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Jun 1, 2015

How Copywriter and Entrepreneur James Chartrand (of Men with Pens) Writes

Writing can be a lonely sport, whether you re running a digital agency, or slaving away on the next great novel. In this week s episode we ll examine the writing process of James Chartrand, a prolific online publisher, copywriter, and digital entrepreneur.

It s hard to settle on a specific title for my guest because James wears so many different hats — founder of the popular blog, web design, and copywriting agency Men with Pens — as well as an author, educator, and writing coach.

James s many accomplishments have been chronicled in such high profile publications as Forbes, Newsweek, and The New York Times, and we got the chance to sit down and talk shop.

In this 26-minute file James Chartrand and I discuss:

  • How Wearing Many Hats Can Boost Your Productivity
  • Why Simplicity Helps You Stay Focused
  • The Cathartic Feeling of Crumpling Up Post-It Notes
  • The Hardest Question in the World
  • Why Good Ideas are Like Fishing
  • The Difference Between Making Friends and Making Money
  • Why Every Writer Should Have a Therapist

Listen to The Writer Files: Writing, Productivity, Creativity, and Neuroscience below ...

The Show Notes

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The Transcript

How Copywriter and Entrepreneur James Chartrand (of Men with Pens) Writes

Kelton Reid: This is Rainmaker.FM, the digital marketing podcast network. It s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at

These are the Writer Files, a tour of the habits, habitats, and brains of working writers, from online content creators to fictionists, journalists, entrepreneurs, and beyond. I m your host, Kelton Reid: writer, podcaster, and mediaphile. Each week, we ll find out how great writers keep the ink flowing, the cursor moving, and avoid writer s block.

In this week s episode, we ll examine the writing process of James Chartrand, a prolific online publisher, copywriter, and digital entrepreneur. It s hard to settle on a specific title for my guest because James wears so many different hats.

She s the founder of the award-winning blog, web design, and copywriting agency Men with Pens as well as an author, educator, and writing coach. James s many accomplishments have been chronicled in such high-profile publications as Forbes, Newsweek, and The New York Times. We got the chance to sit down and talk shop.

In this file, James and I talk about how wearing many hats can boost your productivity, why simplicity helps you stay focused, the cathartic feeling of crumbling up Post-it notes, why good ideas are like fishing, the difference between making friends and making money, and why every writer should have a therapist.

James, it is a pleasure to have you on The Writer Files finally.

James Chartrand: Yeah, no kidding. I m excited to be here. It s cool to meet you and connect with you as well. I m really looking forward to this.

Kelton Reid: Excellent! Well I say we dive into the file and get to the bottom of who you are and what your area of expertise is as a writer, if you care to expand on that.

James Chartrand: I can. I m James Chartrand. I own Men with Pens, which has a top-10 blog for writers — well, so it s been named several times. I suppose that still counts. I also teach a writing course for business owners at Damn Fine Words. I ve been around for a decade in the industry. I guess I m known as a copywriter. I consider myself more of an entrepreneur who writes. I ve also been called a pro blogger. I ve written several books or ebooks — digital books, whatever you want to call them. I m a teacher — general help, advice. I do lots of things. I did some fiction too once upon a time.

Kelton Reid: You wear a lot of hats.

How Wearing Many Hats Can Boost Your Productivity

James Chartrand: I do. I love my hats. The more hats, the wiser I become.

Kelton Reid: Where can we find your writing?

James Chartrand: You can find my writing at You can find me on Twitter, @MenwithPens. You can also find me at Damn Fine Words. I have a lovely newsletter there that I really love. I teach there as well, so I get to have one-on-one contact with a lot of people that become my students, which I really like.

Kelton Reid: What are you working with presently? Can you share with us?

James Chartrand: Everything. Everything and anything. Like any good entrepreneur, I have 40 projects on the go at any given time.

I have three big ones right now. I have an ebook writing course inside Damn Fine Words. I m doing the 2.0 version of that. I m running through everything in cleaning it up and making sure that it s as tight as it can be. I m reworking my entire email marketing strategy at Damn Fine Words. I ve learned some new and cool things recently, so I want to test those out and experiment with them. I ve given myself a challenge of writing 52 posts for Men with Pens. I ve been a little slow on posting in 2014, so I want to get back to that and redevelop that habit of regular posting.

