What’s inspiring? Let me flip that. Here’s what doesn’t work for me. It’s not pat quotes and hammy thoughts on how our souls are speaking through our hands as we laboriously type or write away. It’s not idyllic pictures of nature or photographs of babies and rainbows. What’s inspiring to me, and I think to many other creatives, is learning from others who have made it work. Looking at the writers who live and work around us, the folks that may not have hit it big (yet) but are making a career, pursuing some typically outlandish dreams, and putting cheeseburgers and cupcakes on the table. I draw tremendous inspiration from these folks, our peers in this creative journey that we’ve embarked upon.

And with these words, we kicked off our Thursday series, focusing on the coolest and creative-est freelancers around. Today’s freelancer fits the profile with his combination of guts, talent, and constant surprises.

Keith Ecker is a freelancer new to the fold. A Chicagoan since 2004, he worked for three years at InsideCounsel magazine, a national trade publication for in-house counsel. In June of 2008 he started his freelancing business that focuses on a unique niche: white papers, bylined articles, case studies, PR, and other copy for the legal sector. His niche has translated to major clients and booming business, all on word of mouth and a stellar reputation. In addition to his burgeoning business, Keith is creating a presence in the Chicago comedy world, doing improv, writing sketches, and crafting ridiculously hilarious video bits.

I shared a captivating call with Keith, and talked freelancing, funny shit, and the freakin’ awesomeness of writing as a career. A few excerpts and lessons learned: (Want the whole interview? Scroll down to click through)

On long-held dreams come to fruition (sort of):

I’ve always wanted to be a writer. I remember in 6th grade, for some time capsule project we were doing, we had to say what we wanted to do for careers. I said I wanted to be a writer in Las Vegas. Why Las Vegas? I have no idea. I was a strange 6th grader!

On chutzpah and self-made success:

I’m absolutely doing what I wanted to do. I’m pretty proud of the fact that I’m 26 and in a short amount of time I’ve started my own business. I consider that a big success, and I’m really happy and proud of where my career has gone thus far.

On the big comedy plunge:

I could have easily just shirked away from it, but I knew that wouldn’t make me happy. Eventually I decided I had to throw caution to winds, jump off that ledge, and whatever other writing cliché, and try it. No matter if it ever became or becomes a career, for me it’s an art form and self expression. I need to do it or I will explode.

On breaking rules that need to be broken:

I graduated from the University of Missouri with a journalism degree, and it’s pounded in our heads that marketing and advertising are the dark side. Cross over, and you’ll never go back, ever! I thought for a while it was true. And maybe it is. But I broke that rule. I focus on marketing copy, which pays better than editorial work, takes less time and requires less interviews, and frankly, its often just as if not more informative as editorial work. I never did investigative journalism pieces, and I know many pieces like that are extremely useful. But some of the white papers I write convey just as much information for legal audiences as other editorial articles.

Want to contact Keith? Here’s a few ways to get in touch:

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

QRW: Why freelance?

KE: The main driver was actually comedy. I wanted to have more flexibility in my schedule to do different comedic projects that were taking up more of my free time. So I wanted something to balance that. Add to that the fact that I’m pretty independent minded and don’t work well in a structured hierarchical environment like you have at a magazine, and freelancing was a natural next step.

QRW: What is it about writing that makes you want to get up in the morning, and make a career out of it?

KE: I’ve always wanted to be a writer. I remember in 6th grade, for some time capsule project we were doing, we had to say what we wanted to do for careers. I said I wanted to be a writer in Las Vegas. Why Las Vegas? I have no idea. I was a strange 6th grader!

I remember reading a lot when I was younger, and I always wanted to produce my own work. I never saw it as a chore, but as one of the easiest ways to express myself, my very shy self. Of course, when I got to college I initially pursued electrical engineering. That’s a way to make money, right? It’s practical. But I realized that was not what was important to me. So I decided to pursue my passion.

I’m absolutely doing what I wanted to do. I’m pretty proud of the fact that I’m 26 and in a short amount of time I’ve started my own business. I consider that a big success, and I’m really happy and proud of where my career has gone thus far.

QRW: How do comedy and writing mesh in your life and career?

KE: I do a lot of comedy writing, so it definitely meshes. I write sketches and have done stand up, and generally just do a lot of comedy writing. Freelance for me is marketing or technical, very much like a science. Comedy for me is the opposite. It’s very much abstract, trying to pull things together and make them funny in a creative way. It’s a great balance and the two end up facilitating each other.

QRW: Here’s the million-dollar question for every freelancer. Do you have a routine?

KE: I really wish I had a routine! I really do. Sometimes I wake up at 8, sometimes 10, depending on my schedule. I try to stop working around the same time every day, and shift over to comedy work.

QRW: What do you love about writing, and what do you hate about writing?

KE:It’s definitely a love/hate relationship. Every writer talks about sitting down to the blank page, and how incredibly intimidating that is. Knowing that I have to have a client’s project, or a comedy sketch, completed by a certain day, completed in such a way that I’m proud of the work, is very scary. It’s a lot of pressure. But at the same time, it’s incredibly rewarding.

