Except it often doesn’t. Connie Kwan has seen it from both sides: as a five-time chief product officer, including at a company that helps people quit smoking, and as someone who tried the checklist on herself and still slipped.
Her flip is simple to say and hard to do. The how isn’t the problem. The why is. People don’t change because of tactics. They change because of the story they tell themselves about why it matters.
That idea became Story Habits, a method, a workshop, and now an upcoming book. Here’s how she got there, and what happened when she put me in the hot seat.
Engineers, Hollywood, and Who Tells the Better Story
This one got going early, and I loved it. I came to software from about fifteen years in Hollywood, and my take is that developing a product and developing a movie are close cousins. Both start with an idea, and both need a village to get it made.
Connie pushed back, and she has the background to do it. She studied engineering, where the story you learn is that facts win: run the experiment, write the report, hand it over, and let the reader agree or disagree. That isn’t how a movie works, and it isn’t how a board meeting works either. In the moment you’re debating something, the data is rarely complete.
Her distinction stuck with me. Creativity and storytelling are different skills. You can generate endless ideas and still struggle to put the pieces in an order that makes someone feel something and remember it later. The good news is that it can be learned. She has spent years teaching it to product managers and engineering leaders who got told to “influence better” and didn’t know what that meant.
We didn’t fully settle it. We agreed to keep arguing offline.
Connie’s Flipped Motion: Build, Learn, Reapply
Connie’s career isn’t one dramatic pivot. It’s a pattern.
A decade before the smoking cessation work, she built a startup called Real Meals to help people eat better. It didn’t survive, because the timing and the funding weren’t there. But the goal of using technology to help people change their behavior came back around, and the second time it worked.
Years later, while teaching storytelling, she noticed something linking the two: the people who successfully quit had a story behind the change. She signed up on a whim to lead a workshop she’d never run before, and the method came out nearly fully formed. Three years of testing and refining later, it’s an upcoming book.
Build it, learn from it, catalogue it, reapply it. That’s a product person’s instinct, and it’s a Flipped Story motion. She never stopped being who she was. She took what she’d built and pointed it somewhere new.
The Flipped Habit: A Live Working Session
Then Connie did something I didn’t expect. She offered to workshop one of my own habits on air.
I handed her the whole kitchen sink: health, weight, the evening dessert ritual, my habit of researching things far more than doing them. She made me pick one. Then she walked me through the first steps of Story Habits:
- Set a high-confidence goal. Not the big number on the scale, but a daily action I can actually check off. We landed on no eating after 8 p.m., five days a week, set low enough that I can win.
- Find your anchors. Your values, the things that already drive your life, whether you notice them or not.
- Tie the balloon to an anchor with a “because” string. Mine landed on family: I stop eating after eight because I want to be a healthy dad.
In a short slice of the conversation, I went from a vague list of intentions to a reason I can come back to when I’m tempted. You could see how a full session would go deeper.
Connie’s own example was my favorite part. She wanted to eat less dessert, and one of her anchors is frugality, something she grew up with as the child of immigrants. So she decided she only eats expensive desserts. A $10 slice of cake is allowed, but paying for it hurts just enough that she doesn’t go back for two weeks. She cut her dessert intake in half. As she put it, it only works because it’s tied to her anchor.
“There’s nobody teaching how to solidly establish your why.” — Connie Kwan
🔄 The Flipped Story Recipe Book
Every episode of The Flipped Story adds a recipe to the book, and Connie’s is the step that comes before every other habit book: commit first.
Learn More & Connect with Connie
Find Connie and her work at conniekwan.com. Story Habits comes out in November; sign up at storyhabitsbook.com to be notified. For a preview, read her Substack at conniekwan.substack.com.
Catch the full video interview!
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