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"How Did I Get Here Anyway?" Meet The Rideshare Life Coach

Jim Stern
Rideshare Life Coach & Blogger
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new york city
Editors Note: Our CEO, Jason found himself on a life changing Uber ride. While Jason could have been stuck with a traditional driver he had the opportunity to ride with Jim. The reason why Jim is different is that he not only gets you from point A to point B but he helps you along whatever journey you may be enduring. Jim left corporate life to do what he loves most -- help people, and drive. Ridesharing has provided Jim a way to give back and help his passengers through life coaching, therapy on the fly, venting sessions, and dating advice. Tune in for his stories about his Ubering experiences and all the people he has helped along the way.


Our lives move quickly and before we know it the days turn into weeks, which turn into months and the years fly right on by.  Sometimes you need to take a step back, hit the pause button and ask yourself, “How did I get here, anyway?” It is a question that helps us examine, understand and reflect on our lives.  

When I was asked to contribute to Alley each month it was suggested that I start by introducing myself, so I thought this was a great time to ask this thought-provoking question: How did I get here? What led to this moment? Truth be told, how I got here is a long and winding story, but don’t fret, I will spare you all the minute details and cut to the chase.


These days I consider myself semi-retired, but not necessarily out of choice... and so my story begins. Although I am told I don’t look my age, let’s just say I am of retirement age. My career accomplishments include being an elementary school teacher, video producer, sales executive, and entrepreneur. I enjoyed over forty years of a rich and satisfying career, or should I say, “careers.”  After experiencing a few lay-offs mostly due to company mergers, I decided I needed a break from corporate life. I needed to feel in control again, so I put myself on a self-imposed one-year sabbatical! But I couldn’t just hang out. I needed a purpose, something to do and some cash flow of course. Right around that time, Lyft and Uber were starting up in Boston and I happen to love driving (kind of a hobby and my first word was car afterall).  I truly enjoy engaging with people and the fact that Uber would actually pay me for these interests seemed too good to be true. I figured it was a bit of a no brainer, right?


I have always worked to become a top achiever in my field, and in each career I found ways to think differently and creatively to reach that goal, so why not re-engineer driving for Uber? After my one-year sabbatical ended, I found my age was getting in the way of being hired by the companies where I was interviewing. I realized it was time to rethink things, take full ownership of my Uber persona and just give HAPPY a try.


In thinking back to my earlier days as a teacher, when it was important for me to give back and help young people, it became clear that over 30 years in business had hardened me. I knew that to feel fulfilled I would need to get back to being a kinder version of myself. I wanted to offer my Uber passengers options for conversation—ranging from life coaching, therapy on the fly, venting sessions, and dating advice—and make an effort to actually help them out. After all, everyone has something on their mind that they could use help working through.  Most passengers seem to get a real kick out of these conversational options, and they laugh and take a picture of my offerings (a little signage helps).


Some of the conversations I’ve had with passengers have inspired me so much that I felt a need to start writing about my Ubering experience. This has culminated in a blog that I started called Uber Insights. Ubering has become my happy place, provided opportunities to; 1- give back, 2- gain experience for my writing and 3- engage with people from all over the world. Ubering is simply too enjoyable to give up.


It is interesting to compare our career paths to the game of Dominoes, where each preceding vertical tile collides into the next, resulting in some sort of path, or design, in motion. Over the course of our careers, each position we take contributes to our next move. If you look at your first and last professional roles they may appear to be polar opposites, however take a look at each step along the way and it may make perfect sense. I have learned that unless you take risks, go with your gut, and see where a new opportunity could lead, you are not opening yourself up to change and possibilities.  


In the coming months I will be contributing articles about conversations and inspiring stories from my Ubering experience. I am hoping they will make readers think about things they haven’t considered for a while. So let me ask you, “How did you get here, anyway?”

You can contact Jim at

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