Keep Asking Why


Doodling Rosie from Arbor Fall Festival with a cup of coffee on bed.

The best advice I have ever received (well maybe not ze best but certainly way up there) is to dig deeper.

Rosie, the northern red oak of the Arbor Fall Festival, desperately needs a bow added to her trunk for a certain chapter. I’ve reached a point in the illustrations that requires a bit more detail and, well, I’ve sat on that realization for two weeks. Two whole weeks of stagnant pondering.

Why have I stopped drawing Rosie?

As I began to dig deeper, I discovered little, manageable hints contributing to this ever-present procrastination and conspicuous avoidance.

But first, I think I’ll share the inspiration behind dig deeper. That is, to no one’s surprise, my brilliant scientist, Bryan.

So, my favorite color is brown. I’m not joking; brown is my favorite. The color of a perfectly brewed cup of coffee, aged parchment, the color of trees (hi Rosie!), and dirt, my mom’s curly hair, and honey, I love the color brown. And on the other end of that revelation is Bryan. Every time I remind him of my favorite color, he loves to follow up with “brown, huh? Like a murky lake or other things? Why brown? Why not blue or green? You like those.”

Bryan always has a follow up question: Why?

I love that he always asks himself why, digging deeper, thinking critically, examining, observing without fearless curiosity. So like the wonderful leader that he is, leading by example and not pointing his finger and telling me what to do (oh, never), I’m asking more why questions.

Driftwood coffee beans from Camp Zephyr and a cup of coffee

It is a brave thing to do—ask why. The reason I must dig to get a little deeper (if you allow me to really exhaust this metaphor, please and thank you) is because usually I have layers and layers of cemented walls, heavy soil surrounding buried hurts and pains and insecurities that ultimately motivate my stagnant procrastination, my decisions, my habits. There are more than just the bad feelings buried under there, but when it comes to my sudden halt in progress, well, I attribute that to those buried insecurities.

I’m the queen of she shrugs and mutters, “that’ll do.”

It’s not my best quality, actually it might be my worst. I’m not loving my readers enough to really dig in and present to you well-rounded, deep, real characters and art, as opposed to those on the surface, stereotypical, eh, good enough types.

Why is my remedy to that’ll do. Anytime I’ve muttered or even dared to think the words, “yeah, that’s good enough” I rebut with a why. Why stop here? Why is it just good enough?

And here is the revelation of my neglected Rosie. Why did I stop drawing Rosie? I didn’t know how to go forward.

Okay. Dig deeper.

I couldn’t remember how to use the tools in Photoshop to help me use the same photo of Rosie from before, while allowing me to add a bow on top of that layer.


A Sketch of Rosie with a bow and Birdie

What surprised me was that it wasn’t fear that held back my progress, but simply not knowing how to do the work. I do think I was afraid though to ask the question why, thinking that it was some BIG feeling that I had to work through. But nope. Instead, asking why led to some manageable steps to getting the work started again.

So, I refreshed my memory with some tedious tutorials and played around with the tools in Photoshop.

A few weeks ago, I wrote about my book of questions. I noticed I asked a ton of how to and what questions. I set a goal to ask more why questions, to dig deeper and find the source of the answer. Asking questions takes courage, and for me, especially asking why. Rosie’s bow was remedied by a why and simple manageable steps to get back to starting again.

I hope this helps you find the courage to ask more questions and ask yourself why.

Wishing you a joyous and hopeful season,

If you’re new here—welcome, friend, to the Learning in Public series in which I take you along as I clumsily navigate this thing called learning. If you’d like to read about the origin of this series, here’s the first of many.

Enjoy! I’m glad you’re here.