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How I Conquered Every Lawyer’s Worst Nightmare

by Jay Reeves |

Back in my early days of practice I was haunted by the same recurring nightmare.

I’d wake in the dead of night, heart thumping and mind racing, terrified that I’d missed an important deadline that day.

“What’s wrong?” said my wife on one such occasion, after I’d awakened her by bolting upright in bed.

“I think my career just ended.”

“Well, it’s two in the morning,” she said, yawning. “Not much you can do about it now.”

Always the sensible one, she rolled over and went back to sleep. Meanwhile I held my head in my hands and moaned. I had the sick feeling I’d forgotten to file a key document in the Brockington case. This was back when my entire caseload could fit in a cat litter-box, and the Brockington matter was one of the few that didn’t actually belong there. Now I had gone and blown it.

I thrashed and fretted until my wife politely asked me to leave the room. So I got dressed and went into work a bit earlier than usual, meaning 3 AM.

On the Bridge to Nowhere

I took off in my Datsun B210 hatchback from our Sullivan’s Island home to my office in downtown Charleston. The night was cold and rainy and so dark I could see nothing beyond the pale gloom of my headlights.

It was almost Halloween. Ghosts and witches and vampires loomed on both sides as I puttered through Mt. Pleasant and began the long treacherous climb up the Cooper River Bridge. This was in the 80s, before the renovations, when the old bridge bucked and swayed like a trampoline, and mere inches separated you from the cars whizzing by in the opposite lane.

I made it up the first stretch. The bridge shuddered. The water below was a black slash. But my mind was occupied with darker thoughts of malpractice claims and Bar complaints and my once and future career delivering propane gas, which is what I did before law school.

Halfway up the second steep span, I noticed the red lights flashing on my dashboard and felt the car losing speed. That’s when I remembered I’d been putting off for weeks taking the old Datsun in for some much-needed maintenance.

There might be worse things than having your car die on the Cooper River Bridge on a stormy night with your professional life imploding, but I can’t imagine what they might be.

Salvation at Sam Solomon’s

Somehow I managed to make it off the bridge and coast onto East Bay Street before my car finally gave out. I pushed it off the road and into the empty lot of Sam Solomon’s, where I abandoned it. In a chilly downpour I began the mile-long trudge to Broad Street.

It had been raining for days – back then all it took was a sprinkle to cause major flooding downtown – and I arrived at my office drenched and miserable. With wet, trembling hands I opened the Brockington file.

And for the first time that awful night, fortune smiled. I had not missed the deadline after all. I had another whole week.

For awhile I’d been intending to bring a change of clothes to the office, for situations just like this, but I’d never gotten around to it. All I had was the London Fog overcoat my wife had given me for Christmas. So I peeled off my wet clothes and put on the dry coat, then collapsed on the waiting room couch and fell into a sweet, blessed sleep.

Moments later, it seemed, I woke to find a strange man screaming in my face. The custodian had come in for his morning duties and freaked out to find me lying there in nothing but a trenchcoat.

And that’s when I had an epiphany: I was a procrastinator, and I needed help.

Chasing the Demon of Procrastination

“Misery is optional,” said my friend Nick, the wisest counsel this side of Colleton County. “There’s an easier way to do this.”

“Teach me.”

So Nick helped me set up an actual calendaring system to replace my leaky memory, along with a front-desk backup and enormous wall calendar. Plus he recommended I increase my malpractice insurance limits.

I did these things and began sleeping easier. Sure, I’d still have the occasional blown-deadline nightmare. But they no longer caused palpitations. In fact, I came to welcome them. They kept me on my toes.

Recently I dreamed of my old Datsun B210. That model was also known as the Datsun Sunny. It was the first – and best – car I ever owned, mostly because I’d bought it myself with money earned from my propane gas job.

In the dream, I was rolling along in my Sunny when suddenly it rose up off the road and went flying through the air, up among the clouds, soaring freely, as the lights of my former life twinkled far far below.

About the Author

Jay Reeves

jay.reeves@ymail.com | 919-619-2441

Jay Reeves practiced law in North Carolina and South Carolina. Over the course of his 35-year career he was a solo practitioner, corporate lawyer, legal editor, Legal Aid staff attorney and insurance risk manager. Today he helps lawyers and firms put more mojo in their practice through marketing, work-life balance and reclaiming passion for what they do. He is available for consultations, retreats and presentations.

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