This weekend, I had a chance to visit my daughter at college and we had an amazing daddy/daughter day. After our visit, on the way to the airport, I struck up a conversation with my Lyft driver, who I estimated was in her 40s. I’m always intrigued by the different business approaches that each driver employs.

In this case, my driver had a full-time job, but would drive for four or five hours after work four days a week, targeting $100-150 a day. When I empathized that it sounded like a lot of long days, she downplayed it. She asserted that working hard and saving money were in her DNA, and she shared her goal for the year.

Curious, I asked if she was saving for a specific purpose. She shared that she was determined to get back to her financial footing before the COVID-19 pandemic, which was an important goal for her. By this point, we had established a solid rapport, and she chose to delve deeper.

“I’ll be honest,” she said, “making money is very important to me. When I was 13 my mom made some very different choices in her life, and I was left to take care of my baby brother. So, at 13 years old, I started selling drugs to make ends meet and put food on the table. My grandmother was already working three jobs to keep a roof over our heads.”

We went on to talk about the different careers that she’d had in her life, including being an EMT, which paid surprisingly low for the nature of the work. She also shared her future goals: she hopes to get into MRI imaging and to get her own haircare product business off the ground, as it struggled when she first launched it last year. She also shared that she still aspired to attend college and wished that she had.

I found her work ethic and mindset incredibly inspiring, especially considering the numerous setbacks she had faced. This conversation reinforced a couple different things in my mind.

We don’t start life on a level playing field.

While we may want to believe life is a meritocracy, where the people who rise to the top are always most deserving, the objective truth is different. While many of us likely sleep better at night thinking our success is simply a biproduct of our hard work, the reality is that it’s very challenging to succeed without a strong foundation of emotional and financial support.

Recent studies, based on a wealth of data, have reached a similar conclusion: the single highest predictor of your financial success is the level of your parent’s wealth. Everyone loves a rags-to-riches story; and while those do happen, they really are the exceptions if you examine the data more closely.

I am guessing my Lyft driver works harder than most people I know, but her path upward is much steeper.

Everyone has a backstory.

When asked whether they would hire a former drug dealer, most people would understandably say no. But this conversation is a reminder that you cannot judge someone’s past actions without full context. Everyone has a backstory that shapes who they are and informs their prior experiences; these stories often contain pain, struggle and difficult choices. Having helped over 2,000 people discover their core values, I have seen firsthand a pretty direct connection between values and formative childhood experiences.

In some instances, a backstory may explain current struggles. In others, it can illuminate the adversity hidden behind someone’s success and their tendency to overcompensate. By asking questions and demonstrating genuine interest, you can encourage people to share their backstories and gain a better understanding of who they are today.

As I exited the car, I couldn’t help but ponder the paradox of my college visit—which came immediately before a tour of schools with my second oldest. It’s tragic that my driver likely had the same hopes and drive as my kids, but never had their opportunity.

I tipped the driver the max amount the Lyft app would allow. I told her that I hoped she would enjoy a well-deserved day off and had the chance to attend college sometime soon. It was an important reminder for me of the value of listening, avoiding judgement, and always being kind.

Quote of The Week

“Everyone you meet is fighting a battle you know nothing about. Be kind. Always.”


–Brad Meltzer