Kelton Reid: So you re a little busy these days?

James Chartrand: I m always busy. It keeps me out of trouble, eh?

Kelton Reid: Of course it does. Let s dive into your productivity with all these balls that you re juggling. How much time per day would you say that you read or are doing research?

James Chartrand: I read for pleasure about an hour a day. At the end of the night, just before bed, that s my pleasure-reading time. That s really important to me. It lets me unplug, and it gets me in touch with some really good fiction and some really good books that I have.

In my day-to-day work, I m lucky I work maybe four- to six-hour days, so I pack a lot into those four to six hours. It s tough for me to say how much of that time is reading and how much of that time is working. I tend to multitask and do both at the same time. I know it s a terrible habit, but you can t break me of it.

If I had to give it a number, I d say I guess I m reading maybe two of those hours and writing two to three hours. That comes up to about a five-hour work day. That would work.

Kelton Reid: Before you sit down to write, do you have any pre-game rituals or practices to set the desk?

Why Simplicity Helps You Stay Focused

James Chartrand: I have a super-simple ritual. I wake up every morning at about 5:30, 6:00. I have my coffee. I do not write. I am just waking up at that time. At about 7:30, I get my kid ready for school, put her on the school bus. Then I just I sit down for a few minutes. I think about what I want to work on right after I get up. I get up. I have a smoke. I hit the keyboard, and I m off to the races.

Kelton Reid: Do you have a peak productive time of day would you say and/or a specific locale where you get the most amount of writing done?

James Chartrand: I just recently built a custom home — not by myself. I had a general contractor do it. That s not in my skill talents yet, but you never know.

I have a beautiful office that I absolutely love. I ve made a point that this is the only place where I write. Its job is to make sure the writing gets done here. I ve trained myself that if I m going to write, I come into my office. My best hours for writing, I d say, are between 9:00 in the morning and 11:00. I get a lot of writing done there. I m awake, I m sharp, and my creativity is high. I can do a lot.

When my work is done, when my writing s done, I m out of the office. This is the only place that I ve chosen to write for now.

Kelton Reid: Are you someone who likes to listen to music while you re writing, or do you prefer silence?

James Chartrand: Oh God no! Silence. Oh my goodness! I have to write with silence. I find any kind of noise very distracting. I ve tried music. It just doesn t work. I find it too distracting for me.

It s like words upon words. If you listen to the lyrics, it distracts from what you re trying to do with the writing. I do sometimes keep the TV on very low so that I hear a murmur in the background. But it s more like white noise than anything.

Kelton Reid: How many hours per day would you say that you re actually getting words onto a page, excluding email?

James Chartrand: To be honest, I d say two. That block between 9:00 and 11:00 that is really highly focused writing. I dive down. I m in the zone. I really don t know what s going on around me until I come up for air. That seems to be about a two-hour period.

Kelton Reid: Do you ever take a day off?

James Chartrand: Weekends. I didn t use to. I used to work 18-hour days, until one day I fell asleep at my desk and hit my head. It hurt so much that I learned my lesson. Now I make sure that my evenings are off, and I definitely don t write a darn thing on Saturday and Sunday. I find it keeps me a little bit motivated. By constraining yourself and limiting yourself to not writing, you re that much more eager to get back to it on Monday.

Kelton Reid: Have you ever come up against writer s block?

James Chartrand: Oh my goodness! I don t actually believe in writer s block because that s turning it into a symptom, a thing, a virus you can catch, and that s not the case. Writer s block is usually your own thoughts and mentalities getting in your own way.

Have I had that happen to me? Oh for goodness sakes! All the time. I ve had periods where I can t write at all. I ve had periods where I don t know what to write. I ve had periods where I don t feel good enough. I ve had periods where I hate writing because everything has to be so epic, and I just can t live up to that standard. It s all my own personal thoughts getting in the way. You deal with them, and you get rid of them, and you keep writing again.

