Living a Life of No Regret: How to Live a Meaningful and Purposeful Life with No Regrets with Jordan Gross

Jordan Gross interviewed on The Second Phase Podcast to discuss his book, The Journey to Cloud Nine. The podcast graphic has a photo of Jordan and a photos of his book with a toy airplane next to it.

Jordan is a 25-year-old corporate refuge!   He left corporate to follow his curiosity and passion.  Using his idea of a Cloud Nine life, he is a trailblazer for positive change and optimism, sharing the belief that our daily actions can help us overcome stress and anxiety.

The First Phase

Jordan’s first phase was going through the motions, running on the hamster wheel of get good grades, play sports, go to a good college, get good internships, get a good job and make money.   Basically, Jordan was following what others thought his path should be.

The Second Phase

Jordan is spending is second phase trailblazing a path for others to think about personal development in a new way.  By using fictional storytelling, Jordan writes books, coaches and speaks about how to live our lives on cloud nine!

Cloud Nine

Don’t worry, we are not going to get all dreamy on you.   Jordan uses the term cloud nine to refer to living a positive fulfilling life of purpose.  His most recent book, “The Journey to Cloud Nine” is a fictional story about a man who made choices in his life and at 60 years of age, he begins to see that if only he’d made other decisions, he could have been living on cloud nine instead of living alone and suffering with depression.

It’s Never Too Early

We focus on it never being too late to start something new.  But in this episode, we are really looking at it’s never too early to start the second phase.

Passion doesn’t always mean purpose. If you are not being fulfilled, it’s time to make a change and move on to the next phase.

Jordan began his second phase by writing a book.  The book led to speaking engagements, a TEDx Talk, and a podcast. His second book was published in February 2020 and his third book will be published in the Spring of 2021.

Not everyone finds their gifts so early.   But it didn’t happen for Jordan overnight.   It took a lot of exploration of his curiosity.  The important thing to note is that is a matter of optimizing your exploration of curiosity to find your passion and ultimate purpose and finding the cloud nine.

Are you a Pilot, Co-Pilot or the Passenger?

The passenger

The passenger let’s societal expectations navigate their path for them.  They tend to follow the recommendations of others.

The Pilot

The pilot is the person that takes control of their journey.  They follow their gut, their heart, their intuition. Live and learn through the experience.  Action brings a lot of clarity.

The Co-Pilot

The co-pilot provides the perspective that we don’t have to go through the journey alone.   They don’t take control but provide the right recommendations and guidance.

It’s really hard to go about any journey alone.   The co-pilot serves as the companion on the journey.

Favorite quote

“Somebody once told me that definition of hell:  On my last day on this earth, the person who I became will meet the person I could have become, and those two people are total strangers.”

“But somebody also once told me the definition of heaven: On my last day on this earth, the person who I became will meet the person I could have become, and those two people are identical twins.” – Ed Mylett

In making decisions, you want to minimize the gap between who you became and who you could have become.   In every moment, in every choice, you are making the choice that is going to minimize regret.

Gut, intuition, and feel are so important for making decisions.

You can measure character of a person by the choices they make.  There is never a right or wrong choice but a right or wrong way to view the choice you made.  The approach taken for making the decision is what is important to ensure you aren’t going to look back and regret that decision.   Fully immerse yourself in the decision and be totally content with the decision that you made.

About Jerry

Jerry is the main character, a fictional character in “The Journey to Cloud Nine”.  Jerry’s life was being dictated for him and is who Jordan is warning himself not to become.

It’s very easy to let others dictate our life choices.   Before you can make decisions for yourself and gain the support of others, you have to do the work to evaluate the decision and know you are on the right path.  When people see that you’ve done your work and know the value within your decision, they will be more apt to accept it and support you.   You have to be your own co-pilot first.

Identify Your Co-Pilots

Know who respects you and the depth of your ability to make decisions for yourself.   It comes back to logic versus intuition.   You have to take a step back and evaluate the importance of having what you need versus doing something that you will want to do.   It really comes down to communication and being real and raw and honest when telling people what you want to do or need to do.

Human Connection

As humans we need social contact.  No matter how shy or introverted you are, having a couple of key people to be yourself with is important for self-fulfillment.  Connections add value to your life, but you also add value to their life.

Our daily actions can help overcome stress and anxiety.  Making connections and building relationships can help with decreasing the stress and anxiety too.


Jordan uses his JERI method to write his books.   It changes the perspective of reading self-help books.

J – It’s about the journey, not the destination

E – The emotional connection with the characters

R – Reducing the stress

I – Imagitivetation – imagination + creativity + interpretation + implementation

About Jordan

Jordan Gross is a corporate refugee turned trailblazer for positive change and optimism, sharing the belief that our daily actions can help us overcome stress and anxiety. He is a 25-year-old guy just tyring to create something meaningful for himself and for others.

Jordan is a graduate of Northwestern university and Kellogg School of Management, a writer, a coach, a speaker, and a multipotentialite.He is the best-selling author of “Getting COMFY: Your Morning Guide to Daily Happiness and a TEDx speaker.

Learn more and connect with Jordan

Access free chapters of “The Journey to Cloud Nine”



The Journey to Cloud Nine on Amazon

Learn more about your host, Robyn Graham, click HERE.

To learn about The Brand Marketing Insider by Robyn Graham, click HERE.


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