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


March 29, 2018

It was Friday, my favorite day of the week. I mean, can anything ever go wrong when it’s the day before the weekend?  I usually shut down my Ubering and head home around 2pm, but for some reason after 27 rides that day I decided to pick up one more.

It was Friday, my favorite day of the week. I mean, can anything ever go wrong when it’s the day before the weekend?  I usually shut down my Ubering and head home around 2pm, but for some reason after 27 rides that day I decided to pick up one more.

As I pulled up to a Starbucks just east of Harvard Square, I saw three young guys approaching my car.  It was close to Cambridge Ringe & Latin High, so I assumed they had just gotten off from school.   As the three young men got in to the car (let’s call them Randy, Bernard & Jake), I sensed a little attitude… tough guys.  Hey, no worries here as I figured I have dealt with attitude before. I thought, I will just have to break them down. But in a good way, of course.

“How’s it going guys?” I asked.  I got a couple of nods and then Randy from the backseat snickered and said, “Wait, you offer venting sessions & dating advice?” I told him “Sure, but I never give generic advice, so what’s your issue? I will give you some straight feedback.”

Randy said Okay, that he has an issue, but it’s about a girl and it could be venting or dating advice… maybe both.   I said to him, “Let’s hear it.”  He told me there is this girl he has been seeing for over four years and she is moving to North Carolina. He does not know what to do:  Should they break up, or have a long-distance relationship? I thought, Really? In High School?   I told Randy that he could go in a few different directions. If he didn’t want to break it off, they could meet during vacations or perhaps go to the same college. He could also just end it, move on and be open to meet someone new.   Randy nodded in agreement and said he had a lot to think about.

Jake sitting in the back next to Randy said, “I’ve got an issue.”

I replied, “Go for it, what’s going on?”

“It’s also about a girl I’m seeing,” he told me.  It seems that this girl is cheating on Jake with his friend. “Not a good friend,” he continued. I thought, Exactly!  Jake was not sure what to do about this.  I advised that if he knows for a fact that she is cheating, she is not worthy of his love.  I told him to tell her something like this: I know you have been cheating on me with Ron.  If you are into him, don’t disrespect me by cheating. Just break up with me first!  And speaking of breaking up, I already did, with you last week, but have not had anytime to tell you until now!  See ya!

This joke was a big hit, as all three guys started laughing and giving high fives. Two out of two of my pieces of advice seemed to be on point and I thought I was on a roll.  Sitting at a stop light I turned to Bernard, the toughest one, wearing a hoodie and shades, and possibly silver-covered teeth like a rapper or hip-hop artist. In reality, I think they were just braces with the sun shining on them.   😉 

Bernard said, “No, I too have a few issues, but I just can’t decide which one to talk about.” Everyone in the car laughed. “Okay, there is this girl I like, but I have heard she has a past that is not great.” In further disclosure, Bernard told me she did some questionable things privately that gave her a bad reputation.  I smelled a double standard, but figured that was another issue entirely and we didn’t have adequate time to get into it. I was just happy he was opening up. I asked if he brought up his concerns to her. “Yep,” he said, “I did bring it up and she denied it all.”

I told Bernard, “Look, we all have pasts and we may have done a few things ourselves that we may not be proud of, so it’s never good to judge others. Don’t you think you should give her the benefit of the doubt? It shouldn’t really matter if she is trying to turn a page from her past, especially if she has done nothing to you. In fact, you should be supportive. If, however, it turns out that she was not truthful about her past or she does something that negatively affects you directly, then simply talk to her about it and move on.  But you may be glad you gave it a shot.”

I was happy that Randy, Jake and Bernard could open up to a total stranger and voice their concerns. They turned out to be really nice, caring guys.  I was a little surprised that all three issues were about women in their lives and at such a young age.  Hmm, come to think of it, I have my own set of women issues too… I guess it’s just a topic that has no age barriers.  I think I need to grab an UBER so I can get some counsel too!

  1. Reply


    December 29, 2018

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    December 29, 2018

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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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