Kelton Reid: Let s talk about your workflow over there. What hardware or typewriter model are you presently using?

James Chartrand: I have a beautiful 27-inch Mac that I bought about four years ago, so it s time to be replaced pretty soon. I have a 17-inch HP laptop in the kitchen just to catch up on email and stuff.

Kelton Reid: Would you say that you re going to a specific software or a set of software that you use most for your kind of general workflow and writing?

James Chartrand: Yeah, I use Word all the time. I just love Word. I m so familiar with it, and I can do anything with it. I just use that all the time as my go-to thing. I m a little bit of an old-school traditionalist, so I shun all these new bright, shiny tools. I have just started to learn that Evernote actually can be effective, so I m teaching myself how to use it a little bit. It s good for keeping lists, so I like that.

Kelton Reid: I have heard that it is useful, and I m actually using it a little bit more and more each day, I find.

James Chartrand: Yeah, it s one of those things where you have to consistently use it. Otherwise, you just don t because there s other ways that work just as well.

Kelton Reid: Do you have any organizational hacks that you can share with us?

The Cathartic Feeling of Crumpling up Post-It Notes

James Chartrand: I don t. A pack of Post-it notes and a pen — keep several of them around the house in all kinds of strange places. When you re standing in the shower and you have that great idea, you can just reach out your hand and scribble something on your Post-it note and dry it off later. That s my go-to. It s Post-it notes all the way for the win.

It s really satisfying when you finish something — you can crush them up and toss them into File 13. I get victory out of that.

Kelton Reid: That is a cathartic feeling, isn t it?

James Chartrand: I m all about the wins.

Kelton Reid: I think if we could find you some waterproof Post-its that would be a fun gift to send over.

James Chartrand: I should learn to write on the shower walls. I haven t realized yet that you can actually do that. I keep forgetting that you could just take your finger and scribble something there, and it would actually stay for a while. If it goes away, it will come back the next day on the next shower, but I haven t trained myself yet.

Kelton Reid: Do you have any best practices for beating procrastination?

James Chartrand: I try not to procrastinate because I realize that this is completely a first-world problem. You only procrastinate when you can procrastinate. I try to get honest with myself, and I fix my shit. If something s holding me back from doing what I m supposed to be doing, let s get real about it. Let s be honest. At the very least, be aware of what s going on in your own head. That s what I try to do all the time.

That said, I do procrastinate, absolutely. My two best solutions are a couple of sessions of Candy Crush, Soda Saga — let s go for it.

Start with something really small that would only take 15 minutes to do. I actually keep a list of tiny little tasks like that for those moments. I find that if you get started on one little thing, it s pretty easy to go to the next and the next and the next. Before you know it, you ve beaten it.

Kelton Reid: I love that. How do you unplug at the end of a long day of writing?

James Chartrand: A beautiful glass of red wine. That is my treat. Just one, mind you, just one. I used to have more, but let s not go there. I have my glass of wine. I go outside. I take a deep breath, and I feel grateful for what I have. I feel grateful for what I ve accomplished. I find that makes a really big difference in my productivity and in my outlook.

Afterwards, it s just supper. It s sitting on the couch watching some mindless TV. Deadliest Catch and Survivor are the latest things that I m going to. It s brainless stuff, and that s about it.

Kelton Reid: Just a quick pause to mention that The Writer Files is brought to you by the Rainmaker Platform, the complete website solution for content marketers and online entrepreneurs. Find out more and take a free 14-day test drive at Rainmaker.FM/platform.

Let s talk about creativity, and if you don t mind, your definition of creativity.

The Hardest Question in the World

James Chartrand: That s the hardest question in the world. Can I just say that? That was a killer. I thought about this all week, and the only thing I can come up with is for me, creativity means the ability to come up with something out of nothing in surprising ways.

I thought about it over a wide range of artistic things or those times where I looked at someone s stuff and said, Oh my goodness! That s so creative. It s just because they surprised me so much — that they really had nothing to work with, and what they created ended up being so surprisingly good. That s the best way I can define it.

Kelton Reid: In your line of work, I think creativity is probably pretty important to keeping those ideas fresh, no matter what type of project you re working on because again, you wear a lot of different hats. Do you find that you need some specific creative inspiration? Do you have a specific muse at the moment that s driving your creativity at all?

