August 14, 2018 / Esther Choy

At the start, three months of summer sounds like an extravagant amount of time. Yet at the end of it, many of us will find ourselves asking, “Is summer really over? What have I done?” Every year, we seem to prove the saying right: “The day is long; the year is short.” Here are two ways storytelling techniques can help us make the most of this fleeting season.

1. Connecting Better During the Vacation

Sometimes the best way to take advantage of summer is to take an “unplugged” vacation and enjoy near-monastic solitude. Other times, we take vacations for the sole purpose of connecting with others. When the purpose is to connect, it’s important to be deliberate about those connections.

Connecting with others is often a matter of taking the time to learn their stories. Few people, however–even those closest to us–will simply volunteer the deepest, most important stories of their lives. It takes a good question to bring it to the surface.

My colleague Amanda Hirsch, founder of Mighty Forces, recommends the question “What is something you’re thinking about a lot in your work life right now?” She adds, “if it’s someone I know but we haven’t talked in a while I might ask the same question about their personal life.” These questions can prompt someone to fill you in on the stories that matter most to them right now.

I’ve also found several categories of questions to ask people as I am getting to know them. These include:

Origin: How did this start? What motivated or prompted this? How did people react to the decision in the beginning? This could apply to their business, a relationship, relocation, current project, or the vacation itself.

Why: For instance, why do you do what you do? Continue to ask “why” at strategic points in order to drive the conversation deeper.

Surprises: What has surprised you the most? (For instance, “what has surprised you the most in your career…. new city… new role as a parent…?”) What didn’t you know when you started, but wish you did?

Compare and contrast: How is this different from that? For instance, how is this summer different from the last? How is this place different from home? What parallels can you draw between this and that? For instance, between your work and your hobbies?

Different path: How would life be different if you didn’t ______? For instance, if you didn’t work from home, take this vacation, move away from your hometown, attend your alma mater? If you were to take on the role of _____, what would be different? For instance, if you took on the role of mayor of your city or CEO of your company?

Many, many times, these have helped me push small talk deeper and have the kinds of conversations that make me feel my summer vacation has been well spent. (I have five more favorite categories of questions. You can find those and more in my book, Let the Story Do the Work, July 2017 HarperCollins.)

2. Consolidating and Strengthening Our Memories

Whether you consider summer to be over when the kids go back to school, the first leaf tumbles or the calendar officially tells you it’s fall, take some time shortly after summer is over to capture the story of how you spent it. As the years go by, events tend to mash together in our memory. To consolidate and strengthen your recollection, jot down a list of anecdotes or favorite quotes, or create visual prompts like a photo album or short video.

My go-to is the Splice video editor because it’s intuitive and requires little ‘tech-savviness’ to master its features. Here are two other options that can help you quickly and easily keep your summer memories fresh:

PicPlayPost: This highly rated app is touted for being intuitive. Best of all, if you’re short on time, there’s an “automated slideshow” feature–all you have to do is select the items you want in it. The app is free but with paid features inside.

Unfold: A video editor that was “developed as a digital toolkit for storytellers to create beautiful pieces for Instagram.” Unfold keeps things simple and elegant: your vacation photos will look like pages from a travel magazine. The app is also free but with paid features inside.

You’re busy, so why bother spending more time going through and documenting your memories? We are the story we tell ourselves. Our sense of self and life is only as strong and distinct as the stories that get to live in us. This is time extremely well spent!

Summer is almost over. It’s time to take that vacation and make the most of it.

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If you want to connect better with others or preserve and share your memories, contact us for business storytelling training! Leadership Story Lab trains and coaches managers in storytelling techniques to help them become more engaging and persuasive communicators. Whether you would like to stand out in the interview process, add punch to a presentation, or make a compelling case for a new initiative, we can help. Schedule a complimentary session with us today!

Esther’s new book, Let the Story Do the Work (published by HarperCollins Leadership), is now available!

This article originally appeared on

Esther Choy

Esther Choy founded Leadership Story Lab in 2010 to help others leverage the art of storytelling to create extraordinary opportunities.
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