Interesting people, places, conversations, experiences & insights brought to you by a guy who uses the Ride-Sharing platform to Life Coach his passengers. NOTE: People mentioned in posts will have all their identity changed when needed for privacy protection on any sensitive content that is shared.
Shadows of people walking over a dessert


VIEW POST

View more
Insights » Inspirational Stories

GIRL ON A MISSION

By
on
November 25, 2018

 
 

It was a long day… actually, it was a long week. I was looking for my last ride home.  As I was about to choose my destination as “HOME,” meaning I only pick up rides along the way to my house, I got a ping on my app for…

A white pawn and a black king chess pieces


VIEW POST

View more
Insights » Career/Business

DREAMS DO COME TRUE!

By
on
November 5, 2018

 
It’s not every day you meet someone who had a dream come true, but I did, and you can read about it through my latest article posted to Alley.com ( Posted Below):
••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••

DREAMS DO COME TRUE

We are all dreamers aren’t we? Aren’t you? I know I am, and truth be…

An artwork of a man rolling a ball up a hill


VIEW POST

View more
Insights » Inspirational Stories

MENTAL TOUGHNESS

By
on
October 22, 2018

You don’t have to look too far or deep to notice how mental health issues have mushroomed in recent years.  Just turn on the evening news and it is no surprise anymore to learn of a tragic event caused by someone with a mental health problem.  I personally cannot…

A silhouette of a man holding the sun in his hands


VIEW POST

View more
Insights » Life Stuff

PERSPECTIVE IS EVERYTHING…

By
on
October 8, 2018

A Change in the City

I am not sure people realize how much the Greater Boston area has changed over the past 20 years. A simple glance at the skyline reveals the physical change.  Rough neighborhoods are quietly transforming into revitalized landscapes with new construction at every turn.  This transformation,…

A man standing on a flooded pier


VIEW POST

View more
Insights » Career/Business

HOW DID I GET HERE ANYWAY?

By
on
September 6, 2018

On a beautiful day this Summer I picked up a guy from the Cambridge office of ALLEY 
( www.alley.com ).  Alley is a Verizon venture start-up with offices right now in NYC & Boston… It is similar to WeWork, a co-share work space, but it is more of an incubator…

A woman looking at her watch


VIEW POST

View more
Insights » Relationships

NO ROOM TO DATE

By
on
August 9, 2018

Whenever I get a ride near MIT (Massachusetts Institute of Technology), I never know exactly who might pop in. Let’s see, there was the “RAT NERD” who was obsessed with getting rid of rats in his whole neighborhood, there was the cute Chinese couple that I took to City…

A woman with a clock on her head


VIEW POST

View more
Insights » Inspirational Stories

RUNNING LATE… ZEN STYLE!

By
on
June 17, 2018

Starting my drive just outside of Boston in the early morning, it was a beautiful drive heading down route 117.  I know from experience, if I make it to Waltham without getting that first ride it’s never a good sign, as most pickups in this town don’t seem to…

An artwork of hands and a heart


VIEW POST

View more
Insights » Career/Business

TEACHING KINDNESS?

By
on
May 21, 2018

 
When an Indian man named Sandeep got in my car, he seemed perplexed.  He looked at my sign offering options for conversation and asked, “You offer life coaching and venting sessions?”
 
I responded, “Absolutely, so, what’s on your mind today?”
 
Sandeep
Sandeep is a C-level executive at a start-up company in Boston….

Hands opening wooden boards showing a second chance


VIEW POST

View more
Insights » Inspirational Stories

A SECOND CHANCE TO GET IT RIGHT

By
on
May 9, 2018

 
A Dillema Indeed
What would you do if you were heading to the airport, and your boss called to tell you that he is laying off 250 people and your company may face bankruptcy?
 
I picked Scott up at the airport as he was returning from a NYC business trip. He…

A woman looking out to the city


VIEW POST

View more
Insights » Relationships

NEW JOB, NEW CITY… NO FRIENDS

By
on
April 25, 2018

After a quick pick-up in Brookline, I looked in my rearview mirror at her and asked, “So, how’s BU going?”She smiled and replied, “No, I’m out of school and working.”

Mary

“Oh, great! And what are you doing for work?” I asked. “I’m an animator, but not the kind you may…

Driving Insights © 2021
Greater Boston, MA

INTERESTED IN BEING LIFE COACHED? If so please visit the menu at the top left on home page (on Mobil go to 3 horizontal bars). ••••••••••••••••••••••••••••••••••••••••••••••••• Now more about me... Long story short: I started with UBER (6) years ago as a sabbatical from enterprise B2B sales. I have found driving for Uber in Boston to be one of the most engaging gigs I have ever experienced. SOOOO… I decided not to return to corporate life and use Ubering as a platform to help people through life coaching, conversations and random acts of kindness. I am a very HAPPY camper now!

Subscribe for Updates

Jim’s on Twitter