Here at QRW I advocate one simple rule: break the rules. It’s fun to think about, to write about, and to dive in and do. It’s super fun when freelancing and creative success result.

But here’s the thing: breaking rules can get lonely. You start seeing things differently. You start questioning more. You feel like there are few people to commiserate with and to turn to for advice in this brave new rule-breaking world. Eventually you start identifying with the crazy billboard-wearing dude ranting through a megaphone about robots taking over the White House. (He’s a Chicago fixture. And he’s freaky.)

That’s when it helps to find inspiration through other writers and creatives who have broken the rules, and lived to encourage others to do the same. Every week I profile some of our famous and groundbreaking Writers Who Matter here at QRW, and as the week wanes we look at the writers who live and work and break rules around us, the folks that may not have hit it big (yet) but are making a career, pursuing some outlandish dreams, and feeding their pets/kids/selves. I draw tremendous inspiration from these folks, and feel a little less lonely in this creative journey.

Today, we look at Charlie Gilkey, blogger, productivity guru, PhD candidate, philosophy teacher, Iraq vet, and one hell of a supportive friend. Charlie writes at Productive Flourishing, the blog that’s for…

…people who are sick of learning a new productivity system every month and not getting any more productive…It’s for creative people who will throw up if they see another bulleted list or “Top Ten Ways To Hack Your Mousepad”… and for everyone who wants to spend less time doing what they hate and more time doing what they love.

Charlie throws aside the tired crap about productivity, and gets to the essence of what helps us be creative and flourish. With a perspective informed by an obsession with philosophy, combat experiences, and an insatiable curiosity, he’s gained an ever growing and devoted audience.

I met Charlie last week for a spirited IM discussion, and talked writing, creativity, rule breaking, and multi-year plans. It became quickly apparent I could use some of his “un-ass” yourself coaching to get my shit together, and so might be groveling at his doorstop soon.

A few excerpts from our interview: (Scroll down to click through and read the entire interview)

On why writing is supercalifragilisticexpealidocious:

I enjoy writing because it’s part of my creative process, and because it helps me discover new things about myself and the world around me. I find that as I write more, I have richer and more insightful ideas - and those ideas let me connect with others in ways that I really hadn’t experienced before.

On getting your ass moving:

I do understand block, but it’s mainly because a writer is trying to force their creative energy on something that they shouldn’t be at the time. So, a few ways out of that situation. One, write about something that you feel like writing about. Two, read something that’s theoretically related but different than what you’re trying to write about. Three, do some of the other crap you need to do, but don’t want to do, that’s not writing (otherwise known as productive procrastination).

On making things easier:

I really, really enjoy writing for non-academics. I enjoy bridging the gap between what people think are really hard ideas and the ways in which those ideas manifest themselves everyday for each of us.

On inspiration and excoriation:

The writers I admire most are the ones who have used their unique capacities to help themselves overcome struggles or roadblocks … I absolutely detest rhetoricians that use their talents to confuse, control, scare, and cheat people. I’ll not name names here, for they are all too common in the many spheres of our lives. It’s a vile waste of human potential.

Be sure and support Charlie in the following hotspots:
Productive Flourishing
“Un-Ass Yourself” Creative Coaching

Like this post? Well geez, how could you not?? Tell us about it in the comments, and don’t forget to subscribe by RSS or email for all future writer profiles…

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

QRW: Yo Charlie! You ready for me to grill you??

CG: Heyhey! Sure am. Remember: I’m a vet, and if you misconstrue anything I say, you’re unpatriotic (/snark)

QRW: Good to remember. So - tell me why you got into blogging, and why you enjoy writing.

CG: I got into blogging for two reasons: to have a creative outlet, and to help academics struggling with productivity. I quickly learned that blogging didn’t really fit the academic audience, but that I loved blogging.

I enjoy writing because it’s part of my creative process, and because it helps me discover new things about myself and the world around me. I find that as I write more, I have richer and more insightful ideas - and those ideas let me connect with others in ways that I really hadn’t experienced before.

QRW: How do you see writing fitting in to your life? What I mean by that is this - you’re in school, you’re teaching, you’re working on the house (!), you’re still in the Guard. What role does writing serve you, and does money play into that? Should it?

CG: Writing is a critical component of everything I do. As a professional philosopher, the written word is still 90% of communication. While I’m not teaching right now because of my new position as the Assistant Director of an Ethics Center, I still collaborate heavily with my colleagues (in writing) and am working on research grants with them (more writing).

