Blake Eskin spent the mid-90s as a fact checker for The New Yorker, so he knew the organization well when he became the magazine’s first web editor in 2006. In his six years in that role, he helped make newyorker.com a platform for interactive coverage and blogging and brought the magazine to the digital world of e-readers and tablets. It is the 4th most popular magazine for Amazons Kindle, for example.Eskin has written a book, “A Life In Pieces, The Making and Unmaking of Binjamin Wilkomirski” and was the founding editor of Tablet Magazine, an online publication dedicated to Jewish culture. Eskin left The New Yorker a few weeks ago, and he can’t tell us what his next project will be just yet. In the meantime, he shares his thoughts on online media and writing. He’ll be speaking on the Friday morning ISOJ panel “From desk(lap)top computers to tablets and smartphones: How are journalists responding to the mobile revolution?”

How do you help change the way people do things at a legacy publication so they become more online-oriented?

You can’t just go in and change the way people do things. You work with them, you work with the organization. I knew a lot about the organization and I knew a lot of people there. It’s a place where people still go to work for their whole lives and do the same jobs for 20-30 yeas. There are people who really are used to and care about the message people follow. You have to find places to make change and people willing to make change to think about the online product.

How did newyorker.com change during the six years you served as web editor?

When I started there was no blogging platform. The New Yorker is now publishing 100 blog posts a week on its website. Comment, the lead piece in The Talk of the Town each week, is now a daily online feature. There are blogs devoted to books and film and culture. There are a lot of the things you want to respond to out of the rhythm of a weekly magazine – The Oscars, the killing of Osama Bin Laden. What you can say one or 12 or 36 hours later is different from what you can say the following Monday.

How does the site enhance the New Yorker brand?

The practice of figuring out what is lasting enough to say in a magazine that hits the newsstands on Monday, having to think in that way, that’s really good training even for the people who are writing for blogs and the magazine, and those are often the same writers. There is so much recycling of information out there chasing eyeballs; there is this flood of information. The New Yorker as a weekly magazine is a filter for people to say ‘these are a handful of things that deserve your sustained attention.‘ That kind of training and habit is very important for both online and print thinking.

Why do people still subscribe to magazines like The New Yorker when there is so much content available for free online?

A lot of what I might have once gotten from magazines, the discovery of the interesting, the learning about new things, there are often sites that do a really good job of that and do it faster and more efficiently and in crowdsourced ways like Metafilter. I think of Talk of the Town as the Boing Boing of 1925. But magazines help to define an interest group. They help to describe a sensibility. They also help people discover new things. When the New Yorker appeared in 1925, there were a lot of magazines that heavy with type and ran black and white line drawings. The New Yorker now conveys something unique. One of the challenges is, what is the package that is going to connote quality and allow you to focus and sustain your attention and bring in enough money that people will underwrite the kind of longform journalism that’s going on and needs to be done?

You’ve done a lot of work online, but you are first and foremost a writer. What advice do you have for people who want to get into the writing game?

There are two questions: how you make money as a writer, and why are you writing. That is a question I think about a lot, maybe too much. I would probably write more if I didn’t think about it so much. If you’re writing to get eyeballs because that’s what your job is, that’s one thing, but if you’re writing to add something that people didn’t have another way of knowing about, that’s important. But there is a lot of writing that doesn’t do that. Now, you can write and publish, but it’s a challenge to get heard and get paid for it. My advice: Write. Do it. Write about something you care about. Write about things you are interested in. People need to get over their fear of technology, which isn’t to say everyone needs to be a coder. Everyone needs to understand how their work gets distributed in this world. With tech changing as quickly as it does, understanding your tools and distribution systems will inform what you need to do to write about the things you care about.

Update 4/20/12 at 1:42 a.m.: This Q&A originally misstated Talk of the Town as a daily online feature on newyorker.com. Comment, the lead piece from Talk of the Town, is updated daily.