The actual process of writing for me is like a mental puzzle. I’m trying to figure out how to use words to get my point across. It’s almost like a game, and I really enjoy that element. Once the work is done, then there’s another stage I hate. Going through and self-editing is very hard. I struggle with it, and the idea that I’m compromising what I’ve already written, or that I didn’t reach what I wanted to. Add to that my perfectionism, and editing is a nonstop process.

Once its done and sent off, though? That’s the best feeling in the world. That sense of accomplishment is what drives me to keep being a masochist.

QRW: What writers do you admire and learn from?

KE: As far as comedy writing, I admire a few comedians like Bob Odenkirk. He’s extraordinarily business minded and I can relate to that. My approach to comedy is goal oriented so I feel a kinship there. I also really enjoy Patton Oswalt and his standup. Then of course the old school Steve Martin and Bill Murray are a big influence on my comedy.

QRW: What is it about comedy and comedy writing that compels you?

KE: For a long time I never admitted I wanted to be in comedy. I never really thought of it as a viable option. I love comedians and worship comedy, but I never made a connection that I could be that too. I did some comedic stuff in college, like contributing to their first production of the Queer Monologues and writing for a cabaret show, but they felt like fun little side things.

After college, I didn’t know what to do with my life. I knew I wanted to move to a big city, but not New York. Chicago seemed natural. Then I had this moment where I realized, wait, Chicago is the top place to learn comedy! It took me two years, where I studied the scene, read message boards, and generally got to know people. That’s my journalistic personality coming through. Only after that did I feel comfortable jumping in and producing something.

QRW: It’s a tremendous amount of bravery that you had to have to jump in.

KE: I could have easily just shirked away from it, but I knew that wouldn’t make me happy. Eventually I decided I had to throw caution to winds, jump off that ledge, and whatever other writing cliché, and try it. No matter if it ever became or becomes a career, for me it’s an art form and self expression. I need to do it or I will explode.

Maybe in a few years I’ll move out to LA, but in the meantime I’m seeing what I can do here in Chicago. Is it possible to succeed in comedy here in Chicago? Pursuing that actually suits me, since I tend to produce my own projects. I don’t like waiting around to auditioning for a group or be part of a team or show.

QRW: Every freelancer has successes and failures they can recount. What are yours?

KE: I think my greatest success has just been my ability to generate more than enough business per month to make a decent living! As far as screwups, I have had clients that provide bad direction. So I try to read their minds, and end up turning in something they’re not happy with. That can get frustrating, and it’s really hard not to send an email immediately after their nitpicky one, saying what I really want to say. But I know, especially since I write a lot on eDiscovery and the danger of emails, I have to just sit on my hands, walk away, and then come up with something well thought out and professional later on.

QRW: What rules have you broken along the way to your success?

KE: I graduated from the University of Missouri with a journalism degree, and it’s pounded in our heads that marketing and advertising are the dark side. Cross over, and you’ll never go back, ever! I thought for a while it was true. And maybe it is. But I broke that rule. I focus on marketing copy, which pays better than editorial work, takes less time and requires less interviews, and frankly, its often just as if not more informative as editorial work. I never did investigative journalism pieces, and I know many pieces like that are extremely useful. But some of the white papers I write convey just as much information for legal audiences as other editorial articles.

Marketing writing isn’t this twisted evil thing, always trying to sell. I think it’s a gray area, and an important one.

QRW: All right, favorites time. Who are your favorite writers?

KE: I’m a huge Kurt Vonnegut fan, and have read almost everything he’s written. One of my favorite books of all time is Wigfield by Amy Sedaris, Paul Dinello and Steven Colbert. Such succinct character sketches. Amy and David Sedaris overall are terrific. I also like people like Joseph Heller, the kinds of authors you read in junior high that don’t connect with the rest of the world, that can be depressing. I like that.

QRW: What words do you hate, and what words do you love?

KE: Serendipitous. I love that word.

I hate the word fresh. I hate it especially when its followed by another word that starts with F. Fresh flowers, fresh fruit. Those words can burn in hell.

QRW: Okay then! How about indulgences? How do you indulge yourself?

KE: Besides drug and alcohol abuse??

QRW: Naturally. That’s a given.

KE: Comedy is really my indulgence. It’s my escape and side profession. I’m happiest when creating or collaborating with other people and making something greater than ourselves.

QRW: What do you value in other people, and what do you despise?

KE: I value people that are extraordinarily understanding and empathetic, even when their viewpoints don’t necessarily agree with yours. People can be intelligent but also have different viewpoints. I think everyone has own reasoning for being who they are.

On the opposite side, those that can’t put themselves in others shoes are despicable. That is really a writer trait: you have to put yourself in the minds of other people. You have to become them and see the world through a different lens. People who can’t do that? I don’t understand them.