My friend, author and freelancer Linda Formichelli, just posted a long interview with Dan Baum, former New Yorker staff writer and freelancer. Linda had asked me for questions to put to Dan and so the interview is a blend of her questions and mine. She posted the interview on her blog and by permission (Linda’s and Dan’s), I’m cross-posting it here. (Thanks, guys!) Some interesting advice and insights for freelance writers about the hows of doing longer-form journalism and current and future prospects for working writers.

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Dan Baum has written for Rolling Stone, Playboy, Wired, and other big-name magazines, and is a former staff writer for The New Yorker; on his website, you can download proposals that landed assignments with these magazines. Baum is the author of Nine Lives, and runs a blog called WordWork. The account of his “short career at The New Yorker“ran as a series of Tweets in May.

Many freelancers fantasize about doing the kinds of pieces that you’ve written. What does it take to succeed in that kind of long-form journalism?

The biggest mistake I see other freelancers make is that they don’t work hard enough. I know that seems odd because if feels like we all work really hard. But it always seemed to me that getting the assignment was the hard part; researching and writing the story is the easy part.

The trick is, proposals have to be really detailed. You have to do a substantial amount of the reporting and the writing just to get the assignment. So you’ve got to be clever about that, because if you spend weeks working on a proposal, you’re going to go broke because you might not sell the story.

On the other hand, if you don’t make the proposal really good, really dense, really packed with information and really well thought out, you’re not going to get the assignments. I’ve been doing this now since 1987, that’s 22 years, and I still write proposals that don’t sell. My website has a bunch of them.

Somebody pointed out on some blog that if you read my proposals that did sell and my proposals that didn’t sell, you’d be hard pressed to tell which is which, because there’s just a lot of luck in this business.

Margaret [my wife] and I used to do freelance for newspapers when we were living in Africa and in Montana, and they would only pay us like $150 per story, but they might also pay a little bit of travel expenses. So we would use the reporting that we did for the newspaper story to finance the writing of a magazine proposal; but it’s always this balancing act between doing enough work on a proposal to sell it but not so much that you’re doing too much work for free.

Generally, by the time I get an assignment, a third of the research is done, and at the very least, I know the parameters of where the research is going to take me and I have a sense of the universe of sources and documents that are going to be available. So I can pretty quickly and easily get the story reported and written.

It may be that you don’t need to do that. I’ve never had much success writing shorter proposals. This is just what works for me, and it’s not necessarily what works for everybody. I don’t want anybody to think that I’m saying that these are the be-all-end-all of story proposals, there are plenty up on the site that haven’t worked.

Well, you’re going to laugh because I cowrote a book called The Renegade Writer about breaking the rules of freelancing, and one of the rules you read in all the writing books is that your queries have to be one page long. But when I started writing longer pitches, I started getting into the national magazines.

Portfolio had a rule that all proposals had to be one page, and Portfolio just went out of business. I don’t think they went out of business because they demanded one-page proposals; I think they went out of business because they didn’t have a very clear vision of what the magazine was. But maybe their insistence on one-page proposals was indicative of a short attention span and a certain amount of panic that things had to move so fast. And that was a monthly, so they could have really taken their time.

Your proposals are a lot of work. When you come up with a proposal idea, do you target it only to one magazine or do you say “if it doesn’t work for magazine A I’m going to send it to magazine B”?

Well, you have to write a proposal for the sensibilities of a particular magazine, so when people tell me “I have an idea for a story,” my first question is “You have an idea for a story for what magazine?” Because you can’t say, “I have an idea for a story, and if I can’t sell it Playboyy I’m going to sell it toRolling Stone, and if I can’t sell it to Rolling Stone I’m going to sell it to Harper’s,” because it just doesn’t work that way.

The story and the magazine go together and it’s very hard to re-write a proposal that doesn’t sell at one magazine for another magazine. I don’t think I’ve ever done that.

If you don’t sell that story to the magazine you originally have in mind, probably the smartest thing to do is put it aside, cut your losses, and go on to the next thing. Some people may try to recycle proposals for different magazines; I don’t think I’ve ever been able to do it.

Do you think that’s only for the type of writing you do? Because if I don’t sell something to Family Circle then I’m tweaking that thing for Woman’s Day.

