Reader Friday: Overcoming Your Greatest Obstacle

Reader Friday: Books to help you overcome your greatest obstacle

by Dale Ivan Smith

Writers face many obstacles—time, the day job, family responsibilities, health challenges, etc. Then there are publishing challenges, be it the traditional path, small press, or self-publishing.

However, in my experience, the greatest obstacle we face as writers is ourselves. Whether you consider writer’s block real, there are mindset issues such as managing expectations, procrastination, fear of failure, and many others. Getting out of our own way can make all the difference in our own writing.

Fortunately, there are books to help you get past your greatest obstacle. This retired librarian still likes to provide multiple resources, so here are three:

 The War of Art, by Steven Pressfield. Pressfield spent decades struggling to write, and then toiled trying to break-in as a screenwriter, finally succeeding when he co-wrote the story for the 1986 film, King Kong Lives, the sequel to the 1976 reboot of the original. Unfortunately, King Kong Lives bombed at the box office. Pressfield came to recognize that the biggest obstacle to our succeeding as writers is what he names Resistance, that part of ourselves which holds us back from engaging in a new endeavor that might change our lives, especially creative endeavors like writing. Each brief chapter provides an insight patterned after Sun Tzu’s The Art of War. Pressfield breaks the book into three parts: Defining Resistance, Combating Resistance, and getting Beyond Resistance.

The Mental Game of Writing, by James Scott Bell. The Killzone’s very own James Scott Bell’s provides a tool chest of tips and strategies to help you with your mindset as a writer. He covers the gambit from the importance of deciding to become a writer and defining success for yourself, to creativity, production, joy, to not comparing yourself to others, dealing with stress, being inspired, and many more. Jim packed a terrific amount of very practical advice into this book. It’s a resource you can dip into repeatedly after you’ve read it, to look for help in any area that is an inner obstacle for you. Reading this book was like having Jim as a writing mentor, offering suggestions and tips to improve your mental game.

 Breakthrough, by J. Dharma Kelleher. Thriller writer Kelleher looks at creative self-doubt (akin to Pressfield’s “Resistance”) and how it affects our writing. Right off the bat, she provides tools to get past it: meditation, affirmations, and the power of re-framing how you look at an issue you’ve encountered in your writing or publishing. She discusses the importance of your health, understanding your own creative process, focusing on the work rather than the results, dealing with feedback, understanding the “delusion” of paying attention to reviews, and much more. She provides helpful advice, tips, and an extensive list of additional resources.


Now it’s your turn. Do you believe we writers are our own greatest obstacle to our own writing? What books or resources have helped you get out of your own way as a writer?


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About Steve Hooley

Steve Hooley is the author of seven short stories published in four anthologies, a Vella serial fiction, and is currently working on the Mad River Magic series – a fantasy adventure series for advanced middle-grade to adults. More details available at:

35 thoughts on “Reader Friday: Overcoming Your Greatest Obstacle

  1. The book I return to again and again is Jack Bickham’s Writing Novels That Sell.

    The piece of advice that’s done me the most good is Ernest Hemingway saying something to the effect of “quit writing when you know what’s going to happen next and you’ll never get stuck.”

    My mental resource that’s great fun is a little bar in Key West called The Hideaway where my writing mentors hang out. This tickles me because I am not a bar person, but it works. I never know who’s going to be there. It started out with me and Erma Bombeck having lunch one day with an unexpected aside from Ernest Hemingway, who was playing pool nearby. (He still asks me if I’ve read his books yet. I haven’t, but I swear I will). Tolkien helped me plot out my trilogy the other day. If I’m not sure which story I should work on or which direction to take I pop in there. Someone’s always ready to help and it’s usually someone I’m not expecting (though Hemingway is pretty much a fixture).

    • Great resources, Cynthia. Bickham’s books on writing are always insightful. Hemingway’s advice is one I try to follow myself. I love your mental resource! A writer’s bar you can visit anytime you need, is a handy to thing to have at the ready.

  2. Dale! Welcome! Easy question, easy answer: Atomic Habits by James Clear. It’s not just for writing. The driving point of the book is to set a goal and then develop the habits to get there. It is a quick, entertaining, and helpful read.

    • Thanks for the welcome, Joe. Thanks, too, for the mentioning Atomic Habits. It’s become clear that habits are key to success in any area–otherwise I’d never get any exercise done for instance 🙂 Doubly so for writing, which can be so fraught with inner obstacles.

