is somebody who is more inclined to be happy or very critical about the work you deliver. So I feel much more in control if I am the one who is hiring.

Do you compromise in taking on jobs that have a lower potential for you to be creative, because at the end of the day you need to be able to pay your rent?

I look at my career as a “long con”. I am not in it for quick money here and there. (With each job) I want to become a little bigger. So instead of taking a lot of paying jobs, and write on the side, I’d rather take no jobs if they don’t help my final goal. In the back of my mind, I always have this metaphor of the “long con”, of “I’ll get there”. If (success) would have happened to me right away, I probably would not have become as good a writer. Every time I have gotten rejected, it would light the fire in my belly that much more, thinking that the next book will be the one.

So your master plan determines who you are going to work with?

Yeah. I think as a freelancer, do you just want to make some quick money here and there? No, I think you need to constantly keep an eye on building yourself, and building your résumé up. So eventually people will come to you, and you don’t have to go to them.

I want people to come to me: “What is your next book? I want to read that!” That’s the goal. Yes, you can take money here and there, but if it is not going to progress you, it might be smarter to take a less paying job, that will. It’s so tough as a freelancer; health insurance and all that is not taken care of automatically.

So I would think that if you make the choice to go freelance, you must be in it for the “long con”. During job interviews people always ask “Where do you see yourself in 5 years?”. As a freelancer, I think you need to ask yourself “Where do I want to be in 25 years?” and then keep working towards that. Because that is the final goal that you want to achieve with your career.

Check out Lee’s website and books

more interviews . . .

Why side projects matter

CHRIS NOBLE – Broadcast Producer, Brooklyn

Have a masterplan

LEE MATTHEW GOLDBERG – Freelance Writer & Book Author, NY

Be the good client

WOOK KIM – Freelance Creative, Brooklyn, NY


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