Challenge,  On Writing,  publishing,  Topic of the Night

Topic of the Night: My Seven Keys of a Challenge

Topic of the Night: My Seven Keys of A Challenge

A number of people have written me and made comments on the blogs about how they like the crazy challenges I come up with. Let me give you, in seven points, my reasoning about any challenge.

1st… I have learned it has to be short term.

My memory and attention span is so short that if I try for long-term challenge that can’t be broken down into much shorter challenges, I will stop cold or just forget, which is more likely to happen.

2nd… It has to be something I haven’t done before, or have an element that makes it new.

Again, short-term attention span. If I have done it, why do it again? Now I have run a marathon when I was thirty, but not run since, so this is a real challenge and I am fighting the age thinking of being 65/66, so it is interesting and challenging every day.

Another example: I wrote thirty-two stories in July a year ago, so this year when I started that I lost interest. I had already done it.

3rd… The challenge has to have a goal larger than just the challenge.

Writing a novel gets me another book, running gets me to finally drop this weight and get healthy. Challenge alone is never enough. There always has to be a bigger goal that I feel has value.

4th… The challenge has to be specific.

For the running, I want to get to that starting point in Las Vegas and feel like I might actually have a chance of finishing that marathon in five hours or so. I might not, but getting to the starting point is the key with this challenge.

Year-long goals of trying to write x-amount of words just fail for me. Not specific enough. Doing twelve novels is too general as well. I keep setting up the long-term challenges for myself and then just forget about them in short order. And announcing them here doesn’t help.

5th… The challenge has to fit who I am at this point in time.

That becomes a problem because at this age, after this many years of writing and publishing, challenges that come up are often just a shrug for me with the thought, “Did that.” So I listen to other writer’s challenges and I know they are good, but seldom do they fit who I am.

6th… I never do a challenge for the feedback from others or any kind of praise.

I do the challenge for me only. Learned that lesson early on.

7th… I always need to have fun.

Doesn’t mean a challenge won’t be tough and take a lot of hours and sweat, but it still has to be fun before I will even think of it. In fact, when I am looking at a challenge, if I hear myself say, “Oh, that would be fun.” I know I am on the right track.


So I hope those help some of you as well in setting up challenges. You need to check in with yourself. See what works for you. I just detailed these out to give you a framework to figure out how a challenge might work for you.

Or not work. Realize that challenges are often bad for some writers. Too much pressure of a challenge can freeze some writers down to a chair full of stone. So make sure that isn’t an excuse to not challenge yourself, but if pressure actually doesn’t help you, then avoid challenges.

But either way, remember to have fun. That really is the secret.


  • Harvey

    Wow. It’s like you were living in my closet. I have a 12-novel challenge for this year, but I broke that down into one per month (finishing one per month, regardless of when it starts). A 96000 word thriller threw me behind schedule a little (two days) but most of my novels are 35000 to 55000, so should be easy peasy. It isn’t. I’m one novel behind on the year (even after not writing hardly at all in February and March), but still certain I can make it up. To complicate things a bit, I’m also back to another challenge (I call it the Bradbury Challenge) of writing and publishing a short story at least once a week. You’ll probably remember my previous streak was 70 weeks. Then, like a moron, I broke it intentionally. So my new “overall” goal is to surpass that, but I don’t look at it that way. Again, I’m writing at least one short story per week. That’s it. Of course, it’s a great deal of fun. And always, I’m grateful to you and Robert Heinlein.

  • Mark Kuhn

    Dean, I have enjoyed watching all your challenges. But I really think the best was Stories from July last year. To me, that book was a tour-de-force. Between all the cool stories and the blogs on your writing process, I don’t think there is any writer who can’t learn something from that.

  • Mark Kuhn

    Dean, you always say how much fun you have when you’re writing. Did you ever begin a story and not have fun with where it was going? Did you ever not like a character you were using in a story?

    • dwsmith

      Oh, sure, it happens, but not much anymore. Happened too often in my media days which was part of what burnt me out.