    • Thanks for the recommendations, Harvey. I’m a fan of Block’s books on writing as well. I also recently read your own “Quiet the Critical Voice”–it has excellent advice on surmounting this obstacle. Thanks for writing it.

  3. I’m definitely my own biggest obstacle to my writing. I concur on “The War of Art” and “The Mental Game of Writing” but have not read the third. I think someone else recently mentioned Pressfield & I now read this quote from him every day:

    “Don’t prepare. Begin. Our enemy is not lack of preparation. The enemy is resistance, our chattering brain producing excuses. Start before you are ready.” — Steven Pressfield

    Those 5 words–“Start before you are ready.” are a gold mine.

  4. As I’ve said before, if I wasn’t writing, I’d have to clean the toilets, so I don’t have any obstacles to doing the writing. It’s making it good that’s the hard part for me.

    • Hi Terry, Good reminders for all of us that chores are waiting in the wings if we aren’t writing 🙂 Making the writing good is certainly one of my top challenges as a writer, too.

  5. I am my own Resistance, absolutely. It’s a battle to find the confidence to finish.

    A couple books helped, and continue to help:

    Zen in the Art of Writing by Ray Bradbury

    Break Writer’s Block Now by Jerrold Mundis

    Feeling Good by David D. Burns (yep, an anxiety and depression book by a shrink, but helps in many areas).

    When in doubt, pray.

    • Thanks for the recommendations, Philip. I haven’t read “Break Writers Block Now” but have read Bradbury’s book, a true classic. I used to help patrons find “Feeling Good” at my library, a book that helped so many people deal with anxiety and depression. Excellent point that it can writers deal with resistance.

    • Feeling Good, The New Mood Therapy, saved me in my grad school days, and is still useful – talking back to Depression, accepting that it lies, and knowing that doing almost anything will prove Depression wrong that you can’t do anything – still used half a century later. I don’t think I’ve ever been clinically depressed, but the small day-to-day depression is a bear to deal with.

      That, and the very similar Resistance, with techniques to fight back, are mainstays. Once I realize what’s going on – again (boring) – I start using the techniques, and get back to work. It’s usually something specific that has crept back into my brain under the cover of darkness, and is doing damage by stealth.

      • Glad to hear that Feeling Good continues to help. Awareness of what’s going on, too, is obviously important to us getting past Resistance and other challenges.

  6. Great topic and great discussion, Dale. Thanks for leading this one.

    I do agree that we writers (and about everybody else) are our own greatest obstacle (in writing and in many other endeavors).

    The book that helped me the most to “let go” and “be me” was Breaking the Rules, by Fil Anderson, especially one chapter, titled “Beauty in Brokenness.” Anderson tells the story of a potter coming to visit him and presenting a gift, an ugly cracked bowl that should have gone into the trash. As Anderson sits trying to find words to say thank-you, the potter says, “Fil, for God’s sake, please stop hiding, avoiding, denying, and despising your brokenness.” In other words, quit trying to be perfect. Celebrate your brokenness.

    Have a beautiful, imperfect weekend!

  7. Thanks for the shout out, Dale.

    Anne Lamott has a good chapter in Bird by Bird on mental static titled, ahem, “Radio Station KFKD.” And a hilarious chapter on envy.

    A book that helped me tremendously–even before I decided to become a writer–is You Can if You Think You Can by Norman Vincent Peale. It’s solid, old-school advice, which I took.

    • Thanks for writing “The Mental Game of Writing,” Jim. Love “Bird by Bird,” that’s a heck of a chapter. And thanks for adding Peale’s book to the list for today.

  8. Good morning, Dale, and welcome.

    I am the biggest obstacle to my writing. It’s self-doubt. I’ve read both The War of Art and The Mental Game of Writing and found them both to be helpful. (It’s also encouraging to note that virtually all writers experience the same fears.)

    In the introduction to his book, JSB quotes Shakespeare:
    “Our doubts are traitors
    And make us lose the good we oft might win
    By fearing to attempt.”

    That pretty much sums it up for me.

  9. Absolutely. I’m my own worst critic. Aside from all the amazing books mentioned above, getting back to basics, returning to my favorite craft books again and again, help to quiet the voices. My go-to books are anything by Larry Brooks and JSB. I’ve devoured them all more than once.

    Nice to see ya on the other side, Dale. 😉

  10. Thanks, Sue! That’s a terrific point about how returning to the basics of writing craft can quiet the voices. Having some go-to books to help with that is a great idea.