The strongest bullets on my evaluations as a Guard officer center around my ability to write and express ideas (through operations orders, verbal orders, and presentations.) My career as a military professional would have a completely different path were it not for my writing skills.

Money, unfortunately, does play a big role in what I write, but mainly because I have a lot of things going that I can’t quit right now due to finances. So I have to use my talents in ways that I find enjoyable yet that makes money.

QRW: How does Productive Flourishing fit in to this?

CG: As surprising as it may seem, PF generates income - and this increases every month. But more importantly, PF gives me outlets, opportunities, and ways to develop myself that I would not have without it. Ironically, due to my learning HTML and CSS while messing around with PF, I was able to land my current position in the offline world. Due to a lot of my interests and reading related to PF, I’ve learned a lot of skills that help me in that position, too. The most enjoyable thing for me has been the community of bloggers and friends that I’ve met and learned from throughout the experience (such as yourself). I’m inspired and challenged daily by this community, and I actually owe them a lot for my advances in creativity and insight.

One of the possibilities that has manifested is the Creativity Coaching service. Were it not for PF, I never would have been in the position to do that, and I absolutely love it! It took a lot of pressuring from a few friends to hang the shingle, but I’m really glad I did.

QRW: Do you have any goals on where PF and the writing you do there will take you? Any big dreams that involve writing?

CG: Actually, I do have big dreams that involve writing. At some point in the future, I will write a book. The hardest thing for me right now is deciding between the audiences that I write for. On the one hand, I’m a trained academic, but I’m not really motivated to write for academics. I really, really enjoy writing for non-academics. I enjoy bridging the gap between what people think are really hard ideas and the ways in which those ideas manifest themselves everyday for each of us.

Another book I’ve been thinking about starting revolves around a lot of the stories I’ve heard and experiences I’ve had while growing up. While that sounds really lame, my friends and new people I meet always enjoy the yarns that I spin. What they most enjoy is that most of them are either absolutely true or based heavily on the truth. It would be written mostly in the Southern Lit style, given that that’s the milieu most of them come from.

I’ll start on that project once I’ve cleared a few other hurdles, though. I might start on it in 2010.

QRW: What I find so fascinating about other writers, my peers in this blogging world and the freelancing world, is that we all these kinds of writing dreams. And it’s absolutely awe-inspiring when the pieces fall into place, and those dreams start looking more realistic. I think you might be there, my friend.

Since this series is, in part, about how we writers inspire ourselves, and drag our ass into the next difficult but ultimately rewarding task, I want to know what inspires you. Do you have favorite writers? A favorite style? A surefire way to break that misnomer, writer’s block?

CG: The only time I’ve ever had block was when I was trying to force myself to do something I didn’t want to do. While I moan about having too many diverse irons in the fire, it’s that diversity that keeps my ideas flowing. Between reading and writing philosophy, marketing books (I particularly like Seth Godin of late), books on creativity, writing, and graphic design, Ruby on Rails training books, and classical literature, it’s very rare for my source of ideas to dry up. And that’s not even mentioning the blogs I read and the people I talk to about creativity and productivity.

That said, I do understand block, but it’s mainly because a writer is trying to force their creative energy on something that they shouldn’t be at the time. So, a few ways out of that situation. One, write about something that you feel like writing about. Two, read something that’s theoretically related but different than what you’re trying to write about. Three, do some of the other crap you need to do, but don’t want to do, that’s not writing (otherwise known as productive procrastination).

So, in some senses, I’m going against the “force yourself to write what you’re supposed to” conventional wisdom. But in reality, I’m just recommending doing something that’s helpful during the preparative and incubation phase of the creative process.

QRW: I like it. Makes absolute sense, and helps “warm up.” Let’s change tacks. What do you love and hate about writing?

CG: Writing, for me, is about two things: discovery and getting ideas out of my head. I discover a lot of what I think by writing or talking about what I’m thinking - or at least I understand it more by writing and talking about it. But there are other times when I’m pregnant with ideas and I really just have to get them out. And that’s what I hate about the writing process - I don’t work effectively in twenty to thirty minutes. My creative time blocks are between 90 to 180 minutes, depending on energy levels and such. If I know that I’m going to have to transition to the next activity in a half-hour, the right-brain starts working and the left-brain comes on. So it can be really frustrating for me when I work up to the point where I’m bursting with ideas, and then I’m either interrupted or start disengaging because of meetings and eating.