It may be. I want to keep saying this that this is just my experience. Family Circle and Woman’s Daymight be similar enough. In the small number of magazines that I wrote for, you just couldn’t do it. I mean, if you were writing a proposal for Wired, there’s just nobody else you could sell it to. I tried, I’ve tried, I really have. I really have tried and it just never worked for me.

What does it take to make it — what kind of interests and background do you need to be able to do the kind of journalism that you do? What is your background?

I worked for six years in newspapers and then we’ve been freelancing ever since. What does it take? I used to say that for people getting out of college, working at a newspaper is great training, but newspaper jobs are getting hard to get.

I think it takes relentlessness. When I’m starting to work on a story, I’ll start reading about something, and I’ll just follow every link, and as I’m doing it I’ll make a list in a Word document of the people that I need to find.

I start calling them immediately, and talking to them and taking notes on my computer. The expression I use with Margaret is “I had a red dog day today,” which means I had my nose down on the ground and I was going after everything today. Just hoovering in enormous amounts of information. And when I start a proposal, I try to have a series of red dog days where I am just relentless, going after everybody, and as soon as I encounter somebody’s name I pick up the phone and I call. When I finish the interview I say, Who else should I talk to? Then I call those people.

I don’t put it off — I don’t say these are people I’m going to call later — I do it right then. Man, there are times when in one day I can get enough information to write a proposal that will get me a $12,000 magazine assignment.

When you are calling people and you don’t have an assignment yet, how do you convince them to talk to you?

I say, “I’m working on a story for The New York Times Magazine.” Or “I’m working on a story for Wiredmagazine.”

So you don’t let them know you don’t have the assignment in hand?

No, I say I’m working on a story for Wired magazine and I am. My relationship with Wired magazine at that point is none of their business.

What do you do if they ask when the publication date is?

I say “I don’t know, that’s out of my hands; it’s above my pay grade.”

On to another topic: You have such a broad range of things that you write about. How do you know, when you come up with an idea, that it’s going to fly? If it’s already all over the Internet, how do you know it isn’t already too much in the public consciousness for somebody to want to run it?

Yeah, that’s what you always face. I want to write a story about Masdar, which is this city being built in Abu Dhabi — a zero energy city being built from scratch. I thought this would be a great story for Wired.

It turned out Wired never heard of it but they said they were suffering from Abu Dhabi fatigue — they have too many stories on Abu Dhabi. Then I tried to talk to The New York Times Magazine and didn’t get anywhere. So I dropped it. It’s a great story, but I just dropped it.

I look for stories with interesting people in them, and one of the tricks that I’m always trying to impress upon young writers is that when you’re interviewing somebody, like if I was interviewing the chief solar engineer at Masdar, a big mistake people make is talking to that guy only about solar engineering. You have to throw in questions that have nothing to do with the subject. How many siblings do you have and what number are you? What do you read? What are your hobbies? Are you married? How many kids do you have? Have you ever been divorced? You’ve got to get them talking about themselves. I’m asking these questions that are just none of my business, really personal questions, and I’ll just keep getting in closer and closer and closer.

I’ll ask, What do you earn? And you’ll see this kind of shock of recognition on the person’s face. Sometimes people say “Well, that’s none of your business,” but rarely. I can barely think of a time that’s happened to me. Usually you see the shock of recognition when the person goes, “Oh, that’s the level we’re talking on.”

People like it, when you get them talking about themselves and unrelated stuff. You need time for this, and it’s a hard thing to do on the phone. But when you’re getting all of that then you know this person as a whole person, and then you can fit them into the story in a way that you’re still writing about Masdar and solar engineering, but you can just throw in a few licks to just make that person real.

It’s kind of a New Yorker trick. When you read about people in The New Yorker, they are somehow more three-dimensional than sources in other magazines. They’re not just a font of quotes, or a representative of a point of view — they’re people.

You also mentioned that you pick up the phone and call people. How do you find them?

Oh, people are easy to find. On the net, you can Google them, and you may not find their phone number but you’ll find organizations that they’ve been attached to. It may take two or three calls. I just tracked down Oliver North and it took three or four phone calls.