      But these days I can see no reason to write about anyone I don’t like except as a bad guy in a book. My heroes tend to be nice people, for the most part. The kinds of things I like to read, so I write it.

  • L. N. Nino

    Hi, Dean.

    I have a question that is not about the topic of this post.

    You are an enthusiast of self-publishing, and you recommend that we write a lot and publish a lot.
    The problem is, self-publishing costs money: I have to pay for editing and stock photos.
    For some time it wasn’t a problem at all, but these days, after certain financial setbacks, every dollar counts.
    I can create covers with public domain images (not as good, but hopefully not too amateurish), but I have no one I could
    trust to edit or proofread my texts for free.

    Do you think it is worth to keep publishing the books, even if they have not been proofread or edited by anyone but myself?
    Or should I just keep my writing to myself until I can save enough money to pay for professional editing?

    Alternatively, do you know of anywhere authors can exchange free proofreading of each other’s manuscripts?

    Thank you very much for everything you do for other writers!

    • dwsmith

      L.N., I don’t think you should ever stop getting your work out there. Period.

      We all do the best we can with every story, from the writing to the publishing, but alas, there is no perfect story. And there is no perfect circumstances with money and covers and things like that, either. Sure wish there was, but in forty-plus years of writing and running publishing companies and being involved in publishing, never seen it. Ever.

      So if you are going to be the only one to look at the story because of money, then figure out methods to go carefully through the book. It will take you a little more time, but it does help. For example, cover everything but the one line you are reading. That helps mistakes pop up. Also, read it aloud. That finds more mistakes than you can ever imagine.

      So you will have to spend the time, but then, after you have done the best you can, release it and move on to the next story.

      One nice thing about indie publishing is that if someone reads it and finds a mistake, they will often tell you and you can fix it. Nothing is set in stone in this new world. And as you get better with covers, or find better art for a story, you can always change it out.

      Keep writing and having fun. Getting your stories out there might just help with turning the money situation around.

      • L. N. Nino

        Thanks, Dean! I think your advice make a lot of sense. I sometimes still cling to those fears that things will go awful if I don’t do everything perfectly, and I forget I can just get back and correct things in the future.
        As always, your answers are not only good advice, but also encouraging. Again, thank you very much!

    • Sheila

      There are critique groups online where you can get people to read your work. You’re required to do the same, and most people say they learn a lot about writing by critiquing others’ work.

      You can try to find beta readers, who will read your work and give you feedback.

      You can try to find another writer who will swap stories with you , either to swap edits or to do a cover in exchange for your reading their work.

      You can learn to do covers, maybe, if you have an eye for art and have studied what works in your genre. There are free programs (like GIMP), and images can sometimes be had for free or for a low credit price (some stock art sites are cheaper than others). I got 19 credits for 9.99 a couple of years ago, and ended up with several usable images for less than $1 each, and still have about four credits left.

      Premade covers can sometimes be had quite cheaply, if you search around. New designers will have good deals, and there are often sales. You need to know what works for your genre, so you know what to look for.

      There’s a book called “Self-editing For Fiction Writers” you can get. It has some good information.

      Changing fonts, changing page size, reading backwards, reading aloud, having a device read the story are all often suggested as aids to editing yourself.

      I spend very little to publish my books. I edit, format and do my own covers. Not everyone can do this, I know, but it’s an avenue to explore, at least.

  • Jennifer

    In progress setting up the September through December challenge for 2016 (I know it’s September, it’ll just have to start after labor day weekend). Still deciding the number of novels and which of the endless list of novels begging to be next and acting like cats wanting tuna will be chosen. Also how to throw in some sleep here and there. And do the stuff I’m contracted to do. And run and hike and feed blue jays. And have a secret project launching midmonth. And happier about all of it than I’ve been since I stole your 10 novels in 4 months challenge last September. Thank you for all the shiny ideas, encouragement and examples, and may the odds be ever in your favor with your current challenges!