QRW: Nicely put. What writers do you admire? What writers do you detest?

CG: The writers I admire most are the ones who have used their unique capacities to help themselves overcome struggles or roadblocks (Frankl, Martin Luther King, Russell). It’s an occupational hazard of being a philosopher that I admire people who can take really complex ideas and express them simply, especially if they’re ones that actually make a difference in people’s lives (William James, Immanuel Kant, Plato, Aristotle, Locke, Jefferson, Russell, Whitehead).

I absolutely detest rhetoricians that use their talents to confuse, control, scare, and cheat people. I’ll not name names here, for they are all too common in the many spheres of our lives. It’s a vile waste of human potential.

QRW:Absolutely. Do you have a day-to-day schedule, or does it vary widely? I ask because freelancing is so different everyday, and I assume with all your stuff going on it’s the same. Do you have a set time that you write for the blog?

CG: I used to when I was teaching, but there are a lot of variables in my job that makes me shift time and work blocks around. I now tend to think in creative blocks of time, because I know when I’m usually going to have a lot of creative energy and when I’m not. So I may plug some blog writing in a given block on Monday and then use that block for what I do at work on Tuesday. I have a lot of latitude, but to make it work I usually work 10 hours or so a day to spread things out. It’s really hard, though, because out of that I’m lucky to get five or six hours of creative work done.

QRW: All right - how about writing screw-ups - had any you’ve learned from? And how about your greatest writing successes?

CG: I’ve written a few operations orders and slipped in some wrong details, but most of it was worked out before anyone was injured or killed. Lesson learned: always check times, dates, and names when it matters, and it always matters when you think it won’t.

I’m probably too modest to mention great successes, but I think that I’ve done some excellent writing that helped people understand facets of their selves that they didn’t understand before. It really is awesome to have readers and friends write or call and say “You know, I tried the heatmapping thing, and it worked!” or “I’ve actually started doing less and getting more done - I’m much happier now.” Those types of things are what I write for, so maybe it’s the little daily successes that become a great success over time.

QRW: I think that is the very definition of success in many ways! All, quickfire Proust-like question time. What are your favorite books?

CG: How many do I get?

QRW: As many as you like…

CG: I’ll limit it to ten…
Plato’s Dialogues
Aristotle’s Nichomachean Ethics
Kant’s Groundwork
Milton’s Paradise
Louis Menand’s The Metaphysical Club
Tolkien’s Lord of The Rings
Anthony’s Immortal Incarnation Series
Shakespeare’s Tragedy of Julius Caesar
William James’ Pragmatism
Seth Godin’s The Dip

Oops, there’s more: 1984, Brave New World, Fahrenheit 451, Heart of Darkness, Lord of the Flies, The Iliad, His Dark Materials… Okay, I’ll stop there! One of these days I’ll post a “Stuff I’ve read” list somewhere.

QRW:That last list was especially good. I love me my sci-fi and dystopian novels. What’s your favorite music and artists?

CG: Jack Johnson, Amos Lee, Blues Traveler, Alice in Chains, Coheed and Cambria, Iron and Wine. A lot of Classical that I can’t name. Red Hot Chili Peppers, Indigo Girls, David Gray, Dave Matthews.

QRW: Do you have a favorite trip?

CG: When my wife and I backpacked Europe for the summer. We stayed in Greece for 10 days or so. That’s still recounted as the best time in our lives.

QRW: Nice. Favorite word(s)?

CG: Are we counting words I’d like to be favorite or words I say all the time? If it’s the latter, it’s the trite “sweet”, “cool”, and “awesome”. Besides that, I really like the word “synergy” - thinking in terms of synergy and not in competitive, zero-sum, or one-way value helps make great relationships with people.

QRW: How about words you hate?

CG: Racial, sexist, homophobic, and xenophobic slurs. I need not go through the list, I hope.

QRW: Not at all. I grew up in Iowa. Last question - How do you take a break? What’s your indulgence?

CG: Eating out with my wife. Unfortunately, it’s not good for the weight and wallet, but it helps us reconnect since we’re not distracted by other things. She has a lot of irons in the fire, too - so it’s nice to sit back and relax. We also enjoy camping together for the same reasons, but we really haven’t had the time, energy, and terrain to do a lot of it for a while.

QRW: Terrific! Hope you enjoyed this, cus I did.

CG: Loved it!