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.
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Insights » Life Stuff


May 31, 2021

Covid-19 has definitely changed our lives in many ways, some good and some not so much. In my ride-sharing world with many white-collar workers stuck working remotely from home, I find myself spending more time in the inner-city, picking up essential workers and first responders.  I have mentioned in the past that probably 60% of my riders represent people of color and this is where many of my best conversations take place. If you know me or have read my past posts then you know I am not afraid to dwell into some tricky topics like discussing racism in Boston.  I’m not the kind of guy that dodges difficult conversations… the funny thing is they never really become difficult.  I thought it might be nice to share some perspective from two Black men I recently picked up.


As soon as Randall slid into the backseat he started talking.  I asked how his morning was going… he responded with “AMAZING, it’s so good to be alive! Want to hear something crazy?”  He started describing an incident that happened several weeks earlier. His mother always starts her car to get it warmed up in the morning before she heads out to work, but on this particular morning when she went out to her car, it was gone… like MIA.  Randall immediately borrowed his sister’s car and decided to follow his hunch and check out the neighborhood.  It didn’t take long before he spotted his mom’s car parked in front of some row houses. 

Randall patiently waited until one high school aged kid showed up by the car.  Randall approached him and started questioning the kid, as he wanted the set of keys back, which included his mom’s key to the house.  *Malcolm, the kid in question looked familiar as Randall recognized him from playing baseball for the local high school team where his friend coached.  Malcolm mentioned that Yes, he took the car with a friend but he didn’t have the keys.  Randall persisted and said to Malcolm he needed the keys back and that he would give him $50 for them.  Five minutes later the second kid showed up and Randall made the same plea saying he would pay $50 for the return of the keys and wouldn’t report it to the police.  The second kid held out the car key and Randall said, Come on guys, I need the whole set of keys.  So the second kid dug into his pocket and presented the rest of the keys.  Randall took the keys and paid the kids the promised $50. 

Randall, acting like a big brother, talked to both kids about staying out of trouble and ending this kind of behavior. They nodded their heads, but it did not appear they were listening.  They both took off, running down the street.  “Now here is the crazy part,” Randall said.  He ended up running into his coach friend earlier in the morning and Randall inquired about Malcolm. He asked how he was doing and if he was staying out of trouble.  His Coach friend paused for a long moment and sadly said that Malcolm got mixed up into some gang trouble and was killed the other day.  Randall was shocked hearing the news and as he told me, a tear ran down his cheek as he said, “I just knew things would not end up well for those guys.”


I picked up Dewayne in East Boston from his girlfriend’s house and was taking him to his job located in one of the western burbs close to the city.  Our chat was quite friendly and our conversation quickly turned to some of the recent topics of the day.  We started discussing Black Lives Matter, White Supremacy and the GOP.  I mentioned to Dewayne how I just did not get all this hatred at different races and ethnic groups.  I personally, have always appreciated and welcomed diversity; I just don’t see color and would never treat someone differently because of it. 

I told Dewayne that I was always the guy that appreciated all colors and so for me “All Lives Mattered”… and then I had a sudden awakening when the “Black Lives Matter” movement started.  I told Dewayne, what never occurred to me is what Black people go through every day.  The incidents that happen every day to Black people, that white people never have to deal with.  Some can be subtle like stares or some can be truly blatant like hearing the “N” word blurted out while walking down the street or being followed through a store.  This is the meaning of “white privilege,” which I never truly understood until the BLM movement started…and I am grateful for having that understanding!


I asked Dewayne how he felt about racism in Boston.  His answer really surprised me… he said that he didn’t feel racism in Boston.  He said the honest truth is if someone calls out a name it never bothers him because they are just words… “Words are just words, they don’t hurt me,” he said. Dewayne mentioned that he actually feels more racism from fellow Black people and he didn’t mean the calling of the “N” word from other Blacks because that is fairly common.  He went on to describe the hurtful words he would hear growing up about having big ears or lips… that kind of thing.  He went on to say that he developed an understanding that these were just words and he wasn’t going to let it hurt him.  I thought Dwayne was a wise man with an incredible outlook and mature beyond his years!

I truly appreciated the conversations I had with both Randall and Dewayne.  Both these young Black men had such a healthy attitude about life… their lives in particular and the world they live in.  It made me understand even more the Black Lives Matter movement and what it is really about.  Of course white people can relate to these kinds of experiences on some level, but Black people live a life where things happen daily that white people will never have to deal with.  I wanted these two Black men to know that there are many white people who support their cause and have their backs.  I am one of those white people!

• Names & any identifying information may have been changed to protect the innocent (from post), as I am only interested in writing about our conversations, especially if it might be insightful to others.

© Driving Insights, 2021 +


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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!

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