James Chartrand: It s more of a motivation than an inspiration. It s definitely my business, my lifestyle. What I have achieved, I want to keep it. And I definitely want more of it. It s simply the fact that if I m not creative, I will not have what I have, so you d better keep it going.

Another way that I do find a lot of my inspiration for my creative ideas is that I look to the real world. I go out on the streets. I look at people with brick-and-mortar businesses. I watch what people do in positions of customer service or in their jobs.

There s a lot of analogies that can be drawn between real-world stuff and online stuff, or things not to do and things you should do, or different ways of applying certain marketing strategies. I get a lot of inspiration from that as well. I think my earlier posts reflect that quite a bit.

Kelton Reid: Let me ask you another question about creativity. When you do you personally feel the most creative?

Why Good Ideas Are Like Fishing

James Chartrand: I don t know. I guess it s when I am not actually working to be creative, when it s not a job. I find it much more difficult to be creative when I m here and trying to be creative. It happens when you get away, and you re in some completely other environment having some other totally unrelated experience, like you re skiing in the winter and suddenly you get this most brilliant idea. I guess that s the way that ideas go. It s a bit like fishing. You just have to be in the right part of the lake to catch the big one.

My best ideas have come when I m not actually trying for them and I m completely away from any possible manner of capturing these ideas on pen or paper, which is usually why that big fish I just caught slips away.

Kelton Reid: What, to you, makes a writer truly great?

James Chartrand: I have to look at the writers who make me forget that reality exists, the writers who make me forget that I am reading, that I m sitting in this chair, that I m looking at a screen, or that I m holding a book, or that there s a world around me. They re the people who make me forget my reality and bring me into theirs. That, to me, is just sublime.

Kelton Reid: Absolutely. Who are a few of your favorite authors at the moment?

James Chartrand: I m going to list some fiction authors because I don t think I ve yet found any business authors that I really like. I ve found some business books that I like, but I m not sure if I like the authors themselves.

I like Patrick Rothfuss both for his writing and for who he is as a person. He wrote The Name of the Wind, which got really popular and became a bestseller. I think he s brilliant all around. What he does and who he is and how he presents himself is fantastic.

I love Anne Bishop. I don t know of her — I know her books. Her ability to create a world and bring characters to life is so simple and yet so effective. I ve found myself wanting to know her characters like people. I nearly cry when one of her books is over because I won t hear the stories of that person anymore.

I also like Scott Lynch who wrote the Locke Lamora series. He has great characters as well, but he s so clever in everything he does. His storylines, his plots, — I can t even imagine how he comes up with these things. They re so complex and so beautiful. Those are my three.

Kelton Reid: Can you share one of your own best-loved quotes with us?

The Difference between Making Friends and Making Money

James Chartrand: I might be hated for this one. It s a quote from Kevin O Leary of Dragon s Den and Shark Tank who is known to be an aggressive A-type. He said, I m not here to make friends. I m here to make money. I think we need to get in tune with that. I love that quote. It is so cold and unthinking, and cruel even, but it reminds me not to sit here and be a writer and sensitive and caring and generous and give the shirt off my back. I am here to run a business. It s a little bit of my guiding star when I find myself giving too much away or feeling like I m not taking care of myself, but I m taking care of other people.

This one reminds me to get back to what I m doing here which is running a business. I am here to make money. You can be generous and you can be business-like together. It reminds of that an awful lot.

Another one I really like is in the movie Hercules, the cartoon Disney one. It says, Being famous isn t the same as being a true hero. Zeus said that to Hercules. I like that one because it reminds me tone down the ego. Whoever is famous out there, it doesn t necessarily mean that they re true heroes. The same applies to me. No matter how famous I am, I have to remember to be a true hero at the end of the day.

Kelton Reid: Let s do a couple fun ones. Who is your favorite literary character?

James Chartrand: Locke Lamora. He is so witty and clever and charming and personable and silly and foolish and brilliant all at the same time. I want to be him.

