Jordan Gross — On Storytelling, Building Reading Habits, and Handling Uncertainty

Home Podcast Jordan Gross — On Storytelling, Building Reading Habits, and Handling Uncertainty

Jordan Gross — On Storytelling, Building Reading Habits, and Handling Uncertainty

Jordan Gross is a trailblazer, a son, grandson, writer, speaker, guide, editor, and soon-to-be therapist. He is a Northwestern and Kellogg School of Management graduate where he studied absolutely nothing to do with writing. He’s a former startup founder, restaurant manager, and soccer goalie. A solopreneur, podcast host, and 2 Times TEDx speaker, he is also the #1 bestselling author of Getting COMFY: Your Morning Guide to Daily Happiness, and The Journey to Cloud Nine. His third book, What Happens in Tomorrow World, is scheduled to launch on April 6th. Jordan is also an editor of the widely popular Medium publication, Mind Cafe.


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Jordan Gross on LinkedIn and Medium
61 best personal development books summarized in one sentence
27 best personal development books that use creative storytelling
What Happens in Tomorrow World Book Trailer
Private LinkedIn group “Help-Self” that emphasizes creativity, fun, and storytelling in the personal development world
Animal Farm
Why read a book more than once [Ryan Holiday video]
Tuesdays with Morrie
The Defining Decade
Standpoint Theory
Podcast episode with career and communications coach Michael Thompson


Highlights of the podcast

(2:40) How stories can excite and inspire others to learn and live.

Stories are entertaining ways to learn about topics. My first book was George Orwell’s Animal Farm. It was about the Russian Revolution, but was told through the lens of animals on a farm, and was explained in a clear way. I wasn’t just memorizing facts and statistics, I was speaking (metaphorically) to the characters and understanding the emotions behind the animals. It was my first real glimpse into how storytelling can excite someone to live and learn rather than just go through the daily motions.

(5:30) Why stories are more impactful than self-help advice.

Allegories, parables, and fables provide readers with opportunities to apply lessons to their own lives as compared to prescriptive, “do this do that” self-help. We cannot tell people what to do in order to change their minds and identities. But stories provide the persuasive elements we need to ignite someone’s mind to change.

(7:07) On the importance of rereading books to get more out of them.

My main objective for 2021 is to reread and listen to a lot of books. When you read something when you’re 20 and reread it with you’re 25, the book doesn’t feel the same. That’s because you change and the world around you changes. So neither you nor the book is the same.

One book I’m rereading is The Defining Decade by Meg J. I first read this book when I was 22-23, and it’s like a blueprint about how you should live in your 20s, which I think I’m doing well. But the underserved population that I’m studying in school cannot apply the techniques from this book. I was not thinking about them three years ago. But now I am, because of where I am in my life.

(13:00) On “Imagitevitation.”

Imagitevitation means thinking about who you want to become in the future and working to attain it. It stands for “Imagination,” “Interpretation,” “Creativity,” and “Implementation.” So if I want to write a book, I imagine myself with the book in my hand, what people are saying, how my parents and grandma are smiling. Next, is interpretation, which comes down to why is the dream important? Then comes creativity, which is about making a creative plan in the present moment to get to the goal. Finally, implementation is about acting on that plan. It’s trial-and-error, experimenting, and assessing how you’re doing on the journey to achieve that dream.

(17:45) The importance of embracing uncertainty.

The more we desire certainty and clarity on things we cannot be 100% certain of, the more anxiety and stress we undergo. Sometimes, we have to lean into the unpredictability and build the experimentation mindset as opposed to believing there’s just one way to do things and that if we follow it we’ll get what we desire. When we make peace with uncertainty, we can see opportunities even if we’ve not achieved what we wanted to.

(20:12) How to open up to experiences that lead to uncertainty?

Either surround yourself with people who are doing things that make them uncomfortable, seeking new experiences, and being adventurous. Make them a source of inspiration. Or remove some of the certainty from your own life to create space for uncertainty to enter in.

(28:00) What optimism means in the practical world.

My belief about optimism is not that everything will be great. Rather its the belief that if something goes wrong, I’ll still make things right again. Things don’t always have to be okay, but I’m optimistic that they will be okay again.

(32:02) The best way to manage uncertainty.

It’s not optimism or building a sage mindset. It’s fostering hope, love, faith, and being there for the people who need us. That’s how we put one foot in front of the other and support people who’re not managing uncertainty as well as we are.

(34:00) 3 must-remember points to get better at storytelling.

If you want to tell better stories, imagine your work in form of a story for another human being. How is your work impacting someone else’s life?

When I was a baseball player growing up, I always tried to hit home runs. And when you always try to hit home runs, you swing too hard and a strikeout. So my friend’s dad who was the assistant coach would say, “A single is just as good as a home run. Hit singles, get off base, and get home.” So when it comes to storytelling, aim for singles. Don’t try to tell a jaw-dropping story or hit that home run.

Also, to exercise your storytelling muscle, think of a banal situation in your life and reimagine how it could’ve been. For instance, you bump into a person on the street, said sorry, and moved on. But you could reimagine that normal incident as the person is an old high-school acquaintance who’s now a startup founder and invited you to work at his/her company and that your life changed.

Finally, make meaning out of the mundane. So if you bump into someone on the street, make meaning out of that experience. Appreciate it for what it is — a one in a million chance that you knocked into that specific person, who in turn, responded with grace.

Thus, three tips to flex your storytelling muscle are:

  1. Go for singles instead of home runs.
  2. Reimagine banal incidents on how they could’ve been.
  3. Make meaning of the mundane.

(40:45) Non-negotiable activities in my routine.

My routine changes every day since I’m back at school. But my non-negotiable tasks are:

  1. No snoozing, because the more I hit snooze the lazier I’ll be.
  2. Have human interactions with friends, family members, peers, podcast hosts, and others.
  3. Get outside and take in the fresh air.

(42:50) The advice I would give 16-year-old Jordan.

When I was 16, I was under the impression that I didn’t need to know what I wanted to do with my life. So I didn’t even start to explore it. You don’t have to know exactly what you’re going to do in the future, but you should start thinking about it. Start exploring curiosity, learning about who you are, and who you want to become. And always remember that your stories are YOUR stories. They make you unique, and you’re the star in them.

(P.S. Download a free ebook on 10 simple lessons to create a life you look forward to each day here.)

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