What’s inspiring in our pursuits of passion? Sure, it’s awe-inspiring to look at the greats, the writers who matter, and soak in their awesomeness and quiet rebel-ness. Sure, it’s occasionally helpful to consult a rebellious resource or two for tips, tricks and treats on the way to creative success. Sometimes a skewed view or some Word Porn is all you need to get your ass moving. You know what else is inspiring? Looking at the writers who live and work around us. The freelancers. The bloggers. The aspiring novelists, published writers, and creative innovators. The folks that are poised on the brink, making a career and a path for themselves unlike anyone else. The writers that inevitably break some rules along the way. I draw tremendous inspiration from these folks, our peers in this creative journey that we’ve embarked upon.

Today’s freelancer is a man who makes the interwebs his partner and plaything. Andrew Huff worked PR by day and freelanced by night for years after graduating from J-school. Jumping into the blog world in 2001, he wrote about his family, about his life, and about things that made him passionate outside the official work world. In 2003, his blog caught the eye of a fellow Chicago blogger and designer, Naz Hamid. The like-minded duo became friends and partners, creating the Chicago-centric Gapers Block, THE site for Chicago events, obscurities, intelligent conversation, and other goodies. Gaining an immediate audience and wide-spread acclaim, Andrew began blogging in innumerable side projects for companies and initiatives. Last year he finally cut the cord, and blogs professionally on a full-time basis.

Andrew is inspiring because of his determination and drive, and his refusal to live by anyone’s rules about writing or creativity but his own. His blogs are a pleasure to read, his constant creation of new projects astounding, and his thoughtfulness and encouragement of artistic folks refreshing. And his facial hair is consistently impressive.

I talked with Andrew over IM one blustery October morning in Chicago, covering circuitous routes to professional passion, ideas and ideals, and success in writing and blogging. A few excerpts and lessons learned: (Want the whole interview? Scroll down to click through)

On the tendency for corporate work to turn into a horror flick:

I love playing with words — I can’t resist a good turn of phrase or a punny headline. On the other side, the thing that killed me about PR was having to write the same things over and over again. I used to call it “chuck key PR.” I had a power tool client who’d ask us to put out a news release on every new product. That’s totally fair, except that sometimes the only difference between an old drill and the new one was a new chuck key, or slightly different amperage. The drudgery was soul-sucking.

On the bitch that is the freelancer’s schedule:

The biggest trouble I’ve had adjusting to the freelance lifestyle has been getting out of the habit of working at night. I spent so many years working on this stuff after my day job that I have a tendency to get active in the evening instead of during the day. Which means I spend far too much time working in front of the TV or writing after midnight because I had an event I had to go to, rather than getting work done during the day. I’m slowly turning that around, but it’s been tough.

On the (thin) distinction between personal and professional work:

A lot of the projects I do aren’t about making money. Even Gapers Block was conceived as a labor of love, something to do as a fun side project. But as it grew in popularity — and the staff ballooned to more than 70 contributors, as it is now — I realized I needed to make it part of my job. I’m the only full-time employee, and I also often do double the number of posts that the next highest contributor does. But I love collaboration, so the only project that I think of as strictly personal is me3dia, my own blog. Almost everything else has been partnered with other people, most often my partner Naz.

On the crack-like qualities of these internets:

I spend far too much time reading blogs and other websites that have absolutely nothing to do with what I’m working on. It keeps me connected to the blogosphere, but it’s also just a procrastination tool. I often have difficulty getting work done without deadline pressure, so it’s a (naughty) way to eat up some of the time before I really have to get working.

Discover the coolness of Andrew Huff at:
Gapers Block
Me3dia
Out of 5
Twitter
(And far too many others to list - check his Me3dia page for more)

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Want more from the conversation? Click on through to the other side…

Quiet Rebel Writer: Hey Andrew! Ready for some interviewin’ ?

Andrew Huff: Sure! Good morning!

QRW: Good morning to you, my friend. First off - why writing? Did you always want to be some sort of writer growing up?

AH: It’s funny, I resisted it for quite awhile — I wanted to be a cartoonist for a couple years — but I was always writing when I was a kid. By high school I was singled out for my writing by teachers.

My father was a huge influence in my writing development. He is a writer, with his own PR firm which he ran from home or in an office in our home town for most of my childhood (it’s still there, actually). He involved my brothers and me in it from an early age. We engaged in a lot of word play when I was growing up — puns, plays on words, etc. — and it developed my vocabulary faster than a lot of my classmates.

I joined the school newspaper in high school, but didn’t do much with it. It did, however, make me realize I wanted to be a writer and go to journalism school. Actually, my original plan was to go to art school, then go to journalism school and end up in advertising as an all-around creative, but I couldn’t afford art school, so that got dropped. I’m kind of glad it did, though.

QRW: Sounds like that worked out for the best, right? I know originally you worked with your dad in his PR firm. How did the blogging start, and at what point did you consider freelancing?

AH: Yes, I worked at my father’s PR firm for about eight years (boy, the time flew!) When I graduated from J-school, there were few journalism jobs available, so I got into PR, first at a firm in the city, then with my dad’s firm because it offered a flexible schedule. Everybody there is on flex time, so despite it being an hour drive, I was able to indulge my night owl tendencies and arrive later in the morning.

But I really didn’t enjoy PR — I was pretty good at it, but I had absolutely no passion for it. So I spent a couple years freelancing and doing other stuff on the side. When I graduated from college, I started writing a monthly email newsletter, The Huff Report, to family and friends. Eventually, I realized I wanted to make the older issues available to be read online. So I set up a Tripod account and looked for a way to put them up. I used Microsoft Publisher at first — it was awful — and then came across a mention of Blogger. It made publishing online so much easier! So I moved the Huff Report to that, and as it progressed, I changed it to something more blog-like — posting every day, lots of links, etc. I moved it off Tripod and onto my own domain, me3dia.com, on January 3, 2001.

