What Six Drafts of a Five-Minute Story Taught Me

At Wealthsimple, part of my job is making complicated financial operations understandable to people who haven’t spent weeks working through them. I have to decide which details matter and explain why.

I found myself practicing those same choices in Storytelling Level 1 at Magnet Theater in New York. Over six weeks, we developed personal stories, received feedback, and prepared for a five-minute showcase.

I chose a story about a college friendship. Getting it ready took six drafts, mostly spent deciding what belonged, what needed more explanation, and what I could leave out.

Deciding what belonged

My first draft followed the friendship from meeting in college to reconnecting years later. There were plenty of memories to work with. The harder part was deciding which ones belonged together.

During editing, I considered whether to focus on how we became friends or how the friendship lasted over time. Each direction needed different moments.

Once I focused on how the friendship began, I could leave out the later years. Including them had meant spending less time on the moments that explained how we became close.

That decision gave me a clearer way to edit the next draft.

Hearing what was missing

When I shared my first draft in class, people enjoyed the details. They could picture the places and follow the things we did together.

They also wanted to know more about how I felt.

I’d spent time describing what happened, but hadn’t always explained why those experiences mattered. I knew the significance of each memory and assumed more of it would come through than it did.

In later drafts, I gave more space to my reactions: what surprised me, what made me nervous, and what made me feel comfortable in the friendship. That helped explain why I’d chosen to tell this story in the first place.

Leaving room to tell it

The class discussions also included reminders to slow down and leave a few beats. Which is difficult when you’re trying to fit years of memories into five minutes.

Choosing fewer moments gave me room to do that. I could spend time in a scene, pause after a line, and let people take it in before moving on.

Even if I could say all the words within the time limit, I still needed room to tell the story. By the showcase, I had fewer events to cover and more time to share the ones I’d chosen.

Bringing it back to product

After Women in Product, I wrote about deciding what people should know, feel, and do when communicating an ask.

The feedback on my first story draft gave me a practical way to think about the “feel” part. I’d given people the events, but they wanted to understand my experience of them. Sharing more of my perspective helped them understand why those moments mattered.

At work, there’s also an action to consider. Before your next meeting, ask yourself: What do people need to know? Why should they care? And what are you asking them to do?

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