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.
A crossroad between an easy and hard path


February 18, 2021

Sometimes we travel unfamiliar roads to achieve a goal we have set for ourselves. I know I have done this many times, such as when I took a job teaching in Australia to get that much-needed experience in a first job, or when I decided to become a life coach due to my Ubering experience. So, when I picked up Robin in Boston I knew suggesting an alternate route to one of her goals might be just the fix for her.


Robin, a young Black woman, 20 years old, was upbeat and friendly when she got in my car. I asked how her day was going and we were rudely interrupted by a car who felt the need to lean on their horn for a New York minute (not unusual in this town), so we started talking about how mean so many Boston drivers are (hmmmm, pretty sure I just read that Boston was rated #1 in that department).  Our conversation soon moved on to where she worked, which is at a bakery. She seemed to really enjoy baking.  I mentioned that breakfast and lunch are my specialties and shared some of my secrets for making my favorites for family and friends.  Robin seemed to get a kick out of this, but I sensed something was off so I asked is this is what she really wants to do, and where did she see herself in 5 years?

Robin went onto tell me that she was in college earlier in the year and wanted to be an engineer.  I couldn’t help but notice her eyes welling up with tears, so I asked what’s going on?   She mentioned sadly that in February her twin brother died in a car accident and she dropped out of school. I can’t imagine what she was going through, but I had an idea that might put her back on track. I asked one more time, what do you really want to do? Robin confirmed it was engineering and coding… that’s all I needed to hear.


As I am sure you can imagine, after 35,000 rides, I talk to a lot of people and we exchange ideas, conversations and many interesting topics (have you been following my blog?)… some of them I pass on to help other people, which applied to Robin’s case. Earlier in the year I picked up a young woman who worked for a non-profit I loved! Located in Cambridge, MA, RESILENT CODERS is a non-profit that helps people of color work with technology to make social change.  They have volunteers and mentors, and tech companies as sponsors that teach young people of color what they need to learn in coding and help them get jobs in the tech community.  Their mission statement is: “We believe in social justice through economic empowerment, and in the opportunity for meritocracy in tech. This isn’t about one-off camps or hackathons. This is about meaningful change.”  As their website declares they are, “Training people of color for high growth careers as software engineers, and connecting them with jobs.” This is no understatement as the woman mentioned many of their graduates earn beginning salaries of $90,000+… not too shabby!


As we were nearing her final destination, Robin appeared a little overwhelmed (in a good way) as I explained the organization and possibilities with her.  She lit up as she opened her phone’s browser and searched out the organization.  She mentioned she would definitely be looking into it and get in touch with them. I was happy for her and happy to help!  Sometimes it is the road less traveled that just happens to be the most direct route to the goals we have set.  Do you have goals you are trying to pursue?  Are you stuck on how to achieve them? Perhaps you too should consider a road less traveled…

*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, 2019 +



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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