Every person with a big heart and an entrepreneurial spirit reaches a point where they have to decide.

To stay or walk away.

To do the conventional and expected thing, or take an abrupt right turn.

To follow the rules, or write their own.

I’ve had a few of these moments in my career, but the biggest, hardest, and most amazing happened when I was 27.

I had worked hard and gotten lucky. But my good luck was keeping me awake at night and making me burst into tears over dinner.

Let me rewind. I grew up wanting more than anything to be a writer. I wrote songs and stories, scribbled in journals, and forced my brothers, friends and cousins to perform in half-written plays that never seemed to end (go figure). Once I got my hands on a VHS camcorder, we switched to video (oh yes).

I was at my core a creative person—an independent thinker and daydreamer, and highly sensitive. Self-expression fuelled me. But I also really wanted to be taken seriously. So as a young adult I set out into the world determined to couple my creativity and passion for story with useful, practical work.

I became a journalist, landing a well-paid internship at the biggest circulation newspaper in Canada straight out of grad school.

As a country girl who’d always dreamed of becoming a writer, a big-city newsroom was an exciting place to be. Writers I’d followed for years were suddenly shaking my hand or sitting on the other side of a cubicle divider. I knew that if I worked really hard, I could turn my internship into a longer contract. I could stay on for a year, a year and a half, or longer.

I was becoming a writer. Not the starving artist kind. I was playing an important democratic role, meeting interesting people every day, and bringing home a decent pay cheque.

Laser. Focus. Newsrooms don’t usually spring to life until around 10 a.m., but in the beginning I’d often get to work by 8:30 a.m., and stay late. I did everything my editors asked me to do. When I encountered a subject I knew nothing about—and there were many—I buckled down and worked harder.

My editors liked this. They kept me in the newsroom, on one contract and then another, eventually giving me a full-time permanent job with benefits—in an era of layoffs, buyouts, and general uncertainly in the industry.

I mentioned I was lucky. Very.

But deep down, in that place where you can’t be anyone but yourself, my good fortune was killing me.
 

I couldn’t sleep.

Every night around 3 a.m.—the witching hour—I’d bolt awake, thinking about work. I’d think about someone I’d interviewed who was going to appear in that morning’s paper, which would at that very moment be fanning out across the city in the dark, in trucks.

This interview subject’s story would be running through my mind. They had made themselves vulnerable, to some intent, by speaking to me. Many of my interview subjects were “regular” people without media training. Regular people (compared to media-trained professionals or politicians) usually told the best stories, but rarely understand the potential consequences of doing so.

I remember one couple, a man and woman in their 50s. There was an incident of some kind in their neighbourhood—I don’t remember what. I knocked on their door and asked if they would speak to me. Right in front of me, her eyebrows raised, the woman told her husband that she didn’t trust me.

The husband looked at me—a twenty-something with, no doubt, an incredibly earnest expression on my face—and said:

“Oh, this nice young woman wouldn’t do anything to hurt us.”

And I smiled.

I always had the best intentions. But it wasn’t that simple.

Awake at night, I’d wonder if the people I’d interviewed would be hurt by the presentation of the story. By the headline. The angle. By that sentence an editor had encouraged me to add in. By the details I chose to include or leave out.

The truth was, I might hurt them, even if I didn’t mean to.

I’d move to the couch. My cat would come and lay on my lap. I’d watch TV for a while, or read, usually dozing off a few hours later, usually just before my alarm would tell me to get to work.

I think a lot of good, compassionate humans who also happen to be journalists grapple with the exact same things I did. I am not special. But I was particularly sensitive, and particularly unwilling to live in such discomfort.

I became convinced that I was aging faster than I should have been. Insomnia will do that to a girl.

When I told my editor I was quitting, I told him the truth about why.

I said the job didn’t suit my personality, and that I had to either change my personality or leave. And I told him I happened to like who I was.

His understanding and encouragement was one of the best things that ever happened to me.
 

I went.

The truth is, I didn’t know where I was going at the time. I had some ideas, but that was about it. I wanted to write fiction. I wanted to work for myself one day.

I had no idea what that meant in practice.

But that’s part of the modern entrepreneurial spirit, isn’t it? We know there’s a better way to work and live, even if we don’t know exactly what it looks like yet. Or we have a great idea, but the idea is just the beginning.

And so, we set out determined to make sense of the madness. To find or create a job that’s aligned with our values, personalities and skills. To make, contribute, and grow.

It takes a while. It’s supposed to.

I left that job three and a half years ago and I’ve done several different things since. There have been scary and frustrating moments. There have been times when I doubted I would ever figure it out. But then again, does anyone, ever, completely?

Realistically, all we can do is try to get closer.

I’m getting closer. The best part is that by helping my clients tell their stories and grow their businesses through clear and honest communication, I’m helping other people get a little bit closer too.

I use my journalism background in my business every single day. I ask my clients thoughtful questions and write down everything they say. I find the story, and suggest a powerful way to frame it. I zero in on compelling lines and narrative elements with the potential for unstoppable momentum.

But then I hand the notes and outlines over to my client. Because the story is theirs to tell. My job is simply to help them tell it.

I’ve taken all the parts I loved about my first job and found another way to use them. A better way, for me.

And I sleep like a rock.

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Your writing prompt:

Write about something you gave up or walked away from.

xo,