  11. I’ve heard it said that writers’ block is a sign that you’re writing the wrong thing. I think it’s often true. If the current project seems to be steadfastly resisting you, it may be a sign that your energy, your heart, your muse is elsewhere. If this is the case, rethink your priorities. If you’re facing a deadline, it may be better to work on something that creates energy long enough to be able to power through on the time-critical project.

    • That’s a great observation about writer’s block being a sign you are on the wrong path. I imagine my creative subconscious as standing behind soundproof glass, gesturing at me, trying to get me to see what the problem is 🙂

  12. Those are both great books. I like “Bird by Bird” by Anne Lamott and “Writing From the inside Out” by Dennis Palumbo. I have paperback copies of these so I can underline things in them that speak to me.

    Also, the quote that really kickstarted me back to writing and not worrying about how it turned out is from C. S. Lewis – “What you want is practice, practice, practice. It doesn’t matter what we write (at least this is my view) at our age, so long as we write continually as well as we can. I feel that every time I write a page either of prose or of verse, with real effort, even if it’s thrown into the fire the next minute, I am so much further on.”

    If Mr. Lewis considered anything he wrote to be worthy of the fire, then I’m in good company. Quite often I will name a project “Words for the Fire.”

  13. I can’t recommend a specific book, but for those of us who write professionally, the biggest problem we face is our own bodies. Writing is physically brutal with back damage, carpal tunnel, etc. I’ve had friends who had to use voice-to-text programs because their hands and wrists would no longer work correctly. Others have dealt with back surgery or write lying on a heating pad. For a long-time career, we need to be just as invested in exercising, self-care, and learning proper techniques typing, etc., as we are in learning our craft.

  14. Very important point about how we writers need to take care of our bodies along with our minds, and the importance of exercise. Something I schedule time for everyday.

  15. The first craft book I ever bought about three and a half years ago was by JSB about writing pulp fiction and it is now thoroughly creased, highlighted, and dogeared. Little did I know then that I would learn from he himself, courtesy of TKZ.

    A tip of the hat is in order here.

    There are components to writing a good story that hangs together and grabs the reader by the scruff of the neck, and there is a certain structure, and there are methods within those components and structures that build a good workmanlike story.

    For me, once I sit at the keyboard it takes a little bit of gnawing around the edges of an idea and finding cracks so as to hammer in the wedge and get it opened up. I’ve been doing a lot of mind mapping lately because I think in pictures, and that helps to get me off top dead center.

    Aldo Leopold, author of “A Sand County Almanac” identifies sticking points as “key logs” like the log jams in the rivers of his youth that, once removed, free up the flow of dialogue and ideas. It applies to story writing too.

    Finding the time sit and write and think is an issue and staying on schedule is a problem too. Sap flows from a maple tree at a certain rate and kicking the tree in the shins won’t make it go any faster. If there is a distraction like “Honey, take out the trash.” or Zelda the cat climbs up on my desk and sits on the keyboard it takes me a while to get back in the groove.

    One thing that helps me get started is frequent referring back to the story writing skills of the authors we talk about here. It gives me some inspiration to see how they do things, like watching a skilled mason lay bricks.

    I’ve been reading some Edna Buchanan newspaper stories, John Jakes western stories and a pair of P.J. Parrish novels recently.

  16. Super to have you as a contributor, Dale, my friend. This is a well-written piece and a great premise about obstacles. I look back to my young days when I was a rookie “commando” and we first faced the obstacle course in basic training. The instructors let each of us run it alone. We soon figured out that no individual could effectively run the obstacle course by ourselves. But with teamwork – helping ourselves by helping others – we exponentially amplify our accomplishments.

    I see the same thing in the writing world. This is such a solitary endeavour, and to sit alone is unhealthy. It’s vital to interact with others like we do here at the Kill Zone and make friendships that support, educate, and invigorate. Are we our own obstacles? I’d say yes, and it’s cement shoes without tapping into others for positivity.

    I’d like to suggest these positive written resources that have helped me overcome writing obstacles: “Think And Grow Rich” by Napoleon Hill, “On Writing” by Stephen King, “Elements of Style”, by Strunk & Whyte”, “Wired For Story” by Lisa Cron, and “Thanks, But This Isn’t For Us” by Jessica Page Morrell.

    • Thanks for sharing this additional resources, Garry! Some great titles. I agree that we writers benefit so much from friendships with each other, and count myself fortunate to know you and so many other great writers here at KZB.

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