It takes a certain relentlessness. It takes not being discouraged. Sometimes you’ve got to call 40 people until you find the right one. If you’re looking for somebody’s who’s obscure, you use an online phone book. If you know Mark Riseman lives somewhere in the Midwest, and you look up Mark Riseman and up come with 400 of them, you’ve got to go through and call all the ones that are in the Midwest. That can take an hour and a half and it’s tedious, but you’ll find him. That’s what I’m talking about a red dog day. You just have your nose down on the ground, and you’re on the trail all day.

Do you worry about competition — other writers coming in and horning in on your gigs?

No. For one thing, we’re kind of out of magazines. I think in a way, it’s over. I think the days of being able to make a living as a magazine writer are rapidly coming to a close.

That is so sad.

It is. I’m not boasting here, but I should be able to get work, right? I was on staff to The New Yorker for 3 years, I worked for Rolling Stone for a long time. I have written for the biggest and most prestigious magazines out there and I can’t get work. Magazines are closing, they’re shrinking, they’re going from 12 issues a year to 10 issues a year, and they’re going from 300 pages to 140 pages.

Some of them are cutting their rates.

Some of them are cutting their rates. You know, when we started magazine work in 1989, a dollar a word was middling pay. A lot of magazines are still paying $1 a word.

And for a lot of freelancers, that’s the Holy Grail. “If I get $1 a word, that means I’ve made it.”

Yeah, well that’s what we were getting in 1989. But you know that whole question of dollars per word is a terrible way to judge an assignment.

You really have to think in dollars per hour. Is that how you do it?

I think of dollars per assignment. This is kind of dollars per hour…if a magazine assignment is going to pay me $3000, then I can figure out exactly how many days I can work on that. The LA Times Magazineis a pretty good outlet for me. They paid a dollar a word but they took 5,000-word stories; I could work on that for two or three weeks, and make a living. I don’t care; it’s just as easy for me to write 5,000 words as it is for me to write 2,000 words. In some ways it’s easier. So I don’t worry about competition. People tell me that they like seeing my pitches, and it helps them. If it helps other people, if it improves the quality of writing out there, if it helps younger reporters get started, I’m happy to do it.

How do you feel about what’s going on in the industry?

My sense is this — and this may be optimistic — I think we writers are in for a few bad years, because right now the public is used to getting everything for free. So the magazines are dying and the newspapers are dying and the quality of work is going to decline because nobody has yet figured out how to get the public to pay for quality reporting.

I don’t know how long it’s going to take for the public to say we really miss reading the results of two and three weeks worth of investigative work, and that’s worth paying for. Somebody will figure out a business model to get people to pay for it. Then I think we’re going to be a golden era in journalism. I think it’s going to be spectacular some day.

When newspapers and magazines and even book publishers are no longer saddled with the expense of manufacturing, handling, and shipping atoms, it’s going to free up a huge amount of money and I think it’s going to let a whole lot more people get into this business — and there are going to be a whole lot more venues to write for, and it’s going to be great.

I think we’re going to go through a swale of no work. Until the public figures out that it has to pay for quality research and writing, we’re going to face some lean years.

I’m being optimistic. Maybe the public will never say that, maybe quality journalism is over. I kind of don’t think so.

The paper The New York Times is going to disappear; all papers are going to vanish. I don’t worry about that — I don’t really care what medium people are reading in, if it’s a Kindle or if it’s a reader, I don’t think that’s the issue. I think the issue is, how do we get the public to pay for quality research and writing? Nobody’s figured that out yet because right now the public is excited about getting all this stuff for free. It’s just going to take a little while and I don’t know how long it’s going to take.

Some day it’s going to be great for us.

I hope it’s soon…I make my living almost 100% from magazines.

Yes, we make our living 100% from our freelance writing. I’m 53, Margaret is 55, and right now it feels like we’re back at the beginning of our careers.

It’s scary, but it’s kind of exciting in a way.

Well, it’s exciting when I think about what’s going to follow this period. Although yesterday the Times had a story about digital book piracy, and that’s going to be a problem.

There’s a lot of interesting stuff out there to write about — we just have to figure out how to get the public to pay for it.