So… two years later, I posted something on my blog that caught the attention of Naz Hamid, a fellow Chicago blogger and designer, which started an email conversation about how there needed to be a site in Chicago that covered all the interesting web-based projects and obscure events that weren’t being covered by the mainstream media. We met for an hour and developed the concept of what would become Gapers Block, the Chicago-centric webzine we still run today. We asked about a dozen other bloggers to join us, and they all said yes, and in April 2003 we launched it, to immediate success.

GB brought us a lot of attention, and in late 2004 I was approached by a company in New York to be the editor of a lifestyle blog on the topics of “eat, drink and play” in Chicago in support of American Express’ In:Chicago card. The blog went really well, and it led to other blogging projects, which I did on the side while still working in PR and on Gapers Block. Last year, I had enough work that I was able to quit PR and blog professionally full-time.

QRW: That’s awesome. So you have an extraordinary amount of projects going at once. Some of them you probably consider “work,” some of them “personal.” Do you make that distinction, or is that not helpful?

AH: Good question. A lot of the projects I do aren’t about making money. Even Gapers Block was conceived as a labor of love, something to do as a fun side project. But as it grew in popularity — and the staff ballooned to more than 70 contributors, as it is now — I realized I needed to make it part of my job. I’m the only full-time employee, and I also often do double the number of posts that the next highest contributor does.

But I love collaboration, so the only project that I think of as strictly personal is me3dia, my own blog. Almost everything else has been partnered with other people, most often my partner Naz.

QRW: Does your freelance income derive mostly from blogging gigs with companies? Or somewhere else?

AH: It’s mostly from the corporate gigs, although that’s partly because I still feel a little guilty making money off Gapers Block. I’ve pieced together a few pro-blogging gigs that pay reasonably well, and try to aim for a target income monthly.

QRW: Here’s the million dollar question - do you have a day-to-day routine? So many freelancers seem to want to figure this out. I know mine varies, but I”m always curious about others. How about it?

AH: My routine is very rough. I start the morning with a whole lot of email checking, and looking over GB to see what needs to be done. I have one project that has deadlines on Monday and Wednesday afternoons, so I spend some time on that on those days, and on Friday I spend time on the Party Line, GB’s email newsletter. And we’ve got some recurring features on GB that I edit on specific days, usually at night.

The biggest trouble I’ve had adjusting to the freelance lifestyle has been getting out of the habit of working at night. I spent so many years working on this stuff after my day job that I have a tendency to get active in the evening instead of during the day — which means I spend far too much time working in front of the TV or writing after midnight because I had an event I had to go to, rather than getting work done during the day. I’m slowly turning that around, but it’s been tough.

QRW: Sounds about right! So - QuietRebelWriter is about breaking rules to achieve success (freelancing, writing, creative, etc). Any rules you think you’ve broken on the way to today?

AH: Hmm… Well, most traditional journalists would be horrified to know that I straddled the fence between PR and journalism for a number of years. I did some personal finance writing on the side while I represented a financial institution, for instance — although I didn’t use them as a source. I’ve also hired a lot of friends for various projects — that’s always a big risk.

QRW: You rule breaker you. What is it you love about writing? On the opposite side, what is it you hate about writing?

AH: I love playing with words — I can’t resist a good turn of phrase or a punny headline. On the other side, the thing that killed me about PR was having to write the same things over and over again. I used to call it “chuck key PR.” I had a power tool client who’d ask us to put out a news release on every new product — which is totally fair, except that sometimes the only difference between an old drill and the new one was a new chuck key, or slightly different amperage. The drudgery was soul-sucking.

QRW: Ugh. What do you think is (are) your greatest success(es)? How about major screw-ups?

AH: Gapers Block is easily my greatest success. Who could have predicted that a little group blog could become such a popular and influential site, filled with great writing by such a wide range of people?

Screw-ups … I’ve had plenty of them, typically the result of rushing to get something done. But I think my biggest was not getting professional sooner. I’m still not very good about getting invoices out on time, and I realize that I’m woefully bad at bookkeeping. It’s something I’m working hard to change.

QRW: I think that’s a common freelancer downfall! Do you have any writers you admire, both peers and “famous” folks?

AH: I admire bloggers like Anil Dash and Khoi Vinh for their ability to write engagingly about the web and weblogs. John Gruber of Daring Fireball is a sterling example of a journalist-blogger, mixing in-depth pieces on Apple and its products with the little bits and snippets that make a blog a blog.

QRW: How do you indulge yourself?

AH: I spend far too much time reading blogs and other websites that have absolutely nothing to do with what I’m working on. It keeps me connected to the blogosphere, but it’s also just a procrastination tool. I often have difficulty getting work done without deadline pressure, so it’s a (naughty) way to eat up some of the time before I really have to get working.

QRW: Nice. Last question - since you’re a big fan of words and word play, do you have favorite words? Do you have words you hate?

AH: Favorite words… Well, whenever I have to come up with a random or goofy word, I think “rutabaga,” so it must be in some way a favorite. I try not to play favorites when I’m writing (and obviously rutabaga is hard to fit into most articles), so hopefully there aren’t too many crutches in my writing.

Speaking of crutches, one of my pet peeves is the use of “enter” as a segue. You know, like, “The situation called for an expert. Enter Jim Smith.” It’s a rather lazy transition, and it’s overused. I try to eliminate it whenever I’m editing.

QRW: I’m now going to try to work rutabaga into everything I can think of. And it’s all because of you.

AH: Hah! It’s a fun word to say!

QRW: Thanks Andrew! And keep on rocking the blogosphere like you do so well.