Reflect On The Past To Enhance Your Creativity

For fifteen years, I spent most of my summers taking high school students on service trips. We traveled around the eastern United States and Central America, working on projects that benefited local communities. At the end of each trip, I’d spend time asking the kids to reflect on their experiences.

Each trip, I’d ask the kids to consider three questions. I’m sure, after fifteen years, some of the kids got used to (or sick) of the questions. Though, I think these three questions are the keys to capturing memories. The questions are:

  • What is the best story from this experience?
  • What is the one thing you want to remember in five years?
  • How will this experience change you?

When I left that job at the start of the pandemic, I didn’t spend much time reflecting. I jumped directly from that position to a new company and new career. Plus, there was a whole global pandemic happening. Looking backward wasn’t exactly at the top of my to-do list.

Though here we are fifteen months removed from my career change, a bit of reflection is probably merited. However, this email isn’t about my personal reflection. That’s what my journal is for. Instead, I want to explore how these same questions can guide everyone’s creativity.

These three questions are battle-tested and perfected over nearly two decades of small-group discussions. They are, on the surface, rather straightforward. However, they pull details out of people that may not always be as clear.

What is the best story from this experience?

I love this story because it almost always leads to laughter. When we look back on experiences or past friends and family, we inherently go to the fun times. The happy moments. The things that made us collectively laugh.

Stories imprint somewhere in the deep recesses of our memory. It’s a way all humans learn and retain information. That’s why storytelling is so essential for any creative person. If you want people to remember things, tell a good story.

What is the one thing you want to remember in five years?

Our memories are horribly unreliable. The details of any experience get muddied with time, yet large concepts remain seared into our brains. This question gets to the heart of what is most important about the experience.

When working on a creative project, it’s important to drill down to the essence of what the project conveys. What one thing do you want people to take away from the piece? Is it a theme, a message, an idea? Drilling down to the one vital thing is key for memory retention and ensuring your work remains focused.

How will this experience change you?

This question triggered the most introspection. Sure, stories are fun to tell, and major lessons are worth remembering, but how are you different because of them?

Consider this question why you’re creating something in the first place. Why do you want people to walk away with a specific thought or feeling? Why do you want them to remember a story or act upon an idea?


Asking these three questions not only focuses on our memories and debriefs experiences, but they can also help our creative projects go from good to extraordinary.

Whatever project you are working on, take 10 minutes and brainstorm answers to these three questions. Then, let me know how it changes your approach to creativity.

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