books · novel · On Writing

Use Obstacles to Get Where You’re Going

A choice to be made…

The obstacle is the way…

What do I do now?


The further that I go into writer world, the more that I recognize that it’s nothing like I expected.

What did I expect?

My decision to become a writer was not a linear, deeply considered, logical, and reality-grounded process. It was a quiet spasm that gathered force and built momentum into full-on, hurtling tumble toward a distant, shimmering vision. Once I got past mind-numbing fear, yammering memory, and daunting comparisons with accomplished others, I was enraptured, totally committed no matter what obstacles loomed.

Here’s when I became a novelist for real, for true, for always:

It was January. I’d lurched miserably through my annual National Novel Writing Month adventure, making it to 50,000 words a few days before November 30. The writing was the misery. I was writing by the seat of my pants, trying out an approach extolled by a noteworthy, poetic writer. I figured that I’d fly blind, see what came of a process so different from my typical, sketchy, big scene-only outline map to an inevitable, brilliant ending.

The early NANO days were fine. I wrote furiously, introduced characters, set up the premise, grounded the world. I didn’t know where I was going, but the story was chugging along with its own happy story engine. There were surprises, fun ones that kept me wondering what came next. It felt like this discovering story thing might work.

Then the second Monday slammed down. I sat in my usual place, opened my laptop, and set off into fulfilling my daily word quota. There are no words — none that I am willing to admit — to describe the horror of that day.

My protagonist was walking in the woods near her home. She’d left the front door unlocked. She’d brought along an old-fashioned, film camera. Now what? I had no idea why she was in the woods or why she’d rushed out the door — but I’d learn as we went along, right?

She meandered through well-tended neighborhoods to a tame forest. In the distance, young children swarmed bright colors across the elementary school playground. A snarling dog charged at her from behind a fence. Furtive rustles paused as she passed. Ooh, what was going to happen next?

Nothing. Nothing happened next. She lay down on her back right in the middle of the woods, taking pictures of the clouds through the trees while I agonized over the pathetic daily word count total. I mined my own amateur photographer experience, used all I’d learned in photography classes, to describe her artistic breakthrough, lying there in suburban wilderness, snapping shot after shot, the front door of her house open to the mean guys, lovingly describing birches, oaks, and maples until I finally — blessedly — hit the daily word goal.

For the remaining weeks of NANOWRIMO, I shuffled in daily to throw down thousands of words in wretched despair. I finished the novel, watched the NANOWRIMO team perform their happy dance, and then destroyed everything associated with the abysmal mess.

I quit writing on December 1. From then on, I resolved to do only my beloved morning pages. The relief was pure, heartfelt joy.

In late January, a loved one blasted me with a jaw-dropping catalogue of my wrongs. Shaken and stunned by her long-held resentments, I cancelled my plans and stumbled through the motions of a normal weeknight.

The next day, I found myself seated on the couch, pen in hand, notebook splayed open on the table in front of me. Moments later, I was gulping coffee, jotting writing blurts, short questions, and phrases that entwined into a story.

It was my story so I could write anything I wanted. The beloved, infuriating adversary was dead. Her end was untimely, horrible, filled with shame and regret that she’d been such a jerk. Her undeserving ashes were enshrined in a magnificent ceramic urn.

It was time for a road trip. The long-suffering, wonderful, loving protagonist has been entrusted with driving the urn to the memorial service and final resting place. Her secret plan is to take a few, unsanctioned side trips to places that she and her dead loved one mused about, but never managed to visit together.

The trip begins well. The day is sunny, bright, and clear. The gas tank is full, windows down, music on, provisions stored in trunk. The beautiful urn of tragic ashes is carefully belted firmly in place on the front passenger side, cushioned by soft towels. The urn of dead woman and the living protagonist travel to diners, national parks, antique stores. The road trip is calm, quiet pleasure, the jar cradled attentively in the car, placed gently in place of honor in diners, and carried in a backpack to jaw-dropping sites of natural beauty.

Then there’s a storm. Torrential rain pummels, roads are washed out, tree limbs crash to earth. A drenched person desperately needs a ride. The protagonist cannot force this awkward person into the cramped backseat, so she unbelts the urn, giving the towels to the wet person. The urn is settled in the back seat as a chauffeured, honored companion. All goes well. However, desperate, but now dry person needs to go further and the protagonist agrees. The humans ride in front, the urn in back.

Then — you guessed it — another person is in dire straits, needs a ride. Protagonist cannot refuse the rescue. Again, the urn is shifted, still honored and handled with utmost respect.

Later, another individual joins them — or maybe this time it’s a dog. It doesn’t matter. The urn is moved to the trunk, tucked with care between luggage, snacks, and wet towels.

Journey continues, a merry carload enjoying the music, the road, being with one another.

At a quick stop on the side of the road (one of the passengers is pregnant and needs frequent stops), the protagonist yanks out a water bottle, dislodges the urn. The urn shatters on the side of the road. Ashes mix with gravel, road kill, cigarette butts.

Horrified protagonist has long forgiven the loved one, cannot believe what her clumsiness has done. Whatever shall she do?

A hawk soars overhead. Protagonist looks up, admires the hills and pines. The air is clean, the sky high, broad and blue. This is beautiful country, a perfect resting place. She and the dead person would have loved being here together.

Fade to black. I don’t know what happens next — and it doesn’t matter.

I sketched out ideas, drew a plot map. Just like that, I was a novelist, head down, all-in, delighted, romping writer. I’d tried something that didn’t work for me, so what?

All the obstacles, impossible imaginary hurdles, melt away in the torrent of story. New obstacles immediately arise to block the way. Obstacles are like that, multiplying like hydra heads, reveling in their magnificent complexity and confounding appearances.

However, the first obstacle is the hardest one that you will ever have to face.

Conquer that first harrowing obstacle and you can face all subsequent ones with grace, creativity, and profound, unshakeable faith in yourself to continue on your way, mastering one obstacle after the next.

So, I am a novelist who has learned to appreciate the challenges, the quivers and quavers of unexpected, scary times filled with doubt. I know that when I face obstacles, thank them for their gifts, and manage my way through them that I will get where I am going. I also know that there are so many generous, kind, and bright guides in the world, books such as Ryan Holiday’s mind-altering The Obstacle is the Way, and friends who make the journey worthwhile.

The journey doesn’t get any easier. But it does get better.


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