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.
Faces showing different emotions
Insights » Life Stuff


June 2, 2019
When people pop into my car it’s quite easy to gauge if they want to have a conversation or not.  Some people are so locked into their own world, they don’t look up from their phones or computers. I always respect everyone’s space, but most people immediately engage and off we go.
Frank & Elena
Frank and Elena were a really cute couple in their 20s heading to work downtown (their first jobs after college and where they met). Frank immediately noticed my sign and wanted know what I tell people about life coaching.  I told him I don’t usually give out generic advice, but when given a choice in a life always go with what makes you happy (as long as it doesn’t hurt anyone).  This apparently hit a button with Frank. He immediately lit into a rant about how people just want you to be happy all the time.  He felt people want you to replace your worries, stress and concerns with happy… like disguising or hiding what’s really going on and just act happy whether it’s earnest or not. Frank felt people don’t want to be burdened with other peoples’ problems.
Dealing with Reality
I am not sure whether I agree with Frank’s assessment or not; perhaps he was generalizing a bit.  I do believe sometimes people don’t want to be burdened hearing about other peoples’ realities and only want to hear the good. Piling on other peoples’ unhappiness can sometimes be too much.
We chatted about how masking happiness over one’s worries is not dealing with reality. Who doesn’t want to be happy all the time? But this sentiment doesn’t represent the world we live in.  We discussed how dealing with the realities of one’s feelings actually helps you grow as a person.  Trying to mask them with a false sense of “everything is great” is not being true to yourself and will resolve nothing and actually hold you back. Being honest with your feelings and the realities of stress, worries and concerns will help you grow in life. Facing the challenges in your life directly is, to me, the only way. Being able to tackle worries and stress is actually a gift that most of us don’t appreciate.
Don’t Worry, Be Happy
This brings me to the song “Don’t Worry, Be Happy” by Bobby McFerrin from 1996 (gee, it feels like not that long ago). The premise of the song is that worrying is a waste of time and can double your trouble in your head… so just be happy.  I prefer to deal with the worry head on, don’t mask it in happiness if you aren’t really feeling it… so rather than Don’t worry be happy, I would aim for resolution.  
As I approached Frank & Elena’s final destination, Frank seemed to appreciate the conversation or my option choice # 4- Venting Session.  He turned to Elena and declared… “I’m actually feeling pretty happy right now!”

December 17, 2021

A human figure with a light bulb

September 27, 2021

A businessman rolling dice

July 28, 2021


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