Art, Life & Faith Question of the Week #5: What has been your most challenging artistic work?

[W]elcome to the Art, Life & Faith Question of the Week #5. What has been the most challenging artistic work you’ve ever created? What made this artistic work challenging? Right now, I’m in the middle of one of the most challenging writing projects I’ve ever encountered. How about you? Read on…


What is the most challenging artistic
work you have ever created?

My writing partner, Ken Straw (also my brother-in-law) are doing word-for-word, hand-to-hand combat in the fourth draft of a screenplay we “finished” three years ago. Though the script has already won five awards from Los Angeles to New York, we’re taking it to a whole new level. You might be wondering, “Why?” The answer is simple: We have a love for story and we want to make a good script great. We also want to excel at our craft.

If you are committed to creating great art, your work must be challenging and you must challenge yourself. Let’s face it: There’s a lot of bad art out there. Bad art made by Christians who talk about “excellence in the arts” and giving glory to God in all they do. If your art is not challenging and always comes easy to you, life doesn’t work like that. You’re not working hard enough.

We can do better, which is why I’d love to hear from you. What work has challenged you the most? Was it a book? A short film? A photography exhibit? A painting or assemblage art? A sculpture, composition or difficult piece of music you performed? Maybe a song you wrote? What made it challenging? What obstacles did you face? How did you overcome them? What was the final result? Did you succeed or fail? What did you learn in the process?

Or, if you’re like me, what artistic work are you in the middle of right now and why is it challenging? What do you love about it? What drives you crazy? Are you walking a tight-rope of enjoying the passion of creativity and the hair-raising fear of falling on your face?

I’d love your comments and feedback.

We have much to learn from one another!


In case you missed…

Question of the Week #4: What would you say to an artist struggling with a project?

Question of the Week #3: As an artist, what does a good day look like?

Question of the Week #2: How do you define success?

Question of the Week #1: What is the worst thing someone has said to you about WHY you SHOULDN’T pursue your art?

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  • techne

    it may be a bit of a cop-out, but every new piece is the most challenging work. first, there’s the inertia – you need to build momentum. then there are the questions as to whether or not it’s even worth pursuing. then questions about materials, scale, style/ artistic vocabulary, delivery/ presentation method, the appropriate medium and all the myriad formal concerns. then the many questions as you work – does [this] fit? where should [this] go? what if i change [this]? should i change [that]? what stays? eventually – hopefully – you get to the point of judging whether or not it functions or communicates what you want, how you want. does this art hunt? never mind that you’re still not sure how people will respond, or even if they’ll respond. so much of the process is really an act of faith, of trust.

    • Joey O’Connor

      The creative process is an act of faith and trust. The challenge, for me, is which creative project I want to tackle first and stay with…that’s the challenge, because at some point, I will either get bored, discouraged and lose focus, which requires perseverance and patience to stay the course. Thanks for all the good questions and perspective you raised in your post.

  • Lisa Colón DeLay

    I have to let you artist and creative types know about a project I just finished. It’s on using dreams to become more creative and motivate growth. (In a few days or weeks you’ll be able to remember your dreams almost every night, have lucid dreams (awaken inside the dream and control it) and curb anxiety.

    Every artist needs this guide! (Sparky’s Go-to Guide for Dream Control)

    I REALLY hope you enjoy it.

    It’s FREE on Monday. (other free download days will be posted at my website )

    Will you pass this on to other artists, please?

    • Joey O’Connor

      By all means, thanks for sharing this Lisa! Feel free to offer it also on The Grove Center for the Arts & Media website at

  • Annette

    My children!

    • Joey O’Connor

      Yes Annette…challenging blessings! Works of art in progress…masterpieces in the making…except when they’re driving us crazy!