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An Insightful Uber Rider: The Millennial Mindset

uber driver mindful steward

Written By Sean Grabowski

A passionate ambassador, educator and student of mindfulness and meditation. Advocate for unique experiences and life long learning.

October 11, 2017


Recently, to pass some time before the start day of a fresh work opportunity, I became an Uber drive. Ever since my initial and hesitant sign up to simply cover my expenses in the short term, I’ve realized how fun of a job it actually is. Driving Uber is a blast. It’s an incredible way to meet new people and have interesting conversations with strangers on a daily basis, especially considering the majority of riders are close to me in age. One thing I’ve noticed immediately is the somewhat hilarious tendency for people to treat their Uber drivers as if we are their therapists. For whatever reason, riders open up to us about their lives, their struggles and really, whatever is troubling them at the time. This is dependant on the rider, of course, but it does happen a lot. Last week I drove a business executive home from the city core, while simultaneously receiving an earful about the regrets of his professional and proverbial “climb to the top”. It was simple, but insightful, and I decided to put it on some paper.

It is a chronic millennial tendency to prioritize life over work in the work-life balance paradigm. Maybe it is that we are simply learning from our parents mistakes, or maybe we are just pre-conditioned to this perception from growing up in the technological era where we are constantly bombarded by imagery of “the good life”. In the end, regardless of where it has originated, this view on work-life is a common trend in the millennial mindset and it seems many people from other generations actually do appreciate the fact that we possess this perspective.

“Millennials don’t want to be managed, they like to be led, coached and mentored. This generation is on fire and ready to go. Are you ready to change the world?” – Farshad Asl

My Uber rider was established, highly paid, and powerful in his work life, but he lamented the incessant drive for material wealth he prescribed to for most of his life. It brought him no additional happiness, something he believed he would achieve with each coming promotion and raise. He outlined to me his plan to leave his company to start a unique business of his own over the coming years. His advice to me was simple and not unique, but it really was interesting hearing it first hand, instead of in some lame motivational book. “That additional money they offer you for a promotion is almost never worth the personal deficits you will suffer if you hate what you are doing. You need to find a work life and a lifestyle that engages you, or you will have a lot harder time finding satisfaction. We struggle to manage millennial employees for this exact reason, you guys don’t hope to enjoy your job, you expect to. That is something many people my age didn’t figure out until our mid life crisis”. I wrote down his statement immediately after dropping him off at his massive home in the suburbs.

It might just be me, but I feel bombarded by so much “how to be happier” type content that I honestly don’t even know what is legit anymore. What I’ve come to realize makes me happiest seems to fall into a few simple categories: Consistently striving toward personal betterment, prioritizing my passions and health, and in the long term, I believe shaping a work-life that I enjoy is imperative to all of that (or that is just my inner millennial coming out). The millennial dilemma is that we posses an overbearing expectation for instant success, in terms of happiness and career. This stuff simply doesn’t happen overnight and most of the time it requires some good old fashion hard work. Each of us figures out our needs and goals at different points in life. In my opinion, any progress is good, as long as it is happening. However, as my Uber riding friend affirmed, it is important to consider what real progress actually means for our individual situation. Is it actually getting us where we want to be going, or not.


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