Kelton Reid: If you can choose one author, living or dead, for an all-expense-paid dinner to your favorite restaurant in the world, who would you choose? Where would you take them?

James Chartrand: This question always make me laugh because I don t want to fly anywhere. I m an introvert. Actually going out to meet people is a big deal, and I d probably want to stay at home. Do I have to really go out for supper with these people?

It would be fun to have a beer with Patrick Rothfuss one day just because he s so witty and sharp and clever. I wouldn t want to talk about anything else but whatever rips off our head. That would be a great casual conversation to have.

Kelton Reid: Coo. So you can order takeout and have him over for a beer?

James Chartrand: Bingo! He can fly here.

Kelton Reid: That s right. We ll fly him in.

Do you have a writer s fetish? I know a lot of writers do — I do, admittedly — somewhere hiding there in your office.

James Chartrand: I don t. I have nothing. I ve got nothing, man. I made a room with a view. That doesn t really count. I have a picture of a fox behind me to remind me that I m a clever person. I have a little figurine of Sawyer from the television series Lost. If I press the button, he says, There s a new sheriff in town. Y all best get used to it. That s all I ve got!

Kelton Reid: That s good enough for me.

James Chartrand: I think I keep my fetishes for other areas of my life.

Kelton Reid: Very good.

James Chartrand: Oh that didn t sound good. I did not mean that.

Kelton Reid: Back up. We ll edit that out, or we ll leave it in.

Who or what has been your greatest teacher, would you say?

James Chartrand: Adversity. I wouldn t be where I am today, I wouldn t be the person I am today, I wouldn t have learned the things I ve learned today without adversity. I hate it that you have to become a better person by living through hard times or difficult experiences, but I love it for everything it has taught me and everything it has made it. So — adversity.

Kelton Reid: Can you offer any advice to fellow writers out there about how to keep the ink flowing and the cursor moving?

Why Every Writer Should Have a Therapist

James Chartrand: I think cursors stop moving and ink stops flowing when people get too wrapped up in themselves and their problems. Truthfully, just give yourself a break. It doesn t matter if stuff is good enough or not. It doesn t matter if anybody likes it but yourself. Even if you don t like it — secretly, come on, you do. Give yourself a break about this.

Get over yourself. Get over whatever s holding you back. Get a fix for it. Get a therapist. Every writer should have a therapist. Don t give a shit about it. Just do what you want to do, and nothing else really matters at the end of the day.

I see so many getting caught up because they give too many shits in the wrong places. I think it s important to be selective with what you do and how you do it.

Kelton Reid: Well put. Where can fellow scribes connect with you out there?

James Chartrand: It would be great if people could connect with me on Twitter because I love a good conversation. Boy oh boy, we used to have some good ones on Twitter back in the days. I wish that was there now. It s really lacking. There s a lot of links. I m really trying to get back in touch with people. It s hard. I need people to chat with. If people want to get in touch with me, start a discussion. Say something smartass my way. I ll answer back. It ll be my pleasure. Game on. Bring it. You can find me at Men with Pens.

Kelton Reid: Thank you so much for coming on to the Writer Files and teaching us a little bit about your process. It really has been a pleasure.

James Chartrand: You are very welcome, and I m stoked to have been a guest. It was great to chat with you, and it was great to do this, so thank you. Thank you to everyone listening for putting up with my rambling.

Kelton Reid: Absolutely, and it wasn t. It didn t sound like rambling on this side. It sounded like some really wise words.

James Chartrand: There you go.

Kelton Reid: Cheers.

Writing can be a lonely sport, whether you re running a digital agency or slaving away on the next great novel. That s why it s always so enlightening to talk to other writers about how they deal with the stuff that lives in their heads. If you re not familiar with James Chartrand s fascinating story, you can find a great interview with her by Demian Farnworth on the Rough Draft podcast at RoughDraft.FM. I will link to that in the show notes.

Thanks for tuning in. For more episodes of The Writer Files and all the show notes, or to leave us a comment or a question, drop by WriterFiles.FM. Please subscribe to the show on iTunes. Leave us a rating or a review and help other writers to find us. You can find me on Twitter @KeltonReid. See you out there.