How the world’s worst boss set me free

Ned trusted no one to do the job properly. He grilled us for hours over every detail of every project. He wanted everything done just so, but couldn’t seem to tell you what everything was supposed to be or how to go about doing it.

He drove me nuts. “Here’s what I need from you,” he’d say, then scribble circles, squares, triangles, and arrows in a fruitless attempt to explain. I’d spend hours trying to understand what he wanted. “It sounds to me,” I’d reflect back to him what he’d just said, “that you want A, B, and C.”

“Not really,” he’d respond, then pontificate for another muddling half hour.

“So it sounds like,” I’d try again, “you want D, E, and F.”

“Well, no,” he’d say, and would be off again, on and on, till I had a headache and was no closer to understanding what he wanted.

Yes, Ned was my boss.

Before Ned, I’d had good and bad bosses. There was Stephanie, who encouraged me to take on independent projects while I was still a secretary. Patrick addressed me sarcastically whenever he got the chance. Ken awarded me for my hard work with a staff promotion, while Barbara bad-mouthed me behind my back.

My situation with Ned was less black and white, more complex. Even though he could be such a pain in the ass, he maintained a very human side as well.

The best advice I’d ever heard

Shortly after I started working for him, I went through a rough patch – a dramatic break-up followed by a health breakdown. I was sitting in my office crying when Ned popped in.

“Angela,” he said. “I have an idea.” When he saw my face, his immediately filled with empathy. “What’s wrong?”

“Nothing,” I said, trying to pull myself together. “What do you need?”

“That can wait. Let’s focus on you right now.”

Any other boss, even a good one, would have made an excuse and walked off, muttering he’d come back later. Ned gave me the opportunity to talk.

I talked about my relationship, my work, the dreams I had to be a writer. That’s when, in spite of himself and his odd inability to communicate, Ned gave me some of the best advice I’d ever heard.

“You need to do what you need to do. Before you know it, Angela” he said, “one year will pass. Then five, then ten, and you still won’t be doing what you want to do.”

Of course, Ned being Ned, life revolved around his view of the universe: he assumed I’d find some way to do what I wanted while still working for him.

Ultimately, it was his horrible management skills that pushed me to actually take his advice.

Taking the leap

I woke in the middle of the night, stomach churning, stressed by my work, wondering how I’d ever fulfill my ever-changing job description. All the while, Ned’s inadvertent advice echoed in my head: Five years will pass, then ten and you still won’t be doing what you want.

But how could I quit to write full time? I had bills to pay. What could I do in the meantime?

His words sent me in a panic, but that panic woke me up. Because of Ned, I kept writing. I worked on my memoir and took classes. I volunteered at book fairs and attended conferences. I never left the writing world.

Then one day, when a friend told me she knew someone who quit her job to go to library school, I realized I’d found my answer.

Ned was devastated when I quit. He just stared blankly for a while, then shuffled off like a zombie. I felt guilty. He had always supported me, even rallied for my promotion, but I couldn’t stay in the same job, trying yet always failing to give him what he wanted.

Yes, Ned. He was a horrible boss, but ultimately, I am thankful for that. If not for Ned, I might have gone on for who knows how long, safe in my little box. I wouldn’t have pushed harder with my writing, or considered a new career.

Without him, I wouldn’t have left to pursue my dreams.

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