Interesting people, places, conversations, experiences & insights brought to you by a guy who uses the Ride-Sharing platform to Life Coach his passengers.


January 30, 2018

Delivering 20-30 passengers a day can lead to many variations of engagement. Here are 3 random rides from last Friday:


A pool ride or shared ride involves 1 to 4 people going in the same direction.  Many times people will not strike up conversations amongst each other… unless they they have me as a catalyst to get things going.

On this particular pool I picked up a young Indian woman, Varada, in the Fenway neighborhood of Boston. She was a senior at Northeastern University heading out to Route 128, to one of the tech companies lining that highway.  It was a 40-minute ride and Varada mentioned the ride was way too long and expensive to take twice a day.  She felt she had to move closer to her job, and honestly, I could not argue with her on this. It made perfect sense.  

Four minutes out from reaching Varada’s destination, I got pinged for another pool pick-up. This time it was Riddhi, also a young Indian woman.  Riddhi got in and looked at Varada and they immediately struck up a conversation.  I noticed they were heading to the same address, so I mentioned what a coincidence this was.  Varada divulged that she had to move closer to her job.  Riddhi responded how one of her roommates was leaving and she was looking for a new roomie… you guessed it, a pool connection turned into a living connection.  Kinda cool, right?


My next passengers were two guys; Mike and his young bearded co-worker hopped in.  Mike immediately commented how he loved the emoji text he’d received from me, notifying him that I had arrived as the Uber notification can be delayed at times.  Mike noticed the options I offer for the ride and chuckled and said, “This is great!, I’ve never seen this before. I think I could use some life coaching.”  SO, what is your issue? I asked, as I never give generic advice out. “NO,” he said, “I want to hear your story,” and I gave it to him.  The ride was short, but he said he loves my story and feels he also needs to make a change in his life.

As I pulled up to their destination, I looked into my rear view mirror and noticed that Mike was crying. I asked, “Bro, what is going on?” but there was no time to get into it with him.  As he was leaving I handed him one of my “Gratitude coins” and said, “Whatever I triggered in you, follow it through, and if you need to make a change then make it happen.” I handed Mike a tissue and he thanked me for waking him up to what is really important in life.


I picked up Kate at a very large pharmaceutical company in Kendall Square in Cambridge.  She was very young and quite chatty.  We started talking about her career and to my surprise she has been out of school for six years (I must really be getting old) and is doing cancer research.  Kate told me that her entire department was let go at her company as they decided to get out of her area of expertise.

“So Kate, what’s next?” I asked.  She told me she has 3 options: 1) Pursue her PHD and receive a low-paying stipend; 2) Take a higher-paying research job at a Bio Tech company, but in an area she may not be as interested in; or 3) Accept a job already offered from MIT.  In discussing Kate’s options further, she said the MIT position is in the area which is her passion, however she would make much less then taking a corporate job, but at least her PHD would be covered.

I told Kate that you can never go wrong following your passion.  When your work is your passion then it may take longer to reach your financial goals, but you won’t care, and in time the money usually follows.  Most importantly, you will be happy and happy wins every time!

YEP, that’s a typical morning… just 20-30 more CONNECTIONS to close out the day.

  1. Reply

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Greater Boston, MA

Long story short: I started with UBER (5) 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!

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