Review: Ask Yourself 344 Questions

Reading Time: 6 minutes

I love being a technology writer. The job requires me to stay up on the latest/greatest tech (as much as possible given the exponential growth of new products and services) and it allows me to work from home or the coffee shop or really anywhere else I feel like hunkering down and cranking out a chapter or blog post or whatever.

I wrote my first book back in 2006. That book led to a few more the following year… and then even more the year after that. I set a goal to try and reach 5 or 6 books per year and, thankfully, I’ve been able to hit that for the past two years. But with that goal has come certain problems. The thing about writing technology books is that the contracts often come in waves. I’m frequently working on two books at once, forcing me to have to change mental-gears daily or every other day as I jump back and forth between different topics. One book, for example, might need to be written in first-person and all figure references must be specified in complete sentences in a paragraph… another book might be written in third person and require three levels of headers for sectioning. Writing books simultaneously is tricky from a logistics point of view, but from a creative angle… it’s even more difficult.

This really hit home early this year when I found myself working on three books at once. Three. And all three had similar start and due dates. (I’d also done three books at the same time back in 2010 and told myself never again. I should really listen to myself more often.) When I finished all three, I suddenly found myself with a fourth book starting up and a complete lack of motivation and creativity.

It wasn’t Writer’s Block… it was worse.

I took a month off. Actually, I asked for a month off. I knew it would mess with the schedule a bit, but I also had nothing to lose by asking. I had no real ideas, no energy to sit down and type, and a complete loss of interest in my subject matter. To say that I was a bit worried is an understatement.

I have lots of friends and colleagues who are creatives. Some are web designers, others graphic artists, and many are writers, both fiction and non-fiction. We’ve all dealt with The Block before, and while we know that it will pass, knowing doesn’t make it any easier. At various times, we’ve all read books or articles on getting over the humps and we frequently recommend them to one another. The same goes for videos and motivational talks. But really… after a while… they sort of all begin to blend together. What I want (and probably what others want, too) is The Anti-Block. Something new that can light the creative fire the next time I hit the wall.

And If you’ve stuck with me this far, you can probably guess that I’ve found it. And the good news is that it’s not useful to just writers. I can easily see this Anti-Block working for everyone else who has hit a wall creatively. (And I certainly wish I’d had it in college — would have been very useful during those What Do I Want to Do for a Living? moments.)

I was already familiar with Stefan Bucher’s 100 Days of Monsters. For 100 days, Stefan recorded himself drawing a daily monster. (He’s since gone beyond 100.) I loved this. I found myself checking in and just when I thought I’d found my favorite a few days would pass and another favorite would emerge. I was blown away that with some ink, a can of air, and a pen, Stefan could come up with such unique creations. Didn’t he ever get burned out?!

I became an instant fan and began to search out anything Stefan was involved in, not just the monster drawings (although a copy of 100 Days of Monsters sits proudly on my shelf). So when I heard about his upcoming book titled 344 Questions? The Creative Person’s Do-It-Yourself Guide to Insight, Survival, and Artistic Fulfillment, I requested a copy and then promptly drove myself crazy waiting for it to arrive.

Totally. Worth. The. Wait.

This is not a book you read. You use it. You write in it. You read the questions, write in the frequent response in the colorful and cartoon-ish balloons. You offer up some truths and then use a Sharpie to blacken out those things you hope never see the light of day. Some pages encourage you to tear out a piece after you provide an honest answer in a balloon. Other questions taunt you because you simply don’t have an answer.

There’s a nice little bookmark built into the book because there’s simply no way you can go through the book in one sitting. Or two. Stefan tells you to:

…take it with you when you go to work, keep it in your bag, scribble into it as answers occur… If you keep this book in mint condition, I’ve failed… dog-ear one of the pages right now…

It’s a small book (in size) — 139 pages of questions plus the bios of the creative geniuses (Stefan’s words) who offer up their own short lists of questions scattered here and there. Judd Apatow. Ze Frank (another favorite creative of mine who has a great list of questions on page 31). Tarsem. Tim Carvell. And 35 more.

Some of the questions are dead serious. Others are humorous. Two or three might be insulting. And a few will really make you sit up and think about things. For me, the book really is an Anti-Block tool. It’s not going to write my chapters for me, and it’s not going to magically implant dozens (or 100) ideas in my head. But what these questions are doing (and I’m only about 75% through the book right now) is tricking me into forgetting that my creativity isn’t flowing right now by making me laugh (at myself, mostly) and shake my head and wonder and… the distraction is working.

The only downside to the book? It’s looking like I may have to buy another copy as I’ve taken Stefan’s advice and I’ve ruined this book. (Well, about 75% of it.) It’s full of my hand-scribbled wanderings, most of them actually quite honest and helpful. Maybe 1% are fibs… I’ll need to work on being more honest with myself in some areas.

Geek dads are a creative bunch, and I imagine that many of them are often looking for inspiration, whatever their job, hobbies, or interests may be. The book won’t appeal to just creatives, either… those looking to change careers, find a career, start a business… all of these are addressed in the book with some guiding questions that can really help with the brainstorming.

When I’m done (a few more pages left), I’ll tuck this little book into the inner flap on my laptop bag and keep it around for inspiration. There’s no point in loaning it out, really. Because, ultimately (and I’ll use Stefan’s own words from the Introduction) — My Answers Won’t Do You Any Good.


** Images are excerpted from 344 Questions: The Creative Person’s Do-It-Yourself Guide to Insight, Survival, and Artistic Fulfillment by Stefan Bucher. Copyright © 2012. Used with permission of Pearson Education, Inc